He's done every single leg of the race as part of a duo or a team for the last five years.
But this year, Bend resident John Ostendorff is turning 40.
"I've got a couple of friends turning 40 this year, and this is our way of nipping our proverbial midlife crisis in the bud," Ostendorff said on Thursday.
And that changes everything.
At this year's U.S. Bank Pole Peddle Paddle, Ostendorff won't get any breathers. He's taking on the downhill, Nordic, bike, run, kayak and sprint -- out to prove he can do it solo.
"I'm crossing my fingers that it will all come together nice and gracefully, but most likely you'll see me in blood, sweat and tears at the finish line," he said.
Ostendorff is not chasing after any mugs, nor has he been following a strict training regimen.
"I haven't even honestly ran a full five miles yet, in my training program," he said. "I've been on my kayak once since last year. I don't know if you count nine holes of golf, pizza and beer, but if that counts, that was part of my training as well."
Train or not, it's a chance to be an athlete, for a man who didn't do a lot of sports growing up.
"I'd never really competed in anything," Ostendorff said. "And I think that's why I love the Pole Peddle Paddle so much, because it kind of drew me out, in an event where there are already things that I enjoy doing as a hobby."
He's dreading the run, but is ready for the snow.
"The few amount of times that I really have truly skate-skied, I love the Nordic leg, and I really look forward to it every year."
His strategy for race day?
Pacing himself, holding down the puke -- and most of all, having fun.