Escape Artist

This history major's work is cold, wet, physically punishing, and occasionally life threatening. But he also gets to write about and photograph some of the most beautiful places on earth.


Text by Andy Dappen
Photos by Tom Winter '87

Tom Winter has one of those careers that induces envy. While others complain about jobs incarcerating them in cubicles, Winter, a ski and adventure-sports journalist, is at work while traveling, skiing, surfing, and mountain biking. He’s paid to play—or so his résumé seems to substantiate: He is a senior editor for Freeskier magazine and was a senior contributor to Powder magazine, the publisher of Apex magazine, editor of Gravity magazine, managing editor of Freeze magazine, and the managing editor of Vertical magazine.

During the 15 years that Winter has followed this path, about half of each year has been devoted to working as a staff member for a magazine, the other half as a freelance writer for the likes of Ski, Skiing, Skier magazine (Canada), Xtreme magazine (Australia), and the Denver Post. The writing has taken him all over North America and around the world. In any given winter, he’ll travel to Utah, Wyoming, New Mexico, California, and Montana. He’ll heli-ski in Alaska, British Columbia, and the Canadian Rockies. He’ll visit the French, Swiss, or Italian Alps once or twice. And he’ll log a few exotic trips to destinations like Argentina, Chile, Peru, Egypt, Jordan, Turkey, Cyprus, Bulgaria, or Hungary.

Not that Winter’s life is all fun and glamour. Working for winter-sports magazines has its crunch times as issues go to press during the fall and winter. “It’s like finals week once a month putting out the magazines. You write, edit, massage other people’s work, and fill holes. There’s lots of pressure,” he says.

But freelancing part of the year provides an offset. For example, it’s given Winter the flexibility to spend the month of August skiing in South America—something he’s done five times. “You’ve got to keep pitching ideas to create work as a freelancer. The pay is low, the competition high. There’s no job security. You take abuse from editors who change or scrap your stories. You often wait a year between when you start a story and when you get paid. In exchange, you get to travel the world on someone else’s tab, hang around amazing athletes, and associate with people who are infectiously excited about what they do.”

Winter’s attraction to adventure sports, and most specifically to winter sports, started early. Growing up in Boulder, Colo., he maintains there wasn’t much to do in winter except ski. His father also loved to ski and that passion got passed along. When college years arrived, Winter looked at high-quality liberal arts institutions close to real mountains. He wanted a change of scenery from Colorado but was not interested in the small, ice-coated mountains of the East. That made Puget Sound, with its proximity to the Cascades, one of the few schools that met his dual standards.

Winter made the UPS ski team as a walk-on and competed against Canadian National Team members who were on full-ride scholarships at Simon Fraser and the University of British Columbia. During his junior year, while studying abroad in the United Kingdom, Winter raced in the British National Championships and won a few bronze medals. Now he jokes, “If I were English, I might have had a shot at the Olympics.”

Winter graduated from Puget Sound with a B.A. in history (he once wrote a story about ski touring Hannibal’s route through the Alps), worked temporarily for the Smithsonian as a research assistant, and then started graduate studies at the University of York in England, working toward a master’s in cultural history. In 1989, when the Berlin Wall came down, he skipped classes for several days and traveled to Berlin to witness the momentous occasion firsthand. When he returned, his professors asked what it was like. He told them, “Leave now and you can see and feel everything. You can swing a hammer at the wall and see guards on the other side with their machine guns looking at you. You’ll understand exactly what it is like.”

None of them went. That proved a turning point for Winter. “It floored me. Here were a bunch of historians, some who specialized in European history, with one of the most important historical events of their lifetime unfolding, and none of them went to Berlin. What were they thinking? You have to go to an event like that if you’re a historian.”

But the professors Winter studied under in Britain were mostly interested in seeing the world through books or other people’s experiences. “They were in the Ivory Tower looking out. I was interested in actually experiencing the real world, tasting it, and smelling it, and being there.”

