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.

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!

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.

My 2018 Year In Review: Finally making a good living

It’s been three years since I quit my day job to build the Fearless Salary Negotiation business. It’s finally paying off.

I didn’t think this year would go so well for my business, especially considering that I was almost out of runway only 18 months ago. But my 2018 income is very close to what it was when I quit my day job in 2015, and now I have the freedom, flexibility, and personal satisfaction that comes with making a living from something I built from scratch.

The decision to double down on salary negotiation coaching in 2017 continues to pay dividends as I work with more clients and raise my rates to capture more of the value I create with my work.

That’s the business side of things.

Personally, things are great. I’m fortunate to have a very close group of friends. I’ve gotten better at running, and I’m pretty good at making omelettes. Of course there are things I would like to work on for 2019, but 2018 was amazing!

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

2018 Goal Review

So how did I do this year? Let’s take a look at my 2018 Goals.

Make a good living

The goal was I want to make $10,000 per month in net revenue in 2018. More specifically, I would like to do that by selling $5k in products and booking $5k in coaching per month for the year.

I missed this goal, but not by very much. And each $5k sub-goal is pretty close to what I actually did.

The difference between hitting and missing this goal comes down to a consulting retainer that ended in September after about a year. If that kept going, I would’ve made it.

I also could’ve made it if October wasn’t so horrible revenue-wise.

To be honest, this is bonkers to me. I didn’t actually think I might hit this goal—I just wanted to make sure I set an ambitious-but-achievable goal to maximize my earning potential in 2018.

I did hit a secondary goal, which was to double revenue year-over-year from 2017 to 2018. I did that from 2016 to 2017, and it seems like “do twice what I did last year” is a reasonable goal that can be achieved through good planning, execution, and moderate growth.

More traffic

The goal was I would like to build my organic search traffic to 100,000 unique visitors a month.

This one is interesting. I did hit this goal, but then traffic fell off and settled in around 80,000 visitors a month.

2018 Organic Traffic

The good news is that with more traffic came more revenue, so there was a direct benefit to this goal.

Improve at Sales

Here’s that goal: My goal is that 2% of email subscribers become paying customers within the first 30 days.

This was a huge miss. HUGE miss.

That’s the bad news.

The good news is I did build one funnel—the one that gets the most traffic—that pretty consistently converts 1% of subscribers to customers for a $47 product.

So there’s a lot to build on there.

Help other businesses get more search traffic and email opt-ins

Ehhh, I did some of this but not very much. I worked with a few clients to tweak their SEO, and I worked with some clients on their content strategy. But I just didn’t feel motivated to push this part of the business.

I think there are still things to focus on in my core business and I didn’t want to get too distracted.

Running goals

  • 10k – Sub-8:00 pace Hit it with a week to go in 2017
  • 5k – Sub-7:00 pace (currently 7:14)
  • Mile – Sub-6:00 pace (currently 6:08) Ran a 5:54 mile in August
  • 400m – Sub-60s pace (currently ~64s~ 62.75s)

I’ll write about this later, but I also ran a PR for 15k and finished my first Half Marathon.

A detailed 2018 Year In Review – Business

At the beginning of this year, I felt like the trajectory was in the right direction, but I still had some concerns. I started the year in a bit of a cash crunch as I was still digging out from the financial hole I dug to get through 2017.

To free up cash for 2017 taxes, I had parked some expenses on a 0% credit card. It looked like I would be able to pay it off before the interest rate jumped in August, but it would be close. I also decided all 2018 taxes would be taken off the top and held in a dedicated account so I wouldn’t have to scramble to pay taxes this year.

Saving ahead for 2018 taxes plus paying down that 0% card meant 2018 could be sort of a financial grind. I knew that was likely when I made those decisions in 2017, and now it was time to pay the piper.

January was mediocre, but then things took off: February was my best month ever, and March, April, and May were all consecutively better.

By June, I was out of the woods and starting to replenish my savings. It was almost exactly one year from “Uh oh, I might have to get a day job.” to “This seems to be working and I have some room to breathe again.”

With the exception of a horrible October, the second half of the year was great (but not quite as strong as Q2). I may be doing enough business that I’m able to spot some seasonality, but I’ll have to wait and see.

For now, things are good with the business and I finally feel like I can relax a little and enjoy what I’ve worked to build over the past few years.

Salary negotiation coaching

In June of 2017, I repositioned myself as a salary negotiation coach for experienced software developers. Before that, I was basically positioned as an author who also did some coaching.

That shift in focus is what saved my business.

I kept pulling on that thread in 2018 and it continues to pay off in a few ways.

First, I’ve gotten more and more reps negotiating job offers with big tech firms, so I know their playbooks. This has made me more confident and gives me the tools to pitch my coaching offering more effectively.

Second, I’ve been able to raise my prices so I earn more for my work by reaching a more experienced market where my work has more value. Basically, I’ve enabled more and more experienced software developers and senior managers to find me when they have job offers, and their job offers are usually very substantial, which means their improvements are often substantial.

The combination of those two things is what has really enabled my coaching business to take off.

I also really like what I do. It’s fun to help people who’ve worked so hard to build a valuable skill set actually capture more of the value of the skill set they’ve built.

Product sales

Selling digital products is at once a boon to my business and an enigma. Traffic and sales were up this year, but I continue to suspect that I’m selling far less than I should given my traffic levels, and the quality and value of my products.

This has to be a focus for me in 2019. With over a million visitors to my site in 2018, I should be selling a lot of products.

Email list growth

I hit some pretty big milestones this year. I was this close to hitting 35,000 email subscribers before I pruned almost 10,000 subscribers. Since I started building my list in January 2015, I’ve had more than 60,000 people join my list. About 20,000 of those unsubscribed over time, and I pruned another 12,000 or so.

