The World's Wildest Jobs: 17 Guys Who Dodged Cubicle Life

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The Bush Pilot: Drake Olson
Courtesy Drake Olson 2/17

The Bush Pilot: Drake Olson

What I Do:

Drake started flying backcountry planes in Haines, Alaska, in 1995, four years after walking away from a 13-year car racing career. “I was burned out on the fast-pace of the lifestyle,” he says. Drake cashed in and “wandered aimlessly” until he found himself in the fjord-side town of Haines with a pair of skis, a small airplane, and 6 million acres to explore. He considers his three airplanes tools for accessing the country; he calls Haines, a quirky town of 2,500, his supply depot. In the 22 years since coming to Alaska, Howard has flown 8,500 hours in the bush, most of that time shuttling mountaineers, rafters, skiers to gravel bars and untracked powder lines. “The wilderness is both the draw and the challenge,” he says. He’s intentionally dive-bombed grizzlies to chase them off of skiers, made emergency stops to free gray whales caught in gill nets (using only his serrated knife), and landed his Piper Cub on 6,500-foot peaks so that legendary snowboarder Jeremy Jones and his posse could pioneer new lines.

Experience Required:

Anybody can get a pilot’s license. They just need good eyesight, $11,200 for schooling, and 44 hours of classes. There are more than 3,000 flight schools nationwide, with Anchorage’s Land & Sea Aviation among the best. What takes time, and a whole lot more money, is owning and maintaining a plane and learning to fly in mountains as rugged as the Chilkats. “Sometimes there are bad results — you hit stuff, things break,” Drake says. He’s his own mechanic, and he usually works 75 hours per week, much of it meticulously maintaining his planes. “An economist will tell you I’m making fucking $4 an hour doing this job,” says Drake. “I’ll tell you it’s totally worth it.”

Why Olson Always Carries a Grain Shovel:

Early in Drake’s career, he flew a mountaineering guide to the Davidson Glacier, a tongue of ice flowing away from Glacier Bay, so the guy could set up a camp for his clients. Over the past week, 15 feet of fresh snow had fallen. He didn’t realize it was still soft until he touched down. One ski sank, tilting the plane and burying a wing. “Nothing was broken,” Drake says. But his plane was wallowing in a sea of powder. Fuel was leaking from the tank. “The guide was, let’s say, expressive,” says Drake. “ ‘We’re fucked. Call the Calvary.’ ” Instead, they grabbed the grain shovels Drake carries with him everywhere. In 15-degree temps, they uncovered the plane and built a ramp out of the pit. “I fired the engine but wasn't going to risk getting bogged down again,” Drake says. The guide, and his 700 pounds of gear, stayed behind in the snowfield. As Drake took off, snow started falling again. “The guide loved it,” Drake says. “Getting paid to lounge in a tent with hundreds of pounds of food and no civilians to watch over for two full days — it was a paid vacation!”  -Kyle Dickman

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