Is This All There Is?

For twenty years, I had one goal sitting underneath every other goal: financial freedom. Not the number itself, but what the number would buy me — enough passive income that I never had to work another day if I didn't want to. That was the finish line, as I saw it back then. Full-time freedom.

In January of 2023, I got there. I stepped out of the last active role I held in one of our companies. Two decades of building, and I'd arrived.

I celebrated. Within a few weeks, the celebration went quiet.

It felt like I'd spent twenty years climbing a ladder, only to reach the top and realize I'd leaned it against the wrong building. It was colder up there than I expected, and lonelier too.

The question that followed surprised me: “Is this all there is?” Right behind it came a second one: “What's next?”

I'll confess, that second question rattled me more than the first. If I needed a “what's next” the moment I finally got everything I said I wanted, maybe the goal was never really the point. Maybe, somewhere along the way, I'd built my sense of worth on top of achieving things, and once I stopped achieving, I didn't know how to feel valuable.

I'm not a trained counselor, so I won't pretend I've fully worked this out. But here's what I've come to believe: if my identity depends on the next win, I will always need a next win. There's no version of “enough” that satisfies a worth built on performance. There's only ever a taller ladder.

For me, sorting through this has meant going back to something steadier than achievement — trying to remember I'm a beloved son before I'm anything I've built or earned. I'm not pushing that framework on you here. I'm just challenging you to consider whether the goal you're chasing right now is the destination itself, or another ladder against another building.

If you've hit a goal recently and felt strangely empty instead of settled, you're not broken, and you're not alone. You may just be finding out what I found out in January of 2023: freedom without a settled identity underneath it doesn't feel like freedom. It feels like standing at the top of a ladder, wondering why you're still cold.

What building is your ladder against right now?

Dave.