The churn is normal. The pruning is sort of controversial among my peers. But the bottom line is I had a ton of people on my list who were not opening or interacting with any of my emails, and I don’t think it’s good for anyone if I keep emailing those folks.

So I’ll end 2018 just shy of 30,000 active email subscribers. That’s crazy to me. I had 600 subscribers after my first full year doing this. Now I get more than that in a typical business week.

Now I just need to get better at aligning my product offerings to my email subscribers’ needs.

Consulting retainer

I also had a fun opportunity to consult with a very successful business. It was an unusual arrangement without any real parameters: Just come hang out, observe what we’re doing, and make suggestions to help us improve.

It worked really well for a while and it was a ton of fun, but the business itself eventually became so active that I found myself lost in the shuffle. I would love to do more of this sort of thing, and it’s good to have this experience so I can help define the desired outcomes—for myself and for the business—of this sort of engagement better in the future.

Essential Salary Negotiation Email Pack

Last year, I made a small product called The 15-Minute Counter Offer. I was trying to learn more about how I could help folks finding when they needed help negotiating a job offer.

What I found was that most of those people were in a real hurry—they had just a few hours from the time they found myself site until they had negotiated their offer.

So I built The Essential Salary Negotiation Email Pack to help with their specific needs in a very short timeframe. That product, plus The Salary Negotiation Crash Course—a more in-depth-but-still-streamlined, end-to-end job offer negotiation course, offered as an upsell to the email pack—made almost $12,000 in 2018 and I didn’t start selling it until April.

This is by far my most successful new product and I hope to create a similarly successful offering for folks who aren’t sure how to ask for a raise in 2019.

Overall stats

Here are some high-level stats for 2018 (all as of December 26):


There were 1.023 million New Users on, and 90% of those were from organic search traffic.

My email list

Here’s an updated list of end-of-year email subscribers:

December 2015: ~700
December 2016: ~2,500
December 2017: ~11,500
December 2018: ~28,500

In 2018, I had 24,300 new email subscribers, but since I pruned about 12,000 recently, active email subscribers is “only” 28,500.

Here’s a graph of my email list growth in 2018:

2018 Email List Growth

No hockey stick this year—just consistent growth.

Conversion rates

They’re basically the same as they were last year—about .4% of email subscribers purchase something from me in the first 30 days. The consistency is a little deceptive as I did significantly increase conversions for one funnel, and I also significantly increased opt-ins for all other funnels.

Last year, I said, “If I hit [5% opt-ins and 2% conversions] by the end of 2018, I should be able to hit my revenue goals.”

On one hand, it’s really frustrating to see such a huge miss. On the other hand, I almost hit my revenue goals anyway, so if I actually find a way to get those sorts of conversion rates I’ll be doing very well.

A detailed 2018 Year In Review – Personal

Two things stand out when I think back on this year: traveling and running.


2012 was the beginning of a years-long plan to build a business and stop working for other people. That’s vague, but it’s about as specific a plan as I had in mind.

I started by getting a good-paying day job to leverage my prior career experience and newly-acquired MBA. I used that income to start paying down debt as aggressively as I could, and I began slowly acquiring the basic skills I would need to (eventually) build a successful business.

For the next few years, I was either paying down debt or saving up a runway while basically working seven days a week on my day job and side projects.

In 2015, debt free and comfortable with my runway, I quit my day job to focus full-time on building a business. For a little over two years, I worked really, really hard seven days a week. I think that sort of work was necessary to build the basic infrastructure of my business, but it was also very taxing.

In 2017, I decided the seven-days-a-week schedule needed to end, so I sort of re-entered normal society and focused on community. Either the foundation I had built would facilitate a real business or it wouldn’t—it was time to find out.

So I stopped working so much, but I still wasn’t earning enough to take non-business trips or anything like that. I had to pass on a number of super fun trips to avoid burning too much of my savings.

That changed in 2018 as my business actually started to take off.

Ski trip

I went skiing for the first time since high school and I loved it. My friends go on a ski trip every year, and I was always a little jealous I couldn’t make it. But I also remembered absolutely hating skiing, so it didn’t sting too badly to miss that part.

I figured I would give it a shot this year, mostly so I could say, “See! I went skiing and it’s still awful!” But it turns out I really liked it, and that getting ski lessons is actually very useful. Who knew?

I had a blast and I can’t wait to get back out there in 2019.

Our group at Vail


I also went to Boston with a couple college buddies in June. It was amazing. I hadn’t taken a trip like that in a very long time, and it was everything I hoped for.

Classic Allen face

I have a lot of “Allen makes this face at a sporting event” photos

Running stuff

At the end of 2017, I asked “Am I a runner now?” In hindsight, that question was pretty naive. The answer is vey clearly no.

Runners run a lot more than I do. I am a hobbyist and I made progress on my hobby this year.

My first 15k

In January, I ran my first 15k and it did not go well. Turns out that running a 15k with the flu just isn’t a great idea. But I finished and my time wasn’t terrible (for a guy with the flu).

My first 15k

Sub-6:00 mile

One of my original running goals was to run a sub-6:00 mile. It took me a few tries and about 18 months, but I smashed that goal with a 5:54 in August.

My six-minute mile time with 400m splits

This may have been my most satisfying PR yet because it as almost exclusively mental. I had to try and fail a few times to understand exactly how to run a fast mile, but once I understood it I was able to knock it out.

15k PR on a training run

I was prepping for a Half Marathon and I ran an 8:00-flat pace 15k. This wasn’t even on my list of goals, but it felt pretty good. When I started running at the beginning of 2017, I set a goal of running this pace for 10k. So it’s cool to run that time for a longer distance.

