Great Falls outside of Washington DC

in Year in Review

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

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

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

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

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

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

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

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

2021 Goal review

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

Increase business revenue by 50%

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

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

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

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

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

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

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

Be more generous

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

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

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

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

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

Small things. But targeted specifically to their needs.

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

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

2021 Year in Review – Business

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

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

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

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

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

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

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

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

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

Revenue by month for my career so far

Ok, let’s look at some stats.


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

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

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

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

Coaching revenue

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

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

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

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

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

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

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

Product revenue

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

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

2021 Year in Review – Personal

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

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

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

Pickleball mania

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

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

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

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

The Pickle Palace
Working on blocks with the Tutor

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

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

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

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

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

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

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

New boots in Breck

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

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

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

80s Day
The best house we’ve ever rented

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

RV trip

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

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

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

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

Great Falls outside of DC

New kitchen and other home improvement

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

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

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

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

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

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

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

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

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

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

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

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

My kitchen before the remodel
My kitchen after the remodel

New friends

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

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

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

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

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

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

The annual Manor Christmas Party

Less disc golf and running

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

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

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

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

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

Tried yoga for the first time

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

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

2022 Goals

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

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

Build and launch a new salary negotiation course for software engineers

I think it’s time.

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

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

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

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

Increase business revenue by…50%?

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

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

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

Get to a 4.0 level in pickleball

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

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

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

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

Ski the top of the mountain at Breck

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

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

Travel more (for real this time)

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

Something something cooking?

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

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

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

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

Be more generous

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

Summing it all up

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

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

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