Sixty Years of Firsts and I Still Get Butterflies

We Don’t Have This Figured Out. That’s Most of the Fun

I was eleven years old, standing at the top of a hill that looked like a mountain. The bike was a little beat up, and the roads were wet from the rain. My stomach did that thing—the pit, the tightness—and I pushed off anyway.

Broken bones. First concussion. And weirdly? I’d do it again.

Here’s the thing about firsts: they never get easier. You just get more familiar with the feeling. Sixty years of life, 18 years running a business, and I still get that pit in my stomach before something uncertain. The butterflies still show up when it works.

I’ve watched the world shift from analog to WWW to AI. Each time, the same question: Will this work? Each time, the same fear dressed up in new clothes.

But I’ve also had people see something I couldn’t yet see.

The teacher who noticed my struggles wasn’t about the lessons—they were about boredom. The employer who trusted me with remote work before anyone called it that, and let me run with it. The clients who hired me when I was brand new, and the ones who’ve stuck around for years. Those moments weren’t about having it figured out. They were about someone saying, “Let’s see what happens.”

Now I watch opportunities multiply because technology—and AI—have leveled the playing field in ways we couldn’t have imagined. We’ve got influencers, vibe coders, and genuine risk-takers building things that would’ve been impossible a decade ago.

But here’s the kicker: it’s still not smooth sailing.

I wrestle with what to do with WP Site Success and how DigiNav Compass fits into it. Part of me wonders if I should retire one for the other, chase what’s next. But then I remember the people who still need my brain—not for the shiny new thing, but for the thinking that comes from 18 years of showing up.

It’s not all or nothing. It’s figuring out how to make the best parts fit.

The overwhelm is real. The ethical questions about all this tech keep me up some nights. The challenge of staying human in a totally connected world? That doesn’t have an easy answer either.

And this space—this little corner I’m carving out—isn’t about the experiments or the new rules of business. It’s not “you should be doing this” or “that was so yesterday.”

It’s messier than that.

It’s brain dumps and nostalgia. Things that work outside of business and software. Lessons learned from missteps and the “holy crap, I did that” celebrations.

Because here’s what I’ve figured out after 60 years of firsts: we don’t have this all figured out. Taking steps toward it is most of the fun.

That pit in your stomach? It doesn’t mean you’re doing it wrong.

It means you’re doing something that matters.

And the butterflies when it works? That never gets old.