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. You can review their link building packages that helps you to build up your marketing strategy.

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

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

My kitchen before the remodel
My kitchen after the remodel

New friends

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

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

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

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

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

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

The annual Manor Christmas Party

Less disc golf and running

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

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

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

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

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

Tried yoga for the first time

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

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

2022 Goals

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

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

Build and launch a new salary negotiation course for software engineers

I think it’s time.

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

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

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

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

Increase business revenue by…50%?

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

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

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

Get to a 4.0 level in pickleball

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

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

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

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

Ski the top of the mountain at Breck

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

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

Travel more (for real this time)

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

Something something cooking?

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

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

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

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

Be more generous

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

Summing it all up

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

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

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

My 2020 Year in Review: Riding it out

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

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

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

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

2020 Goal review

Increase revenue by 50% again

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

Sub-7:00 pace 5k

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

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

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

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

Sub-60-second 400m

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

Travel more

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

Be more generous

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

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

2020 Year in Review – Business

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


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

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

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

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

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

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

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


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

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

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

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


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

Coaching revenue

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

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

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

Product revenue

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

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

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

Strategy paying off

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

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

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

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

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

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

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

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

Monthly income for my entire career to date

Investing in the business

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

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

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

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

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

2020 Year in Review – Personal

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


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

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

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

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

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

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

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

Ski trip

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

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

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

2020 Ski Trip Crew

Birthday bash, just under the wire

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

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

2020 Birthday Dinner

Survivor Fantasy League goes International

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

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

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

An epic RV trip

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

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

Sunset on Black Balsam Knob in North Carolina

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

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

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

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

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

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

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

Weird football season

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

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

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

Florida vs Texas A&M Football, 2020

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

Five years since I quit my day job

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

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

My first disc golf tournament

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

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

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

First tee of my first disc golf tourney

2021 Goals

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

Increase business revenue by 50%

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

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

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

Be more generous

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

Here’s to a better 2021!

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

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

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

Setting the stage

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

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

Making a plan

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

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

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

Starting to write Fearless Salary Negotiation

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

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

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

Quitting my day job

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

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

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

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

Publishing Fearless Salary Negotiation

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

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

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

Sunsetting TaskBook

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

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

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

Building the Fearless Salary Negotiation Business

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

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

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

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

Easing into salary negotiation coaching

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

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

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

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

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

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

By the Fall of 2016, two things had happened:

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

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

Focusing on helping Software Developers

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

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

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

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

Saving the business by focusing on salary negotiation coaching

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

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

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

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

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

I decided to make a big change.

Raising my rates

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

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

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

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

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

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

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

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

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

Breaking even on my previous day job salary

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

There’s still a lot of work to do

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

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

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

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

Big Strides in Breck

Last day on the slopes in Breck

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

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

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

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

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

And now, on to the recap…

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

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

ANYWAY, it was slow going at first.

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

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

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

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

Beaver Creek

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

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

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

Staying forward and poling around turns

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

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

Letting my edges do the work

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

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

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

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

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

Looking up from the base at Beaver Creek

My first full-on spa experience

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

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

Vail (semi-fail)

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

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

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

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

Moving day

Part of my plan this year was to extend my trip so I could get more ski days in and more rest days. I decided to contact experts from Big T Moving & Delivery to carry my belongings carefully and I think this is the perfect time to take a rest day on Tuesday since we would be relocating from Beaver Creek to Breckenridge by the end of the day.

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

Beaver Creek Chocolate Chip Cookies

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

It was a good day.

Back at Breck

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

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

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


This is what we woke up to on Wednesday morning:

Our view from the porch in Breck

It would be beautiful like this all week.

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

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

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

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

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

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

2020 80s Day in Breck

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


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

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

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

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

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

2020 Thursday in Breck

Friday (rest day)

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

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

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

Downtown Breck


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

Cimarron at Breck

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

Our crew for the Luge

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

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

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

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

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

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

Odds and ends

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

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

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

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

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

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

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

My 2019 Year in Review: Finally paying myself back

What a year.

