How to Find the Perfect Adventure Buddy

There are times, more than I’d care to admit, an hour and a half into a trainer ride in my freezing garage, staring at my bike avatar move through virtual landscapes of Zwift, when my gear is growing moss and the walls are closing in the way do at Disney’s Haunted Mansion ride, that I suddenly feel the urge to shed the cloying comforts of home and go for some long trek through a foreign landscape.

If only, I’ve often thought, I had an Adventure Buddy—someone who would always be there, nodding along as I detailed my latest hazily conceptualized scheme: I just read about the most remote pub in the UK. They’ll buy you a beer if you hike in. It takes a few days. You up for it? To complicate things, my mind never seems to drift to the local, the achievable (say, a day-hike in the Poconos) for which I might actually drum up a companion. I generate quixotic ideas that call for veritable Sancho Panzas.

The trusty companion of trail and tent is an idea—almost a romantic longing—that haunts the world of outdoor exploits. You think of famous climbing partnerships like Conrad Anker and Jimmy Chin, or Tommy Caldwell and Alex Honnold. If you’re me, you think of writers like William Finnegan, in his surfing memoir Barbarian Days, cavorting around the globe with his buddy Bryan Di Salvatore. Finnegan once evinced the bromance aspect of the whole thing. “You go to extreme lengths, and you do it together, so these friendships really get tested,” he told Alta Journal. “You want that great wave, but it’s much greater if your friend sees you get that great wave. It’s a dense sort of homoerotic world you live in.” The same, of course, can be true of female adventure friendships.

I’m not alone in my hunger for shared adventure. You see it on the partner boards at shops like Denver’s Wilderness Exchange, where people put up cards listing their preferred pursuit and available dates (“Always,” being my favorite). You see it in endless online queries from people new to a town who don’t have anyone to join them in the outdoors. The URL adventurebuddy.com will take you to a site, based in Alaska, looking to pair people up. “What a great idea!” one commenter wrote. “Just what Alaska needs … So many things to do, but not always easy to find the people to go with.”

Indeed.

As it turns out, I actually do have an ideal adventure buddy in mind: my friend Wayne Chambliss. Wayne—currently doing post-graduate work in London on geography, part of which involves him being “inhumed,” or buried underground—is pretty much up for anything, no matter how grueling, how ill-advised, how quasi-legal. He’s got an outdoor CV that is impressively outlandish.

All this raises a question: What, in fact, makes for a good adventure buddy?

There was the time near Utqiagvik, Alaska, that he had to outsprint a polar bear—this just after he’d taken bolt cutters to his wedding ring, chucking half of it, in some Tolkienesque rite, onto the frozen Beaufort Sea. Or the time, for lack of planning, he was forced to do a fifty-one-mile single-push circumambulation of Oregon’s Three Sisters volcanic peaks. He’s been submerged in a homemade submarine, along with its maker, off the coast of Honduras; he’s been airlifted into the wilds of Canada for a kayaking trip, without much knowing how to kayak. He’s crossed the Grand Canyon from rim to rim to rim, walked through Chernobyl’s zone of exclusion, and traversed Death Valley on foot (twice). Wayne is also a ferocious magpie of information, an endless spinner of theories and weaver of connections, a writer of feverish, private dispatches. Once, when I was asked him for any off-the-cuff thoughts for a potential story on treasure, he responded immediately:

“Hey, Tom. An interesting question. I’ll give it some thought. In the meantime, are you considering botanical rarities like ghost orchids or Pennantia baylisiana, or last surviving speakers of languages, or the gold that Rumiñahui ordered hidden in the Llanganates Mountains, or the Nazi gold hidden in Lower Silesia, or the one viable REE mine in the U.S. (now owned by a Chinese concern), or how antimatter (of which less than twenty nanograms have been produced thus far, I believe) costs ~$62.5 trillion per gram, or the lone copy of Once Upon a Time in Shaolin (which would be a great opportunity to interview the Wu-Tang Clan, and maybe Bill Murray), the disassembly of the Codex Leicester…”

I will cut it off there. But it went on. And it was the first of three emails. Suffice it to say, we could spend weeks on an outing without running out of things to talk about. There is just one problem in all of this: Wayne and I have never actually done any adventures together. Our failure to connect can be explained away by that tangled alchemy of time pressure, work commitments, having a family, and the general financial state of the creative precariat. Call it real life.

