BrooklynFans Of Books: Chris Gethard On How To “Lose Well”

Lose Well

By Chris Gethard

HarperOne, an imprint of HarperCollins Publishers; hardcover, $26.99

Comedian and cult hero Chris Gethard knows a thing of two about losing, and failing is an art form, as he argues in his new book Lose Well.

Let’s face it, everyone wants a seat at the cool table, a great job, and loads of money. Most of us won’t be able to achieve this widely accepted, black-or-white, definition of winning, which makes us feel like failures, that we’re destined to a life of loserdom. This is the conventional wisdom, and Gethard thinks it’s bunk.

The host of the eponymous TruTV talk show and the wildly popular podcast Beautiful Stories from Anonymous People, Gethard sets fire to vision boards and tosses out the “seven simple steps” to achieving anything.

“I want you to know that I believe in you,” writes Gethard.

“Some caveats:

“First: I don’t really know you. You are at this point an abstract thought to me, a theoretical reader who has purchased, borrowed, or stolen this book at some point far in the future. That being said – I believe in you. Because you are a human being and you have some latent ambition inside you that remains unacted upon. I think that ambition can come out and should come out. In fact, not only do I think you have a right to put it into action, I think you have a responsibility to do so.

“A second caveat: While I believe in you, I absolutely do not believe in your ability to succeed. Far from it. You are going to fail. Of this, I am certain. You’re going to unlock your ambition and it’s going to betray you; you’re going to fall right on your face. You’re going to put a plan into action and it will end in humiliation, or even worse, be met with nothing but ice-cold apathy. You’re going to waste your savings chasing a dream. You’re going to strike out. Lose. Come up short. That’s the statistical likelihood, and only a scant few of you are going to defy those numbers, break out, and make something happen. Prove me wrong. I want you to. But my guess is, most of you are going to lose. To the extent that I believe in you, I only believe in your right and responsibility to fail.

“But here’s a secret – once you do, you’ll be fine.”

Gethard’s personal and professional manifesto is illuminated with hilarious and ultimately empowering stories about his own set-backs, missteps, and public failures, from the cancellation of his Comedy Central sitcom after 10 episodes to rediscovering his comedic voice and life’s purpose on a public access channel.

Like a down-on-his-luck David Sedaris, Gethard employs his trademark wit and inspiring storytelling to teach us how to power through our own hero’s journey, whether we’re a fifteen-year-old starting a punk band or a fifty-year-old mother of three launching an Etsy page. Using personal anecdotes, Chris reveals:

  • How a deli-counter spat with a little old lady schooled him on interacting with different kinds of people;
  • Why he changed his definition of success;
  • When vomiting on his “cool guy” shoes on his honeymoon taught him to more freely admit to his own limitations;
  • How to find strength in “loser moments”;
  • That success takes hard work, sacrifice, and luck. And sometimes requires jumping into a (literal) giant pile of garbage.
  • Why it’s important to “always be terrified” when it comes to reaching goals.

In the process, Gethard shows us how to fail with grace, laugh on the way down, and as we dust ourselves off, how to transform inevitable failures into endless opportunities. It might get a little messy, but that’s exactly the point.

“How do you know when a dream is worth the sacrifice?” asks Gethard. “In my experience, it’s when it shows up in your life and leaves you with no choice but to pursue it.

“From a young age, I knew that I wanted to make people laugh. When I was seven years old I’d climb onto the coffee table and impersonate comedians I saw on TV to make my mom giggle. Making my brother laugh felt like a major accomplishment. It still does. I was never the best at sports, the most confident in life, or particularly great at anything – but when I could make the other kids laugh, I always felt strong and safe.

“Still, I didn’t know that was a thing one could really do, so for many years it wasn’t a dream of mine. It remained dormant, asleep somewhere inside me, waiting for the right moment to strike.

“And when it did, it arrived amid chaos. I never expected it and barely even asked for it. I didn’t sit down with a pen and pad and brainstorm until I came up with a dream. Instead, foundations shifted and crumbled, and there it was.”

Gethard writes of his current podcast and what went into its creation, “At the beginning of any new creative venture, I like to drill myself on three simple questions:

“Why this? Why here? Why now?

“All three of these questions are simple, to the point, and intended to help me remain focused on my goals.

“If my answers to these questions feel muddled or – worse – don’t come, I know that I need to flesh out my ideas more. If I can’t explain why a thing is necessary in this time and place as its creator, I assume anyone asked to consume it will be confused as well. But if I can answer those three questions in a straightforward, simple, and confident fashion, I know there’s something at least worth bringing to fruition. Like all endeavors, odds are that it will fail, but asking myself these three questions gives me permission to at least try.”

The guiding principle of this book is that the first step in living on your own terms is learning how to lose well and, more often than not, the revolutionary act of failing lets us witness firsthand what awaits us on the other side.

Lose Well is an entertaining read, but also quite worthwhile, as Gethard has created a unique self-help book of sorts from his experiences.

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