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

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

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

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

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

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

2019 Goal review

Double revenue again

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

Product revenue

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

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

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

This decision was driven by three challenges:

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

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

Services (coaching) revenue

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

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

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

Sub-7:00-pace 5k

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

Sub-60-second 400m

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

More trips

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

2019 Year in Review – Business

This year was an unequivocal success.

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

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

I had two issues with my day jobs:

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

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

Monthly earnings throughout my career

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

Two milestones to close out the year

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

Income from my business now exceeds my day job income

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

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

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

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

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

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

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

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

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

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

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

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


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

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

Salary negotiation coaching

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

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

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

My old fee structure

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

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

Here’s what the fee structure looked like:

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

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

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

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

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

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

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

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

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

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

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

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

My new fee structure

So I totally changed my coaching fee structure in April.

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

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

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

So what to do?

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

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

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

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

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

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

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

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

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

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

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

So how’s it going?

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

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

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

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

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

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

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

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

Mistakes were made (by design)

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

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

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

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

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

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

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


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

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

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

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

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

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

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

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

This is what running a business looks like

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

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

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


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

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

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

2019 Year in Review – Personal

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


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


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

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

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

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

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

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

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


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

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

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

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

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

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

Eye surgery

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

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

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

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

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

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

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

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

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

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

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


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

In Breck for the Breckpocalypse

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

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

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

Me in my 80s Day onesie

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

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

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

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

Central Park - NYC


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

Best possible outcome

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

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

2020 Goals

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

Increase revenue by 50% again

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

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

Sub-7:00 pace 5k

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

Sub-60-second 400m

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

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

Travel more

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

Be more generous

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

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

Our group in 80s gear

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

80s day was a hit

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

  1. Authentic retro 80s attire. Maybe half the group went this route, wearing headbands, sweaters, jackets, and pants that were either actually from the 80s or could’ve been.
  2. Caricature 80s attire. And about half the group wore stuff that I describe as “What people today think people wore in the 80s.” I was in the camp, wearing a super loud 80s onesie.

Me in my 80s Day onesie

We picked the perfect day to do this since it was relatively warm, the sun was out, and the sky was blue all day. The groups pics we got at the top of Peak 8 made the whole thing worthwhile (the rest of the day was gravy).

Our group in 80s gear

Our group playing our air instruments

Slow and steady progress as a skier

This was basically my second time skiing. Technically, I skied a few times in high school, but I don’t count those because we were on east coast ice, and no one ever actually showed me how to ski. So I was terrible and I hated it.

Last year was the first time I skied on anything resembling powder and I also took lessons, so I immediately felt better about it and made progress quickly.

This year was interesting because I was the worst skier in our group, so I was the one holding things up most of the week. But I wanted to take my time and work on some things to make sure I was actually improving as a skier and not just ramping up the difficulty.

First day on the slopes

Our first day on the slopes, I felt pretty uncomfortable on my skis. Skiing is not like riding a bike—and I felt like it was my first time out. But after a few runs, things started coming back and I felt a bit better.

By the end of our first day, I felt like I was pretty much back to where I left off last year. I could comfortably cruise down most of the blues, occasionally feeling like I wasn’t quite in control. This was a super long day because we went out early-ish and came home late-ish. We did a bunch of runs and those runs were challenging for me since my form was so rusty. I was totally spent at the end of the day.

Second day on the slopes

I decided to take our second day and just focus on technique—specifically turning and maintaining my speed while staying in control. My friends would frequently say, “Wow, you really flew down that one! You’re getting a lot better!” And I would say, “Well, that’s because I only have two speeds—Stop and Go. Once I’m in Go-mode, I’m just trying to stay upright until I can slow down.”

I wanted to feel in control most of the time instead of feeling like I was just trying to stay upright and avoid wipeouts. So I stuck to blues and slowly improved.

Although I didn’t move up to more difficult runs as quickly as I did last year, I made a lot more progress in my first couple of days on this trip. By the end of the second day, I actually felt more like I had control, I could slow down when I wanted to, and I was able to choose my lines rather than just taking wide S turns and hoping for the best.