15k training run - 8:00 pace

My first Half Marathon

I was planning to run a Half Marathon earlier in the year, but the aforementioned flu ruined my training and I bailed. Plus, the Half I was going to run would be during the winter and the weather was going to be awful.

A wise friend told me, “Do you really want your first Half Marathon to be a miserable experience? Why not just wait for a better one?” So I did.

I ended up running a Half in sunny, 60º weather and it was a pretty good experience. The one hitch was that the course was only 12.1 miles, so I literally had to go the extra mile to finish.

At least we got cupcakes at the end.

My first Half Marathon (with cupcakes!)

I ended up with a pretty good pace of 8:24. I was very happy with my race strategy as I felt I did the best I could, and I’m certain I could go quite a bit faster with better training.

That said, I doubt I’ll run too many more Halfs. I’m glad I did it, but it really took a toll for like two weeks after the race.

2019 Goals

I’m going to keep things pretty simple this year.

Double revenue again

I have no idea if this is possible or how I will do it, but I don’t think it’s a crazy goal.

Can I double product revenue? I think I can, although I don’t quite know how. I have the traffic and products to do it. There are also a lot of sub-goals that I won’t write about here, but which I think will help with this high-level goal.

Can I double coaching revenue? Yes, by more consistently booking clients and continuing to raise my rates.

This year, I earned pretty much what I earned in my last year of full-time employment. That feels amazing. But I didn’t quit my day job to make the same money I made before. I quit my day job to earn multiples of what I was earning before (among other things). So I want to continue pursuing that as long as it doesn’t require me to return to being a hermit.

Sub-7:00-pace 5k

I’ve been chasing this one for a while, and I probably should’ve tried to knock this out when I ran the sub-6:00 mile earlier this year. Unfortunately, I was battling some injuries and decided to slow down before I really hurt myself. I would like to check this one off the list.

Sub-60-second 400m

I’m honestly not sure if I can do this or not. For one thing, I’ve got nagging injuries that basically prevent me from sprinting. But if I can get healthy, I think I’ve learned enough about proper running that I can do this.

This wasn’t one of my original running goals (I wasn’t sure I’d ever break 70s), but I think it’s still an achievable stretch goal. Or maybe it’s not. I dunno.

More trips

I travel to relax, and I’d like to do that more this year.

I’d like to take another trip with the Boston crew this summer. That trip was a lot of fun and I think the three of us are pretty much an ideal traveling group.

A trip to Europe would also be great—I miss Italy—but I don’t have anything specific in mind yet.

My 2017 Year In Review: Making a living

In May of 2017, my business was in real danger. I had finished 2016 on a high note, finally breaking even for a few months in a row. But revenue began to slow in January, and my savings account was shrinking. I cautiously began looking for day job opportunities or something to bring in a little revenue while I figured out how to bring my business back from the brink.

One night, I mentioned this to a friend, and we talked strategy for several hours. Long story short, I needed to shift my focus to coaching as quickly as possible.

The next day, I flipped some switches on, updated my onboarding emails to emphasize coaching, and formally narrowed my positioning to “Salary negotiation coach who helps software developers get more high-quality job offers and negotiate higher salaries.”

June was my best month ever and I was cautiously optimistic that I had finally found a formulate that worked. July was strong and so was August. September was even better than June, and I knew I was on to something. Closing out 2017, the streak continues: Every month since May of 2017 has been better than any month through May of 2017.

I’m finally making a living and it’s an enormous relief.

Here’s a Table of Contents so you can jump ahead if you want:

2017 Goal Review

Let’s start out with a look back at my 2017 goals.

Make fewer new products, more new sales

I did pretty well on this one. The new products I made were all versions or subsets of previous products. And all of them were designed to test my own theories about how I could best help people in their current situation.

Focus on helping developers

I did really well on this for coaching, and totally failed for products.

My business has two primary revenue streams: coaching and products. My coaching is positioned specifically for Software Developers (the headline is “Software Developers: …”), and that’s where most of my revenue comes from. I haven’t niched down products because I don’t quite know how to do it given the volume of traffic my site gets from organic search (mostly Google).

Fearless Salary Negotiation was initially written for W-2 employees who want to get paid what they’re worth. So the articles on are deep dives into my strategies and tactics, which are mostly job-agnostic. That makes it tough to niche down my product focus because so many people who could be helped would think, “That’s not for me.”

I’m working on this now.

More traffic

My goal was 100,000 visits from organic search per month, and I missed this goal by quite a bit. I’m currently a little over 50,000 organic visitors per month.

It would have been a stretch to make this happen, but I think I could’ve done it if I moved it up my priority list. The reason I didn’t do that is I realized “more traffic” is meaningless if that traffic doesn’t turn into customers. So I switched my focus from “more traffic” to “more email subscribers from existing traffic” and now to “more customers from email subscribers”.

I’ll loop back on traffic some time in 2018 as a natural part of optimizing different areas of my business.

Make a decent living

Check! I’ll write more about this later on.

Finally finish my audiobook

Fail. I tried to make a push early in the year and even tried to hire someone to help me finish editing it. But that person stopped replying to emails and I lost steam editing it and just sort of let it languish. I’m not even sure how much revenue this would drive, so it’s basically a bucket list item to “Publish an audiobook” at this point. That’s not a strong motivator for me, so I’m not sure when this will get done.

2018 Goals

If 2017 was the year I made a living, I want 2018 to be the year I make a good living from what I’ve built.

Before I quit my day job, I was making a good living. I had a good job on a good team at a good company, and it was a nice life. But I wanted to know if I could build something on my own, and specifically I wondered if I could capture more of the value of my own abilities by doing my own thing.

