Try it again


On Thursday, one of my colleagues and I received an interesting invitation.

We flew to Bend Oregon to present at the annual Bend Design Conference. The gathering ended on Friday, but we decided to stay until Sunday morning so we could enjoy Fall in the Pacific Northwest. We asked around for advice on what we should do while in town.

One of the conference organizers, Cassondra, happened to be an Expert Mountain Biker. She and her husband own one of the town’s premier bike shops.

“Would you like to go mountain biking on Saturday? We’ll take care of everything for you. I really think you’ll love it.”

At first, we were unsure. There were a slew options for our short time in Bend. Mountain Biking sounded interesting, but we had no experience and no idea what to expect. But after a little research we learned that a local trail complex, Phil’s Trail, includes some of the best trails in the country and it was only 20 minutes away. It would have been foolish for us not to go.

“We’re in.”

On Saturday, we stopped by Sunnyside Sports to pick up our gear – top of the line Mountain Bikes and helmets. Mike, Cassondra’s husband and the shop’s co-owner, suggested  the best route for us to take in the Phil’s Trail Complex: Ben’s Trail + Lower Whoops. Since we didn’t have a truck, we had to ride from town to get up to Phil’s. That was more challenging than we’d be expected. We were tired before we even began the actual trails. Still, we couldn’t wait to begin.

We caught Ben’s trail, and quickly found ourselves facing steep climbs, hairpin turns, jagged rocks, and narrow pathways between trees. With each new obstacle we learned how and when to shift and how to trust our tires in tricky situations. It was nice that it had rained the day before. The dirt was perfect: tacky and tight so there was no dust. Mountain bikers call it Hero Dirt…because you ride like a hero.

The last bit of that half was especially steep. It was the section directly before Lower Whoops. We kept panting and breathing hard. At times, I could tell Aaron was really struggling, and vice versa. In those moments, we paused, drank some water, peered at the amazing forest, marveled at the moment we were sharing, high-fived, and kept riding. Though the ride was arduous, our spirits were buoyed by the beauty of the terrain and the overall wonder of the experience.

Lower Whoops

At the end of Ben’s Trail is the famous Lower Whoops descent. It’s entirely downhill and full of jumps, table tops, turns, and challenging situations. We were advised to lower our seats, stand on our pedals, lean back, and hold the brakes. I listened to most of that, except for the last part.

What happened next changed my life.

As I began the trail, I realized I was entering the mouth of a monster. I was about to be swallowed by the mountain. The jumps were some of the most most aggressive things I’d ever experienced. Several times, I mishandled a landing and thought I was going to flip or face-plant into a tree. Every time I made it past a jump or a turn, I was faced with two options:

  • a) Be grateful I made it through the challenge and then slow waaaay down.
  • b) Be grateful I made it through the challenge. Think through what worked. Try the next iteration on the next jump.

I went with “b.”

Aaron popped out shortly after me. He’d felt the same incredible rush and was glad to have to made it through in one piece.

I’d wanted to try it again, but it seemed crazy. The trail was way above my skill-level and I was exhausted from the day. But when someone offered to take me and my bike back to the top in their truck, I couldn’t resist.

Before my second descent, I remember considering the same options as before: Be grateful & slow down/stop? Or go for it?

There’s something powerful about that moment – choosing to re-face something that scares you. In the words of Nic Lamb, a world-champion Big Wave Surfer,

“Pushing through is courage. Pulling back is regret.”

I did it again, this time with more confidence. There were a few hiccups, but I made it to the bottom, fairly unscathed and challenged by the speed, views, and thrill of the ride.

Wherever you are, there will be times when you travel through challenging and uncertain situations. If you make it through in one piece, maybe you should just be grateful and move on – never to look back.

Or maybe, you should try it again.

PS: Here’s a video of Lower of Whoops taken by another rider: