Above the Tree LineAbove the Treeline

41 Boys, 11 Leaders, and a Few Things I Got Wrong

June 5, 2026  ·  6 min read  ·  by John Bishoff

41 Boys, 11 Leaders, and a Few Things I Got Wrong

Happy Friday. I just got back from Moab.

Took 41 boys and 11 leaders for four days in the desert with our church group. Big trip. A lot of logistics. Food for that many people, transportation, tents, sleeping arrangements, water, the kid who didn't read the packing list. The spreadsheet was long.

But here's the part I want to tell you about. I didn't plan most of it. The older boys did.

I've run enough of these trips to know how they usually go. Adults plan everything, kids show up, kids participate politely, kids go home. It works, sort of. The buy-in is shallow. So this time we did it differently. The older boys, the ones the younger kids actually watch and quietly imitate, planned the activities. They chose the hikes. They argued over routes. They decided what this trip was going to be. And then we grouped the boys into tent crews on purpose, with the planners as tent leaders and their friends with them, so the ownership ran all the way down through the group.

Short version: it worked. The boys had a great time. The buy-in was real. And I made a couple of mistakes I want to talk about, because they're more useful than the parts that worked.

What Worked

Most of the trip just ran. The boys hiked, ate, talked, slept, and got up and did it again. A few tents were a little crazy, which is what you sign up for with 41 teenage boys, but most of them were genuinely engaged. I didn't have to manufacture enthusiasm. It was already in the group when we got there, because the kids the younger boys look up to had built the thing.

The thing that surprised me most was how much fun they had with the unplanned hours. Cell coverage was bad, so the phones mostly stayed put. The boys used downtime to explore. They caught crawdads. They goofed off. They were just being kids, which is something I hadn't seen that much of in a while.

I had planned the activities and built the spreadsheet, but the best parts of the trip were the gaps between the activities. The parts I didn't plan at all.

I keep thinking about that. We spend so much energy designing experiences for kids, and then it turns out the magic happens in the cracks. When we leave them alone long enough to find a creek and a bucket and each other.

What Didn't

A couple of things didn't work, and they're both about the same thing.

The first night, we let the kids serve themselves at dinner. The food didn't last, there was waste, and a few kids ended up short. After that, we started serving them. Suddenly there was enough to go around, and a lot less ended up in the trash. Same boys, same food, completely different outcome.

One kid came to me at dinner because he'd gone to his tent instead of getting in the food line. By the time he came back, there was nothing left. I gave him the rest off my plate and told him next time he needed to actually get in line. He had plenty of time to eat. I didn't feel bad about it. But it stuck with me, because the whole problem was solvable with a little more structure on the front end.

The bigger one was the hike to the waterfall.

I'd told the boys to wait for me while I took a couple of leaders over to show them Potato Salad Hill. We got into a good conversation about jeeps and what it takes to get a vehicle up something like that. By the time we walked back, all 41 boys and 3 leaders were gone. They'd taken off on the hike without us.

They made it to the waterfall fine. But on the way, they walked past a panel of petroglyphs I'd wanted to show them, and most of them never even saw it. And by the time we caught up, they were jumping off the rocks at the falls.

I didn't want that to happen. People get badly hurt up there. Grand County Search and Rescue carries someone out almost every week, and the injuries are not small. Compound fractures. Things that change a kid's life. The boys didn't know that. They were just doing what teenage boys do when there's water and a drop.

That one's on me. I had handed them ownership of the trip and then I underestimated what that actually meant. Ownership doesn't pause while I have a conversation about jeeps. They were ready to go, so they went.

The Contradiction I'm Sitting With

Here's what I'm still working out. It's a little contradictory, and I'm going to leave it that way because pretending it isn't would be dishonest.

I learned it's okay to not have everything planned. The unplanned hours were the best part of the trip. The boys' ownership of the schedule worked. Letting them lead was the right call.

And I wasn't as organized as I should have been. The food situation was a setup problem I could have seen coming. The waterfall thing was a leadership lapse, not because I let them lead, but because I let them lead without making sure they had the information they needed before I stepped away.

Both things are true. Letting go worked. And I let go of a few things I should have held onto. I don't think those cancel each other out. I think that's just what leadership of this kind actually looks like, and anyone who tells you they've got the balance figured out is selling something.

The skill isn't choosing between control and trust. It's knowing which parts to keep and which parts to hand over, and being willing to admit when you got that line wrong.

What I'm Taking Home

I'm going to do another trip like this. The model works. The older boys planning it, the tent groupings, the unstructured hours, all of it. I'd change a few things on the operations side. Serve the food. Brief the group on safety at the actual destinations before we get there, not just before we leave the parking lot. Make sure nobody starts a hike until I'm with them, even if I'm in a great conversation about jeeps.

But mostly, I'm taking home something quieter. Forty-one teenage boys had four days outside, mostly off their phones, mostly in each other's company, mostly running their own trip. They caught crawdads. They hiked to a waterfall. They saw Delicate Arch and rafted on the Colorado River. They came home tired and a little sunburned and a little more themselves than when we left.

That's most of what I wanted, and I didn't have to plan most of it.

Where in your life are you doing too much planning for people who'd be better off if you let some of it go? And where are you using "trust" as an excuse for not setting them up properly in the first place?

Both questions matter. I'm asking myself both of them.

See you above the treeline.

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