The Truth About Embarrassment & Entrepreneurship


headshot jess
By: Jessica Myers, CEO, Digit Keeper

When was the last time you put yourself in a situation where you were uncomfortable or embarrassed? It’s probably tough to recall because as a general rule, we all avoid discomfort like the plague. But when is the last time you engaged in a bit of schadenfreude (finding amusement in another’s discomfort)? I did it the other day when I laughed at my husband as he accidentally stepped in a giant puddle. It’s easier to laugh at or with others than be laughed at ourselves. And the fear of it happening is sometimes paralyzing. It’s the reason you don’t raise your hand in class, pipe up during a strategy meeting, or act on the idea you’ve been carefully nurturing in the back of your mind for months.


There are over 180 million working-age adults in the US, but only 11.4% of us own our own businesses—why aren’t more people pursuing their ideas? It’s because being an entrepreneur is risky and error-prone. Most people pass it up because they’re afraid of being embarrassed. And the people who are willing to risk what others won’t are often ridiculed and considered a little crazy, or hell, really crazy. Jeff Bezos is a great example. He had a great job on Wall Street, was newly married and about to have a baby, and decided to quit his job to sell books on the internet. Everyone thought he was nuts, but Amazon is now one of the largest, most successful businesses in the world. Looks like he had the last laugh.

Sara Blakely has a hilarious story about founding Spanks and having her own booty as the before and after picture for the first five years she was in business. She got invited to sit down on Oprah with her “team” and she didn’t have a team! Sara asked her friends to join her and pretend to be on her Spanks team. She is such a great example of overcoming embarrassment and doing what’s necessary to bring an idea to life. Could you imagine if she had decided to pass on Oprah because she was embarrassed? Me neither. I am learning every day that fun, triumph, and growth are on the other side of fear.

Elon Musk said if you need a cheerleader to stay motivated, being an entrepreneur isn’t for you. And I won’t sugar coat it either—starting a business is hard work. Sometimes I feel like a lunatic, other times I feel like a genius. It’s a rollercoaster, but I am so confident in my mission, message, and services that I don’t care if some people think I’m crazy.

Embarrassment is inevitable, but the people who eventually succeed learn to embrace those moments as opportunities for growth. Give up the fear of embarrassment, because the reward is worth so much more than the fear of what other people think. And if you fail or people keep saying you’re crazy? Don’t worry, you’re in good company. Just keep pushing and you’ll get there.


Need a little extra encouragement? Read Kobi Yamada’s What Do You Do With An Idea? I guarantee you’ll walk away feeling inspired to love, nurture, and grow your ideas.

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