I don’t talk about this much, but the investment I’ve made in building this business is pretty substantial, especially in terms of opportunity cost. I understood that going in, and it was a risk I wanted to take because the potential upside of learning how to build a profitable business with my skillset could be substantial.

I say all that to emphasize that I did not quit my day job to “do ok” or even “make a living”—I was already doing that. I quit my day job for a shot at making a much better living than I could as a W-2 employee capturing only a small fraction of the value I created. I’m over-explaining this because I realize this next goal may sound greedy, and shooting for even bigger goals beyond that might sound outright ridiculous. But I did not make this move—quitting my day job and starting a business from scratch—to break even. This business is an investment where I want a multiple on my return.

Make a good living

Talking about revenue is a little out of character for me. But once I get past “pay all my monthly business and personal bills with a little left over”, describing the next level of growth without using actual numbers is challenging.

So here’s a quantified goal: I want to make $10,000 per month in net revenue in 2018. More specifically, I would like to do that by selling $5k in products and booking $5k in coaching per month for the year.

This is a stretch goal because averaging those numbers for the year will be very challenging given that I’m starting below that average. But I like shooting for the average because it will incentivize me to keep pushing even if I hit those numbers for a month or two. “Yes, I hit the $10k goal two months in a row, but I need to do better if I’m going to average $10k over the entire year.”

More traffic (continued)

I would like to build my organic search traffic to 100,000 unique visitors a month. I’m currently at 50,000, so I need to double my monthly traffic to hit this goal. In nominal terms, adding 50,000 visitors a month seems like a stretch, but in relative terms, “Double my traffic in 2018” seems relatively easy compared to the growth I’ve seen over the past two years.

There’s also a risk here because almost all my traffic eggs are in the organic search basket. I will also spend some time working to add new traffic sources in 2018, but I’m not sure how I’ll do that just yet.

Improve at Sales

Selling products and services is the goal that I had in mind when I set about building the infrastructure of my business. The entire point of my book, website, outreach, and other business activities is to reach more paying customers.

My goal is that 2% of email subscribers become paying customers within the first 30 days.

This is probably my most important goal for 2018. If I hit it, a lot of other goals will be easier.

Help other businesses get more search traffic and email opt-ins

This one is less quantitative, but is something I’ve really enjoyed in 2017. Part of building a business is learning new skills, and I’ve gotten pretty good at getting organic search traffic and turning some of that traffic into email subscribers.

I can help other businesses do that. I like doing it. And it’s extremely valuable, especially for businesses with established, profitable sales funnels in place. For them, more traffic and opt-ins means more revenue.

Running goals

I set these goals after I began running earlier this year, and I’ve only gotten one of them so far.

  • 10k – Sub-8:00 pace Hit it with a week to go!
  • 5k – Sub-7:00 pace (currently 7:14)
  • Mile – Sub-6:00 pace (currently 6:08)
  • 400m – Sub-60s pace (currently 64s)

I’m confident I’ll get the 5k and mile times eventually. I’m not sure I can do a 60s 400m, but I’m so close I have to keep trying.

These posts are normally business-focused, and this one will mostly be business-y. But this year was a lot about personal growth and experience, so I’ll talk about that too.

A detailed 2017 Year In Review – Business

This year, I focused on building on the foundation I laid in 2016. Last year’s one-sentence summary was “Build infrastructure to turn the book into a business.” This year’s one-sentence summary is “Make a living.”

The real key to 2017 was focus. Early in a new business, I think it’s extremely important to try lots of things to see what works and what doesn’t. As much as we want to believe we can engineer a perfect business, that’s just not how it works.

But once things start moving—people are aware of your product or service, you have some sales, you’ve seen a few things work for you—focusing becomes extremely important. In 2017, I focused on building my traffic, building my brand, and building my business. I avoided distractions and that was key to my survival.

Ultimately, shifting my focus from “build a robust sales funnel for my products” to “leverage my skillset and knowledge in the most valuable way possible (coaching)” was the one thing that saved my business and unlocked real growth for the first time since I started.

Products and Services

Ultimately, my business is all about offering the right products and services to the right people at the right time.

In 2017, my coaching revenue more than doubled; my product revenue more than quadrupled. When I step back and look at my business, those are both extremely encouraging signs, especially considering I feel there’s a lot of untapped potential within the infrastructure I’ve built.


In June, I turned my focus to booking coaching clients and it paid off in a big way. I’ve worked with clients negotiating with the Big Five (Apple, Amazon, Facebook, Google, Microsoft) and many other big names. My portfolio speaks for itself, and I’m learning how specific in-demand firms negotiate their job offers. This knowledge is extremely valuable and I am starting to capture the value of the knowledge base I’m building.

I have also begun working with a new niche: graduating physicians. I initially started doing research to write a book for them, but I think the best way to start is to offer coaching. The common wisdom is “doctors’ contracts aren’t negotiable”, but that’s simply not true. Not only are they negotiable, but the value of negotiation is tremendous—even more than software developers in some cases.

The 15-Minute Counter Offer

I’m pretty sure I only created one new product in 2017: The 15-Minute Counter Offer. It was a companion product for the free email templates I give away on my site. I was curious if people would pay a little bit for more help writing their counter offer email, and it turns out they would.

This is slightly different than products I’ve created in the past. Those products were explicitly designed to make money. This product was designed as an experiment to learn more about how I can best help my audience. It’s subtle, but this shift belies a move from “try to make some money” to “optimize my business”.

The Salary Negotiation Crash Course

The Salary Negotiation Crash Course is a focused version of Fearless Salary Negotiation that is designed to help folks who already have a job offer become effective salary negotiators in less than 90 minutes. This is a good product, and it’s also an experiment as I learn more about the best way to offer valuable help to people who are looking for salary negotiation advice.


