No Longer Mandatory

Read time: 5 mins

Home run.

It was his professional at-bat. And he catapulted the ball over the fence.

His name was Tim Wakefield. A lanky first baseman for the Single A Watertown Pirates.

Wakefield had a bad habit. He liked throwing a knuckleball around the infield during practice.

He threw it so much, the manager, Stan Clinburn had to urge him to stop and throw the ball straight. Wakefield didn’t listen. It wasn’t mandatory that he throw the ball a certain way.

He was slotted to be a home-run hitting first baseman. Why throw a knuckleball? It was a circus pitch.

But his swing had a few holes in it too. Wakefield struck out 92 times in 256 at-bats in his first two seasons. And that was in Single A.

How could a player who struck out 36 percent of the time make it major leagues?


Everyone knows as soon as you make something mandatory, it becomes the opposite of what you want to do for a living.

Jessica Hische, Learn the Tools

People do not like to be told what to do.

My first job was a sports information director at my alma mater. It’s a fancy way of saying I was the middle man between athletes, coaches, and the media.

One of our tasks was transcribing quotes of coaches and athletes. This way we did the media a favor. Reporters could easily pull a quote for their story or deadline.

I grew to hate it. Because it was a mandatory part of my job.

Six months ago, I found myself watching a long interview with Jason Fried. The Chicago Founders’ Stories series, hosted by Pat Ryan, asked Jason questions about Basecamp, his company. It was a fascinating interview.

So much that I found myself playing a few parts back. One specific part where Jason discusses the advice they received from Jeff Bezos.

A few minutes later, I started transcribing what he was saying. This was a task I used to hate. But here I was transcribing an interview in my free time just because I could.

It was no longer mandatory. I found myself wanting to transcribe other talks like this 1997 Q&A with Steve Jobs.

Today, I transcribe about an interview a week. It started as me hosting them with my favorite web app Draft. And now it’s morphed into a side project on my personal site.

I’ve done 23 total and you can check out the full list at people.hotdogsandeggs.com/list.

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I’m getting a lot out of this side project.

By listening to other people, it’s helped with my writing and making it more conversational. I get ideas for blog posts like this one and get to share the advice and inspiration with other people. I’ve traded emails with people I respect like Derek Sivers.

All because it was no longer mandatory.

It’s sparked other ideas for more side projects too.

Tom Haverfoods Meets Dale Carnegie

I used to hate reading in high school and college. Your assigned to read to chapter 13 by next Tuesday or 250 pages by the end of the week. It was mandatory. And no fun.

After college, I found myself reading more. I would rip through a book in a weekend and enjoy every minute of it. Because it wasn’t mandatory.

If I could recommend any book to you it would be How to Win Friends and Influence People by Dale Carnegie. Ignore the cheesy title. It’s timeless lessons in how to be considerate.

Carnegie has 30 principles in the book. Smile. Try honestly to see things from the other person’s point of view. Ask questions instead of giving direct orders.

The problem was finding all the principles in one place. Since the book was published in 1936, yes almost 80 years ago, it’s a bit outdated. I could find PDFs online and a list of the 30 principles.

But it just didn’t feel right. That’s when I found inspiration from an unexpected source.

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Parks and Rec is a hilarious sitcom. Aziz Ansari’s character has a skit where he fires off different slang for foods. And then someone made the site, tomhaverfoods.com.

Reload the site and you’ll see a new slang term. Honey is bear drool. Ice cream is milk on the rocks. Milk is cereal sauce.

It’s amazing.

I found it really interesting how the site was built. It’s so simple. Just one phrase per page. How did they do that?

That’s when I decided to marry to the two ideas. What if Tom Haverfoods could work for Dale Carnegie’s principles?

And now I give to you, dalecarnegieismyhomeboy.com. Reload the page and find a new principle.

This side project taught me how to build a site that delivers dynamic content when the page reloads. Javascript is boring, but man is it useful. I practiced writing code and designing a website too.

All skills that help me learn. And all because reading was no longer mandatory.


Tim Wakefield wasn’t going to make it to the Major Leagues as a power hitter.

Woody Huyke was a scout for the Pittsburgh Pirates. He noticed Wakefield throwing that knuckleball around in Spring Training. Then he asked Wakefield to throw it off the mound.

Wakefield pitched 19 years in the Major Leagues.

He won 200 games on the mound throwing that knuckleball. A feat only 112 pitchers have ever accomplished. He struck out over 2,000 batters. And he won two World Series titles with the Red Sox.

It wasn’t mandatory for Tim Wakefield to throw the ball straight. So on the side and during practice, he threw it a different way.


Find the things in your life that are no longer mandatory. Do them on the side. And you might just discover your knuckleball.



Rock onThanks for reading!

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Find me on Twitter @cjgallo or GitHub @gallochris or Instagram @heygallo.