My turns got much tighter and I was intentionally hitting spots that seemed easier to navigate. I actually went in about an hour ahead of most of my peers because I was still beat from the first day, and I felt I had accomplished what I wanted for the second day.

Third day on the slopes

I asked a couple of friends where I could find the easiest black run at Breck. The answer came back: “Dukes.” It was a relatively short run that used to be a blue, but they turned it black so intermediate skiers wouldn’t get spooked. So it was technically a black, but only just.

My goal for the entire day was to get more comfortable and eventually do at least one black run, so I pretty much mapped out the day to slowly move toward that goal.

Powder, powder everywhere

Even before I started going on this trip last year, there was much lamenting that fresh snow never arrived. It was almost like this specific trip had some sort of jinx on it so that it was always warm and sunny with no new snow during the trip.

That all changed this year, and we made up for lost time. In our last two days at Breck, I think there was over a foot of snow and it just kept coming.

So I swapped out my regular skis for “powder” skis to start the third day. At first, this was kind of frustrating because I had to re-learn a lot of what I had worked on the previous day. Turning was harder, stopping was harder, maintaining control was harder. Everything was harder.

But once I got used to the new skis, they were much better and easier to control.

A solo run for my first black

After several good blue runs, it was time to make my way to Dukes, the easy black my friends recommended. I actually scoped it out during my first run of the day since it starts from a common catwalk that we use to move between peaks.

I was going to run it with a friend, but he ended up stopping early, so I was on my own. But before we parted ways, I asked if he had any suggestions—he had three:

  1. Stay to the right, away from the moguls.
  2. Wait for a big opening so I could do “my run” without traffic around me.
  3. If I felt like I needed to slow down to regain control, turn slightly back up the mountain to regroup.

And off I went.

The lift dropped me about 100 yards from the top of Dukes, so there wasn’t too much time to think about it once I was off the lift. I initially planned to get to the top of the run and give myself a minute or two to gather my courage, but it turned out I didn’t need that kind of time.

I got to the top of Dukes, looked at it and thought, “Meh, that doesn’t seem so bad. Let’s go.” And I was off. Overall, it was a pretty good run and I used all three of my friend’s tips.

I actually made it down the steepest part without any issues, but I relaxed too early because I didn’t realize there was a second steep part that was also icy and bumpy. All of a sudden, I realized, “Uh oh, I’m going too fast and this is all bumpy ice. Need to slow down… or need to at least try to maintain control until I can slow down.”

I didn’t quite succeed, but I didn’t quite fail either. I basically ended up spinning out so that I didn’t technically “fall”, but came as close as I could’ve. After a few very ungraceful flailing spins, I found myself stopped, skis splayed, hands on the ground in front of me, holding me up. I regained my composure and it was easy from there on out.

I remember getting to the bottom and thinking, “Huh. That wasn’t so bad.” I almost talked myself into doing it one more time, but I thought better of it and made my way back to our house.

Right after my black run on Dukes

Fourth day on the slopes – or not

I finished my third day on a real high. I finally felt comfortable on my skis, I felt more in control than I had at any other time this year or last, and I did my first black.

But I also felt like I had been pretty lucky so far. I had been really tired a few times during the week, but had managed to get good runs in despite the fatigue. I also had a strained right adductor to watch out for.

Before I went skiing, my doctor said, “Sure, you can ski. But don’t do anything crazy and stay off the tougher blacks.” Remember the spinout I mentioned on Dukes? It was exactly the kind of awkward motion that could’ve reinsured the adductor. I’d been rehabbing that stupid thing for 5 weeks, and hadn’t run in almost 10 weeks because of it, and I wasn’t looking to re-injure it if I didn’t have to.

So I had a really tough time deciding whether to go back out for our fourth ski day, or if I should just take it easy.

