I'VE BEEN snowboarding for 12 years. But despite being able to tear down double-blacks and through waist-deep powder, I?still find leaving the ground terrifying. Ollies, boxes, rails, and the biggest of all terrain-park horrors, the halfpipe—they haunt me.

Which is why I'm shaking in my black freestyle boots right now. I'm standing at the top of a 22-foot halfpipe on Oregon's Mount Hood Glacier, hoping to find the courage and skill to drop in and fly over the lip on the opposite side. "Halfpipe riding is probably the most technical discipline in snowboarding," says my coach, Reed Silberman. "Any imperfections in your form will come out."

Um, thanks?

Silberman, 33, is head coach at Windells, a 22-year-old ski-snowboard-and-skateboard camp that, thanks to the glacier, stays open year-round. More than 90 percent of all X Games snowboard medals have been won by athletes who passed through Windells, including Shaun White.

My goal was more modest. I showed up for six days of private instruction last June hoping simply to learn to soar—no tricks or style points—out of the pipe. My lessons began on some blue and green runs with fundamentals, going over things I had forgotten or long ignored, like keeping my shoulders parallel to the board and bending my knees more.

When rain ate at the snow and ice—which it did for half my stay—Silberman took me to a vert ramp in Windells's 184,000-square-foot skate area to work on "pumping the transitions." In a halfpipe, you build speed by crouching as you enter each curved transition and extending on the flat bottom and the vertical sections of each wall. I managed on the skateboard but had a much tougher time on snow, which has a lot more variables. If I turned my shoulders, I lost balance and fell short on the far wall. Same thing if I made a sloppy turn, crouched late, or sprang early—time and again I ended up stuck low in the pipe's trough.

I found more success outside the pipe. After lessons on weight distribution and body alignment, Silberman eventually had me doing ollies, 180s, and box slides over small jumps and obstacles. The trick, I?realized, was less about learning the skill than knowing I already had it. If I?approached an obstacle confidently and fully committed, my momentum would simply carry me over. As for landing, that just involved being on the snow, which has never been my problem. The last day would be my one chance to put this all together in the pipe.

But after five hours, I still haven't. As my fellow campers spin below me under the June sun, I drop in for my last run and am shocked when I?can suddenly see over the lip on the far side. Unfortunately, only my head makes it that high. With my board stalled about a foot below, I do a quick ollie and slide back down. So I?didn't air it out over the pipe, but I?can catch air now. And I plan to spend a good part of this winter above the lip.