My 2023 Year in Review: Still here

Career Earnings to Date

Although this is a Year In Review post for 2023, it will mostly pick up where my 2022 post left off. I finally got around to publishing that post in June and had already been through almost half of 2023 when I published it, so I won’t recap all of that time and will probably pick up from this post: My business is struggling. Here’s my plan to save it.

In many ways, this has been an amazing year. I find myself feeling particularly grateful for my family and friends, my community, my town, and my life in general. I have much to be thankful for.

But financially, this has been probably my most stressful year yet. When I was under contract for the house I bought in October 2022, I felt that my business was slumping a bit. At the time, I didn’t have enough information to know for sure if I was just having a down month, or if the business itself was in trouble.

Part of deciding whether to go through with the house purchase was gaming out the possibilities in front of me. At one end of the spectrum was something like, “I’m currently having a slow month, which happens occasionally, but everything is actually fine with the business and the new house will be no big deal.” At the other end of the spectrum was something like, “Worst-case scenario is my business is tanking and I’m about to 2-3x my monthly expenses at the absolute worst possible time.” As it turns out, I was pretty close to the worst-case scenario.

My business brought in about 50% less revenue this year than it did last year. Worse, it brought in less than 40% of what it made in 2021. That’s after growing every year since I started it in 2016.

That being said, the final few months of this year are looking up a bit. More than half of the business’s revenue has come in since September 1, which is when the downward slide started last year. It’s not “back”, but it seems to be trending in a good direction.

I’ll unpack a lot more of that later on, but for now that’s a high level overview of my year.

2023 Goal review

Things were so dire by the time I wrote my 2022 Year In Review that I only set one goal…

Survive to 2024

And I did!

Barely, but I’m still here, running my business and paying the bills. And so far I’ve managed to do this without taking on any debt (other than some cash that I’ve borrowed just in case, and which is parked in an interest-bearing account).

Obviously, just surviving is not fun, and I’m relieved that things seem to be turning around, but I continue to live in survival mode.

I think I’ll just leave this as-is for now since I’ll be unpacking a lot of the specific tactics that helped me meet this goal later on.

2023 Year in Review – Business

Where to begin?

As I mentioned above, revenue was way down this year, under 40% of where it was in 2021. It might be helpful to remember that 2022 was down about 32% from 2021 (after actually running ahead of pace for the first half of 2022). That matters because it shows just how bad the second half of 2022 was, and then how bad 2023 was.

This is all the result of an extremely lean period from around October 2022 through August 2023.

Here’s my updated “Career Earnings to Date” chart, which I’ve been maintaining for over a decade now. I won’t digress about how mind-blowing that is, but it’s pretty mind-blowing. Anyway, here’s the chart:

Career Earnings to Date


Here are the stats that I typically track:

  • Visits to This was down, but I’m unsure how much because Google Analytics overhauled their product and I can’t figure out how to get stats. It was 720,000 in 2022 and I’m guessing it was around 700,000 in 2023
  • Unique page views: Same issue as above, but I’m guessing this was also down and under 1M
  • Total email subscribers at the end of the year: About 26,000 (down about 5% year over year)
  • Product sales through the site: About 40 (down from about 100)
  • Coaching applications: 26 (down from 99)
  • Coaching clients: 11 (down from about 22)
  • Coaching conversion rate (from application to client) was 42% (up from 22%)*

*This number is probably too high. I got some clients who came through entry points that previously didn’t exist, and therefore who did not complete applications. I also had leads from those new entry points that did not convert. My best guess is I closed about 33% of people I talked to about coaching this year.

Coaching revenue was down about 50% year over year.

I think the best way to think about the business this year is from two perspectives: macro and micro.

The Macro view

The boring view is the macro view. If you zoom out far enough, the business is more or less the same is it has been for the past several years (since 2017 or so when I started focusing on coaching full-time). Most of my revenue came from coaching, which is my primary focus, and I also sell my book and courses on the product side.

I’m still a salary negotiation coach, just like I have been for the past six years or more.

The Micro view

While my business is pretty much the same thing from the outside looking in, I’ve made lots of changes under the hood. “Overhaul” might be too strong a word, but only just.

Focusing on high earners

The overarching change I made this year was to broaden my positioning as a salary negotiation coach to a much more general demographic: high earners.

I previously focused on software engineers and engineering managers going to big tech companies. That was a great market in 2021 and a horrible market in late 2022.

I had actually started planning this exact change in positioning—from “engineers going to big tech companies” to “high earners”—way back in 2020. As I began thinking through that change, the first part of my plan was to redesign and rebrand my website. As I worked on those projects, I was careful to create new branding that would appeal to the big tech market and be durable enough to appeal to high earners later on.

Many of the branding and logo ideas I considered had visual cues that would appeal to software engineers and people in tech, and I ended up going with something which was less tech focused and more broadly looked like a “luxury” brand.

I’m really, really glad I did this because it made the pivot to high earners trivial in terms of branding rather than requiring an overhaul.

Anyway, the big tech hiring slowdown that began in late 2022 served as a forcing function that caused me to revisit my original plan and move on it as fast as possible.

I rolled out the new positioning in the middle of the year (June) and then began the uphill climb of figuring out how to find high earners who needed my help.

If you want to read a lot more detail about my positioning change to high earners, this post is a deep dive into that project:

My business is struggling. Here’s my plan to save it.

Starting from scratch with marketing

The biggest challenge with my repositioning to high earners is how to find those folks and make them aware that I exist and that I can help them negotiate their job offers.

Until this change, my entire coaching funnel was SEO-based. Back in 2017, I got very good at SEO and I built a site that would rank high for specific things that software engineers and engineering managers going to big tech companies might be searching for when they had a job offer in hand.

This was effective for two reasons:

  1. There wasn’t much competition (yet) for these search terms.
  2. Software Engineers and Engineering Managers basically make a living by googling solutions to technical problems and finding the best solution. I got really good at making my site the solution to their “What do I do once I have a job offer from a big tech company?” problem.

But I couldn’t rely on this strategy for high earners for a couple reasons:

  1. Over the past few years, there has been a lot more competition for search traffic in my space. For a while there, I was basically the only person or company doing what I do. I still am, but there are a lot of other people and companies doing something similar, and they also jumped on the SEO strategy. Some of them even copied my work, published it to their own site with minor changes, and ramped up their own marketing efforts to outrank me. There were a few times when I would see a new site outranking me (I had been, say, #2 and was now #3) only to discover that they had repurposed my own content on their site and leapfrogged me. Not good.
  2. More broadly, high earners and software engineers look for solutions to difficult problems in different ways. I don’t think they’re googling “How do I negotiate [company] job offer?” Instead, they’re asking friends and family, looking for trusted sources, possibly listening to podcasts, or asking other professionals with adjacent expertise (law, accounting, executive coaching) for help, and searching places like YouTube rather than Google. They’re “search” is more like asking a colleague or mentor, “Hey, I think I’m about to get an offer that should be pretty good. Do you know anyone I can talk to that will help me avoid screwing this up and leaving money on the table?”

So I needed a new marketing strategy to replace my “inbound SEO” machine that had helped me grow the business for the past five years.

Before I even started working on a new plan, I realized that pretty much anything I did would be a long-term play. There was not going to be a magic bullet that would cause high earners to magically appear and ask me for help. This was simultaneously encouraging and discouraging.

Encouraging because I felt that once I figured out my new plan, it would be more robust and would work well for longer.

Discouraging because my runway was shrinking during the drought.

But I knew that if I was going to save the business and hopefully put it back on a growth trajectory, these were the changes I had to make.


I have never really used LinkedIn. For some reason (I honestly don’t remember why), I included a link to my LinkedIn bio in my book, which meant I slowly grew a network of about 1,000 contacts as people would send me connection requests.

When working with software engineers, I just didn’t focus on LinkedIn as a way to connect because that group is constantly inundated with recruiter spam, and I think they tend to ignore the platform. But with a focus on high earners, who I think use LinkedIn more traditionally than software engineers, it seemed like LinkedIn might be a useful way to find high earners and connect with them. This would be my first attempt at outbound marketing.

So far, I’ve added a couple thousand more connections so I have around 3,000. I think this is worth pursuing, but I still don’t know for sure.

Email strategy change

I’ve never been great at email marketing. For a while, I was pretty good at acquiring newsletter subscribers via SEO (I had about 60,000 subscribers at the high point), but my email list has shrunk as I’ve removed cold subscribers and lost my SEO mojo over the years. My list is around 26,000 right now.

Although I was pretty good at getting new subscribers, I was never great at selling my book, courses, and coaching to folks via email. I think I was better at this than I realized at the time, but still not good at it.

Over time, I had built more and more urgency into my email sequences and automated campaigns. My assumption was that folks who found my site were likely in pretty urgent need of help, so I didn’t have time to “nurture” them with weeks or months worth of emails before telling them about things that I sell.

When I launched Salary Negotiation Mastery, I ramped this up even further so that my email strategy was to offer a three-day discount on the program as soon as they joined my mailing list.

Not only did that not result in sales, but it resulted in very high attrition (via unsubscribe rates) while I tried it.

I think this was on experiment worth running, but the result was “this doesn’t work.”

The truth is that I really don’t like that sort of urgency-based hard-sell strategy anyway. It’s not me, and it’s not how I approach sales for my coaching service.

A few months ago, I started implementing a totally different strategy: slow, permission-based marketing buttressed by high-value newsletters. Basically a 180 from what I was doing before. No more urgent sales. No more “send all the Black Friday emails to everyone on the list and let them unsubscribe if they don’t want to see them”.

Now everything is based on my weekly newsletter, and subscribers will essentially raise their hand to hear more about a promotion or product that might be helpful to them. Everyone who joins my newsletter gets a five-email series that essentially lays out my worldview vis-a-vis career management and salary negotiation. My goal is to teach something profound and to set expectations for what it’s like getting emails from me. Then, if they choose to stick around, they’ll get my weekly newsletter.

For the weekly newsletter emails, I’m working hard to make them as valuable as possible so that every one of them offers some kind of “Whoa!” moment for the reader. Occasionally, I’ll include a PS or a note that says something like “By the way, based on what you’ve told me, I think this product or service I offer might be good for you. Want to hear more? Click here and I’ll send you some info.”

This is a totally different approach than what I’ve done for the past few years. I’m early in this transition and I think 2024 will be when I’m finally all-in on it, but I’m happy with how things are going so far. It feels more natural to me and I think it aligns better with a luxury-based business approach. Luxury brands don’t generally use high pressure sales tactics—instead, they just continue existing and making excellent things while their future customers move toward them.

Referral program

I also created and rolled out a new referral program so that I’m more top of mind when someone—a former client, newsletter subscriber, friend, someone who hears me on a podcast or finds my work online—knows of someone else who might need my help.

I have always gotten clients through referrals, but with my focus on high earners and as I move the brand to something more akin to a luxury brand, I think a referral program makes a lot of sense. High earners talk to each other about what’s working, and a referral program is a way to encourage those discussions.

One challenge was figuring out how to structure the referral program and to find the right amount for a referral bonus. I decided to offer a referral bonus to folks to send other folks my way, and I chose $1,000 per referral because I think pretty much anyone will perk up when they hear, “Send someone to Josh, get $1,000.”

I literally tested this by telling people about the program and the referral bonus amount in person while I was figuring out what to do. I noticed a distinct eyebrow raise when people heard the number 1,000.

I have already noticed more people telling other people about me, and I’ve been able to give a few referral bonuses, so I’m optimistic this is going to be a longterm benefit to me and my clients.

Coaching price increase

A big change I made mid-way through the year is that I raised my prices for the first time in about 4.5 years.

Last time I tried raising my prices, I had a 10-week drought during the busiest time of the year—literally no one hired me at the higher price.

But my business and clients have evolved substantially since then, and it felt like it was time to try again.

I have continued to work with folks who earn more and more, and who are more senior in their organizations. That means the value I add—in nominal terms—is quite a bit higher (per client, on average) than it was in 2019.

I have also been moving the brand in a “luxury brand” direction, and in the luxury world, high prices themselves communicate a lot about the service being offered.

So the impetus for starting the referral program—the fact that I was moving toward working with high earners—was also a good impetus for raising prices.

I also needed a way to make the referral program work for the business: If I offered a $1,000 referral bonus, that would come out of a $3,000 service fee. That’s a big portion of my margin on the service fee and I just didn’t think the business could afford to absorb that sort of reduction in per-client revenue.

So I raised my service fee to $5,000 while leaving the result fee the same.

This time, people hired me without hesitation and those people told other people about me. In 2019, my business wasn’t ready for a higher service fee, but in 2023 it was.

Here’s the crazy thing: There are several people who have followed my business from day one, many of them from afar, and they had occasionally encouraged me to raise my prices. When I finally did, one of them said, “$5,000? That’s it? I thought you were already charging $10,000!” He wasn’t kidding. I’m not there yet, but I think it’s plausible that a $10,000 service fee will be right some time in the future.

2023 Year in Review – Personal

This year’s Personal update will probably be a lot shorter than the Business update. While my business doesn’t define me, it is how I make my living, and that has been pretty seriously constrained for the past 15 months or so after several years of growth.

When the business was growing, it was easier to just treat it as a separate thing that sent me regular paychecks. When the business stalled and the regular paychecks slowed down or stopped entirely, it had a pretty big impact on my personal life.

All that to say that I’ve spent a lot of the past year trying to get the business on the right path, while trying to survive financially, which means “Business” and “Personal” have been regretfully intertwined. And that means much of my personal update already happened above.

Still, I did some stuff this year!

Ski trip in Breck

Ski trip was a mixed bag this year thanks to an unlucky set of factors. First, I scheduled a private ski lesson for my first day on the mountain. Unfortunately, I also got mountain sickness during the lesson, which was … not ideal. I finished the lesson, but wasn’t able to get as much out of it as I was hoping (because I was just trying to stay out there and survive rather than really engaging with my instructor’s feedback).

The second day, when I was going to try to start working on the stuff I learned in my lesson, our group went immediately to black bowls at Vail and my ski binding got messed up, so I had zero productive runs. That left me with about two days at Breck, and I did make some progress, but nothing like I have in past years.

On our last day out, I was sitting on the lift next to a snowboarder friend. When we went to get off the lift, his snowboard pinned my left ski underneath it. No biggie – that happens sometimes. Unfortunately, my left ski’s tip also pinned my right ski’s tip. If you picture an inverted “V”, that’s what my skis looked like as the lift pushed us forward with his weight on my left ski, and my left ski pinning my right ski. As the lift pushed us forward, the backs of my skis slowly slid apart while the tips were still pinned, so I literally could not move them. Eventually, the backs got so wide that I fell on my back while both of my feet were still locked into my pinned skis on the ground. The result? Two pretty severely sprained MCLs (and I think I was very lucky that I did not tear one or both of them). It took me about two months to recover completely. So I lost about half of my last day as I (wisely) decided to just head back to the house and not push my luck on sprained MCLs.

A freak accident and another unlucky wasted day.

I left this year feeling kind of deflated and frustrated. I made progress, but nothing like what I was hoping for when I booked that private lesson.

Community (and indirectly, The House™)

I’ve been in my new house for almost 15 months (after over 15 years in my previous house), and I big reason I decided to make the move was that my new house would allow me to host a lot more cool stuff for my community.

I’ve been in Gainesville for over 17 years since I moved back (after being here for five and a half years during undergrad), so I have a pretty big community that’s a mix of people from my church and friends who are also townies.

This year, I hosted lots of events, big and small, and probably had a couple hundred people in my house. That is awesome and Josh of even a few years ago would not have believed you if you told him that Josh of 2023 would be saying that.

I am still not even tapping into all the potential I saw in the house when I moved in, and I’m hoping that my business turns around this year so I can keep making improvements and hosting even more cool stuff.


When I first started taking pickleball seriously (mid-2021), my goal was to get to a 4.0 level by the end of 2022. I was making good progress, but then around August of 2022, I tweaked my back at the gym and developed tennis and golf elbow. That set me back quite a bit.

But my back issue resolved earlier this year and the tennis elbow is now more of a nuisance than a hindrance, so I made a lot of progress this year.

I asked my unofficial pickleball coach where I’m at now, and he puts me at “4.0 with a ton of variance”. My serve is my best shot (which he puts at 5.0), and my worst shots are on unpredictable balls and playing from the mid-court (3.5).

What’s weird is that I don’t really work on my serve; other than in-game, I never even think about it. But it’s actually slowly getting better as I try slight variations and just get better at power and topspin. It’s pretty nasty and low-variance.

On the other hand, pretty much every other aspect of my game is high-variance but less high-variance than a year ago.

My next goal is to get to a 4.5 level. I don’t know if that’s possible, but I think it is. It’s possible I’ll make big jumps this year because I’ve finally learned most of the fundamental shots and the changes I’ve been making recently are very subtle changes that result in substantial improvements. For example, changing my paddle angle to be slightly more closed on dinks has made my dinks much better and more offensive while also resulting in fewer pop ups. Another example is that I’ve been laser-focused on not attacking from the transition zone and working on my resets. That’s happening pretty quickly and has made me much better. So I’m at the stage where making a small tweak can provide a big improvement.

I’m not putting a timeline on getting to 4.5, but I don’t think it’s crazy to think it might happen in 2024.

Odds and ends

Conspicuously absent this year: running. My last run was in late February before ski trip.

I had about 380 workouts this year. That is about 150 pickleball sessions (including drill sessions), 150-ish gym workouts, and 70 or so yoga workouts. That’s a pretty good year!

I’ll be crossing 200 yoga sessions in the next few weeks.

2024 Goals

This year, I have two goals (twice as many as last year!).

100% business growth

Last year, hoping for 100% growth would’ve been really ambitious, but now it’s more like, “It would be nice to get the business back on track so it’s getting close to the all-time high of 2021.

Now that I think of it, this is less of a “goal” than a “hope”—if I can do this, then a lot of the financial pressure I’ve felt for the past 15 months will have abated, and that would be really nice for a change.

The good news is that I think I’ve done most of the heavy-lifting to reconfigure the business and set it up for this kind of growth. This year, I’ll get to see if my instincts were right and if the big changes I have made were the right things to do. We shall see.

Make progress toward 4.5 in pickleball

I think I’m unlocking skills that could help me move sort of quickly toward this goal, but I don’t feel confident enough to actually set “get to 4.5” as my goal here. Good progress would be fine.

I’m very aware that, for a lot of players, hitting 4.5 is no big deal. But given where I started a few years ago—literally unable to hit the ball and no understanding of the game—my best measuring stick for progress is myself and my own limitation, and by that standard, my progress so far has been remarkable. Getting to 4.5 would be extremely surprising to anyone who saw me play before, say, mid-2021, so it would be cool to get that done eventually.

My business is struggling. Here’s my plan to save it.

Web traffic totally dead

My 2022 Year In Review was very late to publication. In fact, it’s still not published as I write this in early June of 2023, although I plan to publish it before I publish this piece.


Because it feels bad. The sub-title is “A weird year” and 2022 sure was a weird year.

I want to drill down on one particular aspect of that weirdness: my business turning from boom to bust on a dime, and what I’m doing to try and save it.

DISCLAIMER: This post is bound to get deep into some nitty-gritty detail. If you skip this one, I don’t blame you. But if you want to ride along through a pretty rocky period of uncertainty to see how I make decisions and think through hard problems, keep on reading…

How I got here

First, a brief history of the business. There’s a lot more detail in my annual Year In Review posts, which I’ve been doing since 2015, so if you want lots of detail, check those out. But for now, he’s a high-level summary…

I quit my last day job in September of 2015 as I finished writing Fearless Salary Negotiation. The plan was to publish it, promote it, and live off of the income from it while I built a software business. I quickly realized how foolish my plan was—selling enough books to pay my bills each month would require its own business, which of course needed to be built in addition to the software business I was already building—and that I had to make a choice: Build a business around Fearless Salary Negotiation or go all-in on the software business and hope to get traction before my runway ran out.

I decided that the salary negotiation business was more interesting to me, so that’s the direction I chose. I shut own the software business and went all-in on the salary negotiation business.

When I quit my day job, I had an 18-month runway—enough cash in the bank to pay my bills with no revenue. That might seem like a long time, but a common axiom in the entrepreneurship circles I run in is that it takes about 18 months for any business to really find its stride. So I had the bare minimum runway, on average.

And of course by the time I had the above epiphany and decided to shut down the software business and focus on the Fearless Salary Negotiation business, I had burned about three months of that runway self-publishing and launching the book.

So, for all intents and purposes, I started my business in January 2016 with about 15 months of runway. It grew very slowly and, through trial and error and some careful planning, I managed to find my stride just before my runway ran out. That was May 2017.

Ever since I started the business it has grown every year:

2016: Infinite growth because I started at zero
2017: 150%
2018: 100%
2019: 50%
2020: 15%
2021: 35%

2021 was about 12x the revenue of 2016 and every year showed positive growth (even during the pandemic).

Zooming in on September 2022

Adding to my list above:

2022 (through August): 3%

So basically flat year-over-year, or on pace to be about the same as 2021, which had been my best year ever.

Starting in April 2022, I kept my eye on the local housing market, just to see what was out there. It all started when a friend sent me a link to a really cool house on Zillow, piquing my interest and getting the wheels turning in my mind: “I’ve been in this house—my first house—for a long time. My business is growing and I can definitely afford to upgrade. Why not just see what’s out there?”

I watched the market pretty closely for the next several months and even went to see a few houses, but nothing really caught my eye.

Then I found an amazing house that I immediately felt was the one for me. It was a stretch, but I talked to my wealth manager, accountant, and several smart people to figure out whether it was worth making the move and whether I could really afford it.

The verdict: “Yes, you can afford it. It’s a little more of your monthly spend that the common wisdom says it should be, but your business is healthy and you have no debt, so you’ll be fine. Your disposable income will drop a little bit, but you won’t be strapped for cash and will still be able to do all the stuff you do now. But instead of socking all of the leftover away in the bank, you’ll be spending some of it on a mortgage and upkeep.”