He left the University of York (a revised thesis paper short of his master’s), moved to Vail, Colo., and plugged into the ski bumming life with no real plan. “It completely freaked my parents out. I was attracted to the lifestyle but the menial work associated with ski bumming made me realize I needed to keep the wheels upstairs turning.”

He took an unpaid internship with Powder magazine and the first article he wrote was published. Compared to the research, documenting, and writing affiliated with his history studies, writing about adventure sports was easy. And that proved an epiphany. “My reaction was, ‘I can do this for a living! This is the kind of scam I’ve been looking for!’”

That’s not to say it was easy establishing himself after the internship ended. Specialty magazines exploit the oversupply of wannabe writers to keep their rates low. At the same time—and almost paradoxically—it’s difficult to earn the trust of those tight-pursed editors. Writers must produce quality work, meet their deadlines, handle material creatively, and hold their tongues when rewrites or last-minute changes are mandated. It took two years for editors to view Winter as a valued contributor and assign him enough work to actually pay the bills. “Until then, I moved a lot of furniture, fried a lot of fries, tuned a lot of skis.”

Winter credits personal drive and a good education for his fast transition into journalism. “The education I received [at Puget Sound] was excellent. It really made things easier for me, especially when it came to writing. Many freelancers I edit clearly didn’t get the same type of education, and it shows in their work.”

One of the downsides of his career has been the physical toll placed on his body. He’s broken his leg, ankle, wrist, and three ribs; endured four knee reconstructions; cracked his skull, suffered several concussions; and separated a shoulder. Because he maintains a high level of fitness and works at stretching, Winter says, “I don’t feel the weather yet, but if I ever lapse into a couch-potato lifestyle, I’m going to be hurting.”

Injuries, according to Winter, are the cost of doing business in the extreme-sport world. Sometimes the cost goes beyond injury—several of his colleagues have died while on assignment. With his snow-sport emphasis, avalanches are the biggest threat to life, followed by falls. “On some of the terrain where we work, mistakes are fatal. But the more intense the moment, the happier I am. If I weren’t doing this, I’d probably be a war correspondent.”

The danger factor, and his propensity to live out of a suitcase for months on end, doesn’t make Winter a man women clamor to marry. “Most of the women I’ve been serious about eventually say, ‘This isn’t what I imagined’ when I’m gone for three months. The travel is glamorous, but most people don’t want to spend their life traveling.”

That may change during the spring of 2006, when Winter is scheduled to marry Aileen Gilmour, a talented surfer, passionate skier, and the owner of a travel company. “Her career fits well with mine. We both can travel at will and have plenty of flexibility. She ‘gets it’ when it comes to my career, and the icing on the cake is that she can join me on trips.”

Relationship details, however, aren’t what the envy-crowd wants from Winter when they learn of his profession. Most pump him for information. They want to know which skis and boots to buy. (Answer: Most of the gear these days is excellent, but fatter skis are better.) They ask whether they should ski Europe. (Definitely! Even if the snow is bad, experiencing skiing as a way of life in the Alps is a must.) They inquire about his favorite American ski resorts (Vail, Jackson Hole, Silverton Mountain, Crystal, Taos—though not necessarily in that order) and the best Canadian resorts (Whistler Blackcomb, Fernie, Red Mountain, Kicking Horse). They ask for insider secrets on what not to miss. (All experts should ski La Grave, France, and everyone should ski Chile.)

All of this expertise—none of it particularly world shattering—creates some anxiety. Occasionally Winter, who is now 41, worries he is not serious enough. He wonders whether he should be tackling heavier topics and about the importance of his contribution. But then he also knows he’s a purveyor of dreams. “I show people activities and lifestyles they can tap into. I provide an escape for the masses that are stuck in New York City. Maybe it’s enough to get people excited about their next vacation or to show them the exit ramp from their current lifestyle.”

And then there are those special moments. “When I’m standing at the top of La Grave with some of the best skiing on the planet below my boards, it’s pretty easy to say, ‘OK I can live with this.’”


Andy Dappen is the author of three books and the editor of His writing has appeared in Sports Illustrated, Outside, Men’s Health, National Geographic Adventure, and many other magazines.