Re-entering the Arena

Reflections on 2022, and towards a more ambitious year ahead.

It is not the critic who counts; not the man who points out how the strong man stumbles, or where the doer of deeds could have done them better. The credit belongs to the man who is actually in the arena, whose face is marred by dust and sweat and blood; who strives valiantly; who errs, who comes short again and again, because there is no effort without error and shortcoming; but who does actually strive to do the deeds; who knows great enthusiasms, the great devotions; who spends himself in a worthy cause; who at the best knows in the end the triumph of high achievement, and who at the worst, if he fails, at least fails while daring greatly, so that his place shall never be with those cold and timid souls who neither know victory nor defeat.

—Theodore Roosevelt, “The Man in the Arena”

2022 was a good year.

I want to get that out of the way, because much of what follows could be construed as complaining, but it’s really not.

Life is good.

In 2022 I earned more money than I have in my entire career—almost entirely from my own businesses. I was able to take a two-month family holiday without any professional consequences. I surfed 48 times and ran nearly 1,000 miles. I watched my kids continue to grow into wonderful, fascinating little creatures.

Last Run

The view from my last run of the year. Among my good fortunes is living in a hell of a beautiful place.

Yes, I turned 40 and that stung a bit. Yes, my body seems to be falling apart at a rate that outstrips my increase in physical activity, so I’m getting slower on the trails and catching fewer waves every day. Yes, my kids wake me up earlier than I want and leave me completely exhausted at the end of every day. And yes, I worry that maybe I’ve stagnated, professionally.

But before getting into that last part, I thought it was worth taking a moment to appreciate what I have.

In this—my sixth year-in-review1—I reflect on my past year, and talk about how I hope to tackle the remaining shortcomings in the year ahead.

2022 in review

First, a short review of the year.

The plan

My plan going into 2022 was to work on two major projects. SaaS Pegasus—my Django SaaS boilerplate—would be my main source of income, and Project Griffin—a name I chose for an amorphous attempt at do-gooding—would be my main source of impact.

I aimed to prioritize these projects equally, and thought that if I could keep up the progress I’d made in 2021, I’d be happy.2

Pegasus chugged along

With Pegasus, everything went roughly to plan.

I invested in it consistently throughout the year, and the results were good. My customers are happy and business continues to grow. I no longer publicly share my profits, but they’ve been solid—more than I need to live on, which is basically all that matters.

Glowing review

I set up TrustPilot this year, and glowing reviews like this one are one of the most rewarding parts of building Pegasus.

The biggest change of the year was onboarding a second developer onto the project. Together, we were able to ship features big and small, and make major improvements to the codebase and surrounding infrastructure.

The end result is that both Pegasus-the-product, and Pegasus-the-business are in a substantially better place than they were a year ago.

Griffin flopped

In contrast to Pegasus, Griffin was…a failure.

It wasn’t for lack of effort—at least in the beginning. I spent a lot of time on Griffin. I read a lot, consumed a lot of podcasts, drafted and discarded a lot of writing, and even built and discarded an entire product!3

But, around mid-year, I just…stopped.

Griffin time in 2022

My time spent on Griffin over the course of 2022. By mid-year I’d all-but stopped working on it.

I stopped for several reasons:

First, I got completely overwhelmed by the problem I’d tried to bite off—which eventually ballooned into something like “fix polarization, media and online discourse”. It was too big, and I had no idea how to even make a dent in it. I could barely define it!

At the same time, I lost interest. To some extent, this was a result of succeeding (not alone, but as a movement) in winding back some of the things I had grown most concerned about—specifically, divisiveness and authoritarianism around Covid. With the acute Covid era closing and life returning to normal, my motivation to work on the underlying societal causes fell away.

Finally, mid-year, Pegasus was struggling—and I realized that investing in my livelihood had to take priority over…whatever it was I was doing with Griffin.4

I never officially sat down and said I was giving up on Griffin—it kind of just…petered away. In practice, I quit. I quit because it was too hard, and I didn’t care enough anymore. And somewhere in the back of my head I was at peace with that.

No pain, no gain

So Pegasus chugged along with steady, incremental progress, and Griffin got hard and I bailed. Overall, things were good, but there was a big missing ingredient: risk.

With Pegasus things are stable. I add features, fix bugs, do marketing, and poof! That’s a month. Yes, it’s work, but I know what I’m doing. It’s predictable, and—to some extent—easy. It’s comfortable.

Griffin was supposed to be my opportunity for growth last year—only…I gave up.

Combined, this meant spending the year almost entirely in my comfort zone. I had a nice time, made some money, and, ultimately, stagnated.

And stagnation sucks. I may be middle-aged, but I’m not ready to stop learning new tricks.

Motion is life. Stagnation is death. Japanese Proverb (according to ChatGPT)

I’m actually unclear whether this is a real proverb. Hello, confusing AI future.

Fighting stagnation

This coming year I’d like to keep the good things going, but overcome some of the stagnation I felt in 2022.

I’ve come up with three ideas to help with this.

Re-entering the arena

The best antidote to stagnation is to keep being challenged. To be “the man in the arena” from the quote at the beginning—striving for “high achievement”, and “failing while daring greatly”. To take bigger risks, shoot for bigger successes, and expect bigger failures.