I ultimately decided to take an actual vacation day and just hang around the house, and there were a few factors at play there:

  • I felt like I had been pretty lucky that I didn’t re-injure my adductor despite some close calls.
  • I accomplished my primary goal for the trip—do a black run.
  • The conditions were very powdery, but I wasn’t good enough to really take advantage of that. And powdery also meant cold, snowy, low-visibility.
  • It was the Saturday beginning Spring Break, and I knew the lift lines would be long (so I’d be waiting around a lot, and wouldn’t do much skiing for the time I would be out there).
  • I hadn’t taken a real vacation day—a full day off to just relax—in…I can’t remember the last time I did that, but it was years ago.

It was basically a coin flip that came down to, “I’ve checked all the boxes for this trip and I didn’t re-injure my adductor. I finished on a high and I am anxious to get better and ski more when I’m healthy. Maybe I should just quit while I’m ahead.”

I decided to just take the day off. If my adductor had been healthy, I would’ve gone out. But I knew that if I went out, I would want to try tougher blacks, and that would make re-injury more likely.

Even in hindsight, I’m not quite sure if this was the right thing to do.

A great trip with friends

The coolest part of the ski trip is that each day essentially has two major events: Skiing and hanging out.

Skiing is typically over around 4:00 at the latest, and that means we have another eight hours before we go to sleep. We typically try to squeeze in all four of these things after skiing:

  1. Hot tub time
  2. Dinner
  3. Crepes a la Carte—an amazing crepe place in Breck
  4. Games (usually Body, Body, Body, but not always)

We checked all those boxes a couple times and hit three of four every night (I think).

We had some amazing food—The Canteen, Michael’s, Giampietro, Empire Burger (the sides and sauces are amazing)—but I didn’t document any of it because I was too busy eating it.

And I was finally mafia in Body, Body, Body and got the win. So now I’m one-for-one as mafia, but still only like one-for-fifteen being mafia. The law of averages will eventually catch up and I’ll go on a mafia spree (or maybe I’ll just cheat—ahem, GP—and make it happen on my own)

Surviving the Breckpocalypse

About half way through our trip, it began to snow. And snow and snow and snow and snow. There was a lot of snow.

This made my final ski day a lot of fun, and I’m sure it made Dukes (at least the top part) much easier. My friends said it was the best snow day they had ever seen, and some of them even extended their trip to get more time in the powder.

Here’s a short video of the view off of the balcony…

Short video of our balcony view

Of course, the snow giveth and the snow taketh away… the ability to travel. We had a few rental cars with varying numbers of passengers, and some of the cars had trouble either explicitly getting through the snow, or in driving from Breck back to Denver. My car was pretty lucky because we left early. It took us almost three hours to get to Denver (normally two hours), and we had to stop to manually de-gunk the windshield a couple times, but we made it. There was also an avalanche about 20 miles west of us on I-70, so I’m obviously glad we missed that.

Some other folks either missed their flights after a long (five hours!) drive to Denver, or simply got stuck in the snow in Breck and had to wait it out (this may or may not have been related to an ill-advised decision to rent a 2WD truck despite a steep driveway and a snow-heavy forecast).

When we finally go to Denver, it was 3 degrees outside—the lowest March temperature in like 140 years. Apparently it got as low as -6, so we got there when it was nice and toasty outside.

All in all, this was another amazing ski trip and I can’t wait to get back out there and hit some real blacks next year.

Keeping small pains from becoming big problems

I usually run three days a week, like clockwork. Monday is a track workout, Thursday is a short run, Saturday is a longer run. It usually adds up to about 10 miles a week unless I’m training for something (like a 10k race or a 15k with the flu).

Here we are on January 16, and I haven’t run at all this year. Last time I ran was December 29, 2018, about six weeks after I finished my first Half Marathon.

It’s really frustrating, but it’s also necessary.

I have been battling a couple of overuse injuries for a few months, just sort of hoping they would work themselves out if I kept training with good form. Sometimes that works, sometimes it doesn’t. This time it didn’t work and it made things worse.

I noticed I was struggling to keep up a good pace, and that maintaining good form was more and more challenging as I tried to compensate for various aches and pains. Learning about various treatment options as I navigate here became my hobby. It started getting more difficult.