It’s useful to track stats over time, so I’m going to look back at most of the stats I tracked last year and add a few new ones.


This was a huge focus for me in 2016. I kept working on it in 2017, but not as intensely as last year. The reason is that I realized I had enough traffic that I should be able to do something productive with it if I would just optimize some things.

Before we look at 2017’s traffic, let’s look back at 2016:

2016 weekly organic traffic on

Not bad! Now let’s look at 2016–2017 for perspective:

2016–2017 organic traffic

First, you can see that things are still improving pretty quickly. Second, you can see that I took it easy mid-year because I was focusing on other business priorities.

As an aside, I’m finding that building a business as a solo founder is really just focusing on one thing at a time until it’s time to focus on something else.

In my case, I got to a level of traffic where I thought, “It’s worth my time to focus on turning traffic into email subscribers. If I can make a meaningful improvement to my opt-in rate, I can grow my email list really quickly.”

So I turned to optimizing my site to turn all that traffic into more email subscribers. This was a wise move.

My email list

Subscriber growth really picked up this year as I got more traffic and increased the opt-in rate for my site. Here are the subscriber counts at the end of the last three years:

  • December 2015: ~700
  • December 2016: ~2,500
  • December 2017: ~11,500

Here’s a graph of my subscriber growth for 2017:

2017 email list subscriber growth

You can see the hockey stick in September. That was the result of finally making a change I had been thinking about for months: I moved my free email templates behind an email opt-in form. That one-hour change quadrupled my site-wide opt-in rate.

I’m getting about 2,000 new subscribers a month now.

I want to pause on that number for a minute to put it into perspective.

The entire year of 2015, I got 700 email subscribers. SEVEN HUNDRED. I typically get that many new subscribers every 10 days now. I remember the first month where I had at least one new subscriber a day (October 2015), and that was a huge milestone for me. Now my slow days are around 30.

Conversion rate

This is a new stat, which logically follows the email list stats. By conversion rate, I mean, “How many of my email subscribers become paying customers in the first 30 days?” For me, the answer is embarrassingly low: Around .7%.

And it’s actually not even that good because that number is propped up by a couple experiments I did with extremely low-priced products. It’s probably more like .4%.

My 2018 goal is to improve conversion rate to 2% within the first 30 days.

Overall funnel

If you haven’t already noticed, I just described my “funnel”:

Traffic -> Email opt-ins -> Conversions
50,000/mo -> 2,000/mo (4% or so) -> .4%

Here’s where I would like my funnel to be by the end of 2018:

Traffic -> Email opt-ins -> Conversions
100,000/mo -> 5,000/mo (5% or so) -> 2%

If I hit those stats by the end of 2018, I should be able to hit my revenue goals.

Leveling up my credibility and profile

This year was huge in terms of publicity. I published several articles on and was interviewed live on international TV for the BBC News. The tick-tock of my BBC interview is pretty interesting as it was less than two hours from start to finish.

My work was published or syndicated on Business Insider, Fast Company, The Motley Fool, CNBC, MSN, Yahoo! Finance, AOL, The Telegraph, Forbes, Quartz, The Muse, and lots of other sites.

You can see a running list on the media page.

These opportunities have significantly raised my profile and given me a credibility boost that is paying off for my business.

A detailed 2017 Year In Review – Personal

This may sound crazy, but it’s true: Starting in 2009, I basically worked 7 days a week until the end of 2016. I got into that routine because I was working full time while also studying for my MBA. I would work at my day job during the week, then use weekends to do whatever needed to be done for my MBA.

That lasted until I finished my MBA in 2011. As soon as I finished my MBA, I quite my day job for 8 months. Ironically, I worked more during that 8 months because I was playing a lot of poker, writing my first book, and learning how to build web apps. It was a busy year and I worked some very, very long days and weeks in 2011.

I went back to work full-time in 2012, but I was building ShareAppeal (my first web app) and finishing Heads-Up Tournament Poker while I worked full time. We published Heads-Up Tournament Poker in 2013, but then I started working on TaskBook, which was a nights and weekends project.

I switched jobs in 2014 while I was still working on TaskBook, and then I started writing Fearless Salary Negotiation in December 2014 while still developing TaskBook (my second web app).

I quit my day job (again) in September 2015 to focus on publishing Fearless Salary Negotiation, and then began building that business in 2016 after the book was published. Throughout 2016, I was doing the hard work of building underlying infrastructure to run the business, and that work is pretty much a “volume of effort in correlates directly with results out” situation, so I worked long days all year.

2017 had to be different

But moving into 2017, something had to give. I had chosen to invest my time to learn how to build businesses and eventually become independent. But what was the point of being independent if I spent literally all of my time working? Yes, hustle is necessary to get something up and running, but eventually the hustle has to give way to something better than a 9 to 5.

So as 2016 wound down, I made a conscious decision to stop working so much and start enjoying the freedom I had earned by going independent. What did that look like in 2017?

I began working less and started leaving my laptop in my office at the end of the day. I had more energy because I was working less, so I got off my couch. I went from sporadically attending church to consistently attending. I joined a community group. I started spending more time with my friends just for the sake of spending time with them. I made new friends. I joined a running club and found a new hobby.

Am I a runner now?

My diet is typically pretty awful around the holidays. There’s like six weeks of non-stop snacks and big meals, and then I almost always get a truckload of candy for Christmas. I take on the truckload of candy as a personal challenge, so I eat even more candy than normal for the month of January.

And, uh… well the point is I typically gain a few pounds between like Halloween and February 1. This year, someone said, “Hey, we have a running club that meets once a week to do track workouts. You should come!”

Normally, I would’ve said, “I don’t run.” But the Florida winter was unusually mild and I had a few pounds to shed, so why not?

