This week marks two full years since I left Stripe and started what in retrospect is a new (and likely) final phase of my career as an independent technologist. I didn’t quite know what that would entail at the time: it turned out to be a combination of founder (my work at Buttondown) and managing partner (my work at Third South).

I wanted to put to pen some notes and thoughts for folks considering a similar such change, loosely organized by topic that people tend to ask about:


Work-life balance is, in general, worse and harder than it was previously. This can obviously vary a lot from person to person or season to season — for instance, I could probably work ~15 hours/wk if I was happy to just subsist off of my current engagements rather than wanting to actively try and grow them — but independent work largely means eschewing the safety net that larger companies afford you. I am never more jealous of my friends in industry than when they talk about taking a multi-week vacation and setting an OOO reminder because they know their team can handle it.


That being said, work/life flexibility is at an all-time high. I work a pretty conventional schedule most days, but even then if I have a day that I’m not feeling 100% I know I can take it easy or rest or spend my time in the garden or whatever. (At a wider-aperture level, I get the privilege of structuring my day exactly how I want it: heavily skewed towards focus work, with only a single two-hour meeting block in the late afternoons.)


I am, without question, the most deeply creatively fulfilled I have been in my entire life. My work feels like an extension of my self and my ethos, in a way that feels more akin to an artisan; I feel an extremely large sense of pride and connection with what I produce and manage.


It is fairly lonely relative to the digital/tangible watercoolers that defined and enhanced my time at larger companies. Most of the online communities ostensibly geared towards folks in my position are overwhelmingly oriented towards salesmanship and transactional relationships; I’m grateful to the folks who I’m able to chat with about a variety of business and business-adjacent things (thank you, Nick, Sumana, Shep, and Jo!), but I find myself missing the sense of ubuntu and camaraderie that comes from being able to chat with dozens of people about a shared mission.


I have grown more as an engineer, operator, marketer, and craftsman in the past two years than in any other stretch of my life, bar none. There’s one bit I miss of being at a large company, which is dealing with deeply cutting-edge technical problems, but my ability to analyze information, make decisions, and perform at a high-level has grown very quickly.


It is really hard for me to offer a cogent, good-faith analysis that suggests independent work is, on average, going to bring in more money than working in industry. Buttondown is a very healthy and quickly-growing business, and even then its returns are less than if I had just sat in a ~750K TC FAANG-ish job for the past two years. [1]


In retrospect, this was probably the silliest concern I had when striking out alone. I don’t mean this to sound braggadocious, but I know (and most founders know) that if I decided I wanted to go back into the warm arms of industry I could send a few emails and end up a week later with a job at a company I admired.


Even after two years, I struggle with nouns. I've finally started to kick the habit of referring to myself introductions as "ex-Stripe"; I've never loved the word "founder" or "entrepreneur", both of which strike me as having vaguely startup-ish connotations that don't feel quite correct. Even over the past six months, I've realized that folks who I'm meeting for the first time think of me less as "plucky internet person trying something new" and more as "CEO of company" [2] which is — odd. I am realizing, even now, how much of my identity and sense of self was wrapped up with being X title at Y company, and how strange it is to lose both lodestars.

A few weeks ago, I grabbed dinner with an old friend visiting from Seattle. We were chatting about how our careers had diverged over the past half-decade, and they commented:

It’s really impressive that you spent so much time when you were 25 about doing this and then you just did it. I feel like there’s so many people who joke about leaving tech and buying a farm or whatever and, you know, obviously you didn’t do that, but you still committed to a big change. How did you take the leap?

The answer I gave him — and that I’ve given a few other friends and acquaintances — was this:

When I decided to pursue independent work, I was 29 years old, with no children, a loving spouse (who was bringing in money!), a good amount of savings, and projects that I was actively excited about.

The conditions were perfect, and yet I still didn’t feel ready — my life was good, I liked my job, and it felt very risky to rock the boat and throw away what was a very good and comfortable lifestyle in favor of something new.

And yet. I knew I wanted to try something else eventually. And I kept asking myself: if not now, when? Certainly it would be harder to give up things like health insurance and a steady paycheck once I have children; certainly it would be harder to spend entire days in flow ten years from now than it would be today.

And so. It quickly became obvious in my mind that if I wasn’t going to try going independent now, then I might as well extinguish the thought forever, as the conditions for such a move would literally never be better than they were today.

And I really didn’t want to extinguish the thought forever — my dream for over a decade had been to live my life on my own terms.

And so I quit my job, and here we are.

All of this is to say: creative independence is not for everyone. My experiences may not — probably will not! — reflect yours, and my circumstances and context are probably different than yours.

But if you think it might be for you — if not now, when?

I would be remiss if I didn't end this essay with a deep note of gratitude to my wife who more than any single person pushed me to take this jump, even though it meant she'd have to deal with me being even more insufferable than I already am.

  1. This, by the way, is a good shibboleth for if a person writing online about their experience is full of shit — if they’re suggesting you should do this for monetary reasons, chances are they’re trying to sell you a course. ↩︎

  2. Albeit an idiosyncratic one! ↩︎

Lightning bolt
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