I didn’t ride that day to clear my head.
I rode because if I didn’t, I’d drown in it.
It was the day after I got fired—after fourteen years in sales, after building two companies, after helping grow one from just over a million in revenue to more than $20 million. Seven years of blood, strategy, and belief. Gone. Because someone else didn’t share my vision.
So I clipped in.
Not for Strava. Not for a story. Not for anyone else.
I wasn’t even sure where I was going. Most days I have to piece trails together like a Goonie- Cutting through open fields, ducking under gates, and stringing together dead-end paths like they were puzzle pieces no one else could see. That morning was no different. I just needed to move forward with everything in my world had come to a hard stop.
The music hit before the tires touched dirt. I always ride with music—always. My playlists aren’t just background noise. They’re part of the ride. They set the tone. They speak for me when I can’t get my own thoughts straight.
That morning, I needed a war song.
Something to carry the weight I didn’t have words for.
Something loud enough to compete with the silence I was avoiding.
I started pedaling. Legs cold. Back tight. Mind spinning.
My body doesn’t exactly love me for this habit. I’ve got pain in places I don’t talk about much—discs that don’t move the way they used to, bulges in my spine, a neck that fights back on climbs. But the thing is… the pain from not riding is worse.
Because riding is where I come alive.
That trail—stitched together from access roads, slivers of singletrack, maybe-somebody’s-yard—was the only place that made sense that morning. And somewhere in the climb, when my legs started to burn and my mind stopped yelling, I felt something peel off of me.
Not all at once. Just in layers.
The lie that my worth was tied to a paycheck? Peeled off.
The weight of a vision that no one else believed in? Peeled off.
The shame I didn’t deserve but still carried? Peeled off, mile by mile.
God didn’t speak out loud. But He didn’t have to.
Because the music shifted.
The wind picked up.
And I looked up—really looked up—for the first time in days.
The world hadn’t ended. It had just changed.
And in that moment, I wasn’t the guy who got fired.
I was just a man on a bike—hurting, pedaling, free.
When I got home, I told my wife, “I think I just rode the shame off.”
And that was the first time I called it a reset ride.
Not because I found all the answers. But because I let go of the need to.
I ride almost every day now—sometimes twice a day. Morning for the clarity. Evening for the exhale. It’s not for fitness. It’s for something deeper. Music in my ears, sweat on my back, the chatter of the world finally quiet.
I don’t post about it.
I’m not on social media.
I don’t ride to show people what I’m doing. I ride so I can feel what I’m not saying.
I notice everything out there. The old man walking his dog. The woman jogging with headphones in and tears on her cheeks. The teenager bombing the sidewalk on a BMX bike, pretending he’s not lost.
It’s like the more I pay attention to what’s out there, the more God works on what’s in here.
This blog is called Faith in Failureship, but this series—these rides—are the heartbeat of it.
The world doesn’t teach us how to reset. It teaches us to distract, to numb, to grind until the wheels fall off. But I think real leadership starts when you stop pretending you’re okay and start listening to what your soul actually needs.
Mine needed the ride.
It still does.
So if you’re in that space—heart bruised, head buzzing, unsure what’s next—get outside.
You don’t need a full trail system or expensive gear.
You just need a place to breathe.
To sweat out the fear.
To crank through the questions.
You don’t have to believe that the worst thing in your life can lead to the best.
But just know—it can.
This ride didn’t change what happened.
It didn’t give me my job back or fix my future.
But it reminded me I’m not finished.
And that was enough for Day One.
So I’ll be back out there tomorrow—music loud, wheels spinning, eyes wide open.
Not chasing anything.
Just riding toward whatever comes next.
—Jason
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