Lessons From the Trail: A Metaphor for Life and Gap Year Adventures

I practically had this Substack written in my head before I even got home. Fresh off a hike in New Hampshire’s White Mountains, I was ready to drop all sorts of poetic metaphors about hiking and life.

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I’d even saved a meme that read, “When you reach the top of the mountain, you realize the mountain wasn’t the obstacle. It was you.”

But after what actually went down, this piece is heading in a very different direction. Turns out the better inspiration came from another meme I’d saved: “Remember, all those dead bodies on top of Everest were once highly motivated people. So maybe calm down.”

This trip was supposed to be something really special. Besides my usual hiking crew — Larry, Bruce, and Walter (a few others had to bail) — I was joined by my daughter Leah and her partner Alex. A once-in-a-lifetime trip. And the operative word there is “once.”

Day 1 was billed as the hardest: short in distance but with a brutal 4,000-foot elevation gain. I laced up my boots and hit the trail with determination. There’s something about standing at a trailhead — the beginning of a journey — that mirrors how my gap year started. It’s equal parts anticipation and fear. There’s no clear roadmap, and the goal feels impossibly far. But like choosing a trail, simply stepping onto the path is a commitment. You don’t need every answer right away.

I thought I was prepared. I’d packed what seemed right, made what I thought were smart decisions about what to bring and what to leave behind. Early on, I realized I’d miscalculated on both fronts. My brother-in-law Bruce ended up carrying my pack along with his, hauling it all the way to Madison Hut, our first stop. I was exhausted but grateful. Lesson learned: don’t be afraid to ask for help — and accept it when it’s offered. Life isn’t always a solo climb. Sometimes the people around you will literally and figuratively take the weight off your back so you can keep going.

Day 2 started early. Our plan was to go from Madison Hut to Lake of the Clouds, crossing Mount Washington — the highest peak in the region — a 6- to 7-hour trek. But soon enough, we were hit with wind gusts between 40 and 75 mph, no tree cover to break it, and reports from other hikers that the weather ahead was turning ugly.

That’s where Leah — the most experienced and level-headed of us all — called it: we needed to find a bailout trail. Cue the meme about the dead bodies on Everest.

Luckily, we crossed paths with a group of young Amish men who knew the area and helped us pick the best way out. My pride was bruised, my body more so after a couple of spills, but we started the descent. The trail down was rougher than the way up — a harsh, rocky slog that went on for miles. Bruce still carried my pack, and Alex followed close behind, basically on babysitting duty, thanks to Leah ordering him to keep an eye on me. Neither of them would ever admit it, but I know.

Honestly, I didn’t mind. I was way outside my comfort zone, and my only priority was getting home in one piece. That’s not an exaggeration — I was clearly in over my head. And sometimes the only way you get there is together. Either everyone makes it, or no one does.

Near the end, we managed to get a signal to reach Leah’s friends, Bea and Victoria, who were going to meet us for a third day of hiking. We were out of water, worn out, and banged up. Walter had twisted his ankle, Larry had cracked his knee against a rock — misery loves company. Bea and Victoria, basically wilderness angels, hiked up with water, encouragement, and took on a few more packs. They were a sight for sore eyes — especially for Leah, who had been watching me struggle and needed backup from her BFFs.

Lesson learned: the journey is easier with good friends.

We didn’t even try to do the Day 3 hike. None of us complained. Sure, we didn’t finish the route we planned, but we did finish, in our own way.

So instead of wrapping this up with a grand reflection on “the beauty of reaching the summit” or “the power of the uphill climb,” I think there’s a bigger takeaway:

Adaptability matters. Resilience matters.

Life, like the trail, throws you curveballs. The weather shifts, the terrain changes, and sometimes you have to bail out. That’s not failure — that’s wisdom. It’s okay to ask for help. It’s okay to change course. It’s okay to put safety and well-being ahead of pride.

In the end, the magic wasn’t about conquering the mountain. It was about relying on each other, getting back down safely, and recognizing that the real triumph is making it through together — detours, bruises, babysitters, and all.

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