This Doesn’t Look Like Winning

I’ll be honest. Writing has been hard lately. I haven’t felt creative and I am not sure why and I know it shows in these recent editions. But here I am getting in another rep. Learning each and every week.  

I also realize now, after writing this, that I said I was going to write about my plans for Forged Fitness this week. My bad. Next week, I promise. It’s something I’m truly excited about and as I type this, it may just be the creative spark I’m looking for. 

Some days it sneaks up on me

My alarm went off this morning, and instead of jumping out of bed, full of piss and vinegar to get the week started, I hit snooze.

Then I hit it again.

And then I rolled over and held Kallie tightly.

She didn’t know it, but in that moment, that was the only thing I could do to soothe the heaviness that had crept back in. That broken feeling that shows up now and then. Quiet but loud. Unwelcome, but familiar.

It’s easy to share the highlight reel. And don’t get me wrong—there’s plenty to celebrate right now. Josh and I just bought property number five for Land Stream Capital, with three more in the pipeline. Baby shower is coming up Saturday. Bills are paid. Our family is healthy. We’ve got a beautiful, full life.

And yet.

That broken feeling still slips in more often than I’d like.

Eventually, I pulled my ass out of bed and got the day started. I stepped outside before dawn and sat on the front porch. Cool breeze off the lake, quiet air, just me and my thoughts.

And the question came:
Why do I feel this way when I have so much to be grateful for?

So I did what I always do—I started to analyze.

Truth is, last week was a good one. Discipline was moving in the right direction. Business was moving. Nutrition, workouts, jits, good convos—I felt aligned. Until Saturday.

That’s when the move started. Not to our 100-acre property in Tennessee, but from the garage apartment into my mother-in-law’s house. She offered more space for when the baby comes. It made sense. But something in me resisted.

I didn’t realize it right away. But by Monday morning, it hit:
I’m about to be 39, living with my wife, our newborn, and my mother-in-law.

That wasn’t part of the original plan.

A few years ago, we had our own home, two paid-off vehicles, and six figures liquid in the bank. Now, here I was—feeling tired, not physically but emotionally. Like I was where I was supposed to be. And I hated that feeling.

At one point this morning, I even caught myself thinking…
Maybe I should just get a job again.

That’s when I knew I had to reset.

Because I’ve been here before.

And every time, I have to remind myself:
I chose this.

I could’ve stayed at Progressive. Climbed a few more rungs. Made a quarter mil a year. Retired with a 401k and a hollow sense of “I did everything right.”

But I knew that wasn’t the life I wanted.

So we made some really hard decisions. We sold the cars. Rented out the houses. Moved across the country. Away from my parents. Away from all of our friends. Cut our expenses and burned the safety net.

We made these decisions to build something better. Something slower, richer, freer.

And yeah, I may not have as much liquid cash as I did in 2023, but our net worth is up 45% since then. And yeah, I may life in my mother-in-laws house. But we have two homes in Ohio that make us money every month. We’re healthy. We’re stable. We’re on track. And most importantly, we’re still in the game.

Here’s the truth:
These choices weren’t steps back.
They were steps out—out of the cultural narrative of what life should look like at 39.

I’m not where they are, because I’m not playing their game.

And this season? As uncomfortable as it can be, it’s necessary. It’s forming me. Refining me. Preparing me.

So no, I won’t get a job.
I’ll get to work. Which is exactly what I did this morning after my internal dialogue. My process. 

Because whenever I feel this way I process it and remember that aligned action always makes me feel a big sense of relief. 

And I wouldn’t trade it for anything.

As always, thanks for reading,
Kyle

Song of the Week
“Head Full of Doubt / Road Full of Promise” – The Avett Brothers

There’s a line in this song that always gets me:
“Decide what to be, and go be it.”

Simple. But damn if that isn’t the whole game.

This week, I needed that reminder. That the doubt, the fatigue, the second-guessing—they’re part of the road. But so is the promise. The promise of what this life could be if you keep showing up.

Put this one on when you’re up early, working through the fog, trying to remember why you started. It’ll land.