Wilderness Adventures

The Perfect Trip (Is Almost Always Imperfect)

By Tom Holland May 19, 2025
Group of backpackers trekking through the brush on a rainy day in Alaska.

When I’m asked to reflect on my Wilderness Ventures trip nearly 30 years ago, it’s the imperfect moments that stand out:

Diving into my tent in the Wind River Range, laughing hysterically as the bugs overwhelmed us. Hauling our canoes up the channel between Lewis and Shoshone Lake, soaked by rain during a grueling upstream portage. Being turned around just below the summit of the Grand Teton due to an incoming storm.

These are the stories I still tell. Yes, I made lifelong friends. Yes, I had exceptional role models. But the memories that stuck? They were the curveballs, the challenges we overcame together.

Now, as the steward of this incredible company (Wilderness Adventures), I’ve had the privilege of reconnecting with countless alumni. They all speak fondly of their time with us, but the stories they share – the ones they just have to tell – are about the flat tires, the evacuations due to wild fires, the blisters, the rain, the bugs, the forgotten food, the bear spray mishaps.

Having led trips myself, I see it with former students and campers too. They’ll run into me and start with, “Do you remember the time when…?” And it’s always followed by something beautifully imperfect. A stuck van. A massive thunderstorm. A setback that somehow became a highlight. These are the sticky moments that etch themselves into our memories. The challenges. The unexpected turns. The times when the group’s true character is revealed.

Just recently, I met up with a few students from one of our Gap Semester programs. Their first words? “Do you remember the windstorm?! And the dance party after?!” That’s what stuck.

I’m reminded of this every time I head out on my own wilderness adventure. Before a trip, I dream of perfection – the flawless line, the perfect temperature, the smooth trail, the cloudless sky. But that’s almost never how it goes. And that’s okay.

One of my favorite personal memories was rafting the Lower Salmon River with dear family friends. The final day includes a long flatwater section, so we brought a motor to push us through. The night before, the motor mount broke, completely unrepairable. But instead of panicking, we spent hours crafting a new mount out of helmets, scrap wood, duct tape, and NRS straps. When we launched the next morning and it held? That moment, born out of frustration and teamwork, is now one of my most treasured memories.

Parents often ask how we keep trips “perfect”. We do everything in our power to prevent the preventables. Our protocols are extensive. Our team is prepared. We work hard to smooth the trail, but after more than 50 years of WA trips, we know the truth: every trip will have its surprises. And often, those surprises are what make the trip. They are what your child will talk about when they get home, full of excitement and pride, sharing stories of a trip that was, without a doubt, perfectly imperfect.