For life lessons, look to the comedians

The teletype started tapping this morning and an assignment emerged: what is your favorite thing you’ve ever written?

My favorite thing I’ve ever written is every interview I’ve done with every comedian I’ve ever spoken to (plus some other folks who aren’t comedians, but for this day and since ChicagoNow says NOW, I’ll just mention the comedians).

Comedians specialize in honesty, insight and laughing. So talking to a comedian is a life-changing experience.

Sometimes people ask, “Who was your favorite interview?”

Impossible to say!  I have favorite things about every interview and every comedian. I’ve learned something from each. Much of what I’ve learned has changed my life.

ChicagoNow’s rule is we have to post within the hour, so this is not a complete list or even close– a complete list would be a book! Comedians’ insights are encyclopedic! But here are some of the life-changing lessons I’ve learned.


From Prescott Tolk:

Prescott was the first interview I ever did. He is now a writer and comedian in L.A. One of his bits is about his dad.

“Prescott, I never asked for anything.”

“But Dad! You don’t have anything!”

“That’s my point. You’ve got to ask.”

Lesson: Don’t be afraid to ask. Asking is my weakness. But Prescott’s point brings home the consequences of reticence.

From Paul Thomas:

I’ve been fortunate to speak with Paul several times. He was kind enough to do my first interview on ChicagoNow, although we’d spoken before for TribLocal and the Patch. (Check out Defiant Thomas Brothers now at Stage 773 and more of Paul’s work here!)

Paul once said that a challenge of comedy today – and it’s true of everything – is that even a yacht is hard to see in the middle of the ocean.

Lesson: The information that comes at you these days is the size of all the oceans together. It’s infinite. Don’t give up. Keep putting your work out there even if the challenge feels daunting. If it comes from Paul who is at the very top of the game in every comedy genre, I know it is ok to acknowledge the vastness, but then focus your view on what’s immediately in front of you and keep moving.

From Steve Gadlin:

Steve is the creative genius known for Don’t Spit the Water (the first television pilot funded by Kickstarter), “I Want to Draw a Cat for You” (which started as a lark and ended up a venture funded by Mark Cuban on Shark Tank), Steve Gadlin’s Star Makers and most recently, one of the most energizing, fun appearances I’ve ever seen on Who Wants to be a Millionaire.

He also created the Nairobi Project which had its genesis in a spam email he received from a writer in Kenya. The email offered writing assistance. Where other people would see the delete button, Steve saw opportunity. He wrote back and agreed to the twenty-five dollars for a script with the following specifications:

“A millionaire named Quack Quack Quimby has forgotten the true meaning of the Jewish holiday Tu Bishvat. His daughter goes to great lengths to remind him of its meaning, and make him happy once again….”

The play went on to become a sold-out hit in Chicago. Steve, who is as honest as he is creative, sent the royalties back to the playwright.

Lesson: Opportunities are everywhere. Something else Steve told me is he believes in the principle of getting underwater on a project, is how he put it. Get to that point where there’s no turning back and the commitment is set in stone. If you have qualms about whether a project will work, about your ability, or the sanity of an idea, get over it! Get underwater. You’re in and then you’ve got to take it all the way. Looking at the awesome and highly original results of Steve’s projects, I always have this advice in mind, although I’m not as good at following it as I’d like to be.

From Cameron Esposito:

One time at the Wilmette Theater in 2010, three years into her career, Cameron began her set by letting the audience know she’d be signing her album after the show and that one day it would be worth something because “I’m going to be very, very famous.” These words were spoken from a place of truth, commitment and humor, and they were prophetic.

Coming up on the close of the hour, I can’t list everything Cameron has done since then, but here is her imdb listing.

Lesson: The combination of talent, integrity and focus is powerful. (I do have a signed album. There was no doubt she spoke the truth and always does.)

Hour is up. This is just a short list and even a short list with regards to each comedian I’ve mentioned. I hope to continue to add to it. No! Underwater! I WILL continue to add to it!

What I know: if you want to know what’s important in life, look to the comedians. What they know would fill all the oceans put together.


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