By Joe Byerly
Before I had kids, I used to enjoy placing bets.
I played blackjack at Caesar’s Palace in Las Vegas when I was stationed out on the west coast. I threw down friendly wagers on the game at Super Bowl parties. When I lived at Fort Knox, I even bet on horses at the Kentucky Derby—I wish I would have put my money on Giacomo in 2005. I didn’t.
It’s been years since I’ve stepped foot in a casino or won and lost cash at the track.
I’d like to say I don’t gamble anymore—but that’s not exactly true.
Because eventually, I had to place the scariest kind of bet there is: Betting on myself.
I’ve seen others do it—and hit it big.
I’ve also heard the stories of those who lost everything.
A friend of mine dropped out of college as a freshman to chase a fleeting opportunity. Today, he’s a bestselling author who’s sold millions of books. When you hear his story, it sounds bold—like he went all in and the cards fell just right. But if you ask him, he’ll tell you the truth: it was terrifying. He nearly broke down more than once. But it worked out.
Betting on yourself is a little terrifying.
In 2024, I took my chips off the military table—a table where I’d spent two decades building a strong hand—and moved them to a table of my own.
Here’s the bet I placed: that I could build a life for myself and my family where I wake up every morning, love what I do, and be fully present in their lives.
I was betting on something more valuable than some big payday or even fame—I was betting on the quality of life itself.
When people ask me about that decision, I sound a lot like my buddy: “It was an easy decision to make—but scary as hell to live with.”
Unlike the roulette wheel, the horse, or your favorite NFL team, there’s no one else to blame when you bet on yourself and come up short. You can’t point to a bad bounce, a slow horse, or a blind referee. It’s just you.
And that’s exactly why so many people are afraid to do it.
The unknowns are endless:
Will I have financial stability?
Am I actually any good at the thing I’m betting on myself to do?
What will people think of me when this thing goes off the rails?
We all want a guarantee. But if there were guarantees, it wouldn’t be a gamble—and there wouldn’t be a payoff either.
It’s been over three years since I made the decision to retire. Nearly a year since I took off the uniform for the last time. And there are a few things I’ve realized along the way.
The first is that you have to believe in the decision to bet on yourself. Although I’ve never outright questioned my decision to leave the military, I’ve come close. But I know if I let myself go down that road, it’s wasted energy. When you bet on yourself, you can’t afford to look back and wonder what if. If you do, you’ll spend precious time and energy on the one thing you and I can’t change—the past.
So I believe I made the right decision. And from there, I face forward—not backward.
Next, you have to believe in yourself. Whatever system you came from—military, corporate, academic—might have affirmed you. But when you step away from that system, that belief has to come from within
In the military, my leaders believed in me. Their trust—and the performance evaluations that came with it—helped me reach the next level year after year.
But that’s gone now.
Now, it’s on me.
The military taught me how to work hard—to roll-up my sleeves, crack my knuckles, take a swig of day-old coffee, and move out.
So I know, without a doubt, that whatever happens, I’ll figure it out. I have the work ethic. I have the experience. And I’ve learned to navigate uncertainty.
Whenever we leave a familiar path for the unknown, we can’t discount what brought us here. We have the tools, lessons, scars—and they matter. They’re reminders that in those quiet moments of doubt, we’re more capable than we think.
Finally, you have to believe in something bigger. Whether it’s God, Allah, Fate, Destiny, or the Universe, I believe it’s important to trust that there’s a bigger design at work—something just beyond our comprehension. And within this design, each of us has a role to play. Some major, some minor. But when we lean into the process of discovering what that role is, things start to click. That’s been my experience.
I keep coming back to Joseph Campbell’s words about the Hero’s Journey. He once said:
“You follow [your path] and doors will open where there were no doors before, where you would not have thought there were going to be doors, and where there wouldn’t be a door for anyone else. There’s something about the integrity of life. And the world moves in and helps. It really does.”
So now, a year into this gamble, I can say—it’s still a little nerve-wracking at times. I have no idea how the cards are going to fall.
But I’m enjoying the game.
And maybe that means I’ve already won.
Joe Byerly is a retired U.S. Army Lieutenant Colonel with 20 years of service, including tours in Iraq and Afghanistan, and command of a cavalry squadron in Europe. He earned numerous prestigious awards, including multiple Legion of Merits, Bronze Stars, the Purple Heart, and General Douglas MacArthur Leadership Award. In 2013, Joe founded From the Green Notebook.
A passionate advocate for self-knowledge through reading and reflection, he authored The Leader’s 90-Day Notebook and co-authored My Green Notebook: “Know Thyself” Before Changing Jobs, a resource for leaders seeking greater self-awareness. If this post resonated with you or sparked any questions, feel free to reach out to him at Joe@fromthegreennotebook.com.
