Losing More Than I Won

I’ve lost more than I’ve won.

In gambling, in life, in love, in decisions that felt right at the time but led me straight into the fire. I’ve bet it all—money, trust, pride—and watched it disappear more times than I can count. The worst part? Sometimes I wasn’t even surprised. Losing became so familiar, it felt like a part of me. Like maybe I was meant to lose.

But here’s the truth no one wants to talk about: losing teaches you things winning never could.

Every time I fell flat, every time I got knocked down, every time I walked away from a table, a relationship, a job, or a version of myself that just didn’t work anymore—I learned. I got back up. I dusted myself off. I started again.

I’ve lost sleep over mistakes. I’ve lost friends over pride. I’ve lost money, time, years I can’t get back. But in those losses, I found grit. I found humility. I found the will to keep showing up, even when nothing made sense.

Michael Jordan said it best:
“I’ve missed more than 9,000 shots in my career. I’ve lost almost 300 games. 26 times I’ve been trusted to take the game-winning shot and missed. I’ve failed over and over and over again in my life. And that is why I succeed.”

That quote used to make me mad—like, good for him, he’s Michael Jordan. But now, I get it. Losing didn’t make me less than. It made me more. More resilient. More self-aware. More determined to write a better story.

I don’t gamble anymore—not with my money, not with my peace, and definitely not with my future. I’m not trying to win quick anymore. I’m playing the long game. I’m finally winning at life. Not because it came easy. But because I failed enough times to learn how to win the right way.

And that is why I succeed.

-ryan