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Ideas in Peter Olenick’s world are fantastic in such a way that you never think they’ll come to fruition. “I’m going to do a 25-foot flat five,” he says. And we all laugh it off until the next morning when, over a plate of eggs and pancakes, I see him on the cover of the Aspen Daily News and realize that, well damn, he did it. Not all of his ideas happen though. For a few years, he’s been telling me that the best place in the world to build jumps is Alaska. We’ll live the good life, he tells me. We’ll go to the Bush Company at night and ride pro snowmobiler Paul Thacker’s sleds during the day, cruising around to find perfect terrain for jumps. You’ll shoot photos of dudes on skis doing flips so close to sea level that it will look like they will land in the ocean. Heroic shit. Yet year after year, the trip doesn’t happen. “Set it up, and I’ll be there,” I say, passive-aggressively giving my imagination the space and time to avoid failure.

“OK everyone, we are going up to AK on the 21st and coming back on the 30th.” That simple email from Peter was the culmination of years of shit talking and dreaming, a pile of emails and countless nights of conversations that ranged from “we could” to “we should” to “can we?” to “let’s.” The point is, like that world-record halfpipe air, it happened. Long after every other ski crew was done for the season, Mack Jones, Matt Walker, Joe Schuster and Peter headed north and west, flying into Anchorage on May 21, 2013.

We camped out in the living room of Thacker’s condo for 10 days. The first three days seemed like a failure, crap weather and no sleds greeted us. We responded by boozing, playing hockey on PlayStation and golfing late in the evening under bright grey skies. Then the weather and everything else aligned. Three days of noon to midnight sledding and jumping led into a down day because of bad weather, perfect for the guys to rest their bodies and take a much-deserved trip to the Bush Company, Anchorage’s premier gentleman’s establishment. Then it was back to work for two more days of jumping and a day shooting an ad campaign for Eira, the outerwear brand that sponsors all the skiers and funded this potentially disastrous spawn of Peter’s brain.

But it wasn’t a disaster. Just as a skier who launches a 25-foot air in the pipe before putting his skis down on the steepest part of the transition, the Eira team blasted off for a week. Thacker showed us around, partied harder than us, always seemed to have more one dollar bills for his lady friends and reminded us that even strapped into a bucket seat without use of his legs, he is a better snowmobiler than all of us combined. We built big kickers, then built them closer to the water. None of us wrecked the sleds that Thacker and his friends from Big Lake Powersports wrangled for us. And, when the time was right, we piled into Thacker’s huge, lifted truck and had two of Alaska’s finest young ladies deliver us to the airport with a smile and a wink.

The above text and photographs originally appeared in the 2014 Photo Annual issue of Freeskier, Volume 16.5. Freeskier Magazine is available via the iTunes newsstand.