Week 1 4— The Man With the Clipboard

Do we take our marbles and go home?

52 Weeks
4 min readOct 10, 2021

Starting in the 1940’s, all the parks in the City of Milwaukee came together for an annual chess tournament.

It was held at Hawthorn Glen. A whole field covered in chess sets, lined up in rows.

One year, I even got my picture in the paper.

And the way it worked was, you would play up to three (3) games, and then there was a carnival.

And if you won all three games, you got to come back the next day, and play three more games.

And if you won those, you were the City of Milwaukee chess champion for your age group.

When I was 11, I won my first three games, and got to come back the next day.

I won the first game of day two, which at that point was the farthest I had ever gotten.

And then I won game five, which meant I was playing for the championship. I was literally shaking.

And this man with a clipboard…. one of the counselors… was watching the game.

It was one of those long, tough battles… but I won. I did it. Maybe the greatest achievement of my life.

And I raced to the pay phone to call my dad.

But while I’m on the phone, the guy with the clipboard comes over, and tells me there’s been a mistake. I hadn’t won. There was another kid who was undefeated, and I was going to have to play him. The tournament wasn’t over.

My dad said to call him back...

I couldn’t believe it. Every year it was three games Day One, three games Day Two, you win, you’re the champion, you get a chess set. Maybe your name in the paper.

So they take me to the extra game, and I don’t remember the kid, only the disappointment… that I had to play again.

But I won. Seven in a row!

And the guy with the clipboard said congratulations… again. Maybe we shared a chuckle.

I didn’t even make it to the pay phone this time, when the guy comes over and says he was really, really sorry, but there were soooo many kids in my age group that year, that there was ANOTHER kid who hadn’t been beaten.

And I had to play again.

I just wanted to cry. I was 11 years old. I had it, and they took it away from me twice.

I was ready to tell my dad to come pick me up.

This last kid I remember. He was a tough-looking kid with short hair, and he had four friends with him, behind him, kind of kibitzing, talking smack. I knew it was the last game because it was played on a picnic table instead of the grass, and all the other clipboards were hanging around.

I was by myself.

And at some point, I tricked the kid. I sacrificed a bishop to take a pawn, and while he was celebrating my mistake, I slid my rook all the way down, and his king was trapped behind 3 pawns, and it was checkmate.

And the guy with the clipboard looked at it and said: that’s a checkmate.

And I won the tournament and got my chess set.

(And, yes, it’s still the greatest achievement of my life)

The point of the story is, there’s ALWAYS going to be a man with the clipboard.

No matter who you are, or what you do, someone (or a lot of someones) is going to try to stop you, or change the rules, or put new and unexpected obstacles in your way.

And sometimes, like with the tournament, it’s no one’s fault!

Shit happens. There were a bunch of extra kids that year. Sometimes life throws us curveballs.

It challenges ALL of us at all times. No one gets a pass.

Now, do some people have more obstacles than others? Yes.


And do some people screw up so bad, they create their own obstacles?

Yup, that happens, too.

But whether we got lucky or unlucky (or both), the answer to life’s challenges will always be the same.

And that answer is perseverance.

The question is, when you get knocked down, do you get back up? Or do you take your marbles (or chess pieces) and go home?

We can’t control what other people think about us, or what other people are going to try to do to us, let alone whatever life has in store.

The only thing WE get to control is how we respond to whatever life throws our way.

An obstacle can’t stop us. It might delay us, it might force us to go around it. It might even rob us of a moment of triumph.

(like what happened to those other kids)

But it can’t STOP us. Only WE can do that, by giving up.

When we have perseverance, we don’t just survive — we persevere.

We’re like the Terminator. We don’t stop and we don’t quit.

They change the rules? We adapt our game. They tell us we’re not good enough? We make damn sure we’re good enough.

Perseverance is what separates the screw-ups who make it… from the screw-ups who don’t.


— Get good at it. Perseverance is the last refuge for all of us.