Now, I could tell you this was a solo journey of introspection and self-discovery. But I’d be lying. This ride was powered by bad decisions, Bang Energy, and a rotating crew of friends who joined me at various stages. Only one man rode the whole way by my side: Andrew Clark. The man, the myth, the legend who trained for this trip by not training for this trip.

The Starting Line: Ignorant Confidence and Hawk Hill

We began at the top of Hawk Hill (read: we skipped the first climb and started with a downhill like cowards champions). The descent was beautiful. The kind of cinematic, wind-in-your-hair moment that makes you forget you’re about to grind your body into a fine powder for the next eleven days.

Clark, having flown in from Nashville the day before, hadn’t so much as sat on a real bike in months. His training? Thirty minutes a day on an indoor bike with the resistance turned down. Day One? He walked his bike up a 3% grade. I started mentally browsing Amtrak tickets.

The Crew Assembles

For the NorCal leg, Kyle Cabagon joined us. Kyle is a longtime friend from our CollegeWorks Painting days and a proud dad of a newborn. He managed to carve out two days to join us, which, considering he has an infant, is basically a sabbatical.

Then came Matt Ryback. He took a train to meet us halfway down the coast, got a flat tire, scavenged Gatorade from a methy 7-Eleven, and brought a breakfast wrap so greasy it could’ve lubed our bike chains. He called it "The Dirty Bird." Clark swore by Bang Energy and weed; Matt swore at his tires.

And then there was Daniel Berman. The man biked despite a surgically-repaired knee and joined us on the tail end in SoCal. Legend. (Also: possibly cursed. He needed another knee surgery right after the trip.)

Big Sur: Beautiful, Brutal, and Seatless

By far the hardest leg was Big Sur. We clocked 77 miles and 6,800 feet of climbing. At one point, Clark’s seat literally broke off his bike. No joke. He zip-tied it back on, but the angle was... problematic. Imagine riding 300 miles with a seat poking into your soul. That’s Clark.

And yet, the guy powered through. No complaints. (Okay, some complaints.) But mostly, just him whispering “I hate my life” into the sea fog and then pushing on.

We survived Big Sur by bribing ourselves with fish and chips at Nepenthe, yelling in joy at arriving at our inn, and sharing the road with a mystery cyclist who looked like he trained by carrying boulders.

The Century Day

The hardest day wasn’t Big Sur—it was the 105-mile push from Oceano to Santa Barbara. We biked 35 miles along a freeway. You haven’t lived until you’ve felt an 18-wheeler breeze past your elbow at 70 mph while your butt slowly forgets what comfort feels like.

Nutrition? The infamous Dirty Bird. That and trail mix. Bang Energy. Some tears.

Matt ended that ride by hosting a dinner party for 20 people. Clark and I lay catatonic on his couch, hallucinating Gatorade bottles and padded bike shorts.

Highlights & Gooch Pain

There were moments of glory. The Golden Gate Bridge at sunrise. That downhill into San Luis Obispo. The birthday party pit stop in Long Beach where Kyle peeled off to meet his family. The cheering crowd. The fish tacos. The beach sunsets. The inside jokes.

There were also moments of despair. Like realizing rest days made our legs worse. Or when Clark’s seat kept popping off every 10 miles. Or the flat tire on the highway. Or the moment you sit down on a rock and realize you can’t feel your nether regions anymore.

We called it "Gucci pain." We rode through it until it numbed out.

Lessons Learned

What did we learn? First, that 615 miles is more mental than physical. You just have to keep going. One Bang Energy at a time.

Second, that doing something ridiculous is always better with friends. I’m still in awe of Andrew Clark—this guy had no business finishing that ride, and he crushed it. If I’m ever in a foxhole (or a triathlon), I want him by my side.

Third, that every town between San Francisco and San Diego has exactly one open 7-Eleven, and it’s always 10 miles behind you.

Would I Do It Again?

In a heartbeat. I’d skip the zero-mile rest days (they just made the next day harder). I’d train a little more. Maybe. I’d bring extra padded shorts. And maybe a second seat for Clark.

But yes, I’d do it again. Because there’s something magical about waking up, putting on the same disgusting jersey, getting on a bike, and moving down the coast with your friends. One mile at a time.

And if you’re thinking about doing something that feels ridiculous or daunting or just a little bit insane—do it. Sign up. Show up. Clip in. Let the seat poke your gooch. You won’t regret it.

Unless you forget your spare tube.

Inspired to take on your own wild goal? Head on over to BucketMatch and start your own "What a Year" adventure. Or, at the very least, share this post with a friend who needs a good laugh. Or padded bike shorts.

See you on the road.