“Re-entering the arena” is the first and most important idea I hope to bring to next year. If I’m not scared or uncomfortable or likely to fail with at least some of what I’m doing, then I’m not pushing hard enough.


Thankfully the arenas I operate in are a bit more forgiving than his.

With Pegasus and my businesses I think I know what being in the arena looks like, but with Griffin I don’t.

This presents an interesting wrinkle. I want to enter the arena only…I don’t even know which arena, or where it is.

How do you enter an arena that you can’t even find?

It’s basically the same question that caused me to give up on Griffin last year. To help fight it, I’m bringing in two more ideas.

Bias for action

Bias for action is one of Amazon’s leadership principles. Here’s how they phrase it:

Speed matters in business. Many decisions and actions are reversible and do not need extensive study. We value calculated risk taking.

My interpretation of it is “any action is better than no action”. Doing something, anything, is better than evaluating options, deliberating, and so on.

I spent a lot of time last year reading, learning, talking—-trying to figure out how to do something useful with Griffin, without actually doing much of anything. Looking back, I wish I’d just tried more stuff.

A bias for action puts you in some arena, even if it turns out to be the wrong one. I’ll try to make it my default mode of operation.

Accruing career capital

Career capital is a concept I first learned of from 80,000 hours. They define it this way:

Career capital is anything that puts you in a better position to make a difference in the future, including skills, connections, credentials and runway.

It’s basically skills and tools that set you up better for future success.

If you don’t know your plan, building up career capital is a great fallback. You can think of it like a savings account for your career. You build it up, tuck it away, and then spend it once you figure out your plan. The more career capital you have, the more effective you’ll be at whatever you ultimately choose, and so building it up is always useful.5

Building up career capital is another workaround to the “finding the arena” problem. If you can’t find the arena, might as well practice your swordsmanship, so you’re better prepared when it comes. Or, as a wise person once said: “if you don’t know where to invest yourself, invest in yourself.”6

Getting concrete about 2023

After all that philosophizing, I can finally say something about my plans for 2023.

Taking bigger swings with my businesses

On the business side of the house, “re-entering the arena” means taking bigger swings. This gives me two main business goals for the year.

The first is to shake things up with Pegasus. I have some big changes planned. Things I’ve been putting off for a while, for fear of messing up a good thing. I won’t get into details, but I’m excited and nervous to see how they play out.

The second is to launch a new revenue-generating product. It’s been three and a half years since my last successful product launch (SaaS Pegasus). I’m long-overdue for another one. And there’s nothing more “in the arena” than starting over from zero.

Expanding my reach

So I’ve decided to stop proactively working on Project Griffin. I just don’t have a plan of attack, and my heart’s not in it anymore. Rest in peace, Griffin.

RIP Griffin

Griffin is survived by its father Cory, and its brother, SaaS Pegasus.

In Griffin’s place, I’m hoping to build career capital towards some future, yet-to-be-defined, impact-oriented goal. And specifically—as icky as this may sound—I’m aiming to expand my influence.

Why influence?

For starters, it scales. Influence—which I’m defining as some combination of 1) the number of people I can reach, and 2) how much they care about what I say—is the only asset I can think of that doesn’t hit bottlenecks for a single person as it grows. Publishing an essay or a tweet or a TikTok is the same effort for me, regardless of how many people it reaches.

It’s also the asset that aligns most with how I expect to channel my energy in the future—which, according to my best guess, is through some combination of product-building and communication. Heck, it’s already an indie hacking cliché: build an audience before you build a product.

Finally, it’s aligned with my growth goals. I’d like to be a better communicator. I’d like to have better, clearer ideas. I’d like to be more engaging. And, to use another business analogy—just like the best form of marketing is to have a good product, hopefully the best form of influence-acquisition is to create good content. Exactly what I want to get better at.

For now, I’ll focus on writing.7 My concrete goal is to publish at least six pieces of content I’m proud of this year.8 If people like it, the newsletter subscribers and Twitter audience should follow. If they don’t? Well, at least I’ll have tried.

The author closes his eyes. He smells the dust kicking up from his boots. Hears the hum of the crowd pick up as he draws closer. He takes a few steps forward, and emerges from the long, dark tunnel into an explosion of light and sound. The chaos of the arena is all around him. He brushes his hands together, looks around, and smiles.

It’s good to be back.


As always, if you’d like to see how all this goes, you can subscribe below or follow me on Twitter.


  1. For a recap, here’s 2021, 2020, 2019, 2018 and 2017

  2. For a complete outline of this plan, see last year’s review

  3. A tool to let you adopt someone else’s Twitter timeline. You can read more on my Twitter thread about building it here

  4. Mostly reading, listening to podcasts, and getting depressed. 

  5. Technically, the earlier in your career you are, the more useful career capital is. Picking up a new skill on your deathbed doesn’t help much—though I bet it still feels good. 

  6. Ok…it was me, yesterday. I thought it was a clever turn of phrase. 

  7. I’m also going to experiment with video on my YouTube channel. This is slightly terrifying, because I’m a huge introvert and generally consider myself to be pretty underwhelming in person. But hey, you miss 100% of the shots you don’t take. 

  8. I haven’t decided if this one counts towards the goal or not. It will probably come down to whether I need to fudge the numbers at the end of the year.