I was going through a box of old memorabilia recently — papers, photographs, the kind of random accumulation that happens when you spend decades being a pack rat — and I came across a few pictures from the first time I walked the Camino. That was 1999. I was young and restless and probably had no real idea what I was getting into.
In one of the photos, there’s a woman standing next to me at the start of the trail. We began the Camino together. And I cannot remember her name.
She dropped out three days in.
New boots. Not broken in. No training to speak of. The Camino has a way of exposing every shortcut you took in the preparation, and it did not spare her. By day three, the blisters had made continuing impossible. She turned back. I kept going. I never saw her again.
I think about her sometimes. Not with judgment — the Camino attracts people who don’t fully know what they’re signing up for, and that’s part of its spirit. But I think about the gap between her experience and mine, and I know exactly where it opened up. It opened up weeks before either of us took a single step.
I walked around Charleston that summer in the sweltering heat. Pack on my back, new boots on my feet, miles of sidewalk and neighborhood streets standing in for the trails of northern Spain. It was miserable in the best possible way. But I knew — from years of playing and coaching soccer — what a new pair of shoes can do to you if you haven’t broken them in. I had watched players sideline themselves with avoidable blisters. I was not going to let that happen to me on a 500-mile walk across a foreign country.
So I did the boring, unglamorous, unsexy work of being ready.
Walking Surfside before we ever touched Spain
Four years ago, I walked the Camino again — this time with my son Holden, to celebrate his graduation. And some of my favorite memories from that entire journey aren’t from the trail itself. They’re from the weeks before we left.
We walked our neighborhood in Surfside together. Packs on, boots laced, the two of us making loop after loop through streets we’d walked a hundred times — except now we were preparing for something. We talked about what the Camino would be like. We thought out loud about the miles ahead. And we did the work that most people skip: we broke in the boots, we adjusted the packs, we found out what hurt before it became a problem we couldn’t solve.
That preparation didn’t make the Camino easy. Nothing makes it easy. But it meant that when the hard things came — and they came — we weren’t also fighting the things we could have handled at home.
The college admissions Camino starts earlier than you think
I see this pattern constantly. Students arrive at junior or senior year with real dreams about where they want to go and what they want to do — and then they discover that the years before didn’t quite produce what they needed. Not because they weren’t capable. Because they skipped the preparation.
They didn’t build the transcript deliberately. They didn’t explore their interests with enough depth to have a real story to tell. They didn’t take the time early on to think about fit — what kind of environment they actually thrive in, what they actually want from the next four years. And when the time came to put it all together, the blisters showed up.
Students — the Camino of college admissions doesn’t start senior year. It starts freshman year, or ideally before. Every class you choose, every activity you commit to, every summer you spend building something real — that’s breaking in the boots. That’s carrying the pack around the neighborhood before the trail begins.
Parents — your job isn’t to walk the trail for them. But you can make sure they’re not showing up in new boots on day one.
Five things to do now — before the trail gets hard
Students — the best college applications are built over four years, not four months. Every year you wait is a year of preparation you can’t recover. Freshman and sophomore year are not too early to start thinking intentionally about the path ahead.
Students — breaking in boots isn’t exciting. Neither is building a transcript deliberately, taking a hard class before you’re sure you can pass it, or going deep on one thing instead of wide on twenty. But the people who do the unglamorous preparation are the ones who finish the trail.
Students and parents — there will always be surprises. The waitlist you didn’t expect. The score that didn’t come in where you hoped. The school that changed its requirements. You can’t plan for all of it. But if you’ve handled the things you could see coming, you’ll have the reserves to deal with the things you couldn’t.
Parents — most families don’t know what a competitive college application actually looks like until it’s too late to build one. That’s not a character flaw. It’s a knowledge gap. Fill it early. Find out what the schools your student is dreaming about actually want to see — and then give yourself the runway to provide it.
Students and parents — the Camino Holden and I walked together started in Surfside. The best college application process starts long before the applications open. Use the years you have. Take the campus visits early. Have the honest conversations now. Break in the boots.
If you fail to plan, plan to fail. I know that sounds harsh. But I watched pilgrim after pilgrim turn back on the Camino over things they never imagined would stop them — things that a little preparation would have handled. Some of them were more physically fit than I was. Some of them wanted it more visibly, more loudly, more desperately.
They just hadn’t walked around Charleston first.
The trail is the same for everyone. What’s different is everything you did before you got there.
Carpe diem.
Ready to start building the right application — before the trail gets hard? Entering the Arena gives you the full plan for walking this journey the right way.
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