I’ve never been a runner. The longest I had ever run before this was six miles and that was an awful experience that took me over an hour. I had also run a few miles here and there in college, but it never became a real thing.

There were four to eight of us of us at most of the track workouts. I did not have fun at first—those workouts were extremely difficult for me. I had never done a track workout before, and it took some time to adjust.

But by April, I ran my first 10k race at a 9:00 pace and I actually kind of liked running.

Now I consistently train three days a week, mixing up track workouts (sprints) and medium-distance runs (3–5 miles). A few days ago, I finally achieved the first goal I set this year—I ran a sub-50:00 10k. It felt really good. (Emotionally, I mean. Physically, it was pretty awful.)

I’m also lifting weights three days a week. I’m in the best shape of my life and I can eat a lot more junk with all this running.

Time with people

I’m naturally pretty “introverted”. (Those air quotes are to acknowledge that this term may or may not have any real meaning.) I like to sit on my couch and watch TV or read. It’s pretty draining for me to hang out in groups.

Before this year, I had been working so much that sitting on my couch was my go-to down-time activity. While it was comfortable, it wasn’t healthy, and I decided to change that. Spending less time at work meant I had more energy for hanging out, and hang out I did.

I made a ton of new friends this year and sort of re-entered the social world. I went to Charleston to run a 10k race in April. Spoke at MicroConf later that month. Had a pretty good #SummerOfFun to take advantage of the Gainesville Summer Lull. Split my 4th of July time between a boat and the beach and barely survived a crazy storm. Carved a pumpkin and dressed up like Charlie from Wonder Woman for Halloween. Went to some Gator football, basketball, and volleyball games. Had lots of great dinners with friends. And finished the year off by watching a dozen Christmas movies with friends.

I also spent a lot more time with my family this year, and it was fantastic. No big trips or anything, just small opportunities to have a meal or catch a movie every now and then.

It was a good year.

My 2016 Year In Review: From zero to profitable

University of Florida College of Engineering Interview Preparation Workshop

In September 2015, I quit my job (again) to publish Fearless Salary Negotiation and start bootstrapping a business. So the one-sentence summary for 2015 would’ve been: Write and publish my book.

My one-sentence summary for 2016 is: Build infrastructure to turn the book into a business.

As usual, this is a long post, so here’s a table of contents in case there’s something you want to jump to:

Here we go!

How did I do in 2016?

For 2016, I thought I would just publish the book, build some products to augment the book (video courses), ramp up to enough revenue to cover all my bills and then return my focus to TaskBook. I hoped to do that early in 2016.

If you’ve built a business, you know how silly this plan was, especially considering I was more or less starting from scratch. Yes, I had published a book. But that was it. I had something like 700 people on my mailing list when I launched the book, and somehow I thought I was heading to enough monthly revenue to pay all my bills from digital products early in 2016? Who was going to buy all these products?

On average, I made about half of what I would’ve needed to pay all my bills in 2016. That’s the bad news. The good news is that I finished the year on a five-month stretch of basically paying all my personal and business expenses. So it took me almost a year, but I am paying my bills, and my business is profitable.

Of course, the ultimate goal is to make multiples of my previous day-job salary. But that’s going to take a while, so I need smaller goals in between. The first one was “Pay all my bills”. The next one is “Make a decent living”.

What I now realize is that 2016 was another foundational year. If 2015 was “Write and publish my book.”, then 2016 was: Build infrastructure to turn the book into a business.

Looking ahead to 2017

For 2017 I have a more strategic focus, supported by tactics, to build on the infrastructure I created in 2016.

It feels like this is the difference between working in the business and working on the business. I’m not exactly sure what that means, but I think that’s what’s going on. I’m moving out one level from working in the business—building products, building a web site—to working on it by growing it.

Fewer new products, more new sales

I’ve built a lot of great things in 2016, and now it’s time to grow my business and revenue. Building new products is extremely challenging and time consuming. But now that those things are built, I can reallocate that time to growing my business.

So I don’t plan to create many products in 2017, and will turn my focus to finding my niche and finding the right customers to benefit from the products I have built. I’m sure I’ll build something new, but I’m planning to resist the urge to make make make.

Focus on helping software developers

I think “the right customers” for my business are software developers. I like working with devs and they are generally positioned to gain a lot from my expertise. In many ways 2016 was just a series of experiments with different markets, and every time I worked with devs, or made something specifically for devs, the response was tremendous. For example, this article on How software developers can get a raise without changing jobs has been viewed over 30,000 times so far.

It’s pretty obvious that this is where I should focus, so that’s what I’ll do in 2017.

More traffic (continued)

By the end of 2017, I would like to have 100,000 visits from organic search per month. That’s about 15 times what I’m getting right now. There was a time when this goal would’ve seemed totally unattainable, but I know what I need to do, and I just need to execute.

The problem with this goal is that much of this is out of my control. An algorithm change or something else could wipe me out. The good news is that if I do the right things to drive this number, lots of other numbers will improve. As I’ll talk about in my detailed recap below, organic traffic has been a lagging indicator that I’m doing the right things, and I’m really interested in this stat as a proxy for other things going well. If those things go well and this stat tanks, then so be it.

What’s interesting is I have no idea if this is a stretch goal, or low-hanging fruit. One one hand, 100,000 organic visits per month seems like a huge number. On the other hand, I’ve consistently tripled organic traffic every 60 days for a year. I don’t think that’s sustainable, but I also didn’t think it was sustainable a few months ago and here I am.

If I keep up that pace (again, it sure seems like this is totally unsustainable), I’ll hit 100,000 organic monthly visits in July or August 2017—plenty of time to spare.

Make a decent living

I’m basically breaking even right now—my savings account is no longer shrinking, but it’s also not growing. And I’m living very lean to make that happen. “Make a decent living” would mean replacing about half of my previous day job income, starting to re-grow my savings account, and opening up my personal budget a little bit.