The closest we got was when I randomly discovered we were both in Quito, Ecuador, at the same time. I was working on a magazine piece about a spate of new luxury high-rises built by big-name architects. He was climbing Cotopaxi, the active volcano that shimmers distantly over the city. Flopping on my bed at night after another lavish, wine-heavy dinner, I felt a bit trapped, like Martin Sheen’s character in Apocalypse Now, stewing in Saigon: “Every minute I stay in this room, I get weaker.” Wayne was out there in the bush, getting stronger.

All this raises a question: What, in fact, makes for a good adventure buddy? With the same anxious overpreparation I bring to trip planning, I began making a checklist, interviewing die-hard adventurers and poring over expedition literature in search of an ideal profile—with a nagging sub-thought of whether I myself actually fit that profile.

The simplest answer might be: whoever is available. A blank space on the calendar is probably the number one attribute. The dreary realities of mortgage payments, family obligations and prior commitments have scuttled many of my potential adventures, cooked up feverishly on WhatsApp or a barstool. Here’s a thorny theorem for you budding mathematicians: Take two middle-aged, employed, married dads and try to find three weeks in which they can fuck off into the bush together.

It’s also useful to go with someone who roughly shares your pace and ability. In cycling, I’ve been on both sides of the dreaded “Italian stop,” the group waiting at the top of the mountain for others. Waiting is bad enough, but even worse is climbing full-gas up some incline, only to find your group idling, looking fully reposed, and, saying, with faux concern, “You good?”—then restarting the trip while you’re still trying to bring your heart rate out of the red.

Another desirable quality would be a capacity, or at least some instinct toward, keeping you alive. Not long ago, aboard the NatGeo Explorer in Antarctica, I found myself chatting with the maritime archaeologist Maria Intxaustegi, who spends a lot of time probing ice crevasses. Her partner, she says, “doesn’t need to be my friend; I don’t even need to like him. But when you put your life in the hands of another person, priorities change and other skills are validated.”

Maybe that works for a dive or two. But what if you’re spending weeks together? “The longer the events go on, the weirder it gets,” says Brenton Reagan, a backcountry guide with Wyoming-based Exum Mountain Guides. That’s when mere capability begins to falter; you want someone you can truly bond with. As Joe Cruz, a professor of philosophy at Williams College and frequent long-distance bikepacker, says: “What’s fundamental to me in finding buddies to travel with—and this is the most mundane way of putting it—is they’ve got to be able to roll with shit.” Which means not just dealing with hardship but also “being curious, open, alert, and of a mind to listen, more than tell people how they ought to be.”

It’s of a piece with that “Big Five” personality trait that psychologists call “openness to experience.” As the photographer Alex Strohl—who publishes an occasional series of pamphlets called “Adventure Buddies”—puts it, “someone who can start with ‘what if,’ who’s down to try and can be OK with the decisions you’ve made.”

It is not necessarily a case of just grabbing your best friend and taking them on the trail. “The people you get along with really well in life, or relationally, or at work, aren’t necessarily your best match in an outdoor setting,” suggests Jennifer Pharr Davis, the record-setting through-hiker. “Sometimes going with your best friends is the worst idea.”

Your friends may not share your stamina. They may be “type-one fun” sort of people who blanch at the first sign of trouble. On a recent trip—nothing rugged—with a very close friend, I began to look at him, as a kind of experiment, via the adventure-buddy lens. As someone who likes to move through airports with Teutonic efficiency—I’m sure I’ve got the FKT on any number of jet-bridge-to-curb runs in the United States—I couldn’t help but notice as he constantly struggled with his luggage (which, to my mind, was overpacked), or stopped to use the facilities (what, you couldn’t pre-piss on the plane?), or paused by a TSA kiosk to (unnecessarily) download an (unneeded) app for Global Entry. We joked about it, but I also secretly wondered: How would this play out on a multiday hike? Could I cope with someone so not dialed in?