I made an offer, signed a contract, and sent some cash to escrow.

Within a few days, I felt a disturbance in the force. I couldn’t quite put my finger on it, but something seemed a little off about my business. I had been doing the same thing for more than five years so I just knew how the regular rhythms of the business felt. And something felt weird.

I couldn’t even really point to specific stats or data. But, anecdotally, it felt like there was just less inbound interest in working with me all the sudden. In case you don’t know, I should say: My business was built around helping senior engineers and engineering managers who were changing jobs to big tech companies.

Of course now we know that this was the beginning of a recession in big tech. It turns out that my business was a leading indicator of the health of the employment market in that industry.

But at the time, it seemed likely it was just a blip. My business has had cold spells before—in 2019, I had a 12-week stretch without any new clients—and this might just be another cold spell.

So I was under contract for a new house, which would represent a big increase in my monthly spend, and my numbers were based on a business that had grown every year since it began and was on pace to at least match the previous year’s revenue, which would be more than enough to comfortably make the move to the new house. But I also felt like the business might be slowing down.

What to do?

There were two chances to get off the new-house train: During the inspection period, I could essentially back out, get my escrow money back (which was a big chunk of change), and hit reset on the house-buying process; and before I closed, I could back out and eat the escrow money (which was significant, but was also already a sunk cost).

Remember: All I really had was a feeling that something was off. Nothing concrete. If I decided to pull the plug, it would be based almost exclusively on a hunch.

I only had a 10-day inspection period, and everything came up roses. I considered bailing on the house, but decided that 10 days of “something feels funny with my business” just wasn’t enough of a sample size to make such a big decision. I could still take the next few weeks before closing to see how things went and eat the escrow money if I had to.

Onward to closing.

I now had a checklist with three items on it in order to “thread the needle” on this move without drowning:

  1. Get approved for financing on the new house. The bank was extremely fastidious in this process and sent me a barrage of requests for documents that seemed like it would never end. Although my broker said approval was inevitable, it sure didn’t feel that way.
  2. Sell my old house for an amount that would let me cover the down payment on the new house and put some cash in the bank as a cushion.
  3. Hope my business was only temporarily chilly and not entering a major downturn or dying.

The next few weeks were interesting because I was simultaneously neck-deep in the approvals process for financing on a new mortgage and trying to sell my old house and digging deep into the current state of the business to see if I could figure out if there was a problem or if I was just in a short-term cold spell or something.

It was extremely stressful and I would literally wake up in the middle of the night running numbers, asking myself if I could really afford this, and wondering what would happen if I went through with the purchase and my business died.

I called my wealth manager and accountant again: “You sure I can afford this? What if my business falls off a bit?”

“You’re fine.”

Funky math

Making things even more complicated was a funky mathematical situation that I found myself in. I basically had two options:

  1. If I felt my business might be slowing down for a bit, making my financial situation too dicey to buy the new house, I could just stay put and eat the escrow money (which was a meaningful amount of my cash on hand). That would leave me in a situation where I had not much cash, but also had a still-very-low burn rate which would enable me to make that little bit of remaining cash last quite a while.
  2. If I felt the business actually wasn’t slowing down or the slowdown would be short-lived (a few months, say), then I could just go through with the purchase. That would mean selling my old house, putting most of the equity toward the down payment on my new house, but also pocketing the remaining equity.

The funky math was as follows: Staying put would actually leave me less time on my runway than buying the new house because I would be able to pocket so much of the equity from selling my old house. My burn rate would be higher at the new house, but my savings would be higher still such that I would have more months of expenses covered.

You may already have noticed a complicating factor here: I had not actually sold my old house and therefore did not know what actual amount of equity would be realized when I sold it. If I sold it.

I had a pretty good idea what my house would sell for—recall, I had been watching the housing market for about six months—so I knew about pretty much every house that went on the market in certain areas and certain price ranges. I had a guess what my old house would sell for, but I couldn’t know that for sure until I actually sold it (or try to).

Selling the old house

This brings us to a new conundrum: Selling my old house to cover the down payment on the new house and (hopefully) generate some additional equity to use as a runway if I actually went through with everything.

I was very fortunate that my Mom had recently sold the house I grew up in and she had enough cash in the bank to cover my downpayment in the short-term and help me avoid a home-sale contingency on my offer on the new house. We are not a wealthy family—this was just fortunate timing, and there’s probably been no other time in my family’s history when someone had this kind of cash just sitting in a checking account, but I digress.

Once I signed the contract on the new house, I began trying to sell my old house. At first, I tried to sell it through my own network. I posted about it on Facebook and my church bulletin board and got a surprising amount of interest right away.

I thought it would be cool to sell to someone I knew since I had worked so hard to make my old house comfortable. For all the people I talked to, I offered it at the same price, which was a few percent below what I thought it would sell for if I put it on the market.

I quickly had someone interested, they visited the house, then visited again a week later, and eventually sent me an offer for the amount I had asked for. It was a cash offer, which was great because it meant I wouldn’t need to worry about all the financing stuff and the associated timeline risk.

Let me pause here for a second since I sort of glossed over something that is important: I was under contract for my new house and needed the equity from the old house for the downpayment (to repay my Mom) and also hoped to have enough left over to put in the bank as a cushion in case my business was slowing down. For this buyer, the process from “anyone want to buy my house?” to “offer in hand” was about three weeks, leaving me about a week or so from my scheduled closing on the new house. This was a tight timeline that had me a little nervous.

It turns out that the potential buyer and I could not agree on terms for the contract, so the deal fell through. I had another offer or two from my network, but they didn’t come to fruition either. Now I’m a week from closing and I do not know if my old house will sell or how much it will sell for.

I thought I knew what my house would fetch on the open market, but I was not sure and now I had a few data points that said, “Someone thought about buying my house for a few percent less than what I think the market value is, but they backed out. Therefore it’s possible I have overestimated the market value of my house.” (Shoutout to all the Bayesians reading this.)

Meanwhile, the Fed was rapidly raising interest rates to fight inflation, thus increasing mortgage rates, which seemed likely to cause the market to cool off a bit. To give you some insight into how fast this happened: When I signed the contract on my new house, I locked in at 5.125% on a 30-year fixed-rate mortgage, and by the time these deals to sell my old house fell through, mortgage rates were closer to 7% and rising.

Worst-case scenario would be if the house didn’t sell at all. Then I would not be able to cover the down payment on the new place or have cash in the bank and I would still have a property and a mortgage to take care of in a time when it was unclear how dependable my normally-dependable business income would be.

I hit the big red button: I asked the realtor who sold me my new house if she would help me sell my old house. We got photos, listed it on a Friday, had an open house on a Saturday, had three or four offers on Sunday, had a bidding war on Monday, and I ended up selling my house for … $1,000 more than I thought it would sell for on the open market. Cash.

“All that build-up over like 10 paragraphs and you just end the story like that?” That’s what it literally felt like in real time.

Closing on the new house

Around this time, I was finally approved for financing on the new house. It was a slog, but we got it done.

At least I could check that off the needle-threading list. Now all that remained was actually selling my old house for enough to cover the new house’s downpayment and (hopefully) put some cash in the bank, and hoping my business was still strong.

I was in for the long haul now. Closing for the new house was set, financing was approved, and I had a contract to sell my old house in a timeframe that would work well for the move.

So I had checked one box (financing on the new house) and was on track to check a second box (sell the old house), and was keeping an eye on the business, which seemed to be chilly at the moment (third box).

Let’s pause and I’ll show you a graph. This shows weekly visits to the main pages that drive my business (these are all company-specific pages about negotiating job offers and most of my coaching leads come through these pages).

Web traffic looks ok but doesn't bounce back after summer slump

Normally my search traffic ticks back up after Summer, but not this time

It looks like a pretty normal chart until the marked data point. Typically, around August 1, the summer slowdown starts to abate and the graph heads back up to April-ish levels of traffic. In this way, my business has always been somewhat seasonal, so it’s slower in the Summer months when people are vacationing more and business moves a little bit slower.

The uneasy thing I was feeling at the time was that the traffic to those pages hadn’t returned to pre-summer levels yet, and therefore I had fewer coaching prospects than expected for that time of year.

This is an extremely narrow window to make any real judgements on, but it’s what had given me pause earlier: If this wasn’t just an anomaly and was instead a downturn, what would happen? How long would it last? How bad would it get? And what would the financial ramifications be as I started paying a significantly higher mortgage?

I decided this wasn’t enough evidence to bail on the “buy new house, sell old house” plan, so I moved ahead.

I closed on the new house as scheduled. Then closed on the old house as scheduled. And ended up with a nice cash cushion in the bank, just in case the business was in for a slower-than-normal end of the year.

Covering all my bases

I’m the kind of person who plans for all contingencies. This is both a blessing and a curse. It’s why I was able to plan years out to eventually quit my day job and have an 18-month runway to start something new from scratch. It’s also why I sometimes move slowly and get stuck analyzing and getting input on new ideas rather than just shipping things.

But in this case, it was clear that I needed to make absolutely sure that I did whatever I could to shore up my financial situation just in case the disturbance in the force I felt was a real business downturn.

By the time I closed on my house something was up with big tech. To illustrate this, I just googled “2022 big tech layoffs” and grabbed the first article that mentioned a timeline. Here is is:

Tech layoffs in 2022: A timeline

If you click through to the second page (I’m not sure why the article is paginated), you’ll see that it starts with “Twilio: Sept. 14—850 people”.

This was two weeks into the under-contract period on my new house. Seems small, but it’s something after a huge, years-long hiring boom in big tech.

I needed to hedge my bets, and I had just put a substantial down payment on a new house, so I went looking for options to tap into that equity if I needed to. I started by looking into a HELOC—a line of credit against the equity in my new house—and found that would be the best option. Specifically, I wanted access to a line of credit without having to borrow or pay fees if I didn’t need the cash.

Sure enough, I found a HELOC that was a revolving line of credit that was essentially an interest-payments-only line of credit with a balloon after 10 years. I could borrow, pay only interest, and would have 10 years to pay back the principle. But I didn’t have to borrow or pay any fees if I didn’t want to. It was just a line of credit that I could have in my back pocket if I really needed it.

This was also dicey—I needed to move fast. By the time I moved into my house and the dust settled, I was about two months into a business slowdown and I did not know how long it would be slow. Part of vetting loans is income verification and stuff like that, so I needed to get the HELOC handled before my income dropped off too much. That meant it needed to be done by EOY 2022, giving me only a few weeks to get everything done.

Sure enough, the HELOC was approved and opened before end of year. I had bought and moved into my new house, sold my old house, paid mom back for the down payment money she loaned me, put some cash in the bank as a cushion, and been approved for a backup line of credit that I could use if things got really dire or if I had an unexpected large expense (which is what keeps most homeowners up at night).

For the first time in a few months, I could actually sit back, breathe a sigh of relief and start looking over the business to see what was going on under the hood.

Sliding, sliding, sliding

But I still had that third checkbox: The business needed to return to normal.

It wasn’t looking good.

Here’s the same chart above, through the beginning of December 2022:

Image showing web traffic bottoming out

That bad feeling starts to get real

Ruh roh.

If you run a business and look at metrics, that graph probably looks pretty terrifying. And let me tell you, it was. By then, the big tech layoffs had spread pretty far and the numbers were getting much bigger.

Oracle: 200 people
Microsoft: 1,000 people
Stripe: 1,100 people
Meta: 11,000 people
SalesForce: 950 people
Amazon: 10,000 people
Cisco: 4,100 people
HP: 6,000 people
Amazon (again): up to 20,000 more people

The worst-case scenario that I had been a little worried about a few months earlier was actually coming true. Many of those are the companies whose new hires are my coaching clients. Amazon was the single-biggest driver of my business at the time.

To put a fine point on this: My business was built around these companies hiring new people. A “slowdown” would be a hiring freeze or just a reduction in hiring projections. This was a full on bottoming out: Not only were they not hiring, they were letting everyone go and the entire big tech employment market was seizing up.

People who otherwise would’ve been looking to make a move to a new employer were either being laid off or just sort of trying to keep their heads down, hoping to keep their jobs until the dust settled.

Here’s that same graph through May 2022 (the last full month before I write this):

Web traffic totally dead

This was basically the worst-case scenario, and here’s what it looks like in reality

This time, I have marked the week after I signed the contract on the new house. This is the week when I called a friend and said, “Something feels weird with the business.” It’s a month before the layoffs ramped up, but a month after my inbound traffic fell below the normal expectation for this time of year.

That same friend later said, “Your business was a leading indicator of trouble in the big tech hiring world. That’s remarkable.” It is pretty remarkable. I had dug so deeply into a particular niche that when it started to go south, my business immediately started trending down.

My revenue follows that curve. It’s now down 70-90% from last year’s revenue, depending on which month you look at.

A lifeline with Salary Negotiation Mastery

Just before all of the house stuff started, and before the business started slumping, I finally started working on a project I had been planning for a couple of years: Salary Negotiation Mastery.

It’s a self-serve program where I show the learner how to negotiate their job offer using the methodology I’ve developed over the past six or so years of coaching full time.

I had carved out a pretty narrow niche of people to work with one-on-one, and I was pretty busy with coaching for several years. So busy that I continually narrowed my niche to exclude a lot of people that my methodology would help. This way, I could continue working in my chosen niche and offer something for those outside my niche who wanted to negotiate with my help.

It was long overdue—I probably should’ve done this years ago—but I just didn’t have time to do it because coaching had been so busy. Ironically, I decided to just go for it and then the coaching business dropped off so I actually had lots of time to invest in making it really good.

This was fortuitous because it meant some extra revenue from pre-orders and early sales over the next several months. Forty percent of my Q4 2023 revenue was pre-orders for Salary Negotiation Mastery.

The main business driver for creating the program was that coaching revenue is very lumpy—one month can be fantastic and the next month can be terrible—because it’s a low-volume business. My result fee structure has helped smooth this out over the years by increasing overall revenue, but also just by nature of the lag from the end of each engagement until the payment of the result fee. It’s pretty random, which has a revenue smoothing function overall.

I finished building the program in January and launched it to get some more early sales. Now it’s in the “build a marketing funnel” stage, which is probably the thing I’m the absolute worst at in my business. But if I can figure out how to get it in front of the people who will benefit, then I think it could be a boon to my business.

This is just a working theory for why my business has fallen off

Before I transition to my plans to turn things around, I want to emphasize that my theory as to why my coaching business slumped so hard starting last September is that my chosen niche—Senior Software Engineers and Engineering Managers going to big tech companies—more or less evaporated when big tech companies starting laying people off instead of hiring.

It’s possible that theory is wrong and the business slumped for some other reason. If that is another reason, I don’t know what it is. But if I’m right, then the business is essentially dormant while big tech resets head counts to match the current economic situation.

So my working assumptions are: the business slowed down because my niche has temporarily gone away, the overall economy is actually very good in terms of hiring, and my current niche will come back … eventually.

The problem of course, is the word “eventually” is extremely vague and my runway has a pretty specific length. If there was a magic wand I could wave to understand if and when the current business will come back online, things would be much easier to plan out. But no such wand exists, so all I can do is make some educated guesses and plan for the most likely scenarios.

Where I’m going

So that’s where I am now.

What to do about it?

How and why I chose my current niche

Before we look forward, let’s look back. Here’s my current niche (described through my positioning statement):

I’m a Salary Negotiation Coach for Senior Software Engineers and Engineering Managers going to Big Tech companies like Google and Amazon

That has evolved over time.

How my coaching business started

My first-ever coaching client was a freelance copywriter who was transitioning into a full-time role. While I was writing Fearless Salary Negotiation, a friend reached out because he was negotiating a new job offer. Since I was writing the book, I offered to coach him pro bono so I could test my methodology and see how it held up in the real world.

It held up really well and my friend did well in his negotiation. Once the book was published, I sent him a copy since he had helped me vet the process that I wrote about.

A little more than a year later, his wife reached out and asked if I could help her negotiate. I told her sure, and she asked me what my rate was. I hadn’t really even considered coaching people one-on-one before this, so I didn’t have a rate to quote her. But she was a freelance copywriter, so I said, “Whatever your rate is, that’s my rate.” She said ok and we were off to the races.

We got a good result and I think we were both really happy with the experience. She sent over my payment and then I asked her why she had hired me even though she already had my book and her husband had been through the methodology with me.

“I just wanted you to tell me exactly what to do.”

This was a huge lightbulb moment for me. Even though she had a copy of my book and her husband had been through a negotiation using my methodology, it was still worth it for her to hire me and pay me to walk her through the methodology for her situation.

A couple months later, another acquaintance reached out and asked if I could help her negotiate her healthcare administration offer, and she asked what my rate was. I told her I could help and quoted a rate that was about 60% higher than the what I charged my first client. She instantly hired me.

Interesting. Another data point pointing to coaching as a viable option for my business.

Believe it or not, I was very resistant to this idea. When I began building the business (I was maybe six months in at this point), I planned to create a “passive income”-type business. I wanted to put products online, have people find them, and make sales without manual intervention, so one-on-one client work was more or less the opposite of what I set out to do.

Of course, I had a few friends who immediately said some version of, “You know… this coaching thing seems promising. That is a valuable service and I bet you could make a really good living with it.”

I happened to be attending a conference full of very smart people while I was working with my second-ever coaching client. The sentiment there was the same: This coaching thing could be really valuable. I also got some extremely valuable advice on how to structure the offering, price it, etc.

I went home and (still sort of reluctantly, if I’m honest) put up a landing page for my coaching offering. People starting hiring me pretty much right away.

My first positioning statement would have been: “Salary Negotiation Coach”. This is extremely broad because it implies “…for everyone.” That sounds great! “Everyone” is a huge market! But that’s not how business works.

Narrowing my niche

Still, folks were hiring me. Here’s a list of the types of clients I was working with as I wrote the book and for my first few paid engagements:

Software Developer
Software Developer
Healthcare Admin
Physical Therapist
Materials Engineer
Marketing Manager
Software Engineer
Software Engineer
Software Engineer
Software Engineer
Software Engineer
Software Engineer

You can see a trend develop right away. One of the first public speaking engagements I had was for a (now-defunct) coding bootcamp in Orlando.

Here’s a fun story that I don’t think I’ve ever told anyone. I spoke to this bootcamp twice. It’s a two-hour drive each way, and I was hoping to sell a few copies of my book to help cover expenses. The second time I went, I got a parking ticket that wiped out any profit I would’ve earned on those books. I was obviously doing this mostly for marketing purposes, but it would’ve been nice to at least break even on my costs.

ANYWAY, there was immediate interest for my coaching offering, and I inadvertently created some good content for Software Developers as “sawdust” from that talk. But other people were hiring me too, and from a wide variety of industries.

Eventually, I realized that a lot of Software Developers were hiring me and that Software Developers tended to get bigger results in nominal terms (they were being offered larger salaries and therefore an increase in their comp was worth more dollars).

I eventually decided to specialize and updated my positioning statement to:

“Salary Negotiation Coach for Software Developers”

Much narrower, but still very broad.

I started to build a reputation as the salary negotiation guy for software developers. More and more people hired me.

I noticed that more senior Devs were hiring me and they were getting even bigger results from our work together. I was getting pretty busy, and I realized that one thing driving my business was that my service was so cheap relative to the results I was getting for my clients.

Time to raise rates. I created a complicated pricing structure that was basically designed to charge more for folks with bigger job offers. It worked well enough, and my revenue per client started going up because I was capturing more of the value I created (even if I was doing it in a clunky way).

I eventually changed my fee structure to be simpler: A flat fee to work together (my service fee) and a percentage of the improvement we negotiated (my result fee). The business kept growing.

The Senior Software Developers were becoming the segment that got the most value from my coaching, and I was getting enough business from that segment that it made sense to update my positioning yet again:

“Salary Negotiation Coach for Senior Software Developers”

Narrower still!

Here are the next two iterations:

“Salary Negotiation Coach for Senior Software Engineers and Engineering Managers”

“Salary Negotiation Coach for Senior Software Engineers and Engineering Managers going to Big Tech companies”

You can probably see how these changes happened: I had more than enough work to make a living and the data told me those were the folks benefiting the most from my coaching offering.

This is also a pretty narrow niche (though still huge in terms of the total addressable market).

The benefit of having such a narrow niche is that when those people find me, they know I’m their guy. I’m very specifically describing a group of people which sends a powerful signal that I can help them (especially with all the testimonials I’ve accumulated over the years).

There’s also one huge downside: If that narrow niche hits any economic speed bumps, so do I (see above).

It has always felt restrictive

I think that narrow niche was the right thing to do as I worked to build my business and establish a brand.

But it felt pretty restrictive from the start, and continued to feel more and more restrictive.

I kept narrowing my niche for two reasons:

  1. I could see who was benefiting from my help.
  2. I wanted to work in the highest-leverage situations I could.

I’ve always had an application as the first step for any coaching engagement. The application has been pretty much the same since the beginning (with a few small tweaks here and there).

When I first started coaching, and realized how good Software Developers’ results were, then I would always review a new application by looking straight to the “What is your line of work (industry and job)?” question. I wanted to see “Software Dev” or something like that. Later, I would hope to see “Software Dev” paired with “tech” or “big tech”.

Then I would look at the “What stage are you at in the job hunting process?” question. I was hoping for “Job offer in hand”.


Those were the clients who got the best results and therefore got the most value from my coaching. And “job offer in hand” meant their need for my help was the most acute; they urgently needed my help. Since my fee structure is based on the value I create, that meant more revenue for the business.

Over time, I began to scan the applications differently. Instead of “industry and job”, I would first look at “What’s the annual compensation of your offer?”. I had to be selective about who I worked with because I only had so much bandwidth, so I started looking for folks with higher compensation to work with and hence higher potential result fees.

Since more-senior folks tend to get bigger job offers, I started to evolve my positioning.

I called it “moving up the org chart”. The higher up the org chart, the better the pay and the more leeway to negotiate.

