Maybe Your Best Career Move Is Off the Map

A few weeks ago, I got an email from a former student asking if he could “pick my brain” (side note: can we collectively retire this phrase?). He's sharp, ambitious, and impeccably put-together. The kind of person whose résumé isn't just color-coded, but probably has footnotes and an appendix.

He’d followed the path. Economics degree? Done. Three years in consulting? Yep. MBA from a brand-name school? Of course. Post-MBA strategic role at a big company? Predictably, yes.

Yet here he was, in his mid-30s, reaching out because he had a lingering feeling that despite following the exact steps for "success," he realized he'd reached a finish line he never actually wanted.

It got me thinking that true success rarely looks the way we think it will. Sometimes it looks like wandering, getting lost, or having to awkwardly explain to your parents (again) why you left that stable job to do something that makes zero sense to LinkedIn. The best paths usually seem strange or questionable from the outside.

We love reverse-engineering other people’s success stories, tracing their path backward like it’s some kind of treasure map. Just follow their steps—A to B to C to D—and voilà, success. But those polished tales leave out a lot: the false starts, the stumbles, the cringey "what was I thinking?" moments that only make sense (maybe) years later.

Trying to replicate someone else’s path is like entering their GPS coordinates without checking your own location first. Sure, you'll arrive somewhere, but it probably won't match their endpoint. And that's not a failure. Often, it's the best thing that could happen, steering you toward a destination that's uniquely, wonderfully yours.

Steve Jobs famously said, "You can't connect the dots looking forward; you can only connect them looking backward." Yet we constantly try to preemptively join those dots, terrified of uncertainty. Perhaps it's the wandering, the detours, the scenic routes, and the baffling turns that create the true adventure (and ultimately, true fulfillment).

Psychologists have a term for our reluctance to deviate: "path dependency." It’s comforting to follow known routes shaped by past choices. But what if true bravery is stepping off the path completely, exploring new ground, and creating a journey that's truly your own?

People we admire—the true champions—didn't get there by following a set formula. They took bold risks that seemed foolish at the time, zigged when others zagged, and faced skepticism with courage. They didn't follow a path—they created one.

So if you’re feeling uncertain, lost, or worried that your journey doesn’t make sense, remember this: maybe you’re exactly where you need to be. Maybe the chaos, the unpredictability, and even the occasional self-doubt mean you're not just wandering—you're pioneering.

Edge Thought of the Week

This week, take a moment to ask yourself: Where in your life are you blindly following a path out of habit, rather than true intention? Consider whether it's time to bravely step off that familiar trail and venture into something genuinely new.

Until next time,

Laura