Why I Started The Jolly Outlaw
There comes a moment when you realize the system you’ve been told to trust was never built to support you—it was built to use you for as long as you provide “them” value. For me, that realization didn’t come from reading a book or listening to a podcast. It came from getting laid off. Twice.
The first time, I brushed it off as a tough business decision. Corporations have a fiduciary duty to act in the best interests of their shareholders—which usually means protecting profit and cutting costs when needed. I got it. It was just math. But the second time? It hit different.
I wasn’t just losing a job. I was waking up to a bigger truth: You are dispensable. No matter how hard you work, how loyal or skilled you are—if the spreadsheet says you’re too expensive, you’re gone. And sometimes, the people who stay aren’t the ones doing the best work—they’re the ones who know how to play the game or know someone in a higher position. That’s when it all clicked: depending on someone else for your income is one of the biggest risks you can take.
I started looking around and asking some hard questions—about work, about life, about what really matters. The deeper I looked, the clearer it became: we’ve been handed a version of success that’s built to keep us chasing, not living. And most people are too exhausted—or enslaved by it—to question it.
The Spark That Lit the Fire
That’s when the idea for The Jolly Outlaw started taking shape. The name is a twist on the classic pirate flag, the Jolly Roger—with a Texas twist. A grinning skull in a cowboy hat wearing a Texas Ranger star. It’s not just for style—it’s a symbol.
That grin? It’s for everyone who followed the “rules,” checked all the boxes, and did everything they were supposed to do to keep the appearance of society’s success—but still ended up feeling stuck, tired, or unfulfilled. People who did what they were told but started wondering: Is this really all there is?
The Jolly Outlaw exists for those of us who refuse to settle for survival on someone else’s terms. It’s for those who are done chasing someone else’s goals—and ready to start redefining success for ourselves.
What’s Next
This isn’t about bitterness. It’s about awareness. It’s about recognizing that the system was never going to lead you to success—and realizing that you have the power to take a different path.
That’s the outlaw way. Not lawlessness. Not rebellion for rebellion’s sake. But living with purpose. Acting with intention. Taking ownership of your time, your choices, and your future.
In the rest of this post, I’ll walk through what came after that turning point—and why The Jolly Outlaw isn’t just a brand. It’s a lifestyle, a mindset, and a call to those who know there’s more to life than the grind.
We’ve Been Sold a False Definition of Success
From the time we’re kids, the roadmap is laid out like it’s the only path worth following: do well in school, go to college, get a good job, climb the ladder, buy the house, drive the car, work hard now so you can enjoy life later. And for a while, you might believe it. You might even take pride in following the plan.
But eventually—quietly—something starts to feel off. You’re doing everything right, but you’re still running behind. You’re grinding harder, giving up more, and wondering why the freedom you were promised keeps getting pushed further down the road.
That’s when it hits you: this version of success wasn’t built to fulfill you. It was built to keep you compliant. To keep you chasing. To keep you tired, busy, and too wrapped up in doing “what you’re supposed to” to ever stop and ask if it’s what you actually want. It rewards burnout and calls it dedication. It glorifies sacrifice, as long as it benefits someone else. It tells you to be proud of how much pressure you can handle—without ever asking what that pressure is costing you.
The truth is, this isn’t success. It’s survival—on someone else’s terms. And the more you play by the rules, the more you’re expected to give: your time, your energy, your peace, your presence with the people who matter most.
If you’ve ever looked around at your “successful” life and felt more stuck than satisfied—you’re not alone. You’re not crazy. You’re not ungrateful. You’re not broken. You’re just starting to see the lie for what it is. And once you do, you can’t unsee it.
Redefining Success: What It Actually Looks Like
Once you see the lie, you can’t keep chasing it. And if you’re not chasing their version of success anymore, you’re faced with a better question: what does success look like for me?
That’s where everything shifts. Because real success doesn’t come with a title, a salary, or a corner office. It doesn’t come from impressing strangers or meeting expectations you never agreed to. Real success is personal. It’s being able to show up for the people you love. It’s having time for the things that bring you peace, energy, and joy. It’s living in alignment with who you are—not who the world told you to be.
It’s not about dropping everything and running away to start over. It’s about taking ownership of your life right where you are—and choosing to build something better. That might mean less hustle and more presence. It might mean rethinking what you say yes to. It might mean letting go of status symbols that look good but don’t feel good.
Whatever it is, it’s yours. And that’s the breakthrough: success isn’t something you chase until you burn out. It’s something you define, create, and protect.
Living With Purpose and Intention
Once you define success for yourself, everything else starts to shift. You begin to see that life isn’t about checking boxes—it’s about choosing what matters and protecting it fiercely. It’s not just about doing less or simplifying—it’s about living on purpose.
That doesn’t mean every day is perfect. But it does mean your time, energy, and attention start going where they actually belong. You stop saying yes out of guilt. You stop proving your worth through exhaustion. You stop performing for people who aren’t even paying attention.
And in its place? You start showing up for your family in ways that actually matter. You start having conversations instead of just rushing through days. You start building a life that feels good while you’re living it—not just in highlight reels or future fantasies.
Living with intention means knowing what you stand for and letting that shape your decisions. It means staying aligned when things get chaotic, and having the courage to recalibrate when you drift off course. Purpose doesn’t always come from a big moment or a single mission. Sometimes it comes from how you show up in the small things—how you love, how you lead, how you live when no one’s watching.
When you live with intention, you stop waiting for someday. You start building something meaningful now.
Texas, Adventure, and the Power of Living Fully
When you start living with purpose, you stop waiting for perfect conditions—and you start noticing what’s already around you. And if you live in Texas, you’re surrounded by something most people spend their whole lives chasing: space, freedom, and possibility.
Here, the open road is more than a way to get somewhere—it is the experience. The big skies remind you how small your problems really are. The small towns have a way of slowing you down and grounding you. The backroads, trails, rivers, and BBQ joints? That’s the good stuff. That’s where memories get made.
The point isn’t that you have to do something wild or expensive to “find yourself.” It’s the opposite. Adventure doesn’t have to be epic. It just has to be intentional.
Sometimes it’s packing up for a spontaneous hike. Sometimes it’s casting a line into a quiet river with your kid. Sometimes it’s staying up late around a fire pit, talking about real things with people who get you. These moments don’t require plane tickets or weeks off work. They just require presence.
The more you seek out these experiences, the more you realize something powerful: adventure fuels purpose. It resets your mind. It reconnects you to what matters. And it gives you stories that will outlast any job title or bank balance.
This is what The Jolly Outlaw is about—not just talking about freedom, but living it, right where you are.
Welcome to the Outlaw Way
If any part of this hits home—if you’ve ever felt like the version of success you were handed doesn’t quite fit—then you’re not alone. Maybe you’ve played by the rules and still ended up burned out. Maybe you’ve checked all the boxes but still feel stuck. Maybe you’re just starting to question whether the life you’re living is really yours.
That’s what The Jolly Outlaw is here for. It’s not just a brand. It’s a mindset. It’s a reminder that you get to choose what success looks like, how you spend your time, and what kind of legacy you leave behind.
This isn’t about rebellion for rebellion’s sake. It’s about opting out of what doesn’t serve you and stepping fully into what does. It’s about building a life rooted in freedom, fueled by intention, and filled with the kind of moments that actually matter.
So if you’re ready to stop waiting and start living on your terms—
You’re already one of us.
Welcome to The Outlaw Way. Let’s redefine the good life—together.