In addition to “these folks get more value from my help”, this was the main driver for my continually-narrowed positioning. I was trying to manage demand for my service while staying within the niche I had carved out, so I moved up the org chart through a series of positioning-narrowing moves.

Conventional wisdom is that a narrower niche is easier to cater to because it’s so specific. Basically, the more specific a persona I need to market to, the easier it is to speak in a way that resonates with them.

But I felt very restricted by this.

I think that’s mostly because I was using job title and type of organization as a proxy for the thing I was actually optimizing for: income. The bottom line is I only have so much time to invest in helping my clients, and I need to use that time in the highest-leverage way possible. But I also want to help as many people as possible. It’s a Catch-22 in some ways.

So once the big tech slowdown happened, I had to start thinking deeply about my business, whether it continues to be viable, and who I can help.

Then I had an epiphany (which will hopefully seem obvious to you by now)…

How and why I’m choosing a new niche

Why don’t I just directly work with the folks I had been trying to find by proxy over time?

The conventional wisdom when starting a business is that you choose a narrow niche because it’s easier, cheaper, and faster to iterate and build in a niche. It’s much easier (or cheaper, at least) to start a new company that specializes in making the world’s best athletic socks than, say, a general apparel company. The questions you’re asking that early are things like, “Who wears athletic socks? How do we find them? What do they look for in a good sock?”

That’s pretty narrow, but it might be even easier to start with “men’s athletic socks” or even “men’s tennis socks” because the questions get more and more specific and easier to answer.

If that company starts super broad, they have to answer questions like, “Who wears apparel? Where can we find them?” When you’re just starting out on a shoestring budget and you’re planning your product development and early marketing plans, these answers to these questions (“Everyone!” and “Everywhere!”) are not useful or budget-friendly.

But it’s also true that as businesses grow, they expand—either horizontally or vertically—to serve other niches or simply expand their chosen niche.

“We’re going to sell the world’s best athletic socks” is a narrow-ish niche. And if that company succeeds, they start to realize things like, “Hey. You know what? We’ve gotten pretty good at designing socks, sourcing materials and manufacturing them. How different are t-shirts from socks? We could probably do that too, right?” They expand their scope to leverage the expertise they’ve accumulated over time.

This happens constantly and usually sounds like this at a dinner-table conversation:

“Where’d you get that shirt?”

“ACME co. It’s new. You like it?”

“ACME co.? The yoga pants company?”

“Yeah, they’re selling men’s casual apparel now too.”


This is called “economy of scope”, which is a cousin to “economy of scale”.

They already have designers on staff, know how to source materials, how to negotiate contracts with a manufacturing facility, they have distribution, and so many other things that are needed for the new products, so why not expand into t-shirts?

My new positioning statement

In my case, I already have a methodology that works really, really well in my chosen niche. And I know it works well in a broader niche (people higher up the org chart). Why not expand my niche?

Which leads me to my new positioning statement:

I’m a Salary Negotiation Coach for high earners

I’m a huge fan of “alignment of incentives” and this is similar. For the past few years, I had mostly been trying to work with high earners, but I was doing it through a side door, which made a lot of new-client intro calls more difficult than they needed to be.

Half of my clients over the past 18 months were not “Senior Software Engineers or Engineering Managers”. They hired me despite my positioning statement, not because of it. And I was able to help them get great results.

It’s impossible to know this, but I suspect there were many more folks who would’ve considered working with me, but they self-selected out since they were not described by my positioning statement.

My new positioning statement is an umbrella covering my previous niche

The best part is my previous niche is still perfectly covered with my new positioning statement. Those folks were almost all high earners.

That’s the high-level benefit. But there’s a lower-level, tactical benefit too: All of my current marketing and collateral is still useful for those folks. The landing page, emails, scores of podcasts I’ve been on, articles on my site, and everything else I built to help those folks will still be just as helpful to those folks.

That’s also true for my coaching offering—it will continue to be just as valuable to Senior Software Engineers and Engineering Managers going to Big Tech companies as it was before. And when big tech hiring stabilizes, I’ll be there waiting to help those folks negotiate their job offers.

But meanwhile, I’ll also be helping high earners in other jobs and industries, just like I have been. But now those folks—the high earners who might have previously seen my positioning and thought, “Oh, that’s not for me.”—will feel that my coaching service could be right for them.

Timing is everything

This probably would not have worked when I first started the business. When people hire me, they don’t know who I am so I rely on a lot of credibility-building proxies to help them trust that I know what I’m doing.

For Software Engineers, I had one very nice built-in indicator that I could help them: I am a software engineer. Same for Engineering Managers: I was a people manager. I added “going to big tech companies later”, but only after I had worked with many folks going to big tech companies.

Over time, I built more credibility such that those folks hired me and continually trusted me with more and more valuable negotiations. Eventually, virtually all of my clients were also “high earners”, but it didn’t start that way. And if I had just started out with a focus on “high earners”, I would’ve had a bear of a marketing problem.

What about Salary Negotiation Mastery?

The beautiful thing about this move is it only increases the potential reach and value of Salary Negotiation Mastery. Here’s the short version:

My salary negotiation coaching offering is for high earners who need help negotiating an offer right now or in the next couple of weeks.

Salary Negotiation Mastery is for folks who are not yet high earners but want to be, or who simply don’t have the budget for my one-on-one coaching offering, or who are looking ahead and want to be prepared for future job offers and negotiation opportunities.

Salary Negotiation Mastery is also a great way for folks who don’t know me to get to know me without a formal engagement so they can decide if salary negotiation coaching is right for them down the road.

I have been looking into potential partnerships that would enable me to work with other folks whose audience might benefit from Salary Negotiation Mastery, but it has been challenging because of my current positioning. “Will this work for non-engineers?” is a question that virtually every potential partner asks. “Yes!” is the answer, but it takes a while to explain that.

Now I won’t have to explain it.

“Will it work for folks who are not yet high earners?”


“Will it work for [specific industry]?”


That’s all there is to it. Easy.

What’s next

Now I have a new positioning statement. Ironically, that was the easy part (even though it was really, really difficult to make this decision) and this is when the hard work begins.

The list is long and ranges from “update entire website” to “change twitter bio”.

I have to rework the Fearless Salary Negotiation website (which I have been quietly doing behind the scenes for the past month or so anyway). I need to write some new landing pages. I have to update a whole bunch of email sequences.

And I have to start answering that difficult question, “Where do I find high earners who have job offers to negotiate so I can help them?”

But! Those people are already finding me and (I think) walking right by the store because my previous positioning statement didn’t appeal to them. So my first task is to just make sure the people who are already finding me know they’ve come to the right place. That’s actually pretty easy: Update a few pages on my website and write a new coaching page.

I’m working on that now. (Well, not now because I’m apparently writing a short book about my new positioning, but next.)

How you can help

If you’ve read this far, first of all, thank you for your time.

I had no idea this post was going to be this long, but here we are. As you read, my business has been more or less dormant for about nine months and I’m hoping this new positioning will kickstart it.

If any of these things are in your wheelhouse, I’d be grateful for your help:

  • If you know any high earners (more than $200k income per year) who are changing jobs soon, please tell them about my salary negotiation coaching service. Referrals are my most important way to find new clients to work with.
  • If you know someone who has an audience of high earners, I would love to meet them and talk about ways I can share my salary negotiation expertise with them. This could be a podcast guest appearance, an article on their site, or any number of things with a focus on adding value to their audience. Would you please ask them to get in touch?
  • If you read the previous two and thought, “Well, I know folks Josh could help but they’re not high earners … yet.” Would you tell them about Salary Negotiation Mastery? It’s a fantastic program and it will help them get the maximum compensation next time they negotiate a job offer.

Thank you again for reading this. I think it’s extremely important to document big changes like this because it helps me remember what I did and why I did it. It also helps me avoid falling prey to any number of logical fallacies that are easy to succumb to in the moment.

There’s also a tendency for entrepreneurs to write about their wins and gloss over the hard times. Entrepreneurship is hard and I think it’s a disservice to aspiring entrepreneurs to hide the difficult parts. I’ve fought to avoid that since I started my business and I’m not going to start leaving out the tough stuff now.

I hope I can write a glowing update in a few months or a year, but that’s absolutely not a certainty. If this doesn’t work, I’m not sure what I’ll do. For now, I’m laser-focused on making it work. Wish me luck!

2022 Year In Review: A weird year

NOTE: This post is a sort of sister post to My business is struggling. Here’s my plan to save it. This Year In Review sets the stage for that one.

Well. Paraphrasing an old friend who has since passed on: “I’ve experienced a lot of years, and that was one of them.”

2022 turned out to be a really weird year both personally and professionally. This year in review will probably be a lot different than all of the previous ones because this year was so different.

In fact, it’s probably going to be a downer and my guess is it’s going to be pretty short. But such is life. If you’d rather read something that’s more upbeat, check out my 2021 Year in Review: 2021 Year in Review: An incredible year.

On the personal side, I realized that my years were starting to blur together because I would do the same (usually fun!) things on a sort of loop. Like, before the year began, I could easily get out a calendar and mark 10 or so pretty significant things that were already baked in and would be more or less the same as the previous year. This is simultaneously kind a great—some of those things were “ski trip” and “4th of July at the beach”—and kind of a weird version of Groundhog Day. I was having trouble distinguishing between specific events over the past few years because the events themselves were always the same.

While it’s neat to know I have a bunch of cool stuff on the calendar, it was also a little … I dunno, disheartening? to know that my entire year was pretty much planned out before it began. So I decided that rather than just defaulting to “do the same stuff as I always do”, I would sort of scrutinize each thing and decide if I wanted to do that thing again this year.

For some things, I just left them alone (ski trip), but for other things, I just decided to not do them (4th of July at the beach, the annual RV trip).

I also ended up selling my old house (where I had lived for 15 years) and buying a new (to me) one. So that was a pretty dramatic way to shake things up.

All in all, I feel good about the way I navigated the year, and some really great things came of it. But it’s hard to think of a more dramatic contrast to the previous year, where everything just sort of cruised along as usual, but just more.

2022 Goal review

I haven’t even looked at the goals I set for 2022, and I’m already laughing. I’ll be surprised if I was even close on a single one. Here we go…

Build and launch a new salary negotiation course for software engineers

Ha, well I actually did this and it’s pretty great.

I started building Salary Negotiation Mastery in August and launched it in January. It’s much different than anything I’ve built before, starting with the creation process itself.

I’m extremely happy with how it turned out, and I’ll write more about that later.

Increase business revenue by…50%?


How about “decrease revenue by 32%, landing somewhere between 2019 and 2020”?

Get to a 4.0 level in pickleball

I was actually on track for this until I got injured. I hurt my back doing legs at the gym (either squatting or deadlifting) in August or so. Around the same time I also developed both tennis elbow and gofer’s elbow when I changed paddles.

So since I couldn’t move very well or swing the paddle without pain, I lost about three months of pickleball. Not ideal. ??Worse, when I finally started playing again, I was super rusty and had unlearned a lot of the things I learned earlier in the year, so I estimate that those injuries probably cost me about six months.

I definitely didn’t make it to 4.0, but I did improve in some areas. Mostly, I just need to clean some things up and get more consistent.

Ski the top of the mountain at Breck

Nope. Instead, I focused on fundamentals, and the stuff up top was closed for most of our trip. I think this was for the best—I actually did less difficult stuff this year than I had done last year. But I realized I needed to become a better fundamental skier to raise my ceiling. This would also carry over to 2023, but I guess I’ll write about that next year.

Travel more (for real this time)

Nope. I traveled less, actually. I’m actually happy about that and it was part of the anti-Groundhog Day reset.

Something something cooking?

I’ll call this a push. I had people over much more often, but I didn’t really pick up anything new. Actually, I got pretty good at baking, so that’s progress.

Be more generous

This was a success. I’m not going to write about it here, but I feel good about my progress here and I plan to keep this goal for 2023 as well.

2022 Year in Review – Business

The business got off to a roaring start in 2022. 2021 was my best year ever by a longshot, and 2022 was tracking slightly ahead of 2021 until August. But then the big tech layoffs began and the business basically cratered starting with September being my worst month in six years, then sort of rebounding with several mediocre months in a row. As I write this, I’m in the seventh month of a pretty severe drought and I don’t really see any signs that it will abate soon. If anything it looks like things will get worse before they get better (if they get better). Things are not good.

I ended the year down about 32% in year-over-year revenue. That number itself is pretty bad, but it’s much worse when coupled with “I was actually ahead of pace through August”. The last four months of 2022 were very, very bad.

Here’s the revenue chart I update every year. I did pre-launches for Salary Negotiation Mastery in October and November, or those bars would be much shorter. It’s a pretty dramatic change from the momentum I had built up over the past several years. Notice that I went with a boxless-“2022” badge because the box would’ve obscured September’s revenue. Right next to that low-water mark, you can see October and November were ok by historical standards, but most of that revenue is Salary Negotiation Mastery pre-orders (as opposed to coaching revenue, which has historically been my main source of revenue).

Career earnings to date

One silver lining of the slump is that I had plenty of time to build something new for the first time in a long time. That thing is Salary Negotiation Mastery, and it’s very, very good. I don’t say that lightly—I’m genuinely surprised how good it turned out. Fortunately, I started working on it last August (the month before the downturn), and I launched it in January, so I was able to put all that downtime to great use. I was also able to get some income from that new revenue stream, so that was fortuitous.

Why not look at some stats?


  • Visits to About 720,000 (down from 7880,000)
  • Unique page views: About 1M (down from 1.1M)
  • Total email subscribers at the end of the year: About 27,500 (break-even from the previous year)
  • Product sales through the site: About 100 (down from about 200)
  • Coaching applications: 99 (down from 138)
  • Coaching clients: 22 (up from about 36)
  • Coaching conversion rate (from application to client) was 22% (down from 26%, so basically flat)

Net revenue was down 32% from 2021, and September 2022 was my worst month in about five years.

Coaching revenue was down 28% year-over-year, and product revenue was up about 10% year-over-year, thanks to the Salary Negotiation Mastery pre-launch.

So all that paints a pretty bleak picture of the business in 2022. And you might be thinking, “That seems like it was pretty stressful.” But, as of when I’m writing this at the end of March 2023, it continues to be very stressful, and this isn’t even the half of it (see the personal year in review below).

Building Salary Negotiation Mastery

Looking back, I was very fortunate that Fearless Salary Negotiation was so good. At the time, I felt like I knew quite a bit about salary negotiation, but in hindsight, I actually knew very little. I figured a lot of things out and created a unique methodology that worked really well. It holds up even today and it’s still the basis for what I do with my clients.

But I’ve learned a lot since then—I’ve worked with over 150 people one-on-one, negotiated millions more dollars for people, and generally have a lot of experience negotiating job offers. That experience wasn’t reflected in Fearless Salary Negotiation or in the initial video courses I made because how could it be? I had just started building the business when I made those things.

A few years ago, I decided it was time to build a new course that reflected everything I had learned by doing this full time. It took me a while, and I did a full rebrand and site redesign first, but I eventually got around to building Salary Negotiation Mastery.

I worked with an instructional designer to build a program that would be easy to follow and deliver a learning experience tailored to the learner and their current situation. Right away, there’s a fork in the learning path: If you have a job offer already, skip the module on interview prep.

I also hired a copywriter to write the sales page, and I had 20-30 beta testers go through the course to tell me what they thought.

The look and feel are totally different than the other things I’ve created. Rather than a Keynote presentation with voice over (which is fine!), most of the teaching is me on camera with occasional slides to illustrate a learning point or reinforce an idea. Before I had eye surgery, I never would’ve been comfortable building a thing which required me to be looking directly into the camera for hours on end. But I feel much better about it now, and I’ve actually gotten decent at it. So this made the most sense to me.

Where do I go from here?

I don’t know.

As far as I can tell, the fundamentals of my business are sound. What I do is valuable, people are eager to pay for for coaching and products, but the people I serve are not changing jobs and negotiating new offers right now since hiring big tech is locked up. I have no idea if or when the hiring will get back to normal.

I could continue puttering along, slowly fading until I’m forced to pivot or do something new. Or there’s a world in which the spigot is turned back on, lots of engineers start getting hired by big tech companies, and business booms again. If that latter is what happens, I’m well positioned to capitalize: my coaching offering has stellar results, and Salary Negotiation Mastery is perfect for anyone who can’t or doesn’t want to hire me one-on-one.

I thought things would start getting back to normal in January and I was very wrong. We’re about to begin 2023Q2, so maybe that’s when things will start going back to normal. Who knows? For now, I’m looking at other places where the skillset I’ve built might be valuable, and I have a few opportunities in front of me that are very interesting and which might even be a way to use the same skillset with even higher leverage. Recapping 2023 will be pretty interesting.

2022 Year in Review – Personal

This year was dominated by one pretty big change… ?

I bought a house (and sold one)

I was in my previous house for 15 years, which was far longer than I anticipated when I bought it. Initially, I thought I was buying a starter house, and that I would be there a few years or so and then upgrade.

Unfortunately, I bought it at the peak of the 2008 housing bubble, and the market collapsed soon after I bought it. I was under water for several years with no real way to sell it, so I just stayed put. About five years ago, I started making some improvements, capped off with a total kitchen renovation in 2021.

I hadn’t planned to move in 2022, but a friend sent me a link to a cool house on Zillow and that got the wheels turning. Fortunately, I didn’t get that cool house (it would have been a MAJOR multi-year renovation project as it was built in 1938 and much of the interior was original). But that got me into “check out the local market” mode, which meant that I got a daily email with new listings in my area.

I went to see a few houses throughout the year, but none of them were quite right. Usually, they were older houses that were very cool, but very dated, needing a lot of work. But then I saw a house in August and it caught my eye: My style, recently improved, great location, and even a tennis court in the back yard (which of course would be easily converted into pickleball courts). It was basically my dream house, and I knew it was unusual because I had been watching the market for almost six months and had not seen another house like it.

The downside was the price—it was not cheap. I ran the numbers, then ran them again, then ran them again and decided to go for it and signed a contract at the end of August.

If you read the business review, you’ll notice an interesting timeline overlap here. It was during the inspection period that I started to feel like my business was slowing down after the best 18-month stretch yet.

I had put a lot of money in escrow when I signed the contract, and I could get that money back if I backed out during the inspection period. But by then, I only had a few slow weeks and there were no super-reliable signs that anything was off with the business. So I went through the inspection period and remained under contract.

As the month went on, things started feeling worse in the business and I got more nervous. What if my business was dying or at least headed for a serious rough patch? That would obviously change the calculus on a major purchase like this. I could still back out and just eat the escrow money, or I could go forward and just hope the business came back as it always has.

I decided that if the business didn’t come back, then at least I would have a runway (equity from my old house) and time to figure something out. Worst case, I just unload the new house. On the other hand, if this was a temporary slowdown for my business (which has happened several times before), and I passed on my dream house, I would regret that for a long time.

So I bought the house, closing on the heels of my business’s worst month in like five years. Yikes.

Meanwhile, I had been slow to list my old house because I hoped I might sell it to someone I knew from church or around town. I was trying to be patient, but interest rates were going up and the housing market was cooling off—that was pretty obvious. I was getting worried that I might have bought a new house—requiring the equity from my old house to cover the down payment—and would not actually be able to sell my old house if nobody could get financing. That would’ve been very bad.

Eventually, I put my old house on the market, hoping that it would move fast. Fortunately, it quickly sold above asking. Everything went through so that I had a nice runway and some time to see what happened with the business.

If you know me, you know that I love sleep. I sleep well almost every night. But during this period, I frequently woke up an hour or two early, running numbers or trying to think through off-ramps if things didn’t fall into place. I lost a lot of sleep and actually lost a few pounds as well. I’m not sure I’ve ever experienced that sort of financial stress before.

Of course, the business actually was entering a slump, which has reached seven months now. I’m not sure what I would have done had I known that was coming. But I didn’t know that, and here I am.

Odds and ends

As usual, I went skiing and it was fine. I realized that I had sort of maximized the way I was skiing and I wasn’t getting much better. I started working on some specific fundamentals and made a little progress there.

I also played a ton of pickleball until I got hurt. Then I slowed way down and lost momentum. Still, I improved a lot during the year and my game is coming along nicely. I’m leaps and bounds ahead of where I would’ve guessed my ceiling was a few years ago.

2023 Goals

Survive to 2024

The truth is, this is the thing I’m focused on the most. If I made other goals, they would ultimately roll up to this one.

I’m making improvements that should position my business to rebound in big way if and when the tech market starts hiring again. And I’m exploring other options for revenue if the business as it’s currently configured doesn’t come back.

2022 was a weird year and I’m relieved it’s over. Hopefully my 2023 recap will include “my business rebounded!” or something like that. If it doesn’t, this will be a pretty long year.

My 2021 Year in Review: An incredible year

Great Falls outside of Washington DC

My 2021 was fantastic both personally and professionally. My business grew by about 35% even though I didn’t really make any changes. Personally, I had a great time here in Gainesville, learning new things, making new friends, and just enjoying my community.

On the business side of things, the two-fee pricing structure paid off in spades. By narrowing my focus, reinforcing my positioning (“Salary negotiation coach for senior software engineers and engineering managers going to big tech companies”), and being more selective about the types of clients I take on, I worked with more people and earned more per client to get a nice double-bounce effect that increased coaching revenue by about 70%.

On the personal side of things, everything is amazing and I do not take that for granted. My friends and family all seem to be doing well, and I feel great. But it wasn’t that long ago that I lost two grandparents, an uncle, and a close friend in about a year. I am aware that years like this—when everyone seems to be doing really well—are not normal, and so I’m very thankful for this particular moment in time. I had a great year, did a lot of fun stuff, and can’t wait to see what 2022 brings.

Here’s a Table of Contents so you can jump to wherever you want…

The difference between “my business” and “my personal life”

I just realized that I strongly compartmentalize “my business” and “my personal life”. That’s intentional but not always conscious: I do not see my personal worth or value as associated with the business at all. Conflating those two things can be dangerous, in my opinion. I’ve held this philosophy since I started the business (and probably before), but it was reinforced when I made a conscious decision to engage more in my community and stop being a hermit a few years ago.

