I’m The Real Jason Duncan, back with another Beyond the Grind blog – helping entrepreneurs like you build thriving businesses without sacrificing your freedom. 🚀

Two weeks. Zero emails. No business calls. No “quick questions” from my team.

Just 1,500 miles of Colorado backcountry to test whether I’d actually built the freedom I’ve been preaching to other entrepreneurs.

Most business owners can’t disappear for two days without everything falling apart. I was about to find out if I could.

On July 26, 2025, I left Nashville with three friends, our motorcycles, and one question:

Could I leave my business behind for 14 days straight? Not to check in. Not to monitor. Not even to reply with a thumbs-up.

This wasn’t a vacation. It was a stress test.

We were headed to the Colorado Backcountry Discovery Route – 779 miles of some of the most brutal off-road terrain in North America. The kind of riding that breaks bikes, bones, and egos.

Perfect for testing whether my systems would hold or my business would crumble.

The Ride Begins

We started in the middle of Section 3 of the Colorado BDR pointed south.

The terrain wasted no time.

We crossed Cottonwood Pass, climbed Cumberland Pass, and wound our way through the kind of scenery that reminds you just how small you are.

Within hours, we were dodging rainstorms, sliding through mud ruts, and scanning every switchback for loose rock or deep washouts.

Somewhere along the way, I lost my GoPro – probably bouncing somewhere off the side of the incredibly rough road up Cumberland Pass.

We pushed south until we hit Cortez, Colorado, by way of the highway. We’d skipped part of Section 2, not because we couldn’t handle it, but because we were watching the weather. The storms ahead were growing teeth, and we knew the real fight was coming.

Interestingly, while the terrain was physically demanding, I never felt worn down.

I’ve built #TheExitLifestyle around five freedoms and one of them is Freedom of Energy. You can’t lead well if your body is breaking down. That’s why I train four days a week with weights, TRX straps, and cardio. I don’t do it for looks (although I do enjoy looking better and losing the gut I’ve battled my whole life). I do it so I can show up strong, no matter what life throws at me.

Some of the guys in our group hit a wall early – first-day soreness, second-day fatigue.

But I had margin in the tank.

That margin let me enjoy the ride, stay clear-headed when the trails got technical, and recover fast when the weather turned against us.

That’s the lesson: You can’t wait until the storm to get in shape. You prepare when the skies are clear so you’re ready when they’re not.

Into the Thick of It

After Cortez, we skipped the Four Corners detour because we didn’t feel like adding an extra hundred miles to our day. So, we headed straight into Section 1 of the BDR, northbound.

The next few days blurred together in the best kind of way – cold, wet, beautiful, and brutal.

Rain rolled in hard at times, but it only seemed to rain, hail, and snow when we were at the peaks.

Trails got slick and rutted. Every pass felt like a gamble.

We were soaked. Covered in mud. And fully alive.

That night, just outside Telluride, we set up camp. Every hotel was booked solid, so it was tents or nothing.

Jeff and I shared a tent.

I had packed a lightweight inflatable ground pad to keep me off the cold earth, but I didn’t realize it had a leak.

The first night, I fell asleep on a 1-inch cushion of air and woke up with my spine pressed directly into frozen dirt.

I still slept okay.

The second night?

Miserable. No cushion, no warmth, no deep sleep – just shivering and waiting for daylight. It’s amazing how cold it is at elevation in late July.

But that’s the nature of a ride like this. It wears you down, one night and one mile at a time.

Then came Imogene Pass – elevation 13,114 feet.

It’s the highest drivable pass in the San Juan Mountains. And it’s not just high – it’s hard.

Loose rock. Tight switchbacks. Snow patches. Drop-offs.

It demands every bit of your focus.

Halfway up the climb, I tried to pick a line between two big boulders – and I picked wrong.

The front wheel caught. The rear tire slipped.

The bike tipped right and I went down to the right – away from the drop-off on the left, thankfully.

No injury. No drama. Just a moment.

But it mattered.

Because when I stood the bike back up, dusted myself off, and throttled into the next section of trail – something changed.

I wasn’t nervous anymore.

I wasn’t overthinking.

I stopped wondering if I could make it to the top.

I just rode.

And that’s when everything clicked.

The fear dropped away.

The terrain didn’t get easier – but I got looser.

More confident. More calm.

I reached the summit first. Parked the bike. Walked to the edge.