I should’ve stopped running right after the Half Marathon, but I was too stubborn.

Now it’s time to pay the piper. What would’ve been a week or two of rehab has probably ballooned into a month, all thanks to my stubbornness.

I’ve been thinking a lot about how there’s a fine line between “Just tough it out!” and “Why didn’t you stop before you hurt yourself?!” It’s really hard to see that line in real time, and it seems like the only way to really know where the line is is to look backwards and find it.

But I also think that identifying that line is a skill that can be honed over time.

The best way I know to hone that skill is to constantly monitor pain points: Is it better or worse than last time? How hard is it to aggravate it? Can I work around it? What’s the upside to continuing? What’s the downside if this turns into something bigger?

I’ve been doing this with my business lately and it has helped me identify some small pains that I can resolve before they become big problems. That makes things easier for me and better for my customers.

You can use this sort of analysis with your career. Small pains often become big problems if left untreated, so it’s worth identifying those small pains and thinking about solutions before they become big pains.

It’s the beginning of a new year, so this seems like as good a time as any to start planning ahead to make 2019 more productive by finding and fixing small pains before they become big problems.

Take a few minutes and ask yourself, “What are some small career pains that could become a big problem if I don’t handle them now?” You might find some easy wins with a big payoff for very little effort.

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. But aside from gaming win money, 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.

Going the extra mile in my first Half Marathon

I got peer-pressured into running a Half Marathon a couple weeks ago.

Also I was promised free cupcakes at the end of the race and I have a very, very hard time saying no to cupcakes.

So I did some light training, re-aggravated some nagging injuries, even planned to hire an experienced moto accident lawyer in case of injuries and ran my first Half ever. In sports, accidents are very common. So it is advised to consult experienced injury lawyers for hire to help you claim compensation and legal counseling.

How’d it go?

Overall, I’m pretty pleased with my performance. I ran an 8:24 mile pace and finished in a decent time and I finished 9th overall out of 99.

Half Marathon Split Times

But I also ran out of gas on the back half and I couldn’t find enough energy to push for the end of the race. My mile splits just sort of kept slipping and slipping until I finally finished.

Part of this was my training—I didn’t run more than 9.3 miles before the Half—and part of it was probably nutritional (I should’ve had some gel packs or something).

Overall, it’s a good result and I’m happy I finished.

Nagging injuries

Unfortunately, I went a little too hard in my training two weeks out from the race. I didn’t mean to, but I felt so good on my longer training runs that I just sort of kept going.

I started on Saturday with a 15k (9.3 miles) and smashed my previous PR with an 8:00 even pace. Then I did an easy-ish track workout on Monday, but also threw in a fast 800m (a PR of 2:44). Then on Thursday I ran a fast 5k (7:26 pace).

I felt really good after all those runs.

Then on Saturday, eight days out from the race, I ran a medium-pace 10k (7:54) and that’s when things started hurting. I’ve had a nagging groin injury for a while, and it lit up during this run. Then my knee on that side also started hurting, probably because I was changing my gate to compensate for the other pain. My calf on the opposite started aching too—also probably compensatory. If you are injured to negligence of someone, you can contact lawyers who defend clients against charges and will legal advises.

So I went from feeling amazing to having a few dings that would still be sore on race day.

Fortunately, I was able to get in for a sports massage session, and that calmed things down enough to finish the race.

Still, it’s been 10 days since the race and my calf and groin still aren’t quite right. I just have to take it easy for a while so things will heal.

And this also confirms for me that I don’t think running a full marathon is even remotely a good idea for me.

Pacing myself

Since I hadn’t run this far before, I started off by taking it easy. I held back on my first mile and it still only took 8:15. I was hoping to end up at 8:15 for the entire race, and I felt great at this pace—I thought I might actually hit it!

Once we settled in, I was able to start keying off my cadence and how I felt in general. I felt great for the first several miles, but I also knew I wouldn’t feel too great for the last few miles. So I picked it up a little bit and passed a few people, but still held back.

