How Not to Get Your Indoor Friends Outdoors


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I’ve (mildly) traumatized my friends. Here’s what not to do.

Do you remember your first backpacking experience? I can recall mine with stunning clarity. I was nine and my single night out in upstate New York was punctuated by a stampede of mosquitoes and a very nocturnal, very active family of raccoons. Needless to say, I did not go backpacking again for 14 years.

Since starting again, I’ve gone from a non-backpacker to a thru-hiker. I’ve also tried to evangelize this outdoor way of life, a pursuit that’s left quite a few friends, family members and significant others miserable thanks to ill-thought-out first backpacking adventures. Learn from my mistakes.

Here’s how to not introduce your indoor-leaning loved ones to the art of sleeping in the outdoors:

1. Take Them Hiking in the Rain

Yes, we’ve probably all heard that phrase: “There’s no bad weather, only bad gear.” Well, try telling that to your significant other when it’s hammering rain for the eighth straight hour of their first trek. If you’d like to save yourself some headache, remember that not everyone is totally fine with a slog in nasty weather. And by not everyone, I mean the majority of people.

2. Make Sure They Have Most—But Not All—the Necessary Gear

Over the years, I have accumulated quite a collection of gear that I happily loan out. But early on into my outdoor life, I took my dad on a particularly snowy, particularly steep, particularly slippery hike with only one set of traction devices and trekking poles between us. We made do with a secure step every other stride, but a smart mentor will make sure they provide all necessary gear before heading outside, or pick less-gear-intensive hikes.

3. Seek Out Encounters With Wildlife

Most people—indoor and outdoor alike—are afraid of wild animals. Think twice before choosing a trail the ranger describes as “rife with black bear scat.” (True story.) If my initial attempt at backpacking is any indication, allowing your newbie to encounter wildlife might just keep them out of the woods for 14 years.

4. Start With the Hardest Hike You Know

I love hiking up tough trail, and I can wax poetic about the charm of an empty mind and burning lungs and thighs. My enthusiasm can even cause friends to want to try it themselves. But do not believe indoor folks who claim to want a taste of the hard stuff. They do not. They want the flavor of the hard stuff, but not the real thing. It’s best to start small, perhaps a tiny hill that gets them panting. Backpacking is a bait and switch—and it takes a long while for people to realize that suffering is fun in and of itself.

Sad Campers

Unhappy campers in hour 12 of pouring rain.

5. Discover Their Fear, Then Help Them “Overcome” It

When your mother says she is afraid of heights, trust her. Do not, under any circumstances, attempt to take her up Half Dome. Save the blood-pumping views for another time, another person. Because coaxing someone up and down a death-defying trail is fun for no one.

6. Attempt a Fastest Known Time

People who aren’t used to carrying everything they need on their backs are not fast. Maybe they’re fit. Maybe they’re devoted spin class attendees. Maybe they even take the stairs up to their office on the 12th floor every single day. But still, they will be slower than you. Let your new outdoor buddy set the pace.

7. Crush Butt-Burning Hills

My cycling buddies and I have a saying: Locals lie. As in, locals always think the road ahead is flat (especially when they’re driving it) and it never is. The same thing goes for experienced hikers. Whatever trail you think is flat, your newbie friends are sure to disagree. Look at the numbers—if it’s less than 300 feet of elevation gain, you can be sure it’s truly flat, not your version of flat.

8. Amplify Tantrums

We often think only toddlers have tantrums. The truth is, adults often grow up and continue to have them, especially when they’re uncomfortable in the woods. Remember that when taking your loved ones outside, you’ll probably see some pretty unpleasant sides of them. Be the voice of reason, of kindness, of gentleness. By being gracious in the face of a negative outburst, you’ll keep everyone calm in the long term. Pro tip: Set the trip up on a positive note by telling everyone misery is part of the journey, and we can all help each other stay positive by minimizing complaints and maximizing wonder, awe and goofiness.


It can be hard to introduce people to the outdoors. But with a little preparation, and a whole lot of patience, you can avoid my pitfalls and offer an incredible first (and second and third and …) experience.

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