Why Career Growth Feels Like Mile 20

(And What the Route 66 Marathon Taught Me About Work)

Six weeks before the Route 66 Marathon, I was supposed to be running my goal race — the one I had trained for all summer.

Instead, I was standing on the sidelines at the mile 9 marker of the Chicago Marathon.

I had just pulled my hamstring badly enough that finishing wasn’t an option. After months of early mornings, long runs, and the most disciplined training of my 11-year marathon career, it was a crushing disappointment.

So when Route 66 rolled around, I wasn’t just chasing a personal best. I was chasing redemption.

Race day was hot for late November, with 30-mile-an-hour winds that somehow seemed always in my face. Around mile 20, I hit a long, steep hill. My legs were shot, my pace was slowing, and the voice in my head begged me to quit.

But I kept going — not because it was easy, but because I’d learned something important: discomfort is temporary, and resilience is a choice.

And here’s the thing: work is no different.

Lesson 1: Pace Yourself for the Long Game

In a marathon, starting too fast feels great… until it doesn’t. The same happens in your career. Sprinting without a strategy can burn you out before you reach the milestones that matter. The people who last are the ones who know when to push and when to conserve energy.

Early in my career, I sprinted — chasing every stretch project, saying yes to everything, climbing as fast as I could. And just like a runner who burns out at mile 13, I ran myself into the ground. It wasn’t until I learned to pace myself that I could enjoy the journey and reach the big goals.

Lesson 2: Train for the Hard Miles

No one “accidentally” runs a marathon. You train for the hills, the headwinds, the pain. In work, those “training runs” are the smaller challenges — presenting to a tough audience, taking on a stretch project — that prepare you for the high-stakes moments.

The hard miles in training are what make you strong enough for race day. In my career, those smaller challenges built the muscles I needed for the days when the stakes were high and quitting wasn’t an option.

Lesson 3: Find Your Support Crew

During the race, I could hear encouragement in my headphones from my running group, my coach, my friends, and my family. It gave me energy I didn’t think I had.

Work is no different. Your “crowd” is your mentors, colleagues, and champions — the people who pull you up when you’re tempted to slow down. I used to think I could go it alone. I was wrong. Once I learned to lean on others, I grew faster, stronger, and happier — both as a runner and as a professional.

Lesson 4: Fuel and Recover

Marathoners know you can’t skip water stops or recovery days. In your career, skipping rest catches up to you just as quickly. Sustained performance requires downtime, reflection, and self-care.

For years, I took pride in never rolling over PTO. I knew from the start of my career that rest isn’t a reward — it’s a requirement. The recovery miles make the race miles possible.

Lesson 5: Get Comfortable With Discomfort

That windy, uphill mile taught me that discomfort isn’t the enemy — it’s proof you’re pushing toward something meaningful.

In your career, those “mile 20” moments — when you’re tired, the goal feels far away, and quitting is tempting — are often where the biggest growth happens.

Six years into my career, I had the chance to lead the development and rollout of a major new product. Everything about it scared me: working with senior colleagues I didn’t know, building something with no playbook, and delivering under huge pressure. I came out the other side with more skill, more confidence, and more comfort being uncomfortable.

The Finish Line

When you hit your next career hill — the high-stakes meeting, the challenging client, the stretch assignment that feels just a little too big — remember this: it’s just another windy, uphill mile. Keep moving forward.

Spoiler alert: On that hot, sweaty, windy Route 66 Marathon day, I took 44 minutes off my personal best. And that’s the thing about discomfort — it’s often a sign that the finish line is closer than you think.