The middle of the race was pretty hilly and painful, and I was happy I hadn’t pushed too hard earlier.

Once I got near Mile 10, I thought I might try to push and pick up the pace. I did push, but my pace started slowing as I just ran out of gas. I’m fine with that—I expected to get tired on those final four miles since I’d never run that far before.

My biggest problem was muscle fatigue—my muscles (especially my calves) just were not used to running that far. My cardio felt really good the whole time—I was never even remotely out of breath, had no side stitches, nothing that indicated I need better cardio.

But to go faster, I’ll need to increase my cadence from an average of 171 SPM to at least 175 SPM. To do that, I need better muscle endurance and more late-race energy.

I feel like my plan and strategy were very good. I’m not sure I would do anything differently if I could run this race again.

How I’ll improve for next time

This is actually pretty simple:

  1. Train better. I think I’d be much better off running a few 11–12 mile training runs in the weeks before the race. I think that’s the only way to get my muscles used to doing that much work. It will also give me a chance to slowly push my cadence higher and get used to running faster.
  2. Mid-race energy. I drank a few ounces of Gatorade at the mid-way turnaround, but that was it. I should’ve had gel packs or something for a late-race boost. I don’t know much about this, so it’s something to look into before my next race.

I’m very happy that my cardio was strong for the race, and not surprised that my calves got tired. I can fix that.

Going the extra mile

But the most interesting thing is that I got a rare chance to literally experience a figure of speech: I went the extra mile.

It’s not quite as crazy as it sounds, but it still felt pretty crazy at the time.

This particular race was totally disorganized. It was so disorganized that the actual race distances weren’t right. Not even close, actually.

About 10 minutes in, I realized the course couldn’t possibly be 13.11 miles. It was an out-and-back race, and I could see that the shorter distances (5k and 10k) weren’t right because I got to their turnaround points before I should have.

So I started prepping myself: “Josh, you’re going to be tired when this is over. But you’re also going to need to keep going past the finish to get the full distance. That’s not gonna be fun, but you didn’t come out here to run ALMOST a Half Marathon, so you’re gonna keep going until you hit 13.11 miles.”

Sure enough, I crossed the finish and my Watch said I had only run 12.1 miles. So I ran past the guy handing out finisher medals, grabbed my medal, and just kept going for one more slow, painful mile.

But when I finally stopped, I had completed an actual Half Marathon and I’m glad I did that even if it probably looked a little strange to everyone else at the finish line.

Of course, I’m still a little dinged up—my calf and hamstring are both strained—but I finished a Half Marathon and I got to experience a real-life figure of speech to boot.

Next time I hear someone say something like, “We need to go the extra mile here.”, I’ll know what that’s actually like.

Would I have tricked you with this Halloween costume?

As you can see, my friends and I go all out on Halloween—we do not mess around:

Wonder Woman Halloween Ensemble - 2017

That’s our ensemble costume from last year. I played Charlie, the military-looking guy on the right side (Wonder Woman’s left side). Friends and strangers alike have commented on how much I looked like Charlie, right down to his posture and facial expression.

That’s pretty cool!

But my appearance as Charlie was built on a dirty little secret…

I hadn’t even seen Wonder Woman and I had no idea who Charlie was before I put on the costume.


I did just enough to pull it off. Here’s what I did once we finished my makeup:

  • Watched a one-minute Wonder Woman clip featuring Charlie
  • Studied pictures of him on Google
  • Asked friends to describe Charlie to me

I didn’t need to be Charlie for Halloween, I needed to look like Charlie for Halloween, and I only had to keep it up for a couple hours.

In a weird way, I’ve built an entire business on this concept. My customers don’t need to be negotiation experts—that’s my job!—they just need to know enough to negotiate a job offer or two and then they can go back to their normal lives.

They can do this through self study or even hire me to coach them through it.

Maybe it’s time to update my coaching page to say “I’ll show you how play the role of ‘Expert Salary Negotiator’ next time you get a job offer”.