When I was 21, I promised myself that I’d be working on my own company before 30. I didn’t feel ready at the time (and, in hindsight, I definitely was not … skill issue).

Now, 9 years on, I’ve fulfilled that promise. I recently turned 30[^0], and I’m a year into building Tanagram. Although it’s so much harder than anything I’ve done before, my younger self was right — this is exactly what I want to be doing with my life.

A few things I’ve learned in the past year, in no particular order:

Following your interests is freeing

Tanagram’s problem space — making programming easier and more “obvious” — has been a multi-year area of interest for me. It feels really good to spend my brain cells on this one thing, rather than splitting focus between this and a day job. Now, everything mentally or creatively hard I do is in service of the “right” thing for me, which makes it easier to justify that effort. Similarly, if I’m looking for something to do, there’s always something on the backlog that gets me a bit closer to my long-term goals. Life is a lot simpler this way.

Founder-market fit is key

I wouldn’t have started a company if this wasn’t a problem I experienced first-hand and felt deeply compelled to address.

It’s definitely possible to deeply and rapidly learn about a space in which you have no prior experience and build a company around it, but 1) I don’t think I have the intellectual capacity for that, 2) I certainly wouldn’t have gotten as far as we have so far without my story, and 3) it is much easier to find intellectual stimulation, without the downsides of running a startup, at an existing company.

The first few months of Tanagram were a meandering discovery journey. I didn’t know what specifically I wanted to build, but had enough of a gut instinct to know it when I saw it. A lot of what we’re doing now comes from intuition — we are users of our own product, and limitations in our product bother us. That’s extremely valuable product feedback.

Don’t LARP, don’t grift, and don’t lie to yourself.

Ride the rollercoaster

Some moments, I feel great and energized and we’re inevitably going to make it. Other moments, I feel like nothing is going well and nothing is happening fast enough. These moments can be days, hours, or minutes apart.

At the micro level, these feels don’t necessarily reflect (and they certainly don’t change) my object reality. Just keep going.

Bias towards intensity (but pay attention to energy)

If I do something intensely, I feel better afterwards knowing that I gave it my all. This is a lot more satisfying than doing everything at a chill/relaxed/“sustainable” pace all the time, because the latter always leaves me feeling like I could’ve done more, and that is a draining feeling.

A single big, hard goal is a lot more satisfying (and makes me more productive) than multiple smaller goals. I feel compelled to continue tilting at a goal until it’s done (whereas I’m inclined to take a break after achieving a goal), and a big goal allows me to carry that momentum for longer.

Understanding my energy levels is important to actually make this sustainable. There’s more flavors to energy than just tired or not. I always feel physically restless (and extremely impatient, to an unproductive extent) by early afternoon; the only remedy is a morning workout that gets my heart rate up. After a week or two of intellectually-complex work, my thinking mind will be tired, but the primal exertion of a 15+ mile hike (or 30k+ feet ski day during the winter) will reset that. Some evenings my mind and body are just tired enough to avoid over-thinking, but lucid enough to connect disparate ideas and unblock creative challenges (hopefully not too close to bedtime though, or else I’ll lose sleep).

Keep people close

In relationships, friends, and coworkers (there may be some overlap), focus on people who you enjoy being with and who enjoy being with you. I didn’t realize how important that reciprocity was until embarrassingly recently.

A big part of enjoying being with someone is feeling comfortable around them. Some of this is intrinsic — if someone doesn’t have a sense of humor or takes everything seriously, I likely won’t feel comfortable around them. But in other cases, it’s often a function of time and shared challenges, and I can take the initiative to accelerate this.

Be the person who makes (or finds) plans and regularly invites people to them. Assuming your friends like you at some baseline level, it won’t be annoying; they’ll appreciate your initiative.

It does help to be socially well-adjusted and attuned to how people feel.

[^0]: I woke up that morning to an ache in my knee. The tropes are true.