Although most of my friends probably have a vague idea what I do for work, I don’t think they could really describe how I find clients, what my actual job is, or anything like that. They probably couldn’t make a good guess as to what my business revenue looks like—what does “35% year-over-year growth in net revenue” even mean? I almost never talk about it and most of the time that I do talk about my business it’s because someone else either asks me a question or insists I tell someone new what I do.

Instead, when I’m not working, I focus on spending time with people, working to improve at something, and just focusing on my community. When I’m working, I’m working. Otherwise, my business is an opportunity to make a living doing something I love to do, but it is not who I am.

2021 Goal review

This section will be short this year because I only set two goals. I think the unknown of the pandemic made me hesitant to set a bunch of ambitious goals. Ironically, I got a lot of stuff done even without a bunch of goals. (Which, obviously, makes me wonder if there’s real value in setting goals at all.)

Increase business revenue by 50%

This is weird because I came pretty close to actually hitting this goal, but not for the reasons I expected.

From last year’s “Year In Review” post:

So I would say best case scenario for the year is a slow Q1, the new changes start to take effect in Q2, and both Q3 and Q4 are off the charts.

That’s almost exactly what happened. Q1 was slow. Q2 and Q3 were both quite a bit better. Q4 was off the charts (October and November respectively set and re-set the “best month ever” tracker).

But all the big projects I was working on are still in progress. So what happened? Coaching went bonkers this year.

I think there was a lot of pent up hiring from the 2020 slowdown, and that meant a really busy year for coaching. Usually, the summer is slow, then fall picks up a bit, and winter is pretty strong. Instead, things just got progressively busier throughout the year. It’s always possible that’s just because the coaching business is growing on its own, but I suspect this has more to do with more hiring at big tech companies.

I should have a better idea which it is once 2022 gets rolling.

Be more generous

I feel good about my progress here. I won’t talk specifically about this because this is something I prefer to keep private. ?But I will talk more about my philosophy for generosity in case it’s helpful for others.

It’s easy to experience a sort of analysis paralysis with this sort of thing: “There’s so much I could do. Is this meaningful enough? No, I’ll look for something really significant I can do. … Oh no, where did the time go?”

I think it’s better to look for needs going inside-out. I start with my inner circle: Are the people closest to me in need? If they are, can I help with that need? To be honest, this usually uncovers lots of opportunities to be generous in small ways. And—this is just my opinion, not backed up by any sort of empirical work or anything—small acts of generosity can be at least as meaningful as grand acts of generosity. The more targeted and specific, the better.

Is a friend’s spouse suddenly taking one of their kids to the ER to get stitches? Get them dinner—they’re probably not going to have a chance to cook or even order something tonight.

Is a family member struggling with making a specific type of decision that you’ve faced before? Buy them the book that helped you think through that decision when you faced it, and offer to talk with them about it.

Small things. But targeted specifically to their needs.

I think this is better than, say, “Here’s a big pile of cash to solve your problems!” because even if you give someone a pile of cash, then they have to figure out the best way to use it. Sometimes, that will be obvious to them (and sometimes cash is their greatest need), but going one level deeper and finding the useful thing the cash could buy them will save them effort and time while still helping solve an immediate problem.

It’s also more meaningful to me to help people I know—I just enjoy it more. This may be selfish, but it is a motivator to be generous to those I know, so I lean into it.

2021 Year in Review – Business

I was hoping the business would grow by 50% on the success of two big efforts:

  1. Launch a new brand and website.
  2. Build and launch a new, premium version of my salary negotiation course.

Neither of those happened. And yet the business grew by about 35%.

This was mostly driven by year-over-year growth in two areas: coaching revenue (up 70%) and digital product sales (up 36%).

Since coaching makes up almost all of my revenue (86% this year), big growth in that area has a big impact on the business overall. Product sales are deceptive because they were way down last year (2020), and I’m still way off of 2019, which was my best-ever year for product sales.

So the story of the business is: Coaching is going really, really well.

Stepping back a bit, something I’ve kept track of since I quit my day job is “How much money did it cost me to quit my job and will that eventually be break-even or profitable?” If I had built a business that replaced my day job income, I would’ve felt pretty good about that, especially given how much time and flexibility I have with my job now. But I’m starting to move pretty far past “break-even” and this year’s revenue was more than double my salary at my last day job.

I like to think about what Day Job Josh would think if I went back and told him that. And it’s even more fun to think about what he would say if I told him that and then said, “Tell me how you think that happened? What’s Future Josh doing now to make a living?” Day Job Josh would have absolutely no idea where he was heading.

Here’s my “career so far” monthly revenue chart since I started working, updated for 2021:

Revenue by month for my career so far

Ok, let’s look at some stats.


To keep things consistent, I’ll look at the same stats I did last year.

  • Visits to About 780,000 (up from 660,000)
  • Unique page views: About 1.1M (up from 940,000)
  • Total email subscribers at the end of the year: About 27,000 (down from about 40,000 after an mid-2021 pruning)
  • Product sales through the site: About 210 (down from about 300) This is a little deceptive because I basically doubled prices in February 2021, which means average order value (AOV) was almost exactly double this year. Fewer sales, but more revenue.
  • Coaching applications: 138 (up from 87)
  • Coaching clients: 36 (up from about 16)
  • Coaching conversion rate (from application to client) was 26% (up from 18%)
  • This year’s coaching clients will make a combined $2.9M in additional income over the next four years because of our work

(All of my clients for whom I have records have a combined four-year direct improvement of over $11M. I had never looked at that stat before but ?)

Net revenue was up about 35% of 2021 and the “best month ever” baton, which was previously held by January 2019, was passed not once but twice in back-to-back months (October and November).

Coaching revenue

Coaching revenue was up 70% over 2020. There’s a lot going on here, some of it related to the hiring backlog from 2020, and some of it a little more subtle.

I think the hiring backlog speaks for itself. Once the pandemic hit in 2020, a lot of companies slowed or stopped hiring. As we began to learn how to navigate the pandemic, companies started hiring again. Because they slowed down on hiring in 2020, they had unfilled positions and new positions, which led to a hiring spree, which flowed through to my business.

The subtle things are a little trickier to unpack. For one thing, I’m basically the only person doing what I do, and I’m pretty good at it, so people tell other people about me and that has a snowball effect over time. I’m also dialing in my positioning and client screening to maximize the benefit of my service fee-plus-result fee model for myself, but also for the people I work with.

When I first started coaching, all of my clients came from Google searches, and they had no idea who I was before we talked. My prices were not “low”, but they were low enough for people to take a shot and hire me on the off chance I could actually do what I claimed.

I still get a lot of clients from Google searches, but I have a lot more social proof (testimonials, case studies, podcast appearances, articles, quotes, and interviews on major sites), which makes it much easier for them to take a chance on working with me. A lot of people tell me they’ve been hoping to get a chance to work with me for a while, and this particular job offer is finally their chance to reach out.

The biggest factor is probably just time: I’ve been doing this full-time for about five years. That’s time to build a reputation, get lots of great results, refine my business, and continue to slowly grow.

I also really like what I do, and I think people can sense that as soon as they talk to me.

Product revenue

Meh. It was up this year, but is still way down from 2019. Last year, I had a partnership that generated a lot of product revenue, and that partnership was paused this year as we both redesigned big parts of our businesses. I don’t do any marketing for my products, so I can’t expect too many sales there.

That will hopefully change in 2022 as I build and launch v2 of my salary negotiation course for software engineers and engineering managers. We’ll see.

2021 Year in Review – Personal

This was a great year. Not only did I get to do all the fun things I normally do—ski trip, RV trip, football season in Gainesville—but I added some new things in the mix and made a lot of new friends.

It seems like Gainesville is both growing and becoming a place people want to be for a while. It used to be a very transient town so people would graduate from UF, move away to their real home, and start their new life. Now people graduate from UF and it seems like many of them say, “Gainesville is pretty cool, so I’ll stick around and see if I can find a job here or work remotely.” There are also a lot of people moving here either to work or for medical residencies and things, and those people are sticking around long-term as well.

It’s cool to see and Gainesville is better for it.

Pickleball mania

I tried playing pickleball about five years ago and I was horrible (and even that word is a dramatic understatement). I had never played a racket or paddle sport other than some occasional ping pong, so I didn’t have a lot of the basic skills needed for pickleball competence.

I’m also pretty sure I don’t have real depth perception, thanks to the strabismus issue I had surgery for a couple years ago.

So my first attempt at pickleball failed miserably and I more or less forgot about it until a group started playing on Saturday mornings this year. I went out a couple of times and I was still very bad, but not as bad as I remembered? Interesting. So I kept going out, eventually learned the rules and basic flow of the game, and began my journey to pickleball competence.

Since then, I’ve tried to play at least once or twice a week, and I try to train at least once a week. Some friends built an indoor court, which we call “The Palace” (short for “The Pickle Palace”). We also have a Pickleball Tutor Plus, which is like those tennis ball machines, only it shoots pickleballs, and I’m working with a coach how has helped me get much, much better.

The Pickle Palace
Working on blocks with the Tutor

Compared to Past Josh, I’m amazing at pickleball. Compared to everyone else I play with? I’m not great. But I can play and I’m consistently improving, and that’s all I need to keep at it.

Pickleball reminds me that there are two ways I learn new things:

  1. Just sort of pick it up and run with it. Sometimes I try something new, it comes easily, and I just keep doing more of it and working to improve. Poker was sort of like this for me: I tried it, “got it” almost immediately, and then spent a long time working to get better.
  2. Dogged determination to get better despite difficulty getting started and slow, frustrating progress over time. This is what pickleball is like for me. I am drastically better than I was when I started, but all of that progress has been made by brute force. I’m not naturally comfortable with it or good at it, but I fight through the discomfort to keep improving.

Both of those are fun, but in different ways. Of course it’s fun to pick something up and just “get it”. But it’s also fun to confront the challenge of improving at something where naturally ability or previous experience isn’t an asset. Sometimes it’s satisfying to do the hard things.

Bowling was in the “just get it” category. I had a bowled a lot, but only with a ball drilled for straight bowling. I had never broken 200, and I wanted to get that done. So some friends and I joined a league, I bought a ball, learned to throw a hook, practiced a bit, rolled a 210+ in league play, and eventually topped out at 236.

Skiing was also more of the “just get it” experience. I wasn’t good when I started, but I have been able to make progress pretty consistently by just doing more of it. I don’t feel like I’m fighting to make progress—I just have to be patient and I’ll get better.

Pickleball is distinctly different from those things. All of my progress is earned and it’s a frustrating process. But that makes improvement feel more meaningful.

New boots in Breck

For the past few years, I’ve written a recap of the annual Breck ski trip, but I skipped it this year because it would’ve mostly been more of the same. The first few years, I made pretty significant progress each year—learning how to ski, trying more challenging stuff, getting comfortable skiing black runs—but this year was a marginal improvement to “started working on control for mogul and tree runs”.

I also got my own ski boots, which I think is a great investment that will make me much better. I never felt comfortable in rental boots, and I immediately felt that I had more control once I got my own boots dialed in.

My plan for this year was to hit some of the double-black runs up top at Breck, but all the high-up stuff was closed for most (all?) of our trip, so I didn’t get the chance. Instead, I ran Wanderlust a couple of times, realized I could not make consistent tight turns or manage moguls, and ended up spending the final day (my sixth ski day of the year) looping the moguls on Crescendo. By the end of the day, which ended early because it was so cold that I could no longer feel my feet, I was pretty much zipping down them.

80s Day
The best house we’ve ever rented

For this year’s trip, I think if I spent my first day getting reacclimated to skiing in general, and then spend the second day working on bumps, I should be able to make a pretty big overall leap this year.

RV trip

Once again, we had an amazing summer RV trip. This time, we went to DC, Virginia, West Virginia and Pennsylvania. The cadence of the trip was the same—we crammed into an RV and drove to a bunch of different places to hike and see the sights—but there were also some minor differences from last year to this year.

First, we only had six guys instead of eight, so the RV felt downright spacious. We all had at least a little space to ourselves, and we could all hang out together up front when we drove. The RV was also slightly smaller and much easier to drive, so it was a little less stressful getting around.

I say that, but the first leg I drove was on a narrow, steep, curvy mountain road in West Virginia and that was probably the most stressful driving I’ve ever done. The road basically had no shoulder—you go over the white line and you’re tumbling down the side of a mountain—I couldn’t see around many of the hairpin turns, and I basically had to drive in the middle of the road and just hope nobody was coming the other way. It’s also not fun going down steep grades and wondering, “Are the brakes gonna hold up? Sure hope so!”

We also didn’t have to do as much hiking to get to the stuff we wanted to see this year, so that was nice. I mean, I like hiking ok, but if I can get to a cool overlook by hiking three miles, I’d rather do that than getting to the same overlook with a 20-mile hike.

Great Falls outside of DC

New kitchen and other home improvement

Count me among those who decided to upgrade my house during the pandemic. Every morning, I sit at my dining room table facing my kitchen while I drink coffee and read.

One morning, pretty early on in the pandemic, I was looking at my kitchen and said out loud, “I hate that kitchen.” That’s all it took: in that moment, I decided I would remodel it. I tumbled down the renovation rabbit-hole, hired a local kitchen and bath company, and got to work designing a new kitchen.

I had lots of help and input from friends and family, but I ultimately made every decision about every little detail of the remodel. The most trivial decision I made is hard to choose, but it’s probably something like, “Do I have the drawer pulls installed so they’re vertically centered, or offset by a fixed amount from the top of the drawer?” (I chose the latter.)

Looking back, I think I was aware I would pay a premium for my timing—everything was more expensive because of labor and supply shortages due to the pandemic—but I actually got a decent deal compared to what it would cost to do the same project today. We actually started demo around May and finished everything up in August.

There were two main reasons I decided to invest in such a big upgrade:

  1. Did I mentioned I hated the old kitchen?
  2. I was pretty confident I would have people over more often if my kitchen was more functional.

But there was a more subtle reason that pushed me over the edge: I realized I was probably going to be in my house for a while, so why not make it a place I really like to be? The housing market has been heating up for a couple years, and there are no great alternatives to “just stay in my house”.

I could sell this place and buy another house, but I’m not sure what that would really get me. I like my current house, and upgrading would be super expensive. I would have more space, but I don’t use all the space I have now. I could live in a nicer neighborhood, but my neighborhood is fine.

I could sell this house and rent somewhere, but to rent something comparable would cost about 50% more than my mortgage. That didn’t seem great.

So I decided I would just stay put for now. And instead of getting like twice the house, I would make my current house into exactly the place I want to be when I’m at home.

I also redecorated my master bedroom, got a new roof (out of necessity), got new windows, replaced 3/4 of my exterior doors, had a new fence put in, and started redecorating my office, living room, and dining room. Most of the redecoration stuff is cosmetic, so it’s not that expensive. But it’s making a huge difference in how much I like my house.

My confidence that I would have people over more often with a better kitchen was spot on. I’ve gone from “I hate that kitchen.” to “Why don’t y’all come over and we’ll make a bunch of pizzas?” Between August (when the remodel was done) and November (when having people over for dinner was tough because we were all just trying to get to all the friendsgivings and Christmas Movie Nights), I had people over several times for dinner and it was always a lot of fun. I’ll do a lot more of that in 2022.

My kitchen before the remodel
My kitchen after the remodel

New friends

As I mentioned earlier, Gainesville has historically been a very transient town. People would come here for school, graduate, and leave. Some people moved here to work either at the university or in the huge healthcare industry we have. But even those folks would often leave after they finished their internship or residency or graduate degree or whatever.

That seems to be changing. More people are sticking around after they finish undergrad, more medical professionals are making Gainesville their permanent home, and people just seem more locked in to Gainesville in general.

Here’s an example: Every year, December is dominated by an annual tradition called Christmas Movie Nights (CMN). Whoever is in town will meet up, select a Christmas movie, and watch it together. We do that as many nights as we can before everyone goes home for Christmas. We’ll usually get 10 or so movie nights in, and we’ve done as many as 12 in years past. Typically, we’ll start with a big group (20-25 people) that slowly dwindles until there are only maybe five or six of us for the final few movies before Christmas.

Not this year! This year we watched 15 Christmas movies, we consistently had 15+ people right up until the final CMN, which was December 22. There are just more people who now live in Gainesville and then go visit family for Christmas as opposed to just being in Gainesville and “heading home” for Christmas. Gainesville is home for more people now than it used to be.

This year, there were just more new people who I got to meet and hang out with as fellow Gainesvillians. And since fewer people leave Gainesville every year, my friend group as grown quite a bit. It’s a nice change of pace from a sort of revolving door of friends to a slowly-growing friend group which constantly does fun stuff.

Gainesville has changed a lot since I finished undergrad and pretty much all of those changes have been positive. I love it here.

The annual Manor Christmas Party

Less disc golf and running

For the past few years, I’ve spent a lot of time playing disc golf and working on my game. This year, I made a conscious decision to play less disc golf so I could play more pickleball. I also pulled back on running because pickleball is a pretty intense leg workout, and I realized my legs never recovered when I ran three times a week, played pickleball a few times a week, and worked out at the gym. Something had to give, so I cut back on disc golf and running, and added more pickleball.

My guess is that 2022 will include more disc golf, but probably the same amount of running, but we’ll see.

That said, I did get a couple rounds of disc golf in at the end of the year. We played on teams, and my team won both times, so that felt pretty good (and was a nice change of pace from mostly losing whenever I play pickleball).

A December round in Jonesville
My final drive of 2021 (at Northside park)

Although I wasn’t really training to run, I managed to end the year with some decently fast runs. My last run of the year was 4.5 miles at a sub-8:00 per mile pace. Although I’ve mostly switched that time over to pickelball, I have decided to try to maintain decent running stamina in case I decide to go back to it or set new PR goals later on. So far, so good!

Tried yoga for the first time

This is sort of late-breaking news, but I tried yoga for the first time right after Christmas. Several of my friends go regularly, so I had been planning to give it a shot, but I ended up just going randomly with another friend who had never gone before.

We both survived and it wasn’t too bad. I didn’t hate it, but I didn’t love it. My guess is it’s something I’ll do occasionally, but I won’t end up being a “yoga every morning” type of person.

2022 Goals

I only had two goals for 2021, and I think that’s just because I had no idea what to expect after a weird 2020. Rather than set a bunch of ambitious goals and have them disrupted by another weird year, I decided to hedge and keep things open.

I still had a productive year, but I might have been more productive if I had actually set some goals to pursue. So I’m back to regular goal setting for 2022.

Build and launch a new salary negotiation course for software engineers

I think it’s time.

I made the first version almost six years ago, and I’ve learned a lot since then. The reason I haven’t already updated my flagship courses is … well, it’s because they’re still really good and effective. I frequently get emails from customers saying they increased their offer by a big amount, the ROI is off the charts, and great things like that and I figured “If it ain’t broke, don’t fix it.”

But with the new brand and website, all that I’ve learned over the past several years, and the fact that I’m now known as “the salary negotiation guy” (especially for software engineers and engineering managers), it seems like a great time to build v2.

The original courses I made are very effective for software engineers and engineering managers, but they weren’t designed for them. The new version will be designed specifically for them and it will be good to offer something specifically to folks who can’t afford to work with me 1-on-1, but who want to have my help negotiating.

This will be a major project, but I think it could have a huge impact on the business this year.

Increase business revenue by…50%?

I’m not sure what the right goal is here. I want it to be aggressive but achievable. The wildcard here is how quickly I can get the new course built and launched, and how successful it is.

I have a monthly revenue goal in mind for the course once it launches, and if I could launch on January 1 and hit that goal every month, I would increase year-over-year revenue by about 50%. But it’s more likely the new course is ready some time late Q1 or early Q2, which obviously means I’ll miss a few months of revenue there, so I’ll need coaching revenue to grow some more to fill that gap.

This is a stretch, but I think it’s doable. We’ll see.

Get to a 4.0 level in pickleball

I’ve been working with a coach and we both think this is doable. To be honest, this doesn’t feel like an ambitious goal (I think most people would say “5.0 or bust!”), but I think it is.

I’ve been making very slow, steady progress for several months. But progress is difficult and I have no idea what my ceiling is. I’m pretty sure it’s above 4.0, but 4.0 is also quite a bit ahead of where I am now, so we’ll see.

I’m always trying to find a fun thing that I can work on to see steady improvement over time. A few years ago, it was running, during the pandemic it was … video games, I guess? And now it’s pickleball.

I’m not quite sure how to measure this, but I think it’s something like, “Play a tournament and win at least one pool game at 4.0.”

Ski the top of the mountain at Breck

I wanted to do this last year, but just didn’t get the chance. Ironically, I think this stuff will be pretty easy for me because I’m very comfortable on groomed black runs. The stuff up top isn’t necessarily groomed, but it’s steep and flat and not very technical. This one should be pretty straightforward.

A stretch version of this goal would be “do the Windows run at Breck without dying”.

Travel more (for real this time)

Assuming the ski and RV trips are more or less locked in, I’d like to take one more trip this year. It’s been a while since I went to Europe and I have a giant pile of credit cart points burning a hole in my pocket, so this would be pretty easy to do but for the uncertainty around pandemic restrictions. If I can’t get to Europe, I’ve never been to Chicago before, so maybe that’s something to try.

Something something cooking?

I can’t think of an actual goal here, but I want to cook more and get better at cooking more stuff. This also includes baking.

I have a few things I’m pretty good at, my not many.

Make my own pizza dough? Make fresh pasta? Master the four classic Roman pasta dishes?

I’ll use this goal as an excuse to have people over more often.

Be more generous

I want to call this out to make sure it’s a focus for me this year. I tend to just take opportunities as they come, but I would like to be more intentional about seeking out opportunities or even creating opportunities to be generous.

Summing it all up

When I started writing this year’s recap, I underestimated how good this year was. The last thing I do before publishing these posts is choose the title. I was really stumped this year. So I sat back, thought about it, and realized, “Wow, this was an incredible year.” And there it was.

