My Journey with Climbing

Climbing is all a head-game for me. Every start I overthink how hard it will be, and every end I look back at how silly I was being.

7 years ago, I was just getting into cycling as a sport. I had purchased my first road bike and started going to a Wednesday night group ride regularly, put on by the local cycling team.

This ride took riders on a 15-18 mile route out to Wellesley and back making sure to hit a couple of quick, but steep, climbs. There were 3 paces, the fast, the medium, and the “leisure” group. As a new rider and a slow endurance athlete, I kept to the slowest group. In retrospect, I’m lucky this ride didn’t completely put me off riding in groups, because the local men’s racing team would argue over who had to lead the slow group and was overall a little disdainful about having that section (not a great look for the organizers, but it was one of the few local group rides at the time and I was under the misconception that I needed to “train” versus have fun riding).

I still remember one very specific moment when we were coming back over the last hill before the mile downhill back into the end and beyond. One of the racers road up next to me and said, “Looks like you left your legs at home” then road off like I was doing a track stand. It was extremely discouraging. Their complete ease of riding made me feel completely inadequate.

Why am I bringing up this story now? Because just the other day I rode out and back to a teaching gig in Wellesley wearing casual clothes on my steel frame touring bike and a randonnuering bag full of stuff with little thought to the fact that I was taking a “hilly” route. I rode on almost the same route and over a lot of the same hills. It was while I was going up the 1.5 mile gradual hill that I had this moment of self-reflection. I am casually commuting on the same road that I hated and built up in my head. I was aware that I would need to conquer this hill, but it didn’t scare me the way it had in the past. My feeling was more annoyed (because there was no way around a hill) than worried.

I wish I could tap myself on the shoulder 7 years ago and say it gets better. Am I a spectacular climber now? Hahahahah, no. Am I a better climber than most riders, still no. It’s just that I stopped being so hard on myself. I don’t need to be the fastest up the hill, I just need to be confident in myself that I can make it. I can see a marked difference in my ability to climb hills today compared with even 2-3 years ago. The more you ride, the easier it gets. Add to the fact that I know a lot more about riding (i.e. technique, my personal fueling needs, etc.).

The hardest thing for me is remembering this sage advice. On my recent ride in Maine they talked about this one really big hill coming up after lunch. I spent the whole day stressing about it, not sure if I’d make it. By the time I reached the top, I couldn’t believe how insecure I had been. I build up these “hills” in my head and then completely overthink it. Hopefully in 7 years I can look back at myself today and continue to see improvements in my mental fortitude.

There are a handful of things you can do to improve your climbing experiences beyond just riding your bike a lot (honestly being a full-time bike commuter did wonders for my stamina) all of which I do or should apply, such as changing my mindset, doing repeats, properly fueling up ahead of time, and attacking the finish.

However, for me the biggest thing is overcoming the head-game. Which is easier with friends and with each subsequent climb. Now I look back at that final climb on my way back from Wellesley and think how much I didn’t know then. How, if that male racer had talked to me instead of teasing me, he might have realized I was close to bonking because I wasn’t eating enough pre-ride and not snacking during. With a little advice and encouragement I would have felt more confident and grown faster instead of being embarrassed to join group rides outside of these anonymous strangers.

Remember, when all else fails… sing “Just keep swimming” or “I think I can, I think I can” as loudly as you feel comfortable until you reach the top!


If you’re really serious about improving your climbing skills, Selene Yeager the Fit Chick, is one of my favorite go-to resources. She has several books and is a Bicycling.com writer. I don’t know her, but I read her book Ride Your Way Lean (which pointed out that taking off a few pounds also improves climbing…) and found a lot of really helpful advice. She has a new book called CLIMB! that I may be checking out this winter.

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