I’m not really swinging for the fences here, but that’s because I’ve learned that this is likely to be a slow, steady grind forward. Hopefully I blow this goal out of the water, but I’m not counting on it. Maybe “Make good money” will be a goal for 2018.

Finally finish my audiobook

I managed to re-record about 70% of my audiobook after learning some tough lessons earlier this year, but then I ran out of steam. I would like to get this project finished, and I’m hoping to get back to it early in 2017. We’ll see.

A detailed 2016 Year In Review

Here’s a look back at what I built in 2016.

Products and services

Most of these things are new things I built in 2016. Plus there’s a TaskBook update for those who are curious.

Video courses

I started the year by building video courses to accompany Fearless Salary Negotiation. I know a lot of people learn visually and need action items and next steps, and I wanted to give them a way to learn and apply my strategies and tactics.

This was the hardest part of 2016 by far. Not only did I have to create all the content (about 400 slides, each one scripted word-for-word), but I had to learn how to record and edit audio, video and screencasts. Meanwhile, my monthly revenue was close to zero and I had to spend about $2,000 on my car.

It took me about 10 weeks of non-stop work, but I got everything done and I’m very happy with the result. The result is over three hours of quality screencasts that augment the book and visually illustrate key concepts so they’re easier to understand and use.

I started out here on Once I picked a title for my book, I registered and published a few sales pages, but I still kept writing and pointing everything to

In March this year, I realized that Fearless Salary Negotiation was its own brand and that I needed to start treating it that way. So I redesigned the site, moved to a new platform, and started publishing new content there. At the time, had about 10 pages total. Now it has over 150 pages, and I’ve built every single one.

About 60 of those pages are the online version of the book. The rest are a mix of articles, landing pages, and sales pages.


I’ve been coaching people since I started writing my book because I needed to know exactly what was happening in interviews, salary negotiations, and raise and promotion discussions. At first I didn’t charge anything and I worked with friends and family, then friends of friends. I did that for over a year.

Then I got a call from a friend who said, “I have a big job opportunity and I don’t want to mess up this negotiation. What’s your consulting rate?” I…didn’t have a rate, but I knew she was a freelancer, so I said, “Whatever your rate is.” She charged $75 an hour, so that’s what I charged. Then another friend reached out and since my first client didn’t flinch, I charged $120 an hour. Again, no hesitation, so I knew I needed to raise my rate again.

Fortunately, I went to BaconBiz Conf during this $120/hr engagement, and I talked to my pals Josh Kaufman and Jim Gay. I was pretty proud of myself for getting up to $120 an hour and planning to “Charge more!”, but they had other ideas:

“Why are you charging hourly?”

After a 30-minute conversation, I was planning to charge $1,500 for a fixed-fee engagement with a money-back guarantee. I would promise to increase my clients’ base salary by at least $10,000, so this would be a slam dunk ROI calculation.

Looking back, I’m not sure I actually believed I could find clients who would pay me $1,500 to coach them. (This was classic Imposter Syndrome at work.) Sure, I had made people tens of thousands of dollars. Sure, I knew what I was doing and my previous clients (paid and pro bono) had loved working with me. But would strangers really pay me $1,500 to help them bump their salary by $10,000?

You bet they would! But they didn’t much care about the $10,000 promise and I think it actually worked against me early on. $10,000 is a lot of money to some people, but it’s not much money to other people. For those other people, a $10,000 promise just wasn’t compelling (if you’re making $150,000 a year and I promise to help you get to $160,000…that’s not an exceptional jump for you). So I dropped the $10k promise and stuck with the money-back guarantee.

Since then, I’ve worked with folks negotiating at Google, Amazon, Tesla, Samsung, Verizon, and other companies you’ve heard of. And I’ve raised my rate to $2,000 with a plan to raise it again soon.

I was obviously nervous about offering a money-back guarantee, so I mitigate this risk by holding the money aside until my client tells me they’re satisfied. But so far, none of my clients have asked for a refund. (I’m sure this will happen eventually—it’s just a part of doing business. But it’s nice to have a perfect record in 2016.)

My coaching offering has been a huge boon to my business this year. About one-third of my revenue was from coaching.

The Interview Cheat Sheet

Initially, I made The Interview Cheat Sheet for my coaching clients. I found that I always gave them the same homework before their job interviews, so I figured I would make a nice cheat sheet for them. I hadn’t launched any tiny products, so this was a good chance to try that.

It only made a few hundred dollars, but that was just gravy since I made it for my coaching clients anyway. And now I include it with all my eBook and video course bundles as well.

Get Your Next Raise

Any time someone buys Fearless Salary Negotiation, I ask them “Are you negotiating an offer for a new job or looking to increase your salary at your current job?” The responses are pretty evenly split.

Then I ask some followup questions to see where they might be stuck. I found that I had a really good offering for people who were stuck on interviewing and negotiating and wanted more help from me, but I didn’t have much to offer for those who were hoping for a raise.

So I built Get Your Next Raise. It’s a pretty unique self-paced and guided course that walks students through step-by-step process to ask for a raise while I get them feedback along the way. I launched it at the end of November and I plan to promote it heavily in 2017.

This is also the first product I have built by working backwards from the specific need I saw to a solution (the course) to a free offering that offers value and helps potential students determine if the course is right for them.

Shutting down TaskBook

I’ve decided to focus 100% of my time and energy on growing my business around Fearless Salary Negotiation, which means I’m sunsetting TaskBook in 2017. This is tough because I still have people reaching out who say, “Why can’t I sign up for TaskBook?”, and I know it would help them. But I simply don’t have the resources to grow two businesses.

