How We Leveled Up
BestSelf turns ten this year.
I've been wanting to write this email for a long time. I kept waiting until I had something wise to say about it. Until I had the right framing. Until it felt less like I was just… admitting things out loud.
There's a saying that you'll overestimate what you can do in a year but underestimate what you can do in ten. I've never felt that more than right now, looking back.
When I came out with the idea for the Self Journal, I didn't think I was building a company. I just wanted a product to exist. Something I couldn't find anywhere else. I figured I'd make it happen somehow and see what came of it.
And then I've just been figuring it out as I go along. That's the whole story, really. Ten years of figuring it out. Still doing it. Still learning. Still staying curious about what's actually needed, what's actually working, what I'm actually getting wrong.
That's the thing nobody tells you when you build something for a long time: you don't accumulate certainty. You accumulate more experience with how much you don't know.
Had I known what I was getting into, I'm not sure I would have started.
I'm glad I did. But I want to be honest about that.
There's the version of this company people see publicly: Inc. 5000, Shopify Build a Business finalist, products in the hands of people we really admire, collaborations and opportunities I couldn't have imagined when I was trying to figure out how to ship a journal. That part is real.
The private version is real too. A business partner who held 50% of the company for three years after he'd mentally checked out. An inventory manager I found out was embezzling. Late nights that didn't feel entrepreneurial; they just felt scary. A marriage ending in 2017, the same year the company looked from the outside like it was thriving. Container costs going from $4,000 to $24,000 overnight. Selling to private equity. Buying it back when they nearly ran it into the ground.
Both of those things are true. I wanted to say that plainly.
Leveling Up
Here's the frame that's helped me make sense of it: I think of building this company like leveling up in a video game. If I'd been dropped into the problems I'm dealing with now right at the start, I wouldn't have lasted. I didn't have the skills, the resilience, the pattern recognition. I would have quit.
But you don't face the hard problems until you've already leveled up enough to handle them. Every year of this company made me slightly more equipped for what came next. The embezzlement happened after years of building. The private equity situation happened when I finally had enough context to fight for it and win it back.
I'm still leveling up. I still don't know what I'm doing in a lot of ways. And I've stopped treating that like a problem to solve.
What Actually Kept Me at It
What I did learn, the thing I think actually kept me at it, was to stay curious. About what customers actually needed. About what wasn't working. About what would happen if we tried something different.
At some point we made a shift from being a product company to being a problem company. The question stopped being "what should we build next" and started being "what problem actually needs solving, and does it even need to be a product?" That reframe changed everything.
- The Self Journal came from one question: how do I follow a framework to actually achieve my goals? I couldn't find a planning system that fit how my brain worked. I got an ADHD diagnosis in 2018; it explained a lot. So I built one.
- The Intimacy Deck came from a different question: how do you create a framework that feels like a game, that makes it easy for couples to build real intimacy and strengthen how they communicate? Not a workbook. Not therapy. Something that felt like play.
- Helm came from watching my relationship with technology get worse after COVID and not being able to look away from it. I remember my daughter picking up random things around the house, holding them to her ear, pretending they were a phone. I put my phone down that day. Then I built the thing that makes it easier to keep it down.
- The Self-Discovery Deck came from wanting a structured way to actually figure out who you are; not in a therapy way, but in a "sit down, go through these prompts, and come out the other side knowing yourself better" way. 100 cards, 200 prompts, five phases. It's the most personal thing we've made.
- Helm macOS; I'm using it right now to write this email, after procrastinating on it for way too long. It goes both ways: block what you're trying to avoid, and then there's Mission Mode, which is my personal favorite. I haven't seen anyone else doing anything quite like this.
We didn't plan a product line. We just kept following the problems.
Ten years in, I can finally see it as a complete picture: know yourself, plan yourself, protect your focus. Three things. We built all three by refusing to stop asking what was actually getting in the way.
That's what learning does. It keeps you from getting stuck in your own answer.
If I'm being honest, "trying to" was the version of me that almost broke all of this.
Trying to have it figured out. Trying to grow fast enough. Trying to look like I knew what I was doing when I was terrified. Trying to hold things together that probably needed to fall apart.
Learning is different. Learning assumes you're going to be wrong. It means you can pick up what you got wrong and actually do something with it, instead of defending it.
I didn't fully understand that distinction until maybe year six. Cost a lot to get there.
Here's what I'd leave you with:
If you're building something (a company, a project, a version of yourself) and you're waiting until you know what you're doing before you go all in, you might be waiting a while.
The people I've watched do this well aren't the ones who figured it out. They're the ones who stayed learners. Who treated every hard thing as data instead of evidence that they shouldn't be there.