What’s really fun is that I already have so much planned for 2022. A new brand and website for the business, and lots of personal things I want to try or spend time on but which don’t rise to the level of setting an actual goal. The problem with using the word “incredible” for 2021, is it doesn’t leave a whole lot of room for improvement in 2022, and yet I feel like 2022 could be even better. Still, I think it’s apt so I’m going to run with it.

If I end 2022 trying to find better adjectives than “incredible”, then that will be a great problem to have. And if 2022 doesn’t turn out as well as I hope it will, then at least I didn’t waste an opportunity to describe 2021 as the incredible year it has been.

My 2020 Year in Review: Riding it out

I want to resist the urge to start this post talking about the pandemic but, since I write these posts for posterity, I think I have to start there. It was a weird year that affected my business life much more than my personal life, but the pandemic’s effects were felt throughout the year.

My business actually grew by about 15% in 2020, but that’s a deceptive summary. The underlying components of the business experienced some big and interesting swings in revenue even though the top line looked pretty steady. I almost said I was lucky but … there’s a little more to it than that. A combination of luck and conscious decision making have made the business more resilient (or maybe it’s more accurate to say “anti-fragile”) just in time to weather a big economic storm.

Personally, I had a great year that confirmed something I’ve been noticing for a while now: My family and community are the most important things I have. If my relationships with those are strong, everything else is much more consistent.

For both business and personal things, past investments have led to a stable year in the midst of substantial global upheaval.

2020 Goal review

Increase revenue by 50% again

This was a pretty big miss since the business grew by “only” 15%, but I also didn’t factor in a global economic catastrophe when I set this goal, so I’m giving myself a pass. If I had incorporated that into my projection, I think I would’ve said, “Gosh, if that’s going to happen in 2020, then I guess breaking even would be a very good year.” So the fact that my business grew at all feels like a huge win.

Sub-7:00 pace 5k

Miss, but just barely. I almost hit this one in a training run very early in the year—I had a 7:03 pace 5k on the Hawthorne trail—and if I had just had a different view of the real-time stats on my Apple Watch during my run, I would’ve gotten it.

Then I ran a race in February and ended up at a 7:06 pace, but that’s deceptive because it was 45 degrees out that morning and very windy. In fact, I was pretty much on track to hit this goal until I turned into a super strong headwind that slowed me way down for the final mile.

So I think I would’ve gotten this one but for some bad luck (wrong real-time stats on my Watch followed by non-conducive weather in the race). As misses go, this feels like a hit.

My overall time from the 5k I ran I 2020 was 21:54 and 7:06 per mile

Sub-60-second 400m

I didn’t even try this one. In fact, I’m not even sure I did a single track workout this year. Maybe I’ll hit this one in 2021 (but probably not).

Travel more

Again, this is relative thanks to the pandemic. I got the normal ski trip in just under the wire in February (actually, I extended the trip by a few days this year), and I went on a week-long RV trip with some friends in June. I would say this is actually a win.

Be more generous

This is a win—I think I succeeded here. Could I have succeeded more? Sure, but that will always be true. I was intentional about finding opportunities to be generous and to be generous in meaningful, specific ways that would really be useful.

I’m not sure how to write more about this without seeming braggy, but I do think I might be able to share some more thoughts on this in a tactful way that could be helpful to others, so I’ll try to do that either later in this post or in a separate post entirely.

2020 Year in Review – Business

The business grew about 15% this year. What’s strange is that when I drill down one or two layers into individual stats, things could look very different depending on which stats I choose to focus on.


Before unpacking that intro, I should address the elephant in the room: COVID-19. It very clearly had a huge impact on my business this year, especially on the product side. Organic search traffic took a big hit in January with a Google algorithm update—that’s not unusual. But then it mostly recovered until the second week in March when it fell off a cliff and basically never recovered.

That drop in traffic shifted my email list growth from “steady” to “zero”—my email list has been treading water all year. Search traffic leads to email list growth, which leads to product sales. So with fewer new email subscribers came fewer direct product sales.

Meanwhile, a few pages on my site that are specifically to help folks navigate negotiations with big tech companies actually had a material increase in traffic this year. The traffic to those pages does not generally lead to product sales, but does lead to coaching clients. So traffic to the coaching side of the business was up this year.

All that nets out to more coaching revenue, less product revenue, and modest growth for the business this year.

That’s what things looked like from my side of my business. But clearly this reflects much more substantial issues for folks who were either job seeking in 2020 or would have been job seeking in 2020. It sure looks like companies slowed or stopped hiring altogether and people probably didn’t look for new opportunities as aggressively as they normally would’ve because of the substantial economic uncertainty as we navigated a global pandemic all year.

So I’m thankful that my business grew, and I know that what I described above reflects a lot of economic turmoil for a lot of people.

I’m leading with this because it colors everything else I’ll say in my business recap. There’s just no way to talk about the business without accounting for COVID-19.


I normally end with stats, but I’m leading with them this year because of COVID-19.

Visits to About 660,000 (down from 1.2M)
Unique page views: About 940,000 (down from 1.7M)
Total email subscribers at the end of the year: About 40,000 (down from about 46,000 after an early-2020 pruning)
Product sales through the site: About 300 (down from about 800; about 20% of the 2019 product sales were a single partner promotion, so this is still a huge drop, but not as huge as it seems)
Coaching applications: 87 (up from 63)
Coaching clients: 16 (down from about 30)

Conversion rates are more or less the same as last year.

The one thing I’ll point out now and unpack later is that the drop in coaching clients was intentional. To help unpack this, I added a new stat this year: Coaching applications. That number went up by almost 40%, but the number of clients I actually worked with dropped by almost 50%.


I was focused on working with more senior engineers and executives, looking for opportunities where my service would add the most value possible. I wanted to be sure I had maximum time available to give the best service possible to the clients I did work with because I knew that each client would probably need more of my attention given the complexity of their negotiations.

Coaching revenue

The overall growth was driven mostly by growth in coaching revenue. But even there, digging down selectively would make things look quite a bit different. As I mentioned above, I actually worked with fewer coaching clients this year than I did last year—that seems bad. But my average revenue per client is up quite a bit—that’s obviously good.

This is one of the strange parts about running a business and making changes with an eye on the future: Even though the coaching results this year were more or less exactly what I was hoping for when I changed my fee structure and positioning, it still feels bad to see that I worked with fewer clients. This was by design and yet a declining stat feels bad.

One fun fact from 2020: A single coaching engagement generated more revenue than my business generated for the entire year of 2016 (the first full year I operated the business).

Product revenue

Product revenue was even weirder. It’s basically flat for the year, but a lot more of my sales came through partnerships than in previous years. Overall website traffic was way down due to combination of Google algorithm changes and the pandemic, but partner revenue was up thanks to connections and relationships I’ve built over the past several years.

Again, drilling into specific stats could lead me to say “Oh no! That’s bad!” Or “Wow, that’s great!” But the net result is flat product revenue for the year.

Given the pandemic, I’m very happy with this.

Strategy paying off

Last year, I made two explicit changes that drove significant growth in the coaching business and helped that part of the business to continue to grow through 2020.

First, I changed to a two-fee model: service fee up front; result fee based on the result we negotiate. Second, I continued to position my coaching further up market to work with more-senior software engineers, managers, and executives.

Either one of those changes in a vacuum would’ve netted an increase in revenue, but combined they drove a significant increase in revenue while reducing the number of clients I worked with. This is one of the few times where the outcome of a change I made pretty much exactly matched the intent behind the change.

By moving up market, I am positioning my service for clients where my expertise will generate more nominal value. What I mean by “nominal value” is “real dollars created as opposed to percent increases (marginal value)”. For some of my clients, both the nominal and marginal value are greater than for clients I’ve worked with in the past, which has an additive effect on the monetary result.

By moving to a fee structure that includes a result fee, I also capture more of the value I create and align my incentives with my clients.

So I’m creating more nominal value and capturing more of the value that I create, which has a sort double-bounce effect: I work with fewer clients but generate more revenue. That’s exactly what I was hoping for when I made those two changes, and it’s satisfying to see them work as I hoped they would.

As I mentioned above, I’m also fighting against the tendency to hone in on specific stats (eg, “number of clients booked this year”) which make me less happy. I designed the business to allow me to work with fewer clients, and yet it feels weird to work with fewer clients. Everything is fine, but it feels weird.

Last year, I shared my lifetime career earnings trajectory, and I’ve updated it to include 2020. You can see that this year looked a lot like last year.

Monthly income for my entire career to date

Investing in the business

This year, I also began make substantial investments to improve the business over time. I’m working on a rebrand and site redesign, and I’m investing in training to get better at selling courses to help more people. Just those things will cost about 10% of my 2020 revenue.

I haven’t begun rolling out the new branding yet (and won’t for a while), but here’s what it looks like:

On one hand, this is sort of scary because I don’t know whether and how this work will pay off. That’s the uncomfortable part of being a solo entrepreneur: the buck stops with me. Not only do I have to decide where and how to invest, but I alone absorb the consequences of those investments. So far, the cumulative investments I’ve made in my business have resulted in continuous growth. But there’s no guarantee that trend will continue.

The upside to a growing business is that I have more revenue to reinvest, so each successive investment can be larger. That means a potentially larger nominal return, but also means a potentially larger nominal loss. Since my personal and business finances are a hair’s breadth apart, this can be pretty scary.

But that’s the deal I made with myself when I quit my day job, and if I could make big investments when I was slowly going broke, I can certainly do it when business is better than ever. I just hope the investments I’m making now continue the trend of positive returns.

2020 Year in Review – Personal

This was a good year for me. I almost didn’t write that because I know this has not been a good year for a lot of people. But I feel I can acknowledge two seemingly conflicting things at once: I had a good year; many people did not.


Just like with my business review, it makes sense to start here for my personal review.

And I don’t want to bury the lede: I had COVID-19 right in the middle of the year. My experience was very mild and I only really felt symptoms for about 24 hours. I also know many people who have had COVID and all of them are fine. I feel very fortunate that this has been my experience.

My birthday was in March, and I planned a pretty big party for March 15. One week earlier and I wouldn’t have even considered COVID when planning it. One week later and I almost certainly would not have gone through with it. But on the 15th, things were still very much up in the air and after talking with everyone involved, we decided to go ahead with the party.

After that, everything changed. While my year was more confined than usual, I live in Florida where the response to the pandemic has been different than it has in a lot of other places. This has undoubtedly affected my experience in myriad ways.

I have a small, close-knit group of friends who I navigated the pandemic with. Many of them are medical professionals, so I was able to keep up to date with all the latest information, and I had good, real-time insight into how things were going here.

My family lives nearby, but I wasn’t able to see them as much as I normally would because of COVID. In fact, we took some family photos on March 14—again, right on the timeline tipping point—and I didn’t see them again for a while after that.

Overall, my personal life was affected much less than my business life. I’m extremely thankful for this. My friends, family, and community are all far more important than my business.

Ski trip

I made some big strides in Breck this year. Not only was I totally healthy this year, but I was able to build on everything I’ve learned the past few years to make some big leaps forward.

I did a lot of black diamond runs, and generally felt more comfortable on skis than I have before. It took me a while, but I think I’m a decent skier now.

We managed to get this trip in just under the wire—about two weeks after our trip, things started shutting down. During the trip, we talked about COVID-19, but it was more of a “What’s that all about? Should we be worried?” type of atmosphere.

2020 Ski Trip Crew

Birthday bash, just under the wire

In March, I had a really fun birthday party where I hired a private chef to prepare a nice meal in a house I borrowed for the evening. I didn’t know it at the time, but this was simultaneously a commemoration of my birthday and a last hurrah before everything shut down.

I had been planning to do something big for my birthday, and I decided to go with the most “Josh” thing I could: A nice meal, friends, and conversation. As for the meal itself, the apps and desserts were all fantastic. The entrees were good, but not amazing. But what I was really after was the experience and that delivered in spades.

2020 Birthday Dinner

Survivor Fantasy League goes International

My friends and I have a Survivor Fantasy League, which I realize sounds ridiculous, but which is also basically the most fun we have every week. Unfortunately, we didn’t get any new Survivor this year, so we did some digging and discovered that several other countries also have Survivor, and some of those countries have had epic seasons.

So we went and found one of the best seasons of Australian Survivor and we’ve been watching that all year. And I mean literally all year—we started in June and we didn’t finish until January 2021. We’ve pared things down a bit—no weekly challenges, no draft—but we still watch all the episodes and find ways to make it interesting. I actually won a free meal at Outback Steakhouse (heh) since I won our Survivor Survivor this season.

On one hand, it’s absurd that this season of Australian Survivor has like 30 episodes. On the other hand, I think we’re all really happy we found something to help us fill all the time when everything (especially sports) was paused this year.

An epic RV trip

In June, a friend of mine turned 30 and wanted to celebrate in a big way. The initial plan was some sort of international weekend trip, but COVD-19 shut that down, so we stayed stateside. A group of us rented a big RV and drove around the southeast for a week, doing as many cool hikes as we could.

The entire week went off without a hitch and we had a blast. I hiked about 45 miles that week, visiting some of the coolest overlooks and seeing some of the most beautiful sunsets I’ve ever seen.

Sunset on Black Balsam Knob in North Carolina

One thing that was, um, interesting about the trip was driving a 38-foot RV on winding mountain roads. We eventually learned to bungee the fridge and cabinet doors shut to avoid everything dumping out onto the floor during a sharp turn. And something that felt very 21st Century was that a few of us brought our consoles and tethered to our phones to play video games to pass the time. Even in the mountains, our connections were all pretty good and it was weird to think that we were playing games online against people all over the world while we drove along the Blue Ridge Parkway.

A big highlight of our trip was actually a Pizza Hut experience. We had been hiking all day (this was one of our longest days and we did at least three hikes that day) and got off the mountain so late that we had to race the sun to get off a three-mile trail before it got too dark to see.

We were famished, so we started looking for open-late dinner options only to be supremely disappointed pretty much everywhere we went. We tried a few different places and they had all closed for the night. Finally, we found a Pizza Hut that seemed to be open late enough for us to race over before they closed.

Unfortunately, they had closed early, so we sat in the parking lot trying to figure out what to do. One of the guys suggested we just go through the drive through to see if they were open, and most of us laughed and joked about how Pizza Huts don’t have drive throughs. Finally, another guy decided to just walk up and knock on the door. Someone came out, they talked for a while, and he came back to the van and said, “They’ll take us. Just go around to the drive through.”

Apparently Pizza Huts do have drive throughs, and this particular Pizza Hut with a drive through was run by manager who said, “I’m not gonna turn down money. Come on around.”

We ordered over $120 worth of stuff from Pizza Hut, raced back to the RV (we were in a van for the day) and ate like kings.

Another food highlight was a quick stop for Taco Bell as we raced between RV parks. We were super tight on time, so we drove the RV unreasonably fast down winding roads to hit Taco Bell and get to the camp in time to check in. I ended up spending $20 on Taco Bell and I ate every bite. That may not sound like much, but take a look at the Taco Bell menu next time you’re there and ask yourself how much food you can get for $20. Hiking burns a lot of calories.

Weird football season

This is one of the strangest football seasons I can remember. For the first time in over a decade, the Gators had a dynamic offense with one of the best college quarterbacks to ever play the game (this may seem a bit like hyperbole now, but I think it’s really likely Kyle Trask will be very good in the NFL and would’ve been one of a kind in college if he got to play more than a couple seasons). Unfortunately, we also had one of the worst defenses Florida has ever put on the field, so we totally wasted a generational offense.

Meanwhile, we were in the middle of a global pandemic, which made the schedule weird, and the in-stadium experience even weirder. And yet I went to more games this year than I have in a very long time. (I’m pretty sure I went to five games, but I honestly can’t remember.)

The stadium atmosphere was very strange. Quarter-full stadiums feel empty and there’s no energy, so most of the games felt more like a scrimmage than a real game. Texas A&M had lots of fans and it actually got pretty rowdy, and the Florida vs. Georgia game in Jacksonville ended up being pretty crazy (although that might just be how I remember it since we won). But in general, it was really eerie watching a football game when my nearest neighbors were six feet away and masked up.

Florida vs Texas A&M Football, 2020

My main takeaway from the season was that it was really fun to watch Kyle Trask, Kyle Pitts, and a bunch of other dynamic Gator players run beautiful offense, and I’m glad I got to see them do their thing in several games this year. This team will have some guys playing in the NFL for many years.

Five years since I quit my day job

September 18 2020 marked five years since I quit my day job. I’ll eventually add that story to my blog, but for now here’s a link to the twitter thread for posterity: 5 years since I quit my day job

The cool thing is that I’ve also been tracking each year in these yearly reviews, so I’ve got a much more detailed version here on the blog. It’s so strange to look back, especially at the early summaries, because I had no idea what I was getting into. But I managed to find my way to a growing, successful business doing something unique and valuable that also affords me the chance to set my own priorities and totally control my schedule.

My first disc golf tournament

Although I’ve been playing disc golf for most of my life, I had never played a tourney until this year. There’s a pretty active disc golf community called the Chain Hawks here in Gainesville, and they have an annual tournament called the Chain Hawks Open where they play the two best courses in Gainesville (which also happen to be the two courses I’ve played the most).

This year, a friend and I decided to play and see how we did. We both signed up for the “Advanced” division, which was one level below the open division where all the pros played. I actually played pretty well, shooting even par on Day 1, +4 on Day 2, and +4 on Day 3 for a total of +8 to finish middle of the pack.

Overall, I was really happy with my play, especially on Day 1. It was really windy and I made most of my putts. Days 2 and 3 were both much tougher because of pin placements, and I was frustrated to leave several strokes on the course by missing putts on Day 3 (I literally missed five very makable putts off the metal, including three consecutive birdie misses on the final three holes). But the overall result was pretty good considering it was my first tourney, and I was really fortunate to play with good guys in every group.

First tee of my first disc golf tourney

2021 Goals

This year’s goals are simple. I’m not making any new running goals because I’ve changed my workouts to facilitate recovery from leg workouts over progress in running times. I would like to hit some of those goals from years past, but that’s not a priority.

Increase business revenue by 50%

I almost balked on this one, but this is what I had in mind before the year started. I say “almost balked” because I’m still writing this in February and January was my worst month in about two and a half years. So this goal seems kind of crazy.

But! I’m making some substantial investments in the business, and if those investments pay off then this goal is achievable. Namely, I’m doing the first rebrand and site redesign since I started the business over five years ago. I’m also updating my product offerings to be more streamlined and more valuable (and hence, more expensive).

I think all of these things stacked together could have a multiplicative effect, but it will still be at least a few months before those changes are in place. So I would say best case scenario for the year is a slow Q1, the new changes start to take effect in Q2, and both Q3 and Q4 are off the charts. As always, it’s basically impossible to predict what will actually happen, but this scenario isn’t totally implausible. We shall see.

Be more generous

Same goal as last year. My business is still doing well overall, and my life is pretty simple. There’s a lot of room for me to be generous, and I enjoy it. So I will do more of it this year.

Here’s to a better 2021!

It’s been five years since I quit my day job

This is the story of the first five years of the Fearless Salary Negotiation business. I initially shared this as a Twitter thread, and I’m publishing it here because it’s a personally significant document and it might be interesting to other folks as well. This is exactly as I wrote it in that Twitter thread, but I’ve corrected a few typos and added section headings to make it easier to skim.

Today marks 5 years since I quit my day job. I’ve been thinking about that this morning and my thoughts are surprisingly sort of scattered. I thought, “Why not share some of those thoughts?” So here we go…

Setting the stage

I didn’t quit my job on a lark; I had been working in that direction for about five years before I actually made the jump. I did a trial run after I finished my MBA in 2011: I quit my job to take about eight months and just do stuff I found interesting. That sabbatical was very useful because I learned something important about myself: I did not need a job—fixed schedule, clear responsibilities, steady paycheck, co-workers—to be productive. In that eight months, I was probably more productive than I had ever been. I did some traveling (Las Vegas, Seattle, Vancouver), played in the World Series of Poker Main Event (and a lot of other poker), started writing Heads-Up Tournament Poker, learned Ruby on Rails, built my first web app, and lived on savings the entire time.

To set the sabbatical up, I had saved most of my income for the previous 15 months. So I had essentially run a test and written my own playbook for the next time I would quit my day job and try to make it permanent: Save as much money as possible, pay down debt, have a plan.

Making a plan

By early 2012, I had rejoined the full-time employee world and I had a plan to quit my day job again, but permanently this time. I described my multi-year plan to friends during a round of disc golf, so I vividly remember when I realized, "I’m actually going to try to do this.?" The plan was as follows:

  • Pay down all debt (mostly student loans) except my mortgage, which I refinanced to a super low rate.
  • Save enough money for a 15–18 month runway.
  • Learn to write useful software.
  • Build a software business.
  • Make the jump when the time was right.

For those of you who know me as "the salary negotiation guy", you might be thinking, "Wait. Build a software business? What am I missing here?" But that was the plan! First I shipped ShareAppeal—a proof of concept social sharing app that was very cool. Then I started TaskBook. TaskBook was a B2b (small business) app for managing recurring tasks on teams. At first it was for small retail shops. Then I began focusing on agencies and consultancies (project management applications). It was ALSO a cool app. By the end of 2014 I had some paying customers.

Starting to write Fearless Salary Negotiation

Meanwhile, I had been noodling on the idea of writing a career management book, which I formally started writing in late 2014. I had made some really unorthodox career decisions and people asked me about career stuff all the time, so I thought, "Why not write about this?"

Maybe you noticed I said "career management" and not "salary negotiation". At first it was a much bigger project, more like a textbook. I called it "Take Control of Your Career: A Career Management Guide" and I totally understand if you nodded off while reading that boring title.