There’s an alternate timeline where my first big project is Fearless Salary Negotiation, and it fizzles out because I don’t know how to sell or market. Then I take what I learned and build TaskBook, which takes off like a rocket. But instead, I started with a SaaS (pro tip: Don’t do this!), didn’t know how to find customers, and got distracted by a shiny new thing, which is growing into a business.


I mentioned this was a foundational year, and I think that will show through in this section. Here are my high-level stats from 2016.

My email list

A big metric for businesses like mine is “How many subscribers do you have on your list?”

  • December 2015: ~700
  • December 2016: ~2,500

That’s a decent growth rate considering I haven’t done any meaningful paid acquisition (Facebook ads, etc.). One thing I need to work on is learning more about what folks need when they join my list or download a free guide from me. And I need to provide more value and build a better connection with everyone on my list.

In September, switched to a new Email Service Provider (ESP) called Drip. ConvertKit was great for getting from zero to almost 2,000 subscribers. But as I tried to do more with my list, engage more effectively, learn about people, I kept bumping into limitations. Drip seemed like the best way to get to the next level, so I switched. To ConvertKit’s credit, many of the things that I left for are starting to show up in their product, so it seems I was just a few months ahead of them.


After BaconBiz Conf, I spent an extra day in Philly. I decided to walk to a little coffee shop and found myself crashing a post-conference work session attended by many of the conference’s speakers (many of whom are already my friends). Not one to let a good opportunity go to waste, I coaxed a little advice from the group (this was not difficult), and the main message was:

You’re doing the right things, you just need to do more of them and get more traffic.

At the time, I really didn’t know what that meant, but I started doing things I thought would help. I was already doing a podcast tour, inspired by Kai Davis among others, and had begun looking for opportunities to write guest blog posts. (See a summary of my podcast appearances and guest posts here.)

I also began writing and promoting more content at so I would have more content to point people to when they asked questions, and so Google would have a greater surface area of things to find and suggest for search queries.

My focus has been on Organic traffic (when people Google things and click through to find the answer) because I think that’s a lagging indicator of all other types of traffic. If I get lots of traction with my content, podcasts, guest posts, social media, etc., that will eventually translate into Organic traffic.

Here’s my 2016 weekly organic traffic:

2016 weekly organic traffic on

As you can see, it’s growing pretty steadily and quickly. I have basically tripled traffic every 60 days this year, so I went from almost zero traffic in January to almost 2,000 visits a week now.

Book sales

I’ve sold almost 1,200 copies of Fearless Salary Negotiation so far. Most of those sales were on Amazon, which is why I launched on Amazon. One cool thing is that I have steadily raised my price and sales continue to improve. So I’m making more sales and getting more revenue per sale. This has been a nice surprise.

One concern I had about launching and selling on Amazon was “You don’t know who your customers are!” (this is a common thing I hear in the self-publishing community). This is partially true—I technically don’t know who buys my book because Amazon doesn’t tell me.

But! 10–15% of Amazon buyers subscribe to my email list because I point back to my site, where I offer free worksheets and email templates to accompany the book. Some of those folks have eventually become coaching clients, so I see the Amazon version of my book as a sort of combo product/marketing tool/calling card.


I worked with about a dozen different clients this year. Not bad considering I didn’t launch my coaching offering until mid-year. I’ve intentionally grown this part of the business slowly because I want to make sure my clients get great value for the price, and because I wanted to iterate on the offering as I got to know more clients.

I’ve found that the folks who benefit the most from working with me are experienced software developers moving to larger companies like Amazon, Google, and Tesla, so that’s who I’ve been working with lately.


University of Florida College of Engineering

I had a chance to do about 10 talks this year, and they were a lot of fun. As I write this, I realize that all but one of those talks were to engineers or software developers—another sign that focusing my efforts on helping software developers is a good idea.

This talk on salary negotiation for software developers for Orlando Devs and The Iron Yard, Orlando was my first of the year and it has almost 7,000 views on YouTube. I also gave several talks at a local code school called Gainesville Dev Academy, where they buy a copy of my paperback for every student.

The really fun thing is that talks are easy for me to do—I’m extremely comfortable with public speaking. And they give me a chance to meet developers and see what they’re struggling with.

Podcasts, webinars, quotes, and guest posts

Here’s a one-page summary of my podcast appearances, webinars, quotes, and guest posts.

I was on more than 20 podcasts this year. Most of them were software developer podcasts (yes yes, another checkmark for “focus on helping software developers”), and the response was fantastic.

I think the highlight for me was talking with my pal Patrick McKenzie on his Kalzumeus podcast. Patrick’s detailed blog post Salary Negotiation: Make More Money, Be More Valued was an early inspiration for me to learn more about salary negotiation, try it for myself, and eventually write Fearless Salary Negotiation.

I also participated in three or four webinars, which was great practice. I’m extremely comfortable in the podcast format (probably more comfortable than public speaking), but not as comfortable with webinars where I sometimes need to be on camera, and where the audience is live but invisible.

I did four guest posts and was quoted in a article, so that’s pretty nifty.


I’ve decided not to share my revenue numbers publicly because there are some drawbacks and I can’t think of any real benefits.

That said, I’m basically paying all of my personal and business expenses each month. That’s a big deal for me because it means I’m not spending my savings anymore. Hopefully in 2017 I can replenish the savings I burned through earlier this year.

Wrapping up 2016

It was a good year. It started slow and stressful, but things turned around mid-year and most of the important graphs are moving up and to the right.

I am learning a lot about building and running a business—this experience is invaluable. I’ve spent the past several years getting to know some very smart people, and their guidance has helped me keep focused on the right things and ignore the things that don’t matter.

I’m really looking forward to seeing how this business grows in 2017.