Tommy Caldwell told me that, early in his career, “I was so objective-focused, I would always be like, I want to go to this place and do this climb—then I would just find the other people that would go with me.” Now, he says, “I’m like, here are the people I want to go with—what’s going to be the best possible adventure?” More than sheer technical ability, he says, he looks for “a certain vibe with that person.” Call it people before peaks.

When I told Caldwell about my airport experience, his answer surprised me. “I tend to prefer people that are really good at rolling with the punches—those are not usually the people that are super buttoned-up in life.” Caldwell’s regular partner, Alex Honnold, might not seem the picture of laid back. “He’s Type A in certain things, in that he wants to train in this very specific way,” Caldwell says. “But on my first trip with him to South America, I gave him this whole list of stuff to bring and he brought like a third of it. We just had to figure out how to climb these big mountains without any of the right stuff. The fact that he wasn’t bothered by that was kind of nice.”

This rang a bell for me. In being so rigid about my airport routine, I wondered, was I theoretically setting up my own expedition for failure? I was asking myself a question every right-thinking person should, at least occasionally, put to themselves: Wait, am I the asshole?

Adventure can test people, and relationships, in all kinds of ways. Adversity can strengthen partnerships. But long expeditions also bring a unique range of stressors, from fear and anxiety (an avalanche, a near fall) to outright boredom (stuck for days in a tent in a blizzard). A partner can be either a lifeline or dead weight. There may be people who can keep up with you, who share your peak-bagging thirst, who would be ideal companions on paper, but whose presence on the trail begins to feel like added weight. Things can always go wrong, says Reagan. “But I mean that’s why you try and pick somebody that’s really good. So even when it’s bad, it’s not as bad as it could be with somebody else.”

In David Roberts’s 1970 classic, Deborah, which details a climb undertaken with his friend Don Jensen, the eponymous mountain in Alaska’s remote Hayes Range is just one of the central antagonists. The other is the relationship between the two men themselves. Even before the expedition, the reader senses a rift. “Don and I both knew how badly things were going,” Roberts writes. “Yet we persisted in planning for Deborah with a kind of fatalism.” On the mountain, things got worse. Small traits that first seemed endearing hardened into annoyances.

Hence what the sociologist Diane Felmlee has called fatal attraction among romantic partners: the initial draw to a certain quality turns to resentment over that same trait. But we’re just talking about climbing, aren’t we? “Our situation was, of course, something like that of lovers or married people,” writes Roberts, “except that, instead of a bond of physical love, our bond was danger and the mountain.”

That’s another thing that makes Caldwell’s partnership with Honnold work: They have a shared comfort with risk. “Alex’s is certainly way higher than mine,” Caldwell says. “But I think I’m the closest he’s found.” The alchemy doesn’t always work. In the National Geographic program Arctic Ascent, Honnold comes to an impasse with fellow climber Mikey Schaefer—who has been dodging “death blocks” of loose rock from above— over whether to proceed up Greenland’s imposing ice wall Ingmikortilaq.

“You have poor risk assessment at the moment,” Schaefer tells Honnold.

“Someone is being really grumpy at the moment,” counters Honnold.

“No, I’m not being grumpy at the moment,” replies Schaefer. “I’m being real.”

Which brings up the H word. Reagan, the mountain guide, who is in a sense always surrounded by new and ever-changing groups of adventure buddies (i.e., his clients), says that for him, a sense of humility—the sort not particularly on display in those moments in Arctic Ascent—in a partner is key. “It’s a cliché to say we should always be humble in the mountains, but even when you’re making a really technical and proficient assessment that you’re confident in, you still have to have the sense of I’m dealing with Mother Nature and there are unknowns.”

One way to instill humility is to find a partner who has as little experience as you do. One day, years ago, a British marketing professional named James Whittle received a simple text from his friend Tom Caufield: “Fancy a row in the Atlantic?” Caufield’s mother had participated in a trans-hemispheric yacht race, and his ego was challenged (i.e., “Shit, my mom is cooler than me.”). The pair, old pals who’d met working for Red Bull, then rowed from the Canary Islands to Barbados in a boat called Roberta—with virtually no rowing experience.

