A Packing List for the Trail—and for Life
An old backpacking adage says, “We pack our fears.”
If you’ve ever found yourself sweating under the weight of a backpack stuffed with “just-in-case” gear- rain gear for a 10% chance of showers, a backup to the backup headlamp, three pairs of socks for a two-day trip- you’ve lived this truth.
We overpack when we’re uncertain. We imagine every possible scenario, every what-if, every worst-case outcome- and then we carry it all on our backs.
The irony?
We go into the wilderness to simplify. To strip away the noise, the clutter, the chaos of everyday life. But in trying to be ready for everything, we forget why we’re out there in the first place.
I’ve seen it a bunch- new adventurers, excited and anxious, showing up with a 50-pound pack for a weekend hike. They’re not weak or naive. They’re just afraid of not having enough. And that fear adds up, ounce by ounce, until it becomes the very thing that slows them down, frustrates them, and sometimes even ruins the trip.
On the flip side, I’ve also watched people learn this lesson the hard way by not bringing enough. A forgotten insulating layer or first-aid kit can turn adventure into an epic. There’s a fine line between minimalist and miserable.
So… what’s the balance?
The same question applies to life after big transitions. Divorce. Career upheaval. Identity shifts. We want to be prepared. We want to avoid pain. So we try to carry everything: old habits, outdated roles, resentment, fear, and the stuff we think we might need again someday.
But some of it is just weight.
Whether you’re packing for the trail or starting a new chapter in life, the goal is the same:
Take what you need. Leave what you don’t. Trust that you can handle what comes next.
That’s why we created a Crooked Trail Packing List not just to tell you what gear to bring, but to model how to plan, assess, and pack with intention. This is a living document, updated regularly and packed with examples, gear links, and pro tips. Whether you’re heading into the woods for a three-season backpacking trip, prepping for a winter camping adventure, or corralling kids for a family river weekend, it’s built to flex with your needs.
👇 Download your free copy below
TL;DR:
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- Overpacking often comes from fear, not need.
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- Underpacking comes from inexperience or overconfidence.
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- The sweet spot is being intentional- with both your gear and your mindset.
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- Our downloadable packing list helps you find that balance.
Pro Tip:
After each trip, take five minutes to review what you actually used and what stayed in your bag. That’s where the learning lives.