From up there, I could see the others working their way up – tiny headlights tracing narrow switchbacks along a cliffside trail that looked more like a goat path than a road.

From my perch, I could see what they couldn’t:

• Which corners were deceptively soft
• Where to throttle steady vs. coast
• Which lines gave just enough margin

So I called out through our helmet comms:

“Stay left on that turn.”
“Throttle steady here.”
“Watch that boulder on the right.”

And I realized – this is leadership.

You get far enough ahead to see clearly.

Then you turn around and guide the next rider forward.

That’s what coaching is.
That’s what business leadership is.
That’s how we help others summit what we’ve already survived.

I’ve ridden some nasty terrain in business too.

I’ve survived lawsuits. Lost partners. Led a million-dollar company through the moment we realized it was unsellable – because it was too dependent on me.

I’ve rebuilt from that.

And now, whether it’s a rocky mountain trail or a broken business model, I know how to ride the line, and I know how to coach someone else through it.

Riding Alone & Staying Present

Most of the ride, I was in the back of the pack.

That wasn’t by accident. I took on the role of capturing footage and photos for the group, so being in the rear gave me the best view of everyone ahead.

We used Sena helmet intercoms to stay connected while riding. Most of the time, we could talk in real-time, call out hazards, or share quick trail updates.

But one morning, just after a rest stop on the descent from Imogene Pass, things went sideways.

The guys took off before I had my cameras set up and my comms turned back on.
I wasn’t ready – and suddenly, I was alone.

No communication. No visibility. No idea how far ahead they were.

And now I had to ride solo on a trail that was still plenty technical, unsure if I’d missed a turn or gone off track.

Eventually, I reached an intersection.

No bikes in sight.
No clear direction.

So I flagged down a nearby side-by-side and asked, “Hey! Have you seen any motorcycles come through here recently?”

He pointed up the trail and said, “Yeah, three just went that way.”

I pushed on, still frustrated, and caught up with the guys a few minutes later. They were pulled over on the side of the trail.

I rolled past and keyed in on the comms:

“I guess this is how we’re riding now – just take off and hope nobody needs anything?”

I was hot – both physically and emotionally.

They tried to explain. They thought I was with them.
But I made it clear: That’s not how we do it.
You check. You wait. You don’t leave someone behind.

By the time we got into Ouray for lunch, the tension had passed.
That’s how it is with good friends. You let it out. Then you move on.

Still, there was a lesson in that moment.

Even when you have the right tools, the right systems, and the right people, you can still find yourself alone.

And when that happens, frustration is natural. But responsibility is still yours.

You ride on.
You find your way.
You don’t stay mad forever.
And you don’t let one breakdown define the whole trip.

The End That Wasn’t

On our final day of the ride, we headed north through Section 6 of the Colorado BDR, the last stretch before reaching the Wyoming state line.

It was quiet. Open. Peaceful.

The terrain had flattened out by this point – no more high passes, river crossings, or brutal ascents. Just rolling two-track through big, empty country.

We rode for hours through wide valleys, fence lines, and endless sagebrush until we hit the cows.

Dozens of them.

Loose. Loud. Barreling down the trail like it was running of the bulls in the Colorado high desert.

We slowed up, dodged left and right, weaving through a cloud of dust and hooves.

It was absurd and amazing.

No traffic. No towns. Just loose cattle and the hum of our engines.

And then we reached it.

The end.

Only… there was no marker.
No sign.
No line in the dirt to say we’d made it.

Just a gravel intersection in the middle of nowhere.

We slowed down. Looked around.

“This is it?”
“Yeah… this is it.”

So we did what you do when no one’s watching.
We took a few pictures. Fist-bumped. Laughed about how anticlimactic it felt.
And then we turned the bikes around and started heading south back on Section 6 and through a stretch of Section 5 toward Buena Vista.

The whole thing stuck with me: There’s no parade at the end of your business journey.

No confetti.
No closing bell.
No magical voice that says, “You did it.”

You don’t get fanfare. You get a dirt road in the middle of nowhere.
And if you’re lucky, you get a few good people by your side who understand what it took to get there.

Everyone else is too busy riding their own trail.

That’s not sad. It’s just real.

So if you’re building something – freedom, an exit, ownership – you better decide what success looks like before you arrive.

Because when you hit your version of “Wyoming,” there won’t be a crowd waiting to validate it.

Only you will know what it cost.
Only you will know what it meant.

