I'm not a jock. I'm not a hey-bro outdoor warrior. I have never run five Cascade peaks in one day like those lunatics in Bend do. Skiing might be my one true talent in life, only because I've done it for 47 years. I'm a middling surfer, a novice rock climber, and a passable mountain biker.

My friend Matt Compton, on the other hand, is definitely a jock. He's also a type-A venture capitalist who likes to milk his weekends to the last drop.

For his 50th birthday, he hatched a plan to do five sports in one day, which was a lot, even for him. And he wasn't talking about a low-hassle combination like tennis-pickleball-bocce-basketball-soccer. He wanted to ski, rock climb, mountain bike, surf and then run.

"Come on," he said. "You're one of the only people I know who can do all of these things."

It's true—and I have all the gear. So, what the hell, I said. I'm in.

Soon after I committed, I learned that Mount Hood would likely be a sheet of solid ice and the surf would be quadruple overhead because of a massive swell in the North Pacific. Worse yet, there would be king tide—a really high one—which means there could be logs in the water. But I had made a commitment, and Matt was really excited. I had to go.

Here's what it looked like:

4:30 am: Skiing

I wake up in the back of my Subaru in the climbers' lot at Timberline, after getting about four hours of real sleep between parties of Red Bulled climbers showing up at all hours and shouting "Dude!" into the cloudless night. I eat a cold egg sandwich and discuss the day with Matt and the other sucker he conned, a really nice guy named Greg Mills, who, like Matt, looks a lot tougher than me. I stow my mountain bike in the car with a Kryptonite lock on it and hope that no one steals the surfboards off the roof.

We start skinning up the Palmer chairlift and thank God that I have ski crampons—two bent pieces of aluminum that ride underfoot and keep me from sliding back and smacking my face on the ice. Skins just aren't enough on this shit.

We reach the top of the Palmer just as the sun comes up. I marvel at the dawn colors, and at how cold my hands are. We decide not to go any higher because the snow is so bad. I ski down on the hardest ice I've seen since a race in western Massachusetts in the late 1980s. I know that if I fall, I'll end up smashed against the back wall of Timberline Lodge.

We return to the cars around 8:14 am. The transitions are key, Matt says, so I hustle into my climbing gear and we drive off in three cars packed with gear. I start listening to a podcast about Ötzi the Iceman, the 5,000-year-old hunter they found, perfectly preserved, in the Alps in 1991. There is much detail about his gear: a copper ax, a backpack, shoes insulated with grass. Sleep-deprived, I feel a strange bond with Ötzi.

9 am: Rock Climbing

We arrive at French's Dome, a tower of olivine basalt left by an extinct volcano on the west flank of Mount Hood. I haven't climbed in years, but I remember how to put on a harness. Matt cracks a chemical hand warmer, stashes it in his chalk bag and leads the route. I'm next. Matt is nervous about time, and the rock is ice cold and wet, so I try to get to the top quickly. I fall off a few times, but I'm on belay. My fingers go numb halfway up. At the top, I vow to do more of this in the summer when normal people do it. I rappel off, and Greg goes. He is a pro.

11:00 a.m.: Mountain Biking

We arrive at Sandy Ridge and gear up. Greg has an e-bike and tows us part way up the fire road. We still have to pedal, but it's a hell of a lot easier. I crack open some caffeinated Clif Bloks at the top and wonder if you can free-base them for extra energy. I crash my bike on a sharp corner and bend the fingers on my left hand backward. They hurt and I'm glad we decided to bike after rock climbing and not before.

We return to Sandy Ridge parking lot, and I wonder if I'm going to have to cut my wedding ring off one of my swollen fingers to keep from developing gangrene. I think about poor Ötzi, dying on an alpine pass with an arrow in his back. He'd be great at this.

2:30 p.m.: Lunch

I drive west on 26, searching desperately for a Burgerville. I know I'm not supposed to stop, but I'm getting a milkshake, dammit. Why else would I do this? I learn there is a McDonald's at every exit in Hillsboro. Screw it. I stop at the fifth one and get a large fries and a strawberry shake. I lose the straw after 10 seconds in the litter of gear in my car. I've already lost and found my wallet three times with all the wardrobe changes. I finish the shake and chase it with a few more caffeinated Clif Bloks. I learn that Ötzi ate fatty goat meat for energy, the poor bastard.

4 pm: Surfing

We arrive at Short Sands, unload the boards and walk down to the beach. Matt's family joins us. I ask his wife how she keeps up with this maniac. She laughs and says something about pawning him off on friends. I confess to the milkshake. The waves are huge, but the tide isn't dangerously high. We can surf the broken junk inside and not die.

I get in the water and get worked by walls of whitewater. The sky turns about the same color as it was at dawn: luminous light blue with pink streaks. I catch three wavelike walls of soup and call it good. Greg, who has only surfed a few times, appears to be a natural.

5 pm.: Running

Matt dons his singlet and short shorts from Sheldon High School, where he was conference champion in the 400 meters and the 4×400 relay in 1989, and where he unsuccessfully tried to grow a Steve Prefontaine mustache. He strikes a few Chariots of Fire poses for the camera, and we take off down the beach and run until dark, which, thankfully, is in about 15 minutes.

I'd like to say that we all had beers around a bonfire after, but while Matt and Greg had beers, and there was a bonfire, I have a nonalcoholic beer because I'm doing Dry January, and I'm orthodox about it. I have a can of Athletic Brewing, which tastes pretty damn good. And this way, I won't fall asleep on the drive back to Portland.

8 pm: Home

Arrive at home, unload all my gear, eat a pile of pasta, collapse and think about Ötzi. I imagine him wearing a wetsuit and carrying a pair of skis. His hand is swollen, and he's looking in vain for a Burgerville, in the Alps.

THE OREGON PENTATHLON, MAPPED: