Did you learn to ride a bike the easy way or the hard way? I did it the hard way. Alone. On a hill. On gravel. With a barn as my finish line. But, you can’t steer from the top of the hill. At some point, you’ve got to start pedaling.

When I was about ten, I got a new bike. It came with training wheels, like most do. But for whatever reason, my dad didn’t have the time to teach me how to ride without them.

So, I figured I’d teach myself.

I took the training wheels off in our garage and grabbed a ratchet set, teaching myself how to use that in the process, and then I pushed my bike to the top of the hill in the barn lot on our farm.

It wasn’t a smooth hill. It was mostly gravel, weeds, and patches of grass. But it was steep enough for what I had in mind.

I climbed to the top, sat on the seat, looked down that hill, and told myself, When you get to the bottom, you better be pedaling—or you’re going straight into the barn. You have to keep pedaling. You have to keep pedaling.

So I did it.

I rode down the hill, shaky and wide-eyed. I pedaled hard when I hit the bottom. Miraculously, I didn’t wreck. I didn’t even fall. So I pushed the bike back up the hill and did it again. And again. Until I figured it out.

That’s how I learned to ride a bike.

Years later, my younger brother wanted to learn to ride without training wheels. So, I did what I knew: took his training wheels off, led him to the same hill, and gave him the same pep talk.

“When you get to the bottom, keep pedaling…or you’re going to wreck. You have to keep pedaling.”

I gave him a push, and off he went. He didn’t fall either. We did a few more runs. We laughed together at the bottom of that hill, proud and out of breath. I didn’t realize it at the time, but we were making a core memory. We were just two brothers and a busted-up hill that somehow turned into something special.

To this day, he still says it’s one of the nicest things I’ve ever done for him.

Looking back, I didn’t realize it then, but that hill taught more than just balance and bravery.

It taught initiative. That sometimes, no one’s coming to show you how, and you have to figure it out yourself.
It taught responsibility. That once you learn something valuable, you don’t keep it to yourself—you pass it on.
And it taught grit. That even a bumpy hill made of gravel and weeds can lead to smooth rides, if you're willing to try, fail, and try again.

I’ve carried that lesson into fatherhood.

I want my kids to be brave enough to take the training wheels off.
I want them to be the kind of people who help others up the hill, not just race down it alone.
And I want them to know that some of the best lessons in life are the ones you teach yourself—because those tend to stick the longest.

Because sometimes, the best way to move forward…
is just to start pedaling.

Who taught you to pedal through the hard stuff?

Maybe it’s your turn to help someone else climb the hill. Share this post with a fellow parent, a sibling, or someone who’s in the middle of learning the hard way.

PS: Whether you're teaching your kid to ride a bike or helping someone in your life find balance again… just remember: they don't need a smooth path—they need a push, a little grit, and someone cheering from the top of the hill.

And if you haven’t yet, subscribe to Grit & Wit—because life’s too short to wait at the top of the hill forever.

Thanks for reading Maury’s Substack! This post is public so feel free to share it.

Share

Downhill Lessons