By Spring of 2015 I had a good amount written, but the outline had MANY more topics to cover. I went to MicroConf in Vegas and lucked out to end up eating pizza with Josh Kaufman and Tim Grahl. I cannot overstate how important this one conversation was. It changed everything. In about an hour, Josh suggested I narrow the focus of the book and gave me the title "Fearless Salary Negotiation: A step-by-step guide to getting paid what you’re worth", they talked me into launching on Amazon, and showed me which categories to target.

Quitting my day job

So now I’m working a full-time job, writing a book, and running a B2b SaaS while saving up money as quickly as possible. At this point, the book was more a labor of love and a chance to try self-publishing for the first time. I was still ultimately planning to focus on TaskBook. As my runway approached 15–18 months and I moved into the final stages of Fearless Salary Negotiation, I started to think about when it would be right to quit my day job. I got more and more antsy while also wearing down a bit from doing so much (I was working seven days a week). I decided on September 18, 2015. Here was my plan:

  • Publish FSN by end of 2015.
  • Ship FSN courses so I would have an info-product tiered offering as soon as possible.
  • Make enough monthly income from FSN to survive while pushing TaskBook up the Long, Slow, SaaS Ramp of Death.

In October, I self-published Mastering Business Email, which was a big part of FSN that I removed when I narrowed the scope to salary negotiation. MBE was a self-publishing test run so I could learn the process before launching FSN in December. MBE did surprisingly well! October was also my first full month self-employed and my net revenue for the month was $103.01. November net revenue was $1.72. I felt the full weight of burning large chunks of cash from my runway every month. I realized that runway would go FAST, so I absolutely had to focus.

I spent the rest of the year prepping and launching Fearless Salary Negotiation. I did literally everything except the cover design (which was done by the excellent Pete Garceau, who of course was recommended by Josh Kaufman at that fateful MicroConf pizza dinner).

Publishing Fearless Salary Negotiation

I launched Fearless Salary Negotiation in December. It hit #1 in two categories on Amazon and sold about 220 copies that month. At the time, my mailing list was about 600 people. I made $602.04 that month, putting me at $706.77 net revenue for 2015 (since I quit my day job).

I don’t usually mention specific revenue numbers, but I think that’s important here. It’s now January 2016, four months after I quit my day job to begin burning through my savings. I had been working relentlessly for four months, made $700, and reduced my runway to 14 months.

I was, shall we say, starting to get a little nervous.?

Sunsetting TaskBook

The plan was "Make enough monthly income from FSN to survive while pushing TaskBook up the Long, Slow, SaaS Ramp of Death." I began to see how hard that would be, realizing I was trying to build TWO businesses at once. I had to choose between building a SaaS and building an info-product business. This was not a choice I anticipated when I quit my day job, but here I was at a crossroads only about four months into my journey.

My original plan was not tenable; I was making a new plan on the fly. This choice was nuanced and I won’t go into every factor here. But it was really a choice between pursuing a moonshot in an area where I had little genuine interest, or building a lifestyle business in an area I REALLY enjoyed.

I chose the lifestyle business, going all-in on FSN. I told the few TaskBook customers that I was sunsetting the product, worked out a plan with them, and turned my full-time focus to turning FSN into a revenue-generating business as soon as possible.

Building the Fearless Salary Negotiation Business

My first order of business was to ship the FSN courses as quickly as I could. Turns out that learning to write and produce video courses is difficult. Who knew?! I had no idea what I was in for and fortunately Justin Jackson and the MegaMaker community were super helpful while Caleb Wojcik helped me figure out the on-camera part. It was a grueling process.

I’m generally very risk-averse and had planned and saved meticulously for this move to give myself the best chance possible of never going back to a day job. But my runway continued to burn, I had already significantly modified my plan, and I started to see how risky this was. I was making steady progress, working seven days a week, but I was worried I had made a mistake and set myself up for failure.

One or two days a week, I felt down—I called them "blue days". Those days didn’t affect my productivity, but I felt tremendous pressure and isolation. I was fortunate to be part of a close-knit community, near family and friends who encouraged me. I also had lots of entrepreneurial friends who had experienced similar things, and they helped me keep the right perspective and keep moving forward. I just had to keep moving.

May of 2016 I went to my second Bacon Biz Conf. The timing couldn’t have been better. I had been in 2014, but mostly to network—I met Josh Kaufman there; it was very info-product focused and I had been building a SaaS. By 2016 I was in full-on info-product mode and ready to learn.

Easing into salary negotiation coaching

Just before Bacon Biz Conf, a couple of people asked me if I would help them negotiate their job offers. I had worked with a friend to negotiate his job offer when I was writing FSN, and now his wife asked if I would work with her one-on-one to negotiate a job she was considering. I said I would be happy to help. She asked, "What’s your rate?" I hadn’t ever considered that, and she was freelancing at the time, so I said, "Whatever your hourly rate is, that’s my hourly rate." We got to work, she got a good result, and I had my first coaching success story.

After we’d wrapped up, I asked her, "You already have my book—I gave you and your husband each a copy of it. Why did you hire me when you could’ve just read the book?" She said, "I just wanted someone to do it for me."???

A few weeks later, a friend from middle school (you read that right) reached out and asked if I would help negotiate a job offer. I told her I’d be happy to, and quoted a rate about 50% more than my first client. "Sounds good!" She also got a good result—my second success story.

Coincidentally, I was visiting my friends Rick and Tina when that second coaching client reached out and agreed to my new rate. Tina said, "This coaching thing seems like it could be big. Maybe you should focus on that?" Until then, I was only pursuing info-products.

And that brings us back to Bacon Biz Conf in 2016. (You didn’t think I forgot about that, did you?) I pulled Josh Kaufman and Sean Fioritto aside to talk about my info-product business and how I could grow it. I happened to mention coaching and Josh immediately honed in on that. Instead of talking info-products, Josh, Sean, and I talked exclusively about coaching and how to structure it so it made sense. "No more hourly billing—fixed-fee instead. Charge $1,500 and share some of the best success stories to demonstrate what a good investment it is."

I went home, set up a Salary negotiation coaching landing page, and a slow trickle of people began to find me and occasionally hire me. One coaching client could easily bring in more revenue than all product sales for that month. I was on to something.

By the Fall of 2016, two things had happened:

  1. My runway was burning more slowly. I was bringing in non-trivial revenue most months. Not enough to cover my expenses, but I was occasionally getting CLOSE.
  2. I noticed that my best coaching results were for software developers.

I finally had some breathing room, and I mostly just kept my head down and focused on building the business for the rest of 2016. That mainly meant growing my newsletter, working on SEO, and writing new articles on the FSN site. It was a grind.

Focusing on helping Software Developers

I had still been occasionally coaching people across all industries. But Software Developers continued to get the best results. I mentioned this to Philip Morgan, who (of course) suggested I re-position my coaching offering to be FOR Software Developers. That made me nervous. I had the usual objections to niching down: "What if I’m missing out on tons of other coaching clients in other industries? What if I can’t find enough Software Devs to work with?"

"I’ll bet you a steak dinner you have at least one non-dev ask to hire you in the first 60 days." He persuaded me and I rewrote the landing page and all of my marketing material to say that I was "A salary negotiation coach for software developers". And of course he was right: More devs hired me AND I still got a non-dev client soon afterward.

Business slowly picked up. But it’s important to emphasize that I was still primarily focused on info-product sales. That sweet, sweet promise of "passive income"—if I could build a good enough marketing machine, I might make a good living without constantly grinding or trading my time for revenue.

Meanwhile, my runway was still slowly shrinking—it was under 6 months. My revenue was consistently better than it was a year earlier, but still wasn’t enough to cover my monthly expenses. I was getting nervous that it would eventually run out and I’d have to go get a day job.

Saving the business by focusing on salary negotiation coaching

In May of 2017, I was at a friend’s house and we talked for several hours about my business and my shrinking runway. "Why are you so focused on selling books when you can make so much more on each coaching client? You should be focused on coaching, not books." He was right.

The next day, I changed my positioning from "Author who also does coaching" to "Salary negotiation coach for software developers (who also sells books)". Another inflection point that cannot be overstated: This change saved my business and turned everything around.

That June I had my best month ever—almost triple my May revenue. Looking backward at my best month before this change, each of the next 16 months was better than that. My revenue in May 2018 was almost 10x my revenue from May 2017. I had pulled out of the nosedive just in time.

As I worked with more coaching clients, I slowly raised my rate to help manage demand and because the service was so valuable. But I was slow to raise rates because of a common fear with the Charge More™? (obligatory hat tip to @patio11) tactic: "What if my business dries up?"

In March of 2018, I had a long chat with Mark Butler. He explained why my current pricing was way too low and not sustainable. He helped me see all the hidden costs of the work I was doing, and emphasized the value I was adding for my clients.

I decided to make a big change.

Raising my rates

I significantly increased my rates and moved to a three-tiered pricing structure that was based on the "Total Offer Value" of the offers I helped clients negotiate. It was a clumsy attempt at value-based pricing, but it was effective and revenue kept going up.

By the end of 2018, I had completely transitioned from "just try to survive" to "how do I make this grow?" For the year, I made almost the same as I had made in my last year at a day job. I could finally breathe and now my focus was on optimizing my business to be sustainable.

I began to run into a problem I hadn’t anticipated: Consumer psychology was making it difficult to continue raising prices. The issue wasn’t the value I offered, but the fact that people just weren’t comfortable paying above a certain amount to hire a stranger on the internet. My top pricing tier was $9k. I rarely got clients in that tier, but I did get them occasionally. The next obvious move to Charge More™? was to go to $10k, but people just weren’t going to pay that kind of money to a stranger on the internet for a fixed-fee, paid-up-front service. I had already gotten some resistance at the $9k point, so I knew $10k wouldn’t work. But since all my tiers were sort of tied together, I had to raise the top tier to raise the lower tiers (where most of my business was). I would need to get creative to raise prices this time.

Changing my salary negotiation coaching fee structure to include a result fee

This brought me back to an idea I had considered early in the business, and which lots of people had suggested: Why not charge a fee based on clients’ results? Maybe a percentage of the improvement we negotiated? I don’t think it would’ve worked early on, but it might work now.

But I had a pretty good thing going! Revenue was up, clients were finding and hiring me, everyone was happy. Why mess with that? I felt that if the business was going to keep growing, and I was going to start actually doing value-based pricing, I had to consider a result fee. This was an even more drastic change that repositioning to focus on coaching (which was already working for me), or niching down to work with software developers (who were already hiring me). This was a wholesale pricing model change on a business that was doing pretty well.

But part of the fun of running my own business and working for myself is testing things and optimizing the business. I had to know if a result fee would work now that I was established. I hadn’t tried it earlier because I could see several pitfalls with result fee-only pricing. The main issue was that I wanted to work with clients who were fully bought into my methodology. Negotiating is scary and I need people to be totally on board for us to get the best result. If I only charged a result fee, they wouldn’t have any skin in the game.

I decided on a service-plus-result fee model: A service fee to work with me and benefit from my expertise, and then a result fee based on the actual improvement we negotiated. I started with a $3k service fee—the lowest tier from my old structure—and a 10% result fee. This is truly value-based pricing and since I had negotiated huge results for past clients (more than a million dollars paid out over four years), I knew it enabled me to charge an amount closer to the value I add to salary negotiations. I moved to this model in April 2019.

It turns out, clients LOVE this model. It reduces their up-front investment and they only pay a result fee when they get an improvement. Bigger result fees mean bigger improvements, of which they keep 90%. They’re happier, I’m happier, my business is happier and more sustainable.

Breaking even on my previous day job salary

2019 was the first year I earned more than I had at my day job. 2020 is on track to be even better. But my five-year path to this point was a bumpy one. I thought I was going to build a SaaS and I ended up building a bespoke services business. I almost went broke 18 months in. I had to turn my business upside down, change my target market and risk alienating a lot of potential customers, change my pricing model drastically multiple times, and take other big risks.

There’s still a lot of work to do

And there are still challenges that don’t have easy solutions.The pandemic killed my product sales and organic search traffic. That part of the business is basically dead. I think it can be revived, but it’s not going to be easy. And that’s why I still love running my little lifestyle business after 5 years. I always need a new challenge.

A couple of weeks ago, I reached out to a fellow entrepreneur who I’ve partnered with to help his audience negotiate their job offers. I love his business and just wanted to know more about how he started. It seemed like he came out of nowhere and found success earlier this year. "So take me through this. How did you get started? It seems like you hit a home run right away." "Well, I actually started about five years ago…"

I should’ve known better. Most successful businesses start with that grind. His story was a lot like mine. Building a business is hard and it takes time. I had to survive long enough to find the thing that works. And along the way, I tried lots of things that just didn’t work. I probably offered 5 different coaching offerings before I found the one that took off. That’s the process. Now I try to make my business as anti-fragile as possible (hat tip to Nassim Nicholas Taleb). I try things because I know they will fail and I want to know how they will fail so I can make my business stronger with that information.

My business is a lab where I always try new things. Five years in, that’s what keeps me interested, engaged, energized. I love trying new things, finding new ways to help people, and learning about myself and other people. It’s been a lot of fun and a wild ride so far. I can’t wait to see what the next five years bring.

Big Strides in Breck

Last day on the slopes in Breck

2020 brought another amazing ski trip and it went much better than I hoped. Yes, it’s been nearly two months since I actually got back and I’ve been trying to finish this writeup the whole time, but things have been…strange since then thanks a little thing called COVID-19.

It’s weird to look back on the last week in February knowing what I know now. I remember being aware of COVID-19, and even slightly concerned that it could become a big deal in the States. But we were still on a ski trip and nothing was materially different about this year’s trip compared to the last couple of years.

But within two weeks of our trip, the resorts starting shutting down. And within three weeks of our trip, Stay at Home orders began rolling out across the country. I didn’t know it at the time, but this was a sort of last hurrah before the shutdown.

And now, as of the last week in April, everything is still more or less shut down. We’re talking about reopening things soon, but that hasn’t really happened yet. I think that’s why it has taken me so long to write this: I can live vicariously through Past Josh, slowly reliving a fun trip with a group of friends who had no idea what was coming.

This was an amazing trip. And the fact that we got it in under the shutdown wire makes it even more special.

And now, on to the recap…

Two years ago was essentially my first time skiing and it was verrrrrryyy slow going. Technically, I skied a few times in high school, but those were all east coast trips where I was on fake snow and nobody ever taught me anything at all about skiing. I literally just put on skis and started going down icy runs with no idea what I was doing and no way to stop on purpose.

So two years ago, when I actually took lessons and skied on real snow, was the beginning of my skiing journey, as far as I’m concerned.

ANYWAY, it was slow going at first.

Then last year I had a busted adductor that held me back and slowed me down even more. Nevertheless, I improved a bit and even skied down my first black run (although everyone knows Duke’s isn’t a real black run).

Last year was particularly frustrating because not only was my time on the mountain limited by my injury, but it dumped snow the last couple days I was there. Unfortunately, I couldn’t appreciate all that powder because I wasn’t very good and had already worn myself out.

This year was different. I extended my trip by a few days so that I could get more skiing in while also pacing myself and building in some rest days. We also got a lot of snow early in the trip, so I was able to appreciate skiing in powder this time.

I skied three mountains—Beaver Creek, Vail, and Breckenridge—so I’ll go through each of those in turn.

Beaver Creek

We headed west at 6 AM on Saturday morning, February 22—it was a long day. When we finally got to Beaver Creek, we grabbed some dinner and then I crashed early back at our Airbnb. We had seven people in a one-bedroom apartment that night, but I still slept great. The crowd thinned over the next few days as people headed back to work in Denver.

My first ski day was on Sunday and I took it easy on greens and blues. Beaver Creek is known for being beginner-friendly, so their greens and blues are easier than a lot of other places. That was good for me because I just wanted to get my skis under me and work on some technique.

That first day, I did two separate runs with very experienced skiers who showed me a couple of really useful techniques that immediately made me feel more comfortable on my skis.

Staying forward and poling around turns

When I start to pick up speed, I tend to lean back to brake—I think it is pretty typical for beginners. Paradoxically, leaning back can both increase speed and reduce control, so it’s a real bad idea.

I immediately felt better by making sure my weight was forward (poling around turns helps with this). I could go faster when I wanted, but I generally had more control and my speed was more consistent.

Letting my edges do the work

Leaning back also makes it harder to turn because it flattens out the skis. And, as I mentioned before, leaning back also makes it harder to control speed.

Until this trip, I was basically getting down the mountain by traversing for a bit, slide-stopping to regain control, turning abruptly, then picking up speed by traversing the other way, slide-stopping, etc. I was taking very jagged lines and had little control while also burning out my quads and hip flexors. Not good.

Now I was leaning forward more, and since my skis’ edges weren’t flatted out as much, I was also able to use the edges of my skis to help me turn. The skis will do pretty much all the work on turns if you just let them.

So by staying forward, poling around turns, and using my edges, I could actually control my descent and I was far less tired after each run. Those two quick lessons flipped a switch that paid dividends all week so I was no longer gassed after every run. Later in the week, I could do tricky black runs and still feel fresh at the bottom. Skiing feels totally different now.

By the end of the day at Beaver Creek, I felt great and started looking forward to trickier runs and big improvements during the rest of the trip.

Looking up from the base at Beaver Creek

My first full-on spa experience

Although I was staying down the mountain at an Airbnb, I was able to take advantage of the ameneties offered by a friend’s resort up the mountain in Beaver Creek. That meant ski in/ski out access, which saved a lot of time, which meant I had some time to hit the spa after I hit the slopes.

I think it would’ve been good anyway, but after several hours skiing with mediocre technique, a suana, jacuzzi, and some time to relax on a heated tiled chair was pretty great.

Vail (semi-fail)

Our next step was Vail—my first time back since the infamous Vail Fail in 2018. The good news is that we didn’t accidentally do any black runs. The bad news is the weather was not ideal. I take that back: for the experts in the group, the weather was great because they got to lap their favorite runs with fresh powder and very little traffic. For less-ambitious folks like myself, it was pretty gross. It was very cold (20s), windy, overcast and snowy. Visibility would spontaneously drop to almost zero.

But despite all that, it was pretty fun! I really only skied for about three hours, and we just lapped some easy greens and blues the whole time. We started out on Swingsville and Cappuccino (technically my first tree run), then did a few laps of Ramshorn.

My big takeaway was that I had improved significantly since the Vail Fail two years ago. I remember even the easiest greens being pretty tough my first time out, and they were easy this time. Even some of the blues weren’t bad (Vail is a little more challenging that Beaver Creek or Breck in general). I also got some time to work on my technique, and I felt like I was ready to start tackling more difficult runs when we moved over to Breck.

We ended up cutting things a little short because of the weather, and because our group dominoed itself down from four to three to two to one to zero people who wanted to go back out after lunch. We ended up getting a good lunch and doing some shopping in Vail Village for a while. It was a great day.

Moving day

Part of my plan this year was to extend my trip so I could get more ski days in and more rest days. I decided to take a rest day on Tuesday since we would be relocating from Beaver Creek to Breckenridge by the end of the day.

I spent the morning reading, catching up on email, and generally relaxing. Then I headed up the mountain to hang out and do some shopping before finally getting to try the famous Beaver Creek cookies. I ate … three? four? They were fantastic.

Beaver Creek Chocolate Chip Cookies

After one last trip to the hottub, we sped (very literally) from Beaver Creek over to Breck to make our dinner reservation at the Canteen, a delicious restaurant known for its brisket, mac n cheese, and giant cocktails among other things. We also played Body, Body, Body and I was not mafia per the usual.

It was a good day.

Back at Breck

Now we’re getting into the normal ski trip I’ve been on the past couple years. Everyone assembles in Breck, we have 15 or so people in a giant house, and we move into our normal routine:

  • Wake up around 8 or 9
  • Get some breakfast
  • Make snacks to eat on the slopes
  • Head out either in one big group or smaller groups
  • Ski, ski, ski
  • Head back once the lifts start closing
  • Hot tub time
  • Dinner
  • Crepes
  • Body, Body, Body
  • Sleep

There are variations on this schedule, but this is our baseline. The strangest thing about it is that it always feels like I’ve put in a full day by the time we’re done skiing, but then we have another 8 hours before we go to sleep. Every day feels like two days.


This is what we woke up to on Wednesday morning:

Our view from the porch in Breck

It would be beautiful like this all week.

My plan for this trip was to use the first part in Beaver Creek to remember how to ski and work on my fundamentals so I could jump right into tougher runs immediate once we got to Breck. So that’s what I did.

We started our first Breck day on a couple green and blue runs, and I quickly found my first black run of the year: Spruce.

Before I go on, I should say that most of the single-diamond black runs in at Breck are basically difficult blues. Spruce used to be labeled blue until several years ago when they moved it to black. But for me, the point is to slowly try harder runs so I’m always making progress. That’s how I approach pretty much everything I learn and skiing is no different.

I wanted to tackle Spruce first because I’ve been eyeing it for the past couple years as I rode the Colorado Super Chair lift over it. I remember thinking, “Whoa. That looks tough.” But our first time up the Colorado this year, I looked at Spruce and thought, “That actually looks…pretty easy?” I wanted to capitalize on that confidence so I went for it right away.

I ended up making two runs and the second was much easier. Sure enough, my skiing has improved. Last year, I did Duke’s run (the bluest of black runs) as my final run of the trip. This year, one of my first runs in Breck was Spruce—a more difficult black run, which felt pretty easy.

After a few laps on the Colorado, our group assembled for our annual group photo featuring our 80s gear. I remember it was very cold and windy, so just hanging out while everyone found their way to us was tough.

2020 80s Day in Breck

I spent the rest of the day doing blue runs and mostly taking it easy and having fun. I think I might’ve run Duke’s once, but I don’t remember for sure. That’s a good thing! What was a highlight last year became an unmemorable afterthought this year. That’s progress.


By now, I had a crew to run with and we decided to head over to Peak 6. This was another step forward for me because I skipped Peak 6 day last year to ski solo and work on technique all day. I felt like I had enough to work on without some of the trickier stuff over at Peak 6.

