How I won, week after week, in a race that was definitely not a race.
When I lived in Oxford, I used to ride the chaingang almost every week for years.
The chaingang is definitely not a race… officer.
Just a “really fast ride” with a group of racers on a set course, ending at a literal finish line—where the first person wins—um, I mean waits for the others.
Racing isn’t the Care Bears.
No one waits for you.
There’s no participation trophies.
Tough. Fast. Thrilling.
Not cruel—that’s just the deal.
Everyone would congregate at the start and set off in groups. The fast group had no speed limits.
My first chaingang: spring, heavy rain, four riders.
We rode as one group. It was brutal. Over a motorway flyover, my cleat unclipped. I nearly crashed. A gap opened up. I couldn’t close it. I got dropped and finished last.
Normally they’d all wait at the finish and ride back to Oxford together—but not that day.
No one waited—it was raining.
I rode into Oxford alone.
The rain was cold, but I was hot, so it was refreshing. It stung where the rain mixed with the sweat in my eyes, and I squinted through the blur of headlights on the wet road.
It was awesome. I loved it.
That was the first and last time I got dropped on the chaingang.
I gradually got faster and ended up in the fast group.
The speed they rode at was crazy. Thrilling.
At first, I was just clinging on.
The last bit of the course had a short, gradual hill (Islip) several miles before the finish.
At the bottom there’s a sharp turn and a narrow stone bridge. The first part kicks steep, then eases off. At the crest you come out of open fields into a clutch of trees — a little forest.
Then it was a flat, wide road all the way in.
The hill was way too far from the finish to make a break stick—or so everyone thought.
It was always a sprint finish.
Same finish every time the muscular sprinters pushed to the front and barged each other. Not dirty — just racing.
I was rubbish at sprinting, so never got a look-in.
But I didn’t complain. It was good training.
I started getting faster. I was good at climbing and breakaways.
I knew I couldn’t get away on the hills or at Islip—but I rode hard anyway.
One time up Islip I attacked and got a big gap, but I waited and let everyone catch me.
A rider said, “Why didn’t you keep going? You had a big gap.”
I said, “It’s too far to the finish. I never would’ve made it.”
But then I started wondering.
Was it too far to the finish?
I got obsessed with time trialling—riding flat-out solo.
Trained all winter. Got strong.
I decided I wasn’t going to wait anymore.
The first chaingang of the next season—
We hit Islip.
I attacked. I really meant it this time.
At the top of Islip I had a gap.
But they chased me down miles before the finish. Sprint finish.
Second chaingang. I attacked on all the hills, softening them up.
Bigger gap. They still caught me—but only just. I could see the finish line.
Another sprint. But they were getting worried.
Third chaingang.
I attacked on all the hills and flyovers.
Then I launched at the bottom of Islip.
By now, everyone knew what was coming.
I got a huge gap.
They chased me all the way.
I could feel them bearing down, furious, like poking a group of bears with a stick then running. My legs were screaming, heart hammering like electric shocks in my chest. I didn’t know if I’d make it.
I crossed the line first. I’d done it.
I didn’t celebrate—I was too stunned.
And that was it.
Every. Single. Week.
I attacked at Islip and rode away.
They still got their sprint, of course.
The same elbows-out dash to the line.
Only now, it was for second.
They started complaining.
They didn’t like sprinting for second.
But that’s racing.
When it was a sprint every week, I didn’t moan.
I didn’t ask them to let me get away.
That’s not how it works. You don’t get favours.
There was no trick. No cheating.
They’d ask, “You going to attack on Islip?”
I’d say, “Yup.”
They knew anyway.
Eventually, some of them started hinting that maybe I should stop.
I said no.
“If you want to stop me winning every week,” I told them, “you’ll have to figure it out.”
One of them even asked me to tell them how.
Seriously.
I didn’t laugh. I just said:
“Why would I do that?”
They never figured it out.
Not because they couldn’t — but because they never tried.
They convinced themselves it was impossible.
But it wasn’t.
They could’ve worked together.
If they’d taken turns attacking me, made me chase, forced me to burn out—I wouldn’t have had the legs left to break away.
But they didn’t want to do that.
They didn’t want to cooperate.
They just wanted to win—alone.
And every week, they lost—together.
The chaingang was brutal.
There wasn’t much sympathy.
If you got dropped, you rode home in the rain.
But there was something honest about it.
If you won, you knew it was for real.
That’s racing.
No one owes you a win.
But if you’re losing the same way every week… maybe try something different.
You can moan about how things aren’t fair, if you like.
And keep losing.
Or you can figure out a solution.
Adapt.
And win.
Don’t play the game. Change the game.


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