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From Triumph to Breakdown: My San Diego Cycling Disaster

Close-up of a damaged bicycle derailleur and rear cassette after a mechanical failure during a long-distance ride, with derailleur visibly twisted and cable disconnected.
When Everything Felt Perfect on the Bike
Some days on the bike surprise you — not because of what goes wrong, but because of how right everything feels. That’s how it started for me on June 1st in San Diego.

I had trained for a full year, preparing for what was meant to be the final leg of my long-distance cycling tour across the United States. I’d already ridden from Las Cruces, New Mexico to Lubbock, then all the way to Florida. All that remained was the west: San Diego to Las Cruces.

Over 6,500 miles of training — much of it on Texas roads — had prepared me for this. I focused hard on climbing, knowing the first two days of the ride would be steep.

When I rolled out of San Diego that afternoon, I felt stronger than I could’ve hoped. The hills didn’t intimidate me. My legs had power. My breathing was steady. I felt ready — not just physically, but mentally.

So ready, in fact, that I pushed beyond the plan. Day 1 was supposed to end before the toughest climb. Instead, I decided to go after it. I’d already climbed 2,800 feet. That next stretch would climb 2,400 more.

A Sudden Mechanical Failure in San Diego
I stopped briefly in a parking lot to eat a fig bar — just a quick break before the big effort. As I reached into my jersey pocket, I unknowingly pulled out part of a microfiber towel I always carry.

Fifteen feet after I got back on the bike, disaster struck.

The towel got sucked into my drivetrain. The derailleur twisted, jammed into the spokes, and the chain was shredded. The hanger was bent. Just 34 miles into the tour, my bike was unrideable.

The Ride That Broke Me — But Taught Me More
I had driven 1,100 miles to San Diego. I had poured a year into this effort. That day started with some of the best riding I’d ever done — and it ended in heartbreak.

The repairs took two weeks. The emotional recovery took longer.

But somewhere in that time, something changed. I didn’t feel anger. I felt clarity.

From Solo Bike Tours to Group Cycling Events
I realized I no longer want to do long solo bike tours. What once felt like peaceful solitude now feels like isolation. The logistics. The risk. The long, quiet days. They’re not calling to me the way they used to.

But I’m not done riding. Not even close.

Going forward, I’ll focus on single-day and multi-day cycling events — one per month from July through October. These rides bring people together. They still demand endurance, preparation, and grit. But they give back energy too.

Looking Ahead: Albuquerque and Redemption
In October, I’ll ride 47 hilly miles in Albuquerque. It’s not a cross-country route. It’s not hundreds of miles. But it’s meaningful.

Why? Because it’s full of climbs — the kind of climbing I trained for. The kind of effort that San Diego was supposed to celebrate. This ride will be my redemption ride. A way to reclaim the confidence and purpose that started with that tour.

Why I Keep Riding — Even After Setbacks
This journey reminded me of something essential: not every ride ends the way we hope — but every ride has something to teach us.

Even the worst ones. Maybe especially the worst ones.

I’m still in the saddle. Still training six days a week. Still chasing challenges. But now, I do it with a new sense of purpose — and a little more wisdom in my pocket.

I may never finish the San Diego to Las Cruces tour. But come October, Albuquerque will be my summit.

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