The Hagakure #85: In The Trenches

A New Chapter for The Hagakure

Six months ago, I started a new role as a startup CTO—and threw myself completely into the work.

After three years spent coaching others from the sidelines, jumping back into the fray wasn’t just a shift—it was a shock. I had to relearn the pace, navigate the ambiguity, and face the constant, familiar, and largely self-inflicted pressure to deliver.

Historically, every time I’ve taken on a full-time role, The Hagakure has gone quiet. This time, now that I’ve found my footing, I want to try something different—sharing what life as a startup CTO is really like, at least from where I’m standing.

There’s no shortage of content out there on these topics—how-tos, guides, and polished advice created for the sake of “content.” That’s not my aim. I don’t have it all figured out. I’m in the thick of it, figuring it out as I go. If you’re up for it, I’ll take you along for the ride—the good, the bad, and the messy in between.

If you’ve ever wondered what it’s like to lead in a role like this, stick around—I’ll be sharing more in the next few posts. And if there’s something specific you’re curious about, let me know in the comments.

It’s good to be back.