Have you ever walked around endless airport highway ramps for more than a mile? When it’s after 10pm and you’ve got your carry-on bags with you?

Yeah, so I did that the other night. Short version: when you land in DFW and are staying at the off-airport Hyatt Regency, you’re supposed to take the SkyTrain to the C gates, and then hike through the parking garage to the entrance. I’ve done it that way before, and it’s not terribly difficult.

This time I was hanging out in the D terminal, working from my favorite U.S. airline lounge, and I decided to walk outside and skip the whole SkyTrain thing. How hard could it be? I’ve been to DFW, oh, I don’t know—several hundred times if not more. Sure, it’s a big place, and there was that time I got lost trying to return a rental car and missed my flight, but still.

It turns out it’s actually quite difficult to walk that way, and it took me more than thirty-five minutes. I first went to the D parking garage, only to realize that it is in no way connected to C. OK, no problem. I could see the hotel about 300 yards away, so I decided to walk across the exit ramp. No big deal.

Problem was, as I approached the end of the exit ramp, it went nowhere near the hotel. Instead, the elevated ramp curved around. Waaaayyyy around.

Thus began the more interesting part of the journey, in which I was passed by approximately seventy-five vehicles proceeding in my direction. I clung to the side of the road and hoped that the shuttle drivers and passenger drop-off cars would stick to their lane and not swerve off to the left.

It was a mistake, for sure, but the whole time it felt like some sort of meaningful experience. This year I’ve been thinking about risk a lot, and this was definitely risky behavior. While I was schlepping down the road with no end in sight, I decided that while I probably shouldn’t have chosen this course of action, now that I was committed, I didn’t wish to undo it.

I thought of the Churchill phrase: “When you’re going through hell, keep going.”

I also thought, you can learn a lot about yourself when you’re scared.

I finally arrived at the hotel drenched in sweat, but I felt like a champion. I don’t run marathons anymore; I just do dumb things like get lost at the airport and decide I can find my way by walking on the highway.

It’s a funny thing: I’ve been to this hotel a dozen times before, and every other arrival has been uneventful. Yet I’m pretty sure that every time I stay there from here on out, I’ll remember my highway schlep.

When we look back at our lives, we don’t remember the times when everything went well. If you don’t have challenges in your life, maybe you should change your life.

If you don’t ever struggle, and you don’t ever fail, maybe your goals are too small. @chrisguillebeau (Click to Tweet!)

Chris Guillebeau is the New York Times bestselling author of The Happiness of PursuitThe $100 Startup, and other books. During a lifetime of self-employment, he visited every country in the world (193 in total) before his 35th birthday. Every summer in Portland, Oregon he hosts the World Domination Summit, a gathering of creative, remarkable people. His new book, Born for This, will help you find the work you were meant to do. Connect with Chris on Twitter, on his blog, or at your choice of worldwide airline lounge.

Image courtesy of Nubia Navarro.