The Most Difficult Thing I've Ever Done - Starting a Company

Years ago, I wrote a post calling the writing of my first book the most difficult thing I've ever done. I meant every word of it. Today I have to walk it back.

Starting a company has taken the title.

The book was a solo slog. The hardest part was never the writing itself, it was motivation. I likened it back then to a hard workout: you push through one set, then another, until at some point you break and rest, and the rest starts to feel so good that getting back up becomes the real battle. However, for all of that, the worst case scenario was small. If I quit, I simply wouldn't have finished a book. The stakes lived almost entirely inside my own head: my pride, my grit, the fact that I really don't like quitting.

The stakes for starting Odo feel different. I uprooted a startling amount of my life for this, moving from Denver to San Francisco, and every month I spend here is a month I'm not spending on some other life or career I could be building instead. The stakes are real, and they're mostly mine. But the part that actually wears on me isn't the dramatic fear of it all falling apart. It's quieter than that. It's the stretches where I can feel something isn't working and haven't admitted it to myself yet.

I'm already two pivots in. We built a tool for product managers that turned out not to solve a problem anyone really had. Then we built one for finding and winning government contracts, which did work, just not fast enough to grow into what we wanted it to be. Both times, the hardest part wasn't the pivot. It was the limbo before it. And both times, the moment we finally said it out loud, the dread broke. What was left was relief, and the excitement of getting to think about the next thing.

So why stay on the ride?#

Because I finally get to do this the way it was never possible before. For years I tried to build Notecards, a study tool, in the cracks between client work. I was alone, with nobody to drive me but myself and my bills insisting I focus on someone else's problems instead. Now I get to build full-time, and I'm not doing it alone. My cofounder Yooni is in it with me.

Those years on the side also never gave me room to learn what I actually love about this. It turns out it's the building, watching people use the thing and getting to talk to them about it. Plus the strategizing. And it's emphatically not the nitty-gritty business of keeping a company running. You only find that out once you finally get to do all of it.

Here's the part that still gets me. At the very end of that book post, burnt out and certain I'd never write another one, I wrote that I'd stick to the things I love: writing blog posts, and most of all, developing apps. Years later, that's almost exactly the life I went and built for myself, just with much higher stakes. Odo is me getting to do the thing I said I loved, full-time, for real. It's easy to forget that during peak stress, but as cliché as it is, it truly is a privilege.

What I'm Taking From This#

The book taught me I could grit my teeth and finish something that hurt the whole way through. For a long time I thought that was the lesson hard things had to offer: proof that you can push through them.

This is harder than the book was. But I'm not doing it to prove I can endure something hard. I already know I can. I'm doing it because, even as the most difficult thing I've ever done, it's still the thing that lets me spend my days building, and still lets me dream as big as I want to.

That's also why I'm writing here again. The book was hard enough that blogging was the first thing I dropped when life got full, and somehow it stayed dropped for years. This time I want to bring you along while it's still happening, the doubt and the pivots and the building, instead of writing it all up safely from the other side.

The book left me with a stronger grit muscle. This is leaving me with something I wanted more: the room to keep building, and to keep dreaming big.