You’ve had the tab open for weeks. Kilimanjaro, Mera Peak or Aconcagua. You’ve read the itinerary three times. You can almost feel the cold air at the trailhead. Then the voice shows up. Not this year. Work.
I’ve heard that voice quoted back to me for decades as a professional mountain guide, trip leader for ITT, and founder of a coaching company for adventurous men. The voice almost always says one of three things.
The Big 3 Work Fears That Stop Trips
If I’m gone that long, they’ll realize they don’t need me.
I’d be letting my team down.
I’m too important. The ship can’t run without me.
That last one hits founders and senior leaders the hardest, because it feels the most true. And here’s what I want you to know, sitting here on the other side of dozens of these conversations: every one of those fears is a story. A real feeling, pointed at a solvable problem.
The Stoic emperor Marcus Aurelius put it this way two thousand years ago: the impediment to action advances action. What stands in the way becomes the way. Your work fear isn’t the obstacle blocking the trip. It’s the first pitch of the climb. Let me show you what I mean with two men I recently guided on a 21 day Aconcagua expedition.
Ben: “Would I even have a job when I got back?”
Ben is an engineer in tech. The always on guy. Returns calls at all hours, prides himself on it. When he signed up for Aconcagua, the fear was immediate and specific: “Would I even have a job? Would they just throw me to the side?”
It got darker. The responsible move was to prepare his team to run without him. But what if he did that too well? What if they realized, in his words, “oh, we don’t need Ben after all”?
Here’s what he did instead of quietly stewing. He shared his excitement. Openly, repeatedly, with everyone. He posted trail selfies and training charts in the team Slack. He showed his colleagues that Wednesday afternoon hikes were part of a plan, and backed it up by putting in hours on Saturday mornings so no one could mistake commitment for checking out.
His CEO was worried at first. A critical team member gone for a month, in a small rapidly growing tech organization? But as Ben kept sharing the dream, his CEO had his own lightbulb moment: “We can just say we’re sponsoring Ben for Aconcagua.” Suddenly there was a story to tell clients.
The whole team bought in. Ben’s advice for anyone sitting in that same fear: take the doubt people hand you and send it back as excitement. “Showing rather than just telling them that it can be done is the most powerful thing.”
And the ripple effect? His teammates started planning their own adventures, excited to cover for each other. One expedition cracked open the whole team’s assumption that work has to be your identity.
Jayson: “The obstacles are in your mind. They don’t live out there.”
Jayson owns his business, which means the ship really does need him. Clients calling. Staff needing support. And on top of it all, training that grew to 16 hours a week. The commitment forced his hand. He had his assistant start filtering his email. He pulled himself out of the middle of processes he’d been clogging for years. And the clients?
They loved it. His assistant answered faster and better than he ever had, because she wasn’t juggling forty other things. Then came the moment that told him everything. While he was heading off grid, a client emailed his assistant, someone that client had never worked with directly, and wrote back: thanks for the great service we’ve come to expect from you guys. Seamless. The client never felt a gap.
Jayson had known for years what needed to change in his business. He calls it the tyranny of the urgent: the important work of building systems always loses to today’s fire. His honest confession is one every founder should sit with. What kept pulling him back into the chaos was “that little dopamine hit” of being the problem solver, the small daily proof that he was valuable.
The mountain gave him something no amount of good intentions ever had: a deadline. “If I hadn’t committed to this timeline, it would have taken me two or three years to get to the same place.” And standing at basecamp, fully present for the first time in years, he summed it up:
“The obstacles are in your mind. They don’t live out there.”
The part nobody expects Here’s what both men discovered, and what I’ve watched happen again and again: the trip wasn’t a withdrawal from work. It was an investment in it. Ben came back to a team that runs cleaner and dreams bigger. Jayson came back to a business that finally works without him gripping the wheel. The fear whispered they’ll find out you’re not needed. The truth on the other side was better: they found out exactly what they’re needed for. The strategic conversations. The leadership. The things only they can do.
So if you’re staring at that tab right now, hearing that voice, understand what’s actually happening. The mountain is already training you. The work problem you’re afraid of is the exact skill the expedition demands: commit first, then build the systems your commitment requires.
Book the trip. Give yourself the deadline. Then go solve the problem you’ve been putting off for years. The obstacle is the way. And the way, right now, goes up.
Chris Strouthopoulos is a professional mountain guide, former Professor of Student Success, and TEDx speaker. He is the founder of Ascent Empowerment, where he works with high achieving, outdoorsy men who feel most alive in the mountains and want to feel that same clarity, energy, and presence at work and at home. If you recognized yourself in this article, you can learn more at ascentempowerment.com