On Taking the Scenic Route

People say “break a leg” to wish you good luck, and 15 years ago, that’s exactly what I did. Fresh out of college and working in Casting at Walt Disney World, I was living the dream—or at least a dream—until I broke my leg playing soccer in an employee tournament.

Does the story get better or worse if I tell you the tournament was called the Disney World Cup?

Yep, I broke my leg during the Disney World Cup. Not just in one place, but two. Because, of course, when am I not being a little bit extra.

Cue the impulsive move to the DC metro area and a decision to pursue an accelerated nursing degree. I know, those two things seemingly had nothing to do with each other—are you seeing the pattern yet?

Yes, I came with receipts. Fast forward (saving some lore for later), and no, I didn’t finish that degree. Instead, I found myself in 7 a.m. anatomy labs, silently swearing over formalin-soaked frogs and wondering what sort of karmic debt I was repaying by choosing to do this. I must have had a lot of fun in a past life. Amidst the chaos, I started working full-time for an attorney with a knack for sidequests—someone who became a major influence on my career.

Here’s the thing: you never know how much you might impact someone. A little kindness when it’s needed most, or some compassion when it’s barely deserved, can have someone writing an ode to you on LinkedIn a decade and a half later—maybe even when they’re being recognized in a completely unrelated field.

This individual was an unlikely source of inspiration, but aren’t those the best kinds? I learned a lot from him, but two lessons really stuck:

• Invest heavily in yourself. Learning is the best gift you can give yourself.
• Don’t let anyone tell you who you are or where you’re supposed to go.

Fast forward nearly a decade and I discovered that many of my own sidequests were likely due to undiagnosed ADHD. That’s a lot of days on earth not knowing why you are the way you are. They call it a "good news diagnosis" because it only gets better from there, but they don’t tell you that "from there" requires developing a lot of the skills you don’t have and will struggle to develop. A story for another day.

Grad students I teach at Georgetown sometimes ask about my career path, hoping for a clear roadmap. It started off like a wild MapQuest printout, sixteen pages long, with turns down roads that might look like dead ends but are actually U-turns leading back to a path meant for you. “Head North, turn left, take a U-turn.”

“Wait…where the hell is North?!”

You’re turning the music down so you can see the road better.

But my career didn’t start with a perfect internship or anything that necessarily made sense at the time. My college summers involved selling drinks on a golf course, waiting tables, and doing remote broadcasts at a radio station. Winter breaks were spent folding jeans at A&F and selling body sprays at Victoria’s Secret (don’t even get near me with the Love Spell). At one point, I was registering bikes for the Virginia Tech police department. And that’s just scratching the surface of the jobs I had in my teens and 20s—but I’ve gotta save some lore for later.

Before I knew it, I had accumulated a wide range of knowledge and experiences that would serve me well in time. The disconnectedness was actually the invisible string that was there all along.

You might find that people are desperate for you to go down one conventional path. But it’s the detours that make life rich. If you play it right, there are no wrong turns—only paths that ultimately may help lead you where you’re meant to go.

So, if you’re still reading, you’re probably late for your next meeting, but here’s the bottom line: you can change your mind. Really. You can work hard to reach a destination, then turn around and ask, “Why the hell was I going this way again?!”

Therapists joke that people always drop the bombshells at the end, so here’s mine: last week, one of my closest friends for many years died unexpectedly. The kind of loss that hits you like a freight train, leaving you wondering how to keep moving forward.

But wait, there’s more!

Yesterday, I got that call. You know the one—the call that comes after four missed rings from a relative, and you just know it’s not going to be good news. It wasn’t.

“Your father had a heart attack.”

Life doesn’t come with a map, and sometimes it hits hard. Really hard. You don’t know what’s coming, or what challenges you’ll face next.

But here’s what I’ve learned: Embrace the sidequests. Tell stories that wander, with three starts and barely an ending. When you realize you’re going the wrong way for you, don’t be afraid to toss out the directions that someone else gave you and start paving your own road.

And sometimes breaking a leg truly is good luck.

There’s no one path, no single decision that will get you to "Destination: Great Career"—or a great life. And at the end of the day, you’re the one who has to live with your choices, your journey, every single day.

So, as you carve out your own path, don’t forget to look back and extend a hand to those following behind. You won’t be able to help everyone—sometimes that guilt will gnaw at you—but maybe you can help someone briefly, and that one act of kindness might be all they needed to keep going.

And who knows? Those sidequests might just lead you to places you never would have predicted—like a spot on the PRWeek 40 Under 40 list and a career that’s richer for all the twists and turns.

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