The Road Trip Secret That Makes Career Change Actually Work

I recently went on a road trip home, and even though I've done this drive dozens of times, I always check the route.

My journey takes me through the worst traffic in the country (thanks, Washington, DC!), so having alternate routes—and patience—is essential.

It can mean the difference between getting home at a reasonable time and taking an extended tour through weird suburbs, cute downtowns, and boring auto malls.

No matter which route I take, the intention to get home safely—to keep moving in the right direction—never wavers.

That got me thinking about people who are navigating their own career journeys. There’s an odd feeling that creeps in when your current job isn’t quite "home" anymore. And you may be left checking your career GPS, looking for a better route.

The truth is, successful career change works exactly like my road trip home.

Just like any journey worth taking, career changers need three essential things to maintain their direction of travel. And before you tell yourself you're not ready, remember: You've been navigating complex routes your whole life. This is just another application of skills you already possess.

A Clear Destination (Not Just "Away From Here")

Where is "home" for your career?

Is it another role in your current field, just with better conditions? Or is it something entirely different—a complete reinvention? Maybe it's that entrepreneurial venture you've been sketching out on napkins, or a return to work that felt meaningful before you got practical.

Here’s what I want you to know: What feels like home to you might have shifted during your time in your current role. The destination that made sense five years ago might not fit who you've become. And that's perfectly okay. In fact, it's evidence of growth.

Your career "home" should be specific enough to guide your decisions, but flexible enough to evolve. Instead of "something better," try "work that lets me use my analytical skills to help others solve real problems." Instead of "less stress," consider "a role where I can maintain boundaries and still make an impact."

That's a destination your GPS can actually find.

Multiple Routes (Because Life Happens)

When I punch my destination into the GPS, it always shows me three options: The fastest route. A secondary path. And the one avoiding tolls (which is hard to do on Interstate 95).

Your career transition needs to have the same flexibility.

A jack-knifed tractor-trailer sprawled across the road can shut down any highway. In your career, that might be a sudden layoff, a management change that turns toxic, or an entire industry disruption. (Ask anyone who worked in traditional media about unexpected detours.)

What are your three routes that you could take?

• The direct path: If everything goes perfectly, you move straight into your target role

• The strategic preparation route: Building your case through side projects, certifications, or volunteer work while still in your current role—showing your capability before making the leap

• The scenic detour: Maybe consulting, freelancing, or project work while you build toward your ultimate destination

Why does this matter for you? Because having multiple routes means you're never truly stuck—you're just recalculating. Just like your GPS recalculates around bad traffic.

Having options means you won't get stuck staring at career gridlock, wondering why you didn't plan for this. It means progress continues, even if the route changes.

Checkpoints Along the Way

When I hit the road, I text my family to let them know I’m on the way. If I've hit traffic or need to take a detour, I give them a heads up (safely, of course). They're expecting me, and they want to know I'm making progress safely.

Who are you checking in with on your career journey? Which trusted colleagues, friends, or mentors know about your route? Who's waiting to celebrate when you arrive?

I also gauge my progress by the landmarks I pass on the highway—that weird water tower, the stadium, the gas station that means I'm halfway there.

What are your career landmarks?

• Are you having more energizing conversations about work?

• Have you updated your LinkedIn to reflect your new direction?

• Are you building relationships in your target field?

• Do you have more clarity than you did three months ago?

• Has someone asked you for advice in your area of emerging expertise?

These markers matter more than you think. They confirm you're moving forward, even when the destination still feels distant.

Here's what changes everything: Most career changers try to map the entire route before starting the engine. But just like my road trip, you only need to know your general direction and the next few turns.

The route will reveal itself as you drive. You've already proven you can navigate uncertainty. This is just another journey where your skills apply.

What's one small step you could take this week toward your career "home"? Let me know in the comments—I'd love to hear about your journey.

I’m Richard Taliaferro. I’m a certified career coach specializing in helping mid-stage professionals gain clarity on their career journey. I’ve written a guide on how to escape the work hamster wheel. Click here to download yours.