“A lot of times, when you have experts in a certain field, and you put those people in a pressure cooker, that’s when friction and resentment happen,” says Caufield. “Whereas James and I, we’ve never had an argument, because we are bound not just by this friendship, but by this partnership in naivete.” A key to that, Whittle adds, is switching up the adventures. “If we’d just carried on rowing different oceans, there might have been more of a varied skill level or different perspectives on challenges,” he says. “In being completely new to this discipline, learning it together, it makes the priority about achieving this thing for the first time, rather than speed or ego.”

This attitude has helped them, Whittle guesses, “be successful in the adventures but also to come out with amazing experiences, not resenting your partner, still friends, enjoying the beers afterward.” That’s at least half the reason to do the adventure, he says. “That beer afterward with your mate.”

In short: A good adventure buddy is one you click with, who is ready to move when you are, who understands the assignment, who won’t always leave you behind, who can face adversity without losing their shit and maybe even laugh about it, who brings complementary skills, who might even save your life.

But sometimes, you can’t find that person. Sometimes, you might not want to find that person. Everyone I spoke to also extolled the virtues of sometimes simply going out on your own.

While solo adventuring brings plenty of opportunity for introspection, one of the joys of shared adventure is retrospection.

For Pharr Davis, solo adventuring has been essential at key moments in her life. “I most valued going out alone in the beginning, when I was twenty-one. I was really still figuring out who I was as an adventurer, and also figuring out who I was a person. I don’t think I would have gotten the same experience if I’d consistently hiked with a partner.” Later, going solo became a kind of pressure valve. “I just didn’t want to deal with other people’s needs,” she says. “I was running a small business and I had small kids, and for a hot second, whatever adventure it was, I just wanted to do my own thing.”

Caldwell notes that early on, he started soloing El Capitan. “You’d be all alone up there on the mountain. It’s a little scary and windy and you’re uncomfortable and you’re just feeling all these things that happen. And all that stuff took on a bit darker tone when I did it alone.” Today, he’s found a happy medium: solo drives to Yosemite to meet with climbing partners. “I get five hours a day with my friends, but then the rest of the time I’m in my van alone, coming up with ideas and getting my work done and having me time.”

While solo adventuring brings plenty of opportunity for introspection, one of the joys of shared adventure is retrospection. “Historically, I feel like many of the people who go and do these things on their own are probably looking for answers to something,” says Caufield. “[Whittle and I], we’re not doing that. We’re doing it so that when we’re eighty years old, we can sit in a pub and be like, fuck, do you remember that time we almost died on that glacier in Patagonia?”

As for Wayne and me, I’m confident that at some point we’ll be out there, together. Just recently, I brought up the idea, again, that we should do something. I envisioned a couple of days of trekking, maybe to that remote pub in Scotland.

“We could retrace the route of Cabeza de Vaca,” he offered. I quickly looked up what that actually entailed. Near as I could tell, it seemed to involve walking from Houston to Mexico City—after first crossing Texas, New Mexico, and Arizona. As tantalizing as this sounded, it would take months, months I didn’t currently have. I added it to my psychic calendar and had the thought, not for the first time, that maybe Wayne is just destined to be my platonic adventure buddy, an idealized partnership never tested by messy reality.

Adventure Buddies Hall of Fame

Some go it alone. But with the right partner, the highs feel higher, the lows sting less, and the journey means more. These duos prove time and again that adventure is often better together.

Conrad Anker + Jimmy Chin

From their 2002 slog across Tibet’s Changtang Plateau to their 2011 summit of Meru, these guys have defined endurance in the modern age.

Emily Harrington + Paige Claassen

Climbing partners and longtime friends, the bond between these two is rooted in mutual respect, type-two fun, and, most recently, motherhood.

Tom Caulfield + James Whittle

Known as the Tempest Two, this duo was forged in 2015 when they rowed across the Atlantic with no support crew­­—the first of many challenges.

Tommy Caldwell + Alex Honnold

“The vibe that you have with that person is so important,” says Caldwell of his longtime climbing partnership with Honnold.

Sir Edmund Hillary + Tenzing Norgay

Hillary didn’t consider himself a hero, but said that Norgay, his friend and partner in the 1953 first ascent of Everest, “undoubtedly was.”

Diana Nyad + Bonnie Stoll

It takes a true friend to help you swim 110 miles from Cuba to Florida—five times. But in 2013, at age 64, Nyad made it, with Stoll’s help.