The Art of Trying Out

You don't know if you have the stuff until you show up to the tryouts.

May 08, 2024

Look at this kid.

This is a proud dad post. Prepare yourself.

But don't worry, this isn't just for parents. There's a lesson buried deep in here, too.

Eighteen months ago, after a semi-successful community soccer season, this 9-year-old told me she wanted to try out for the All-Star team.

The confidence on this kid. Wow.

I knew two things:

It would be a good character-building experience for her to try out for the team.
It would be good because she would NOT make the team.

This much I knew.

So we went for the first day. She put on the shriveled, tattered pinney and ventured onto the field with fifty other hopefuls.

Fifty girls trying out for just 10 roster spots.

My kid had no chance.

But the character-building would be off the charts.

However, after 90 minutes of drills and scrimmages, she was one of the best ones out there. Sharp, decisive, skilled. Direct passes and a great attitude. All-Star stuff.

A friendly parent gave me a “can you believe her?” look.

I was certainly surprised.

This couldn't be MY kid. This kid surely would have inherited my TOTAL LACK of childhood sports-related skills.

Gaze upon this mid-80s nerdery:

When I was nine, I couldn't run up and down the soccer field. Too uncoordinated. They stuck me at goalie.

It wasn’t until 8th grade when my body finally clicked together like Voltron.

But this kid is different.

On the second day of tryouts, she was scoring goals on goals. She made the team.

She had a successful All-Star season as the anchor of the defense. They won tournaments. The medals and pins started stacking up.

Then she turned ten and tried out for the EXTRA team (essentially, a traveling All-Star team that lasts a full calendar year).

She made that team, too.

She's played very hard. She’s not the fastest or the biggest. She doesn’t yell or intimidate anyone. But her elbows are sharp and she learns fast.

She's been front-checked by players, elbowed, kneed, took a soccer ball to the face, broke a pair of glasses, and cried a lot of semi-injured tears.

This past weekend was her final tournament. Two days, four games in Walnut, CA (an hour east of us, outside Los Angeles).

The team won all four games—winning the whole thing—with scores of 4-1, 2-0, 6-1, and 3-1. That's a total of 15 goals and only 3 allowed.

This is Messi-level greatness. (I told you this was a dad post.)

But in the final game, something special happened.

In tournaments like these, they give coaches a special trinket (like a coin or dog tags). The coach is supposed to give them to an opposing player who displays good sportsmanship.

So in the final handshake line after the final game of the final tournament of the year, she was singled out as being a kind competitor.

I guess the character-building happened after all.

And none of it would have happened if she hadn’t asked to try out.

There is no try

Socrates said it best: “Do or do not. There is no try.”

But I’ll take it a step further.

Sometimes, you have to try out before you know what you got.

You may or may not have the stuff. You don’t know.

You have to try out to find out.

Go out there and put up your skills against someone else. Compare and contrast.

Not to win.

But to grow.

To see.

My tryouts

Jerry Seinfeld was recently interviewed about why he continues to do stand-up comedy. He's 70 years old and has enough money to do anything he wants for the rest of his life.

He said something that has been rattling around my brain for a few weeks.

David Remnick: "You've probably made a dollar or two from Seinfeld, and yet you still work so hard. Why?"
Jerry Seinfeld: "Because the only thing in life that's really worth having is good skill. Good skill is the greatest possession. The things that money buys are fine. They're good. I like them. But [nothing like] having a skill."

Having a good skill.

I'm lucky enough to have lots of nice possessions. A nice house, a nice sweater-vest, a nice dog, yadda yadda yadda.

But a skill.

That's something to shoot for.

So here's what I'm doing to "try out."

I'm making two things and I don't know how they will go, but I'd like your help.

Commitment #1 - The Book

I've been on the fence for too long. I'm going to write a book about my experiences as a creative entrepreneur. Over the course of 20 years, I've been a freelance web designer, an aspiring TV comedy writer, an agency founder, an agency seller, a marketing executive, and a guy now making sense of it as I look to the future.

I've failed a lot, succeeded a lot, and have both business lessons and funny stories to share.

I’m giving myself the summer to finish 80-100 pages worth reading.

My goal is to have a draft ready by late summer, with pre-orders by early fall.

My working title: Good Misfortune.

Commitment #2 - The Show

I've posted here about my 2024 commitment for more stage time.

I've done two open mics, and performed three times at The Moth. I've loved the experiences as forcing mechanisms. I’ve even done well:

I've binged hours and hours of podcasts featuring comedians/storytellers Pete Holmes, Mike Birbiglia, Neal Brennan, Nate Bargatze, and more.

Birbiglia was on the Smartless podcast a few months ago, explaining the setup of his shows:

"I just think a typical stand up is basically built on the premise of you have a series of set up, punchline. [But] what I've learned through the years is those jokes can be part of a five minute story.
And if you have ten five-minute stories that add up to a single story, that's really the goal of all my shows. And [I try to make] an emotional payoff at the end."

Ten five-minute stories with an emotional throughline?

This I can do. This I am delighted to do.

I don't know how good I am at it. I don't know if I want the career these other famous names have. Not sure I want to do the same work.

But I’d like to try out. I’d like to go for it.

So I'm committing to, like the book, write a one-hour show that I'll put up on stage in Los Angeles later this year.

That's my commitment to trying out.

Feels scary.

Feels exciting.

Here's how you can help.

I'll take all the encouragement you're willing and able to give. Leave a comment. Text me. Hit reply. Give me some ideas. Check in.

Maybe I’ll do a presale for the book or show. But I won’t get ahead of myself.

I’m preparing to try out.

Here we go.

Thanks for following along.

What are you doing for your tryout?

Anything interesting? I’d love to hear and encourage you!