My 20s: How I Started With Nothing, Had Everything, And Lost It All

I did lose myself completely.

There’s a moment I come back to a lot.

It’s a normal weekday night. My 400 square foot apartment is silent - not the peaceful kind of silence.

I’m lying on the couch, looking around at my new home, wondering if I’ll ever have the answers I’ve been looking for. Marriage over. My first house, no longer mine.

At this point, I had no idea who I was anymore. And more importantly, I didn’t know who I wanted to be.

I had it all — and I lost it.

That moment was two and half years ago.

The Rise

I came into my 20s with nothing but ambition, energy, and this relentless itch to build. To create something that was mine. I didn’t know exactly what that meant yet, but I sure as hell knew what failure looked like, or my perception of it — and I was determined to run in the opposite direction. Nothing had really beat me down to this point in my life, I was incredibly lucky.

I did jobs nobody wanted. First one in, last one out, skipped weekends, said yes to everything. From professional sports to live events to launching three businesses— I was always moving. Trying to make things happen.

And it worked.
By my late 20s, I was the guy that “had it all figured out.”

The Peak

I had multiple businesses running. I was sharpening my skills with a corporate sales job (that I didn’t even need anymore), my calendar was full. My bank account wasn’t empty. I had dogs, a house, a wife. A plan. A future that looked like everything I used to think I always wanted.

My network was growing like crazy.
I felt important. I was slammed, but in a good way.

Looking back
Sometimes, what looks like “having it all” is simply, empty.

The Fall

August 2022 through July 2023 — I call it The Lost Year.

That was the year everything fell apart. And I mean everything.

My marriage ended. I left the first house I ever bought, I left my dogs, I left my inner circle of friends and family.

Everything I thought I knew about who I was unraveled. I kept trying to show up — for work, for friends, for family— but inside, again, emptiness.

It’s wild how quickly your world can shrink. One minute you’re buying properties and building brands; the next, you’re avoiding your own reflection and wondering how the hell you became a stranger to yourself.

I lost more than a relationship, a family, and a house.
I lost my footing.
And honestly, I didn’t almost lose myself. I did lose myself completely.

The Wake-Up

Pain has a funny way of breaking you open.

In the darkest days, I found something I never had in my so-called “peak” — A weird form of clarity that I had never experienced before.

Not instantly. Not easily. But over time, through being alone, writing, reading, uncomfortable conversations, and showing up even when I didn’t want to.

I started rebuilding — not just businesses, but my self.

I realized success without self-awareness is a ticking time bomb. (better late than never, huh?)
I learned who really had my back when I wasn’t “on.”

And most of all, I found a new kind of ambition — not for validation, but for realizing true fulfillment. And I don’t mean finding small, temporary moments of inner peace - sure that helps- But I mean the realization and clarity that comes with really looking at your situation as it currently is, without judgements, and without emotions.

That’s clarity.

The Now

Today, I’m still building. But it’s different. It’s not about chasing “everything.” It’s about creating what matters. Living cleaner. Thinking deeper. Being honest with myself, even when it’s not easy.

I’m building something that lasts — but I’m not measuring the way that I used to, because nobody ever wins when they are constantly chasing a finish line that keeps moving away from them.

If you’re in your 20s, here’s my advice:
Don’t confuse the highlight reel with the real thing.
Don’t build for the likes — build for the long haul.
And don’t be afraid to lose it all — sometimes that’s how you find what you actually needed.