The Ride That Proved It

A few days earlier on BDR Section 4, we rode through the most intense stretch of the entire trip.

It started with Hagerman Pass.

The climb was rocky and narrow, with deep ruts and sharp edges. But the weather is what changed everything.

As we climbed, the skies opened up.

Rain. Thunder. Lightning – real lightning, cracking across the ridgeline while we were fully exposed on wet rock at 11,900 feet.

I was literally praying out loud for God to protect us on the trail.

We were soaked through.
No cover. No place to stop.
Just the trail in front of us, turning into a river beneath our wheels.

At one point, I looked down the mountain and realized:

We’re not riding this trail anymore. We’re riding in it.

Water rushed past our boots. Every inch of brake and throttle had to be perfect. One wrong move and you're sliding off a rock shelf into who-knows-what.

But instead of fear, I felt clear.

Laser clear.

My body was steady. My mind was sharp. My reactions were crisp.
And I knew that this is what I’ve trained for.

Not just physically.
But emotionally. Spiritually. Operationally.

All the work I’ve done to build margin in my life, to create space, to steward energy, to let my business run without me. It all paid off in this one moment.

While the trail was chaos, I wasn’t.

We made it down soaked, smiling, and high on adrenaline.
I don’t think I’ve ever felt more alive.

The Way Back

After reaching the Wyoming border, we turned around and began our final leg south – riding Section 6 in reverse and dipping back into a portion of Section 5.

And honestly? That stretch was some of the most fun of the entire trip.

I actually asked our group leader, Justin, if we could ride that desert section again – because the first time through, I couldn’t stop smiling.
Everyone agreed. And I’m glad we did.

We hit fast, flowy terrain with long whoops that bounced us like a roller coaster, sandy washes that tugged at the tires just enough to keep it interesting, and winding single-track through shaded forest.

Those whoops were incredible.

I’ve never really known how to jump a motorcycle.
But in that long, open stretch… I started learning.

I picked up speed.
Found the rhythm.
Started getting real air.
And had an absolute blast.

After all the mud, snow, and switchbacks of the high passes, this felt like freedom.

We were cruising down a series of whoops when it happened.

I was in fourth position, just behind David, who was riding strong all day.
We were mid-conversation on the comms, laughing and calling out turns.

Then I heard him say, “Oh no, I took too much speed into this corner.”

A tight left-hand turn, followed immediately by a sharp right.
David couldn’t slow the bike down in time and he went down to the left.

It didn’t look like a bad fall. We’ve all laid our bikes down before.
Another rider helped me lift his bike off the trail, and David stood up.
But the second he did, he said, “My ankle’s really hurting.”

He could still walk. He could still ride.
So we didn’t think it was serious.

He told us he’d ride out to the highway, skip the rest of the off-road section, and meet us back at the Airbnb.

We finished the sandy trails and the remaining whoops, grateful we still got to ride them, but the energy had changed.

When we got back to Buena Vista, David was hurting.

We loaded his bike on the trailer, iced his ankle, wrapped it, and kept him on a steady rotation of ibuprofen and cold packs.

It wasn’t until the day after we got home that we got the full story:

David had broken his fibula.
Eight weeks on crutches.

And the crazy part? He finished the ride with a broken leg and didn’t even know it at the time.

That’s how it is in business, too.

You don’t always crash big.
Sometimes the break is quiet.

You don’t notice until it’s over.
You don’t realize how bad it hurt you until later.

And the blessing? It happened on the very last day.
If it had happened earlier, it would’ve changed the whole trip.

Even at the finish line, you’ve got to respect the trail.

What It All Proved

Two weeks.
1,500 miles of off-road.
No email. No coaching. No Signal chats. No Asana updates.

And yes – some things broke.

David fractured his fibula on the final day.
My radiator fan failed deep in a stretch of single track, forcing me to ride by feel and pray I didn’t overheat.

But nothing critical failed.
Not the business. Not the mission. Not the team.

Because I’d built for margin.
I’d trained for flexibility.
I’d designed for freedom – even when things go sideways.

This wasn’t a vacation.
It was proof.

Proof that systems work.
Proof that leadership scales.
Proof that real freedom is possible if you design for it.

Words of Wisdom

“The prudent see danger and take refuge, but the simple keep going and pay the penalty.” – Proverb 22:3

Until next time…

Go beyond the grind,
The Real Jason Duncan 🚀