The Slow Burn: The Year I Stopped Trying to Win

I’m a goal setter and an achiever. An Enneagram 3.

If you’re unfamiliar, Enneagram 3s are wired to win. We measure progress. We chase results. We read the room, understand the scoreboard, and figure out how to climb it efficiently. We’re builders, performers, producers. Put a finish line in front of us and we’ll find a way to cross it…often faster than expected, sometimes at our own expense.

At our best, 3s are disciplined, driven, and relentlessly productive. We know how to turn vision into execution. We can carry responsibility, inspire confidence, and create momentum out of thin air. We’re the ones people call when something needs to get done.

But there’s a shadow side.

For an Enneagram 3, worth and winning can quietly become the same thing. Success starts to feel like oxygen. Approval becomes fuel. And without realizing it, you can begin performing your life instead of living it. You don’t ask, “Is this good for my soul?” You ask, “Does this move the needle?”

Loss becomes unacceptable. Rest feels irresponsible. Slowing down feels like falling behind.

And somewhere along the way, you stop knowing where the finish line is…because you keep moving it.

A while back, some buddies and I started a residential appraisal business.

This year, that firm was nominated as one of the top three appraisal firms in the entire country. We might even take the number one spot. I’ll know in a couple of weeks. Either way, it’s a legitimate achievement. The kind you don’t accidentally stumble into.

It took vision. Long nights. Hard conversations. Systems built from scratch. Hiring the right people. Firing the wrong ones. Carrying risk when the market turned sideways. Saying no to comfort so we could say yes to growth. There were seasons where winning required everything I had.

And I don’t regret that.

But here’s the tension no one talks about.

Achievement has a way of pulling you into the future. You’re always reaching for what’s next…the next milestone, the next metric, the next accolade. And if you’re wired like me, you start living one step ahead of yourself. You’re in meetings thinking about outcomes. At dinner thinking about numbers. On vacation answering emails you told yourself you wouldn’t check.

Presence, on the other hand, lives in the now.

Achievement asks, “What does this become?”
Presence asks, “Who is here with me?”

Achievement is necessary to build something meaningful. Presence is necessary to remember why you built it in the first place.

Somewhere along the way, I realized that winning doesn’t always feel like winning when you’re never fully there to experience it. The moment passes, and instead of savoring it, you’re already calculating the next move. The scoreboard updates, and you’re already chasing a new one.

That’s when I started asking a different question.

Not “How do I win more?”
But “What am I missing while I’m winning?”


And that’s why I’m calling this The Year I Stopped Trying to Win.

Not because I stopped achieving.
Not because I stopped caring.
Not because ambition suddenly fell out of my bloodstream.

But because I finally stopped letting winning define whether a moment mattered.

For most of my life, winning was the lens. I measured seasons by outcomes. Progress by recognition. Worth by forward motion. If something didn’t move the needle, it didn’t count. If a moment wasn’t productive, it felt wasteful. Rest was something you earned after the work…never something that belonged inside it.

That mindset built businesses. It also quietly stole moments I’ll never get back.

This year, something shifted.

I still showed up. Still worked hard. Still pursued excellence. But I stopped white-knuckling every outcome. I stopped turning every interaction into a transaction and every season into a proving ground. I stopped asking, “How do I come out on top?” and started asking, “Am I actually here for this?”

Because here’s the truth I’ve been slow to learn:

You can win the year and lose the moment.
You can hit the milestone and miss the meaning.
You can achieve everything you set out to do and still feel strangely absent from your own life.

Presence doesn’t show up on a scoreboard. You don’t get awards for being fully there. No one nominates you for the way you listened, or the way you stayed a little longer, or the way you resisted the urge to rush to the next thing.

But those are the moments that stay.

They’re the ones that settle into your bones. The ones that don’t need validation because they’re complete all on their own.

That’s the slow burn.

It’s choosing to sit with the cigar instead of rushing through it. Letting it evolve. Letting the conversation wander. Letting the silence breathe. It’s understanding that some of the most meaningful parts of life don’t announce themselves as important while they’re happening.

This year, I stopped trying to win every room, every conversation, every season.

And in doing so, I started noticing something better.

I wasn’t losing…I was finally living inside the moment instead of past it.

That’s what The Year I Stopped Trying to Win really means.

Not quitting ambition.
Not abandoning excellence.
But refusing to sacrifice presence on the altar of achievement.

Because the best parts of life , like the best cigars, aren’t conquered.

They’re experienced.

Light Up & Lean In.