Drift with Purpose

Why the Best Paths Are Rarely Straight—and Why That's a Good Thing

I love to read. Always have. Business, philosophy, economics, history—whatever catches my interest. My tastes are eclectic, and I like it that way. I never know where the next book might take me, and that’s part of the fun. Some books are deeply practical. Others are wildly offbeat. And once in a while, I come across something unexpected that sticks with me. That’s what happened with Louis L’Amour’s memoir, Education of a Wandering Man.

Most people know Louis L’Amour as the legendary Western author behind Hondo, the novel that became a classic John Wayne film. But Hondo was just one piece of a much larger body of work—he wrote over a hundred novels and short story collections, selling hundreds of millions of copies worldwide.

Photo by Luca Baggio on Unsplash

As impressive as that is, his own life story might be even more compelling. Before he ever published a word, he worked as a seaman, a miner, a lumberjack, and a boxer. He drifted from job to job, place to place, reading everything he could get his hands on and letting those experiences shape his understanding of the world. His memoir isn’t a victory lap—it’s a reflection on how real learning happens in the wild. It’s about letting curiosity lead the way. It’s about drifting with purpose.

L'Amour didn’t chase degrees or job titles. He chased stories. He followed instinct. He went where life pulled him, knowing each experience had something to teach. His journey wasn’t tidy or traditional. But it was rich, layered, and deeply purposeful.

We’re taught to believe that success follows a straight path. Pick a major. Climb the ladder. Stick to the plan. But real life isn’t so tidy. Most of us zigzag. We change jobs, move cities, try things that don’t work out. We take detours. And that’s not just okay—it’s often the best thing for us.

The Illusion of the Straight Line

It’s tempting to look for patterns in other people’s careers. To assume they had a clear plan all along. But if you look closer, you’ll usually find a winding road full of pivots and pauses. The myth of linear growth is comforting, but misleading. Growth is rarely linear. It’s layered. It’s unpredictable. And it often looks like drifting.

L’Amour’s story is full of moments that, from the outside, look like delays. His time in the merchant marine. His stints as a boxer and a miner. But each chapter added something essential. Discipline. Grit. Perspective. Stories. These weren’t was

ted years. They were training grounds. The foundation for a voice that would later resonate with millions.

This is a lesson we all need to remember—especially those early in their careers, or navigating a transition. Don’t underestimate what your current chapter is giving you. Even if it feels unrelated. Even if it feels like a step sideways or backwards. Your job is to stay curious. Stay open. Learn everything you can. Store it up. You’ll use it later.

Following What Calls to You

As I reflected on L’Amour’s journey, I started thinking more clearly about my own. I’ve never had a five-year plan that actually lasted five years. I’ve rarely taken a step because it was what I was "supposed" to do. Instead, I’ve chased things that interested me, pulled at me, or just flat-out wouldn’t leave me alone. I started companies because I wanted to solve problems. I taught because I wanted to help students find their spark. I wrote because I couldn’t not write.

And somehow, all of those pursuits connected. Not in obvious ways. But in ways that mattered. The startup years taught me how to take risks and stay calm in chaos. Teaching sharpened how I communicate. Writing taught me to clarify messy thoughts and make them real. None of these steps were wasted. They were steps forward, even when they felt sideways.

When I was asked to step into my current role, it caught me off guard. I hadn’t been chasing it. But when the opportunity came, I realized something surprising: I had been preparing all along. Not in a structured, deliberate way—but through years of wandering across industries, roles, and challenges. The experiences I didn’t think would connect… did.

What This Means for You

If you feel like your path isn’t straight, or like you’re drifting more than advancing—you’re not alone. And you’re not doing it wrong. Some of the most capable, insightful, and effective people I know didn’t come from traditional backgrounds. They started in unrelated fields. They raised families. They pursued side gigs. They took time off. On paper, their journeys don’t always make sense. But in real life, they absolutely do.

Your experiences—all of them—add value. The odd jobs. The pivots. The things you tried that didn’t work out. The time you spent in roles that weren’t a perfect fit. They gave you something. Skills. Grit. Perspective. Don’t rush past it. Don’t write it off.

Your past doesn’t need to match anyone else’s. It just needs to be yours. Look at what you’ve gathered. Then ask how you might use it in new ways.

That’s how you drift with purpose.

Stay Open to the Unexpected

This is another lesson L’Amour teaches. His life was never aimless. It was exploratory. He didn’t drift because he lacked ambition. He drifted because he was collecting pieces—stories, skills, insights—that would eventually become something more. His wandering made him more resourceful, more thoughtful, more equipped to create.

The same can be true for any of us. Whether you’re just starting out or deep into your career, resist the pressure to make every step make perfect sense. Instead, ask: What am I learning here? What am I seeing that I haven’t seen before? What strengths am I building without realizing it?

Your resume might not tell a perfect story. But you’re not building a resume. You’re building a life.

What Organizations Can Learn

At the organizational level, we need to stop expecting perfectly linear backgrounds and cookie-cutter career arcs. The best teams are built with people who think differently, who’ve lived broadly, who’ve taken the long way around.

Great leaders recognize the value in those different paths. They create cultures that reward learning, curiosity, and initiative—not just credentials. They encourage people to bring their full experience to the table. And they look for ways to connect the dots between someone’s past and the problems we’re trying to solve now.

When tough problems show up—and they always do—the answers often come from unexpected places. People who have taken the long way around see the world differently. They approach challenges with fresh eyes. They draw on experiences others might overlook. That’s where the breakthroughs come from. Not from following the script, but from seeing past it.

Let Your Drift Teach You

Drifting with purpose is an art. It’s not about giving up direction. It’s about holding it loosely. It’s about letting your goals evolve as you do. It’s about trusting that the weird job, the difficult boss, the side project, the time away—all of it matters.

L’Amour’s memoir reminded me that the richest lives are often the most winding. That learning is everywhere if you stay awake to it. That you can build something great from pieces that don’t seem to fit at first.

So whatever stage you’re in—whether things are clicking or falling apart—keep going. Stay curious. Read widely. Say yes to things that scare you. And trust that the pieces will come together, often in ways you can’t predict.

The straight path is overrated. Drift a little. Just make it purposeful