Why Successful Comedians and Business Leaders Step Out of the Stream

Joshua Ramirez
Book Bites
Published in
4 min readApr 2, 2020

The following is adapted from Shtick to Business by Dr. Peter McGraw.

Comedians aren’t good rule followers. They’re usually not the kind of people you want leading a boardroom, classroom, or newsroom (unless that newsroom is The Daily Show). But not following rules is a key to success in comedy.

To step out, comedians must first observe the world around them and see the way things truly are — the way others are thinking and behaving. From here, they can take actions that violate the status quo and create novel content.

Similarly, great business opportunities are often novel, and yet too many businesses focus on imitation, thinking that it’s going to lead to success. But if the goal of business is to be the best, then it helps to do something different and new.

Breaking the rules can lead to innovative results, and by taking a page out of the comedian’s playbook, business professionals can stand out from the competition.

The Benefits of Breaking the Rules

Comedian Hannah Gadsby is courageous. She opens her Netflix comedy special Nanette by discussing her discomfort living in a small rural town. Gadsby grew up in Smithton, Tasmania (pop. 3,818), which she loved but had to leave “when I found out I was a little bit lesbian.”

You see, homosexuality was a crime in Tasmania until 1997.

She shares with the audience that in order to make her jokes land, she’s had to omit much of the truth — the trauma she’s faced as a woman and a lesbian in a world that’s not always welcoming to women and lesbians. She then tells the honest account of her struggles and traumas.

The Australian comic breaks the rules of a stand-up special. Her audience comes for a comedy show and instead receives the decidedly unfunny life experience of a marginalized woman.

She closes to a standing ovation.

Gadsby became more famous when she stopped telling jokes and broke the rule about sharing serious subject matter in a comedy special. This kind of courage can lead to great rewards in both comedy and business.

Breaking the Rules in Business

In the same way that comedians like Hannah Gadsby have thrived by breaking the rules, many business leaders have as well. Take Sara Blakely, the creator of women’s compression-wear company Spanx, for example.

Shortly after launching her control-top undergarments, Blakely managed to get the product into Neiman Marcus. Spanx was placed in the hosiery department, a part of the store Blakely knew her customer would not venture.

To ensure her product got noticed, she snuck around the store, waited until no one was looking, and moved the display next to the cash register. Fortunately, the employees assumed that the decision had been approved by some higher-ups. Sales spiked.

Not surprisingly, when she was just starting out in her career, Blakely worked as a stand-up comedian. She was no stranger to breaking the rules, and the same type of risks comedians take regularly — will the audience be angry if I deviate from the norm? — paid off when she made the transition to business.

Step Out of the Business Mainstream

To tap into the boldness and creativity of the successful comedian, I suggest you mimic their mindset and look to step out of the mainstream. You know the clichés…go against the grain, zig when others zag, think outside the box. (Ugh…I promised myself that I would think of an outside the box way of saying outside the box.)

By their own nature and by the nature of their work, comedians must think differently than everyday people — and hence they act differently than everyday people.

There’s a comedic premium placed on novelty, and not only do comedians have to break the rules of the status quo in the normal world, but they must do it differently than the comedians who broke the rules before them.

Often, boldness in comedy pays. For example, comedian Dave Chappelle walked away from a $50 million contract from Comedy Central, and he’s still worth that much! Chappelle does what he wants and is rewarded for it.

Applied to business, this way of thinking can lead you to similarly groundbreaking ideas and opportunities your play-it-safe competitors will never see. People thought concepts like Uber and Airbnb were crazy when they first hit the market, but who’s laughing now? The multibillion dollar companies that took a risk and were willing to break the rules.

For more business advice from the genius and madness of the world’s funniest people, you can find Shtick to Business on Amazon.

Dr. Peter McGraw is a behavioral economist and global expert in the scientific study of humor. He directs The Humor Research Lab (HuRL), hosts the podcast I’M NOT JOKING, and is the co-author of The Humor Code: A Global Search for What Makes Things Funny. Peter’s work has been covered by the New York Times, Wall Street Journal, Harvard Business Review, NPR, and CNN. He’s a sought-after speaker and professor who teaches MBA courses at the University of Colorado Boulder, University of California San Diego, and London Business School.

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