Headwinds & Heart: What a “Failed” Ride Taught Me About Grit and Grace

By Mandy Cloninger

My first attempt at a metric century: 65 miles ended with a Snickers bar and a few salty tears.

The conditions were brutal. Sustained winds of 15–20 mph, gusts even higher, and the constant threat of rain. Every mile was a battle against the headwinds, the kind that steal your speed, your breath, and a little of your confidence.

I missed the first SAG stop at mile 17, and the climb over the bridge was punishing. The gusts were so strong you didn’t get to enjoy the ride – you had to pedal downhill just to move. Near the Space Center, there was a blessed couple miles stretch where the wind finally let up, and I caught a glimpse of what progress feels like: 18 mph and a smile. Then, just as quickly, I was back in the gale.

Those few joy-filled miles near the Space Center with tailwinds and a rocket launch!

At one point, I actually screamed into the wind: “ARGH!” It slapped me right back.

By the second SAG stop, around mile 40, I was spent. My phone and GPS had died, my legs were cooked, and my spirit was sagging, too. I rehydrated, refueled, and complained (lovingly) to Rach and Luna, who were cheering me and the others from the sidelines. Once my phone charged enough, I read messages from my tribe, my encouragers who’ve been my tailwinds all along.

I got back on the bike for a few more miles, but the threat of the second bridge was too much. Around mile 45, I called it. Four hours of slow grit. No finish line. Just wind, willpower, and a little wisdom earned the hard way.

Once in the car, I had my consolation Snickers bar with a few salty tears on the side. It wasn’t my day to meet my goal, but I’ll live to bike another day. I’ll face those headwinds again.

Lessons from the Headwinds

1. Headwinds reveal kindness. Every cyclist who passed me checked in, “You good?” “Need anything?” Even when they were struggling too. In leadership and in life, the people who pause to help when the winds are strongest are the ones who make the journey possible.

2. Headwinds remind us we’re not meant to do it alone. I’ve done plenty of solo rides this year, but I’ve also joined group rides with Grupetto and Tampa Bay Rides. The next time I tackle a century, I’ll do it with a team. Drafting, encouraging, laughing through the pain that’s what keeps you steady. Some miles are not meant to be done alone.

3. Headwinds teach grace. Not every goal is conquered on the first try. Sometimes, despite your best preparation, the conditions just aren’t right. We can’t control the winds of change, but we can build the community that helps us stand (or pedal) through them.

4. Headwinds can’t erase progress. I didn’t make 65 miles, but I’ve made it to 45–50 twice now, and I’ve logged more than 1,000 miles in my first year of cycling. That’s movement, growth, and resilience, even if it doesn’t look like victory.

The truth is, headwinds are part of every meaningful pursuit, whether you’re training for a ride, leading a nonprofit, or fighting for change in your community.

They slow you down, test your spirit, and make you stronger than you realized you could be.

👉 So, what headwind are you facing right now and what small win can you celebrate anyway?

💬 I’d love to hear from you. Drop a comment below and share your story.