But this year, I was ready to give it a shot and I’m glad I did. We ended up lapping Kensho Chair several times, starting with a few laps of Bliss, which is basically a steep blue bowl that I found harder than most of the black runs, and we finished up on Reverie.

I had a pretty big epiphany on my second run down Bliss: I was leaning back when I turned left, trying to slow down and gain more control. Ironically, the result was more speed and less control, which meant I would turn left and then go straight across the slope bouncing over tracks that were already there. Once I realized what I was doing, I started leaning forward more, using the tracks as a guide, and all my runs for the rest of the day were much easier.

This was probably the most progress I’ve made in a single day so far.

We had to head back to Peak 8, so we finished up with a run down Spruce before hitting the 4 O’clock home.

2020 Thursday in Breck

Friday (rest day)

I had planned for two rest days, and I took my second one on Friday after two consecutive ski days. A friend and I decided to head to downtown Breck and see what there was to see and this was a great choice.

We ate gelato for lunch and chased it with pecan praeleans from a local chocolate shop. Then we visited a bunch of other little local shops and just sort of killed the afternoon walking around.

It was a really relaxing day and I was glad I took the time to recuperate so I can make the most out of my last day on the slopes on Saturday.

Downtown Breck


Our final ski day started with a pretty big group going after some tougher runs. We made our way over to Peak 10 via Frosty’s Freeway, which was a fun little black run connecting the peaks. I almost got into some trouble in the moguls at the bottom of this one because I was following a friend’s line, but I made it down ok. I also almost got taken out by two of my snowboarder friends, but we managed to narrowly avert catastrophe.

Cimarron at Breck

Over on Peak 10, we lapped Cimarron a few times and it was a lot of fun. I think the flat, steep runs are my favorite—I don’t like bumps very much. That could change as I get better, but for now this is the kind of stuff I’m after.The big group disbanded and I went back over to Peak 8 with a smaller crew. We started off doing a couple black runs over there—Duke’s and maybe Rounders—before heading over to lap Northstar a few times.

Our crew for the Luge

On the way to Northstar, I asked the more experienced snowboarder in our crew to show us where the Luge is. The Luge is an unofficial tree run off of Columbine, and a lot of Breck veterans talk about it as a staple. Although I planned to do the Luge eventually, I just wanted to get a look at it this time. The pla was to head to Northstar.

But my clever snowboarder friend decided to show us where the Luge was by dropping into the Luge and stopping. “It’s right here. See? Not so bad. This is actually the steepest part. It flattens out right away and you just have to watch the trees.”

By now it was clear that the other two of us would either have to leave him there and meet up with him later, or join him and run the Luge. We both reluctantly dropped in and I immediately hit a tree. I thought I might be in trouble, but the rest of the run actually wasn’t too bad. It was difficult because I don’t know how to ski moguls or make tight turns, but I made it down pretty quickly without any falls. Next time, I’ll try to do fewer three-point turns (my go-to maneuver in the tight channels, apparently).

Once we all made it down the Luge, we headed into Rip’s Ravine, which is a fun little path through the woods. I hadn’t seen this before, but it’s a lot of fun to string together with Northstar. You can get a ton of speed up at the bottom of Northstar, then shoot into Rip’s Ravine and just cruise for a few minutes looking at the scenic path they’ve laid out.

Northstar is a great marker for progress becuase I remember the first time I did it back in 2018: it seemed really steep at the top and the whole run was sort of intimidating. This year, it was our fun run to unwind after a day of black runs capped off with a Luge run. I think we lapped it three times to end our day, and the whole game was “Get as much speed as possible without endangering any children so you can speed through Rip’s Ravine at the bottom”.

This was easily my best day of skiing so far and it left me wanting more.

Odds and ends

In hindsight, last year’s trip was less about progress and more about managing my adductor injury while still having some amount of fun. At the time, I felt a little bad about taking it so easy but it’s clear that I did the right thing. If anything, the fact that I made some progress last year was impressive.

Ramping up to five ski days this year was also the right thing and I think I struck the right balance between maximizing the ski time on this trip and enjoying my vacation. It was cool to ski three mountains and I made huge amounts of progress this year.

I did not have a single fall during a run this year, but I fell probably 10 times otherwise. Sitting next to a snowboarder on the ski lift is apparently dangerous for me, and that accounts for at least three or four falls. I also tumped over a couple times learning how to use my edges just before a run. And my best fall of the week was just before my first Spruce run when I inexplicably fell over between the lift and the top of the run.

Next year, I might get more aggressive so that I have a few more falls during runs. “No falls on a run” sounds kind of neat, but it almost certainly means I’m not challenging myself enough. I’m reminded of a useful poker axoim: “If you never get caught bluffing, then you’re not bluffing enough.”

We had a great crew of people this year. Although big groups of people isn’t generally something I crave, our big ski trip is undoubtedly an asset. We have so many people that everyone can find a few people at their skill level to spend a day with. That makes it a lot easier to learn in a comfortable environment where you’re not holding anyone else back, but you’re also not holding back too much for less experienced skiers.

Next year, I want to hit some harder stuff and maybe even get good enough to hang with the expert-level crew for half a day or so. I’d like to hit Imperial Bowl, Peak 7 Bowl, and Whale’s Tail before the end of the trip next year. And of course I’d like to put in a better performance on the Luge as well.

It took a couple years, but I think I’m finally decent at skiing and it’s fun to have a new winter hobby.

My 2019 Year in Review: Finally paying myself back

What a year.

Looking back on the past 12 months, most of what stands out is personal stuff and business stuff is secondary. That’s surprising because my business still grew by a substantial amount, but the day-to-day struggle and grind of bootstrapping something from nothing has given way to something more like tending a garden or spinning a flywheel.

The foundation and systems I worked so hard to build beginning in 2016 are working and the payoff for all the stress of quitting a stable day job to jump into the entrepreneurial deep end has arrived.

Things are good in the business. I’m not saying I’m complacent and I’m definitely not resting on my laurels, as you’ll see in the Goals section below, but I’m in an entirely new phase of business and life.

Personally, things are fantastic, but there’s an alternate universe where 2019 was a horrible year full of pain and loss. Having had at least one year like that already, I can appreciate how special it is to have avoided virtually all of that potential pain and loss this year, finishing up the year with so much to be thankful for.

So while the business continued to move up and to the right, I was able to enjoy life itself more by appreciating all the great things I experienced and all the terrible things I didn’t experience.

Here’s a Table of Contents so you can jump to wherever you want…

2019 Goal review

Double revenue again

This was definitely a stretch goal and I missed it … sort of. Net revenue grew by about 54% this year, and that’s less than 100%. But it’s much easier to see progress if I break my revenue into two categories since I’m really running two distinct businesses that both happen to be built around salary negotiation.

Product revenue

I sell products like my book, Fearless Salary Negotiation, and other more narrowly-focused products like The Salary Negotiation Crash Course to help people negotiate job offers, get raises, navigate the interview process and that sort of thing.

Revenue for this part of the business was up by about 10% this year.

While I was hoping to double revenue in product sales, I’m still pretty happy to see any growth here because I stopped offering strategy sessions, which generated meaningful revenue in 2018.

This decision was driven by three challenges:

  1. Strategy sessions were somewhat time consuming and were more or less random. I couldn’t plan for them and they could be pretty disruptive to other work, including coaching engagements.
  2. Strategy sessions might occasionally cannibalize my coaching business. I don’t think this happened very often, but occasionally someone might decide to forego my full-service coaching offering in order to just book a strategy session. If they would’ve benefited from my full-service coaching offering, then we both lost—they got less and so did I.
  3. The pricing for strategy sessions cheapened the perceived value of my time and expertise. Although the sessions themselves were not cheap, when compared to my coaching offering, they looked cheaper and that’s not the best way to position a premium offering.

Last year, strategy sessions were about 20% of my product revenue. So that means I eliminated the offering that made up about 20% of my 2018 product revenue and still grew that part of the business by about 10%. I would like to see more growth here, but I’m still fine with it given my primary focus on coaching.

Services (coaching) revenue

Then there’s coaching, which generated most of the revenue and growth in my business. Last year, coaching was about 45% of my revenue. In 2019, my coaching revenue is up about 140% and it makes up almost 70% of my revenue.

This was driven by a greater focus on coaching, eliminating strategy sessions, changing my pricing structure, and by simply continuing to exist as my brand and reach grow.

Overall, I’m very happy with this growth and I expect coaching to continue growing into 2020 and I think I’ll see more substantial growth in product sales next year as well.

Sub-7:00-pace 5k

Miss. I was rehabbing a strained adductor for the first half of the year and didn’t get to 100% until September or so. I’ll have to push this one out to 2020.

Sub-60-second 400m

Miss. Same issue, but even worse because I would have to train specifically for short distance and even now I’m not back to full sprints. I’ll have to push this to 2020, although I’m still not sure if I’ll ever be able to get this done.

More trips

Technically, I took fewer trips this year. But I went to New York for the first time, so I actually chalk this up as a win.

2019 Year in Review – Business

This year was an unequivocal success.

Revenue was up more than 50% overall, and it grew in each of my two main categories—products and services.

I don’t actively track my time, but I’m sure I spent less time working this year than I ever have, so the return on my time is way up this year as well. That’s a sort of hidden side effect of the business I have been building and it’s a huge motivator for me to keep doing what I do and it was a big reason I quit my day job four years ago.

I had two issues with my day jobs:

  1. I thought the way we did work in corporate settings was really inefficient and I could do most of my jobs well in about 20 hours a week. The problem was that day jobs expected me to be “working” 40 hours a week. And that meant I spent about half my time doing my job and half my time performing the role of “person doing a job”.
  2. I was tired of making other people money. I felt that if I really dialed in my focus, picked a direction, and tried to build a business, then I could capture more of the value of my work, leading to higher overall pay.

The nice thing about both of these is that they are testable. If I was right, then I should be able to build a business to capture the value of my work without working excessive hours. So I decided it was time to put up or shut up and I quit my day job in 2015. I haven’t updated this chart since 2015, so I went in and added in my business income since then and here’s what it looks like:

Monthly earnings throughout my career

You can see that the first couple of years were very lean. But things started to take off in 2018, and they accelerated this year. I’m now generating far more value for my customers (millions of dollars over the past few years) than I ever did in my day jobs, I’m generating that value in fewer hours per week than I did at my day jobs, and I’m capturing more and more of that value for myself.

Two milestones to close out the year

The image above directly shows one milestone while indirectly showing another.

Income from my business now exceeds my day job income

It was slow going at first, and month-to-month income continues to be pretty volatile, but my overall income is significantly higher than it was at my day job.

Now I can definitively say that I can generate more value working for myself than I did at my day job and I can do it in less than 20 hours a week.

I’ve recovered all the savings I burned building the business

When I quit my day job in 2015, I had saved up a runway of about 18 months. The initial plan was to use that savings to bridge the gap while I built a business that supported me. Phase one was to publish Fearless Salary Negotiation. Phase two was to use income from Fearless Salary Negotiation to cover my expenses while I built TaskBook (a B2B SaaS app).

I quickly realized my plan wasn’t going to work. It was harder to generate meaningful product income than I thought, and building the Fearless Salary Negotiation business was going to be a full-time job. It wasn’t realistic to build two things that would require full-time effort, so I shut TaskBook down to focus on Fearless Salary Negotiation.

That was a good decision. But I was still burning through my savings pretty quickly and the business was growing slower than expected. Early in 2017 (about 18 months after quitting my day job), my runway had dwindled from 18 months to about three months and things were getting pretty dire. I began looking at day jobs and thinking hard about how to build my business into something that could sustain me and eventually make leaving my day job worth it.

That’s when I flipped the switch to focus on coaching as my primary business and things started moving up and to the right from there. My savings account pulled out of its nosedive beginning in May 2017. And in December of this year, it finally recovered to the high water mark that was set before I quit my day job.

The success of my business has come in several stages: When revenue actually started to turn up in early 2017, then when coaching started to really take off in volume and revenue, and now when I’ve totally replaced my day job with the business I created from scratch, built on a super-niche expertise that I developed over time.

I did not think this was possible even 18 months ago, but here we are.

The question now is how much value can I create and how much time will it take to generate that value?

Last year, I set a goal of doubling revenue in 2019. I missed that goal, but the point of the goal wasn’t so much to hit it as it was to force me to think about what my business would look like if I did hit that goal. It was a thought experiment codified as a goal.

At the time, I was thinking about doubling revenue in each part of the business, products and services (coaching). While it was unclear exactly how I would do that, I understood that doubling product revenue would probably be harder than doubling services revenue. I still don’t have a good answer for how to double product revenue, but I had some ideas on how to grow my coaching offering.


Very quickly, I’ll talk about products. My revenue was up maybe 10% this year, and that’s fine. I didn’t create any new products and only made incremental changes with my sales funnels, so I couldn’t expect much change here.

I’m working on optimizing sales funnels, offering the right products at the right time, and generally trying to earn more revenue from the 100,000 or so visitors that come to each month, but it’s slow going.

Salary negotiation coaching

January 2019 was my best month ever and that is still true. Almost 80% my revenue that month was coaching revenue. But I could sense a plateau lurking and I felt I needed to make a plan to push past that plateau before I got there.

The challenge was that I had worked very, very hard in January making it difficult to see how I could adjust one of the two most obvious levers to repeat or exceed January’s success.

The most obvious adjustments were to either work with more clients or raise my rates, but neither of those was really feasible. I didn’t think I could work with more clients and provide the level of service they deserved. That left raising rates, but that wasn’t really an option either because of some psychological hurdles I had begun to encounter.

My old fee structure

My fee structure at the time was both simple and complicated. Simple because I only charged a fixed fee up front to work with me. Complicated because that fixed fee was determined by “Total Offer Value” (TOV), a number I made up.

TOV was the total of base salary, sign-on bonus, and equity included in the offer. So an offer of $150,000 base salary, a $50,000 sign-on bonus, and $100,000 equity vesting over four years had a TOV of $300,000.

Here’s what the fee structure looked like:

Fee | Total Offer Value
$3k | < $300k
$6k | $300k–$600k
$9k | > $600k

I was able to work with clients in each tier, so it was “working”. But there were occasional objections about the structure like “Why should I pay you more for coaching when I did the work to get the good offer to begin with?”

I had good reasons for doing this, so I was pretty comfortable responding to those objections. Basically, higher-value offers required more work because they would often be paired with multiple offers from other companies and each offer would require more rounds of negotiation with more sophisticated recruiters and comp teams. Higher-value offers would also generate a higher nominal ROI on average, which meant my expertise was more valuable for higher-TOV offers.

There was also occasionally some discomfort around the step-function pricing. If someone had an offer with a TOV of $299k, they would pay $3,000 to work with me. But if their offer had a TOV of $301k, they would pay $6,000 to work with me. This didn’t happen often, but it was awkward when it did happen and I would sometimes make one-off adjustments to alleviate that awkwardness.

Still, it was working! The bigger issue was that I could see that plateau coming. There were two main things that concerned me:

  1. As I approached an up-front fixed fee of $10,000, there was real psychological resistance to paying that much for coaching.
  2. That resistance meant I would struggle to raise my prices beyond the existing fee structure and it meant it was harder to actually find clients in that top tier (which is obviously where I wanted to be).

My business is a weird hybrid of B2C (Business to Consumer) and B2B (Business to Business). My customers are consumers, but they think like businesses.

A major factor in their decision to work with me is “What’s the ROI on this? If I pay Josh for coaching, how much am I going to get back in terms of improved compensation?” That’s how businesses often approach spending decisions.

But when it came to the actual amount of money I charged, they thought more like consumers. “Six thousand dollars is a lot of money. That’s multiple mortgage payments.”

I don’t think this was a real issue before I started approaching the five-figure price point. But even the most business-minded clients would eventually become consumers and say, “I can’t send $10,000 to someone for a service.”

So I couldn’t just “charge more” to generate more revenue and find clients who put a higher value on my work because there was a psychological barrier around that $10,000 price point.

I also had a little bit of a psychological barrier myself: I had coached multiple clients who improved their TOV by more than $1 million, and I had only charged them a few thousand dollars to do it. On one hand, I was making a good living with the current fee structure. On the other hand, selling someone a million-dollar compensation improvement for $6,000 seemed a little … silly. It didn’t feel quite right to charge so little for a relatively enormous result.

My new fee structure

So I totally changed my coaching fee structure in April.

A quick reminder: January 2019 was my best month ever by a wide margin, and almost 80% of that revenue was coaching revenue. So the old fee structure worked really well.

But January 2019 was unusual because I started the month with a glut of clients waiting in the wings due to a weird hiring pause at some of the big tech companies. The last few months of 2018 had been pretty slow because I didn’t actually book new clients—they were all waiting on offers that showed up in January 2019.

Also, I had to work long hours to keep up with all that client work. So I knew if I had another month like that, I would have to work really hard again.

So what to do?

The answer: Switch to a fee structure where the up-front fee is less prohibitive and where I earn more when my clients earn more.

So I did. My new fee structure would be as follows: $3,000 + 10%.

$3,000 up front to work with me (a service fee), plus 10% of the improvement we negotiated in the first year’s total compensation (the result fee).

Still pretty simple, and I earn more when my clients earn more. Remember that client who got a million-dollar compensation improvement? That would’ve netted me a $25,000 result fee because that million-dollar improvement was basically $250,000 a year for four years. Ten percent of $250,000 in Year 1 would’ve been $25,000.

The two issues I felt would lead to a plateau would be significantly mitigated with this model.

Yes, that “I don’t know about writing a five-figure check to Josh” issue still persists, but they wouldn’t write that check unless we negotiated an additional $100,000 in the first year’s total compensation—a much easier check to write since that meant they’d keep $90,000 after writing that check.

Also, the up-front fee fell all the way to $3,000, which meant I would face a lot less resistance at the beginning of the engagement. And if I wanted to raise my rate, I could bump that fee up without tripping over any consumer psychology tied to that magical four-to-five-figure threshold.

Smart people have suggested that I charge a result fee for a couple years, and I resisted because I didn’t want to build my coaching business entirely on contingency pricing. Sometimes my clients don’t see an improvement in their salary—that’s just the nature of negotiating with big tech companies—but it’s not clear that will the be result until it is the result.

I just couldn’t stomach a business model where I might have a very busy month that also generated no revenue.

But since I had proven the pricing model with an up-front, fixed-fee price, I was able to transfer that to my new pricing so that I could charge enough for my expertise to cover my time and ensure I would be able to keep operating even if I had a few clients whose offers didn’t improve.

This makes sense to me because part of the value I bring is in monetary ROI, but for some clients the primary reason they hire me is they just want to be absolutely certain that when they start their new job at a big tech company, their compensation is the maximum possible compensation. I can always provide that reassurance using my proven methodology.

So how’s it going?

I haven’t done detailed numbers for 2019 yet, but there are a few data points that I think clearly indicate this is the right direction.

First, even with limited data, I’m pretty sure my average per-client revenue is higher than it was before even though my current service fee was previously the very bottom of my fixed-fee pricing range. That’s because the result fees I’ve earned have been meaningful.

Second, the clients whose total fees have approached that magical five-figure mark are thrilled to pay it because that means they will earn around $70,000 more in their first year at their new job. The service-plus-result fee structure makes sure that the reason they’re paying me that five-figure number is because they earned so much more.

Third, the revenue is spread out a little bit, which smooths month-to-month bumps and often sets me up for a good month before the month even starts. For example, the result fees I plan to collect in January 2020 (from engagements that finished in December) will make January my third best month ever even if I don’t see another dime of revenue all month. More likely, this January will be my best month ever, possibly by a wide margin, surpassing last January (which was an outlier driven by weird hiring practices at big tech companies late in 2018).

If you’re still reading, I’m impressed! And now we go full circle.

Last year, I set a goal of doubling revenue in 2019, mostly as a thought experiment on “What would my business look like if I doubled revenue?”

While I managed to more than double coaching revenue, product revenue only grew a little bit, so I didn’t hit that high-level goal of doubling revenue in 2019.

But with this new coaching fee structure, and even if product revenue is flat this year, I think I can double 2018’s revenue in 2020 because of this new coaching fee structure.

Mistakes were made (by design)

Before I wrap up, I should tell you about a pretty big misstep I had this year.

As soon as I changed my fee structure to the service-plus-result fee structure, I got pretty busy. Too busy. I had a ton of applications and I was struggling to keep up with demand.

The nice thing about the service-plus-result fee structure is that adjusting to demand (low or high) is easier since I can move the service fee up or down pretty easily.

I decided to run an experiment to see what the price elasticity for salary negotiation coaching looked like: I raised the service fee from $3,000 to $4,000.

I expected demand to fall (price goes up, quantity demanded goes down), but I didn’t know how much. I figured that even if it dropped significantly, I’d be comfortable enough with that $4,000 service fee that it wouldn’t matter.

I was right—demand fell—but I had no idea how much it would fall. As soon as I raised my service fee to $4,000, I entered a 10-week coaching drought where I booked zero new clients. Zero.

This was during a busy season when I still got a lot of applications to work with me (and the application clearly stated the higher price), but none of my prospective clients were actually hiring me.


I did the math later and I suspect I probably lost about $20,000 in revenue with this experiment. I never booked a client at the $4,000 service fee price point and I dropped back to $3,000 in the middle of the year.

I’m ok with this result and I understood it was a possibility before I ran the experiment.

To uncover hockey sticks, I have to be willing to take real risks and run real experiments. In the long run, this experiment will make me much more than the $20,000 I spent running it.

How do I know that? Because I realized that I had bumped into another consumer pricing barrier. People who would hire me at $4,000 had different expectations and required a different approach than those who would hire me at $3,000.

I had gotten lazy with my “pitch” and fell into just describing the features of my coaching service. I would tell people “First we’ll do this. Then we’ll do that. Then I’ll get this information from you. Then the recruiter will ask for this, and we’ll tell them that.” It was very tactical.

That wasn’t ever a good pitch, but it was sufficient up to a $3,000 service fee price point. At that price, the people considering my service didn’t need much persuading, so what I said to help them decide whether to hire me didn’t matter very much.

But at a $4,000 price point, the pitch mattered more and my features-focused pitch wasn’t cutting it. I realized that I needed to focus my pitch on the benefits of working with me, not on the features of my service. People don’t care specifically what we’ll do step-by-step; they care about the outcome we’ll achieve together and how they’ll feel about the negotiation process when they work with me.

I will raise my price again in the future, and I think I’ll be able to continue finding new clients. I’ll start with a smaller jump in price (I think a 33% jump was too much), and I’ll be able to describe the service in a way that’s more compelling to people who might work with me. That’s a win. An expensive win, but a win nonetheless.

This is what running a business looks like

I know most of the people who read this have day jobs and might be wondering what it’s like running a business versus having a day job.

This is what it’s like. I run experiments all the time, and I look for experiments that I’m pretty sure will fail, only to see how much they fail so I can learn from them and apply what I learn back to the business to make it stronger.

It’s the anti-fragile approach to entrepreneurship. It’s uncomfortable and I love it.


Nothing too interesting to report this year other than more steady growth in revenue.

Visits to About 1.1M
Unique page views: About 1.7M
Total email subscribers at the end of the year: ~46,000 (up from about ~26,000 to begin the year after a small end-of-year pruning in 2018)
Product sales through the site: ~800
Coaching clients: ~30
Product revenue: Up 10%
Service (coaching) revenue: Up 140%
Total revenue: Up 54%

Conversion rates are more or less the same as last year.

2019 Year in Review – Personal

Before I really dive in here, let me say that everything is great. Even though most of my highlights were difficult, the year itself was fantastic and I had a great time. It’s just that the things that stand out were pretty tough.


I had a couple of injuries that set me back this year, so I got really familiar with rehab protocols.


For most of 2018, my right adductor was sore and slowly got more sore as the year wore on. At first, I only noticed it during a specific dynamic stretch when I did my weekly track workouts. Then I noticed it was tight at the beginning of most of my runs.

Then I ran a half marathon and my adductor did not like that. I think I actually tweaked it during the penultimate week before the half when I went pretty hard on some shorter runs. The half marathon just pushed it over the edge to the point that it hurt pretty much all the time and it didn’t seem to be getting any better.

At first, I tried just resting for a couple weeks and that didn’t work, so I saw a doctor and a PT who both confirmed it was an adductor strain that would require some rehab.

I decided to take this pretty seriously because adductor injuries are sort of notorious for taking a while to recover and for recurring if you don’t recover fully before pushing it again. A friend of mine has had recurring adductor injuries that lasted years, and even now LeBron James is dealing with an adductor injury that doesn’t seem to be healing. I’m obviously not LeBron, but he has the best trainers in the world and he still can’t fix his adductor, so I knew it was going to be a slog.

It turns out adductor rehab is pretty relentless. For 8–12 weeks, I would spend about an hour a day doing various exercises to strengthen my core and eventually repair the adductor. And of course I couldn’t run at all while this was going on. It was pretty awful, but I just took it one day at a time.

It eventually started to get better, then I did a return-to-running protocol, and eventually I was able to run normally again. Only now, at the end of 2019, do I think I’m back to 100%.

Looking back and talking this over with my PT friends, I’m pretty sure this was an overuse injury exacerbated by a training error (I was running on graded roads, especially leading up to the half marathon, and I think that eventually hurt my adductor).


If that wasn’t enough, I also screwed up my shoulders. This injury was actually at its worst in the middle of 2018, but I tried resting and other half measures that didn’t do much.

The initial diagnosis was that I had biceps tendonopathy in both shoulders, so we started by rehabbing that issue. Early in 2019, that was starting to abate and we were able to see (via palpating, which is a fancy word for poking to see what hurts, and MRI) that the real culprit was likely infraspinatus tendonopathy from overuse, maybe exacerbated by minor impingement.

And so we started another round of rehab that overlapped with my adductor rehab. In addition to the seven days a week of adductor rehab, I added three days a week of shoulder rehab.

I cannot emphasize enough how mind-numbingly boring this was. And what made it even worse was that I was doing the rehab instead of normal running and weight lifting. So I was slowly getting further and further out of shape while spending a lot more time at the gym than I normally did.

Eventually, the rehab worked and I was able to start regular weight lifting again. My shoulder is basically 100%, but it occasionally reminds me that I overdid it last year.

As I finish out 2019, I’m back to normal running and weight lifting activity and I feel great. I’m also focusing on nutrition to make sure I get the most out of my workouts, and I’m paying closer attention to potential overuse injuries so I can catch them before they sideline me next time.

Eye surgery

This is not something I’m comfortable talking about, but it’s a big part of my year and kind of a big deal for me, so I’m going to power through it even if the writing will probably be stilted.

I’ll eventually write a longer post on this, but it’s worth capturing a snapshot for posterity here as well.

This year, I had eye surgery. Not that kind of eye surgery—you’re probably thinking LASIK or PRK—but surgery on my eye muscles. The technical term—mostly for Google—is bilateral strabismus surgery, which means an ophthalmologist moved the attachment points of the medial rectus muscles of both eyes so that they aligned better.

For the first time since I was a kid, my eyes work together. If you know me, you probably noticed this right away when you met me: I had a lazy eye. (Technically, I had “wall eye” since I had full vision in both eyes; lazy eye implies loss of vision in the affected eye). Since I’m left-eye dominant, that meant my right eye would drift.

This is not a great way to make a first impression on people. Fortunately, most people were kind about it and pretended not to notice. Meanwhile, any time I had face-to-face interactions (and I’m including “looking at a camera” with that), anywhere from maybe half to 80% of my mental energy went into trying to mitigate the lazy eye and keep it aligned with my dominant eye.

If there was anything worse than someone noticing my lazy eye, it was having a close-up action shot of the lazy eye show up on someone’s Facebook or Instagram feed. Most of the time, I could control my lazy eye long enough to snap a photo. Video was a totally different beast and I avoided it as much as possible. This BBC interview was cool because it was on international TV, but it was also a mental marathon. For three minutes, all I thought was, “Keep your eye focused on the camera. Keep your eye focused on the camera. Keep your eye focused on the camera.” The answers I gave were all more or less reused from my previous interviews or articles I had written, and it had to be that way because if I lost concentration for even a second, the eye would’ve drifted.

The best analogy I can think of is to imagine that any time you talk to someone face-to-face, you also have to balance a kickball on your head. If the kickball falls, the other person looks at you a little weird and quietly wonders what’s wrong with you. Most of your brain power would be focused on the kickball, and the leftover brain power would be used for that conversation.

That describes pretty much every social interaction I have had for my entire life. I could sort of control it, but it took almost all of my mental energy and lots of little coping mechanisms I developed over time.

Now I’m unlearning all of those coping mechanisms since I don’t need them anymore. I’m less worried about making a bad first impression and I’m slowly becoming more comfortable with cameras.

And while I feel quite a bit different, other people perceive me much differently. It was remarkable how many people had never said anything about my lazy eye, then suddenly I would talk to them and they would say, “Wow! It’s like talking to a different person.”

It’s too bad I can’t redo all those bad first impressions, but at least I won’t make any more.


I only took a couple trips this year, but they were a ton of fun.

In Breck for the Breckpocalypse

I had another amazing ski trip in Breckenridge and skied my first black (without falling!) to finish up the trip. Although I had an amazing time, I limited my skiing because my adductor was still in pretty bad shape.

In hindsight, skiing at all was probably a bad idea since I was only about four weeks into 12 weeks of rehab when I went on this trip. I was fortunate not to reinjure myself and I’m glad I took it easy.

It was still really fun to get back to Breck, and I’m glad I finally conquered a very easy black. I’m hoping to make some big leaps forward on the next trip in February.

Me in my 80s Day onesie

My first trip to New York with a quick stop in Jersey

In June, a friend of mine was coaching in a professional flag football tournament so another friend and I went to New York to see the sights and root for some flag football.

We only got about two days in NYC, but we covered a lot of ground in that time. Not only did we see most of the popular sights, but we ate a lot of great food (and that’s really what I’m after when I travel).

It’s hard to pick standout moments, but Central Park is fantastic, and the 9/11 Memorial was really moving.

Central Park - NYC


Thanks to my adductor injury, I don’t really have anything to report this year. I’ve been mostly doing medium-distance runs of three to five miles a few times a week, and my pacing has been pretty strong. I tried a couple of track workouts later in the year and they went well, so I’m looking forward to doing more track workouts in the new year.

Best possible outcome

I won’t go into detail because this stuff doesn’t have to do with me directly. But this year could’ve been very, very bad in terms of pain and loss for my family. Several family members had significant surgeries and health scares, and all of them emerged on the other side happier and healthier than they were before.

In the early 2010s, I went through a similar stretch where pretty much everything went as badly as it could have. I lost a close friend and several family members during that time, and it was really painful. I’m so thankful that 2019 was the opposite and that my family didn’t have to experience that sort of pain and loss again.

2020 Goals

I’ve been putting this write-up off for the past month or so because I don’t really have new big-time goals for this year. I’m basically still going after the same goals from last year.

Increase revenue by 50% again

Last year, I set a stretch goal of doubling my revenue, and I “only” got to 50%. If I do another 50% this year, I’ll have more than doubled revenue over a two-year span. That would be pretty fantastic.

If I can increase both product revenue and coaching revenue by 50% each, I think that would be a great, balanced way to hit this goal. I suspect the improvement will be more skewed toward coaching, but I am focused on growing product revenue this year, so I’ll just have to see if I can get traction there or not.

Sub-7:00 pace 5k

Since I basically lost this year to my adductor injury, I’m refocusing on this goal and I hope to hit it this year.

Sub-60-second 400m

And while I’m training for faster speeds at shorter distances, I might as well take another crack at this goal. I’m still not sure it’s even possible for me, but I got so close in 2018 that I feel like I need to give it another honest effort.

One of my track workouts before the holidays was a 400m repeat workout and I got all my reps in the mid-80s range. That is better than I thought I’d be after a year off, so there is some hope that I can get this done. We’ll see.

Travel more

I’m carrying this one over from last year. I did ok with 2019, but I’d like to get some more trips in, especially since I have a ton of reward points on a couple of credit cards and it’s a shame for them to go to waste.

Be more generous

Business is good and my personal life is simple. There’s room for me to be more generous in many ways, and I want to be more intentionally generous this year. There are lots of ways to do this, and I don’t have any one way in mind. But “be more generous” seems like a good high-level goal to think about as each day passes.

Surviving Breckpocalypse 2019 (another awesome ski trip in the books)

Our group in 80s gear

I’m back from our annual ski trip and I had a blast. This year was an interesting mix of firsts and caution, and I made a ton of progress. (Last year was great too, read about it here.)

80s day was a hit

This year, we added an 80s day, which got us a ton of attention and made our first day on the slopes a lot of fun. There were two types of outfits:

  1. Authentic retro 80s attire. Maybe half the group went this route, wearing headbands, sweaters, jackets, and pants that were either actually from the 80s or could’ve been.
  2. Caricature 80s attire. And about half the group wore stuff that I describe as “What people today think people wore in the 80s.” I was in the camp, wearing a super loud 80s onesie.

Me in my 80s Day onesie

We picked the perfect day to do this since it was relatively warm, the sun was out, and the sky was blue all day. The groups pics we got at the top of Peak 8 made the whole thing worthwhile (the rest of the day was gravy).

Our group in 80s gear

Our group playing our air instruments

Slow and steady progress as a skier

This was basically my second time skiing. Technically, I skied a few times in high school, but I don’t count those because we were on east coast ice, and no one ever actually showed me how to ski. So I was terrible and I hated it.

Last year was the first time I skied on anything resembling powder and I also took lessons, so I immediately felt better about it and made progress quickly.

This year was interesting because I was the worst skier in our group, so I was the one holding things up most of the week. But I wanted to take my time and work on some things to make sure I was actually improving as a skier and not just ramping up the difficulty.

First day on the slopes

Our first day on the slopes, I felt pretty uncomfortable on my skis. Skiing is not like riding a bike—and I felt like it was my first time out. But after a few runs, things started coming back and I felt a bit better.

By the end of our first day, I felt like I was pretty much back to where I left off last year. I could comfortably cruise down most of the blues, occasionally feeling like I wasn’t quite in control. This was a super long day because we went out early-ish and came home late-ish. We did a bunch of runs and those runs were challenging for me since my form was so rusty. I was totally spent at the end of the day.

Second day on the slopes

I decided to take our second day and just focus on technique—specifically turning and maintaining my speed while staying in control. My friends would frequently say, “Wow, you really flew down that one! You’re getting a lot better!” And I would say, “Well, that’s because I only have two speeds—Stop and Go. Once I’m in Go-mode, I’m just trying to stay upright until I can slow down.”

I wanted to feel in control most of the time instead of feeling like I was just trying to stay upright and avoid wipeouts. So I stuck to blues and slowly improved.

Although I didn’t move up to more difficult runs as quickly as I did last year, I made a lot more progress in my first couple of days on this trip. By the end of the second day, I actually felt more like I had control, I could slow down when I wanted to, and I was able to choose my lines rather than just taking wide S turns and hoping for the best.

My turns got much tighter and I was intentionally hitting spots that seemed easier to navigate. I actually went in about an hour ahead of most of my peers because I was still beat from the first day, and I felt I had accomplished what I wanted for the second day.

Third day on the slopes

I asked a couple of friends where I could find the easiest black run at Breck. The answer came back: “Dukes.” It was a relatively short run that used to be a blue, but they turned it black so intermediate skiers wouldn’t get spooked. So it was technically a black, but only just.

My goal for the entire day was to get more comfortable and eventually do at least one black run, so I pretty much mapped out the day to slowly move toward that goal.

Powder, powder everywhere

Even before I started going on this trip last year, there was much lamenting that fresh snow never arrived. It was almost like this specific trip had some sort of jinx on it so that it was always warm and sunny with no new snow during the trip.

That all changed this year, and we made up for lost time. In our last two days at Breck, I think there was over a foot of snow and it just kept coming.

So I swapped out my regular skis for “powder” skis to start the third day. At first, this was kind of frustrating because I had to re-learn a lot of what I had worked on the previous day. Turning was harder, stopping was harder, maintaining control was harder. Everything was harder.

But once I got used to the new skis, they were much better and easier to control.

A solo run for my first black

After several good blue runs, it was time to make my way to Dukes, the easy black my friends recommended. I actually scoped it out during my first run of the day since it starts from a common catwalk that we use to move between peaks.

I was going to run it with a friend, but he ended up stopping early, so I was on my own. But before we parted ways, I asked if he had any suggestions—he had three:

  1. Stay to the right, away from the moguls.
  2. Wait for a big opening so I could do “my run” without traffic around me.
  3. If I felt like I needed to slow down to regain control, turn slightly back up the mountain to regroup.

And off I went.

The lift dropped me about 100 yards from the top of Dukes, so there wasn’t too much time to think about it once I was off the lift. I initially planned to get to the top of the run and give myself a minute or two to gather my courage, but it turned out I didn’t need that kind of time.

I got to the top of Dukes, looked at it and thought, “Meh, that doesn’t seem so bad. Let’s go.” And I was off. Overall, it was a pretty good run and I used all three of my friend’s tips.

I actually made it down the steepest part without any issues, but I relaxed too early because I didn’t realize there was a second steep part that was also icy and bumpy. All of a sudden, I realized, “Uh oh, I’m going too fast and this is all bumpy ice. Need to slow down… or need to at least try to maintain control until I can slow down.”

I didn’t quite succeed, but I didn’t quite fail either. I basically ended up spinning out so that I didn’t technically “fall”, but came as close as I could’ve. After a few very ungraceful flailing spins, I found myself stopped, skis splayed, hands on the ground in front of me, holding me up. I regained my composure and it was easy from there on out.

I remember getting to the bottom and thinking, “Huh. That wasn’t so bad.” I almost talked myself into doing it one more time, but I thought better of it and made my way back to our house.

Right after my black run on Dukes

Fourth day on the slopes – or not

I finished my third day on a real high. I finally felt comfortable on my skis, I felt more in control than I had at any other time this year or last, and I did my first black.

But I also felt like I had been pretty lucky so far. I had been really tired a few times during the week, but had managed to get good runs in despite the fatigue. I also had a strained right adductor to watch out for.

Before I went skiing, my doctor said, “Sure, you can ski. But don’t do anything crazy and stay off the tougher blacks.” Remember the spinout I mentioned on Dukes? It was exactly the kind of awkward motion that could’ve reinsured the adductor. I’d been rehabbing that stupid thing for 5 weeks, and hadn’t run in almost 10 weeks because of it, and I wasn’t looking to re-injure it if I didn’t have to.

So I had a really tough time deciding whether to go back out for our fourth ski day, or if I should just take it easy.

I ultimately decided to take an actual vacation day and just hang around the house, and there were a few factors at play there:

  • I felt like I had been pretty lucky that I didn’t re-injure my adductor despite some close calls.
  • I accomplished my primary goal for the trip—do a black run.
  • The conditions were very powdery, but I wasn’t good enough to really take advantage of that. And powdery also meant cold, snowy, low-visibility.
  • It was the Saturday beginning Spring Break, and I knew the lift lines would be long (so I’d be waiting around a lot, and wouldn’t do much skiing for the time I would be out there).
  • I hadn’t taken a real vacation day—a full day off to just relax—in…I can’t remember the last time I did that, but it was years ago.

It was basically a coin flip that came down to, “I’ve checked all the boxes for this trip and I didn’t re-injure my adductor. I finished on a high and I am anxious to get better and ski more when I’m healthy. Maybe I should just quit while I’m ahead.”

I decided to just take the day off. If my adductor had been healthy, I would’ve gone out. But I knew that if I went out, I would want to try tougher blacks, and that would make re-injury more likely.

Even in hindsight, I’m not quite sure if this was the right thing to do.

A great trip with friends

The coolest part of the ski trip is that each day essentially has two major events: Skiing and hanging out.

Skiing is typically over around 4:00 at the latest, and that means we have another eight hours before we go to sleep. We typically try to squeeze in all four of these things after skiing:

  1. Hot tub time
  2. Dinner
  3. Crepes a la Carte—an amazing crepe place in Breck
  4. Games (usually Body, Body, Body, but not always)

We checked all those boxes a couple times and hit three of four every night (I think).

We had some amazing food—The Canteen, Michael’s, Giampietro, Empire Burger (the sides and sauces are amazing)—but I didn’t document any of it because I was too busy eating it.

And I was finally mafia in Body, Body, Body and got the win. So now I’m one-for-one as mafia, but still only like one-for-fifteen being mafia. The law of averages will eventually catch up and I’ll go on a mafia spree (or maybe I’ll just cheat—ahem, GP—and make it happen on my own)

Surviving the Breckpocalypse

About half way through our trip, it began to snow. And snow and snow and snow and snow. There was a lot of snow.

This made my final ski day a lot of fun, and I’m sure it made Dukes (at least the top part) much easier. My friends said it was the best snow day they had ever seen, and some of them even extended their trip to get more time in the powder.

Here’s a short video of the view off of the balcony…

Short video of our balcony view

Of course, the snow giveth and the snow taketh away… the ability to travel. We had a few rental cars with varying numbers of passengers, and some of the cars had trouble either explicitly getting through the snow, or in driving from Breck back to Denver. My car was pretty lucky because we left early. It took us almost three hours to get to Denver (normally two hours), and we had to stop to manually de-gunk the windshield a couple times, but we made it. There was also an avalanche about 20 miles west of us on I-70, so I’m obviously glad we missed that.

Some other folks either missed their flights after a long (five hours!) drive to Denver, or simply got stuck in the snow in Breck and had to wait it out (this may or may not have been related to an ill-advised decision to rent a 2WD truck despite a steep driveway and a snow-heavy forecast).

When we finally go to Denver, it was 3 degrees outside—the lowest March temperature in like 140 years. Apparently it got as low as -6, so we got there when it was nice and toasty outside.

All in all, this was another amazing ski trip and I can’t wait to get back out there and hit some real blacks next year.

Keeping small pains from becoming big problems

I usually run three days a week, like clockwork. Monday is a track workout, Thursday is a short run, Saturday is a longer run. It usually adds up to about 10 miles a week unless I’m training for something (like a 10k race or a 15k with the flu).

Here we are on January 16, and I haven’t run at all this year. Last time I ran was December 29, 2018, about six weeks after I finished my first Half Marathon.

It’s really frustrating, but it’s also necessary.

I have been battling a couple of overuse injuries for a few months, just sort of hoping they would work themselves out if I kept training with good form. Sometimes that works, sometimes it doesn’t. This time it didn’t work and it made things worse.

I noticed I was struggling to keep up a good pace, and that maintaining good form was more and more challenging as I tried to compensate for various aches and pains. It started getting more difficult.

I should’ve stopped running right after the Half Marathon, but I was too stubborn.

Now it’s time to pay the piper. What would’ve been a week or two of rehab has probably ballooned into a month, all thanks to my stubbornness.

I’ve been thinking a lot about how there’s a fine line between “Just tough it out!” and “Why didn’t you stop before you hurt yourself?!” It’s really hard to see that line in real time, and it seems like the only way to really know where the line is is to look backwards and find it.

But I also think that identifying that line is a skill that can be honed over time.

The best way I know to hone that skill is to constantly monitor pain points: Is it better or worse than last time? How hard is it to aggravate it? Can I work around it? What’s the upside to continuing? What’s the downside if this turns into something bigger?

I’ve been doing this with my business lately and it has helped me identify some small pains that I can resolve before they become big problems. That makes things easier for me and better for my customers.

You can use this sort of analysis with your career. Small pains often become big problems if left untreated, so it’s worth identifying those small pains and thinking about solutions before they become big pains.

It’s the beginning of a new year, so this seems like as good a time as any to start planning ahead to make 2019 more productive by finding and fixing small pains before they become big problems.

Take a few minutes and ask yourself, “What are some small career pains that could become a big problem if I don’t handle them now?” You might find some easy wins with a big payoff for very little effort.