Is embarrassment your entrepreneurial secret weapon?

entrepreneurial secret weapon

By Kiki Schirr, {grow} Contributing Columnist

When you’re starting your own journey as an independent creator or entrepreneurial marketer, the one thing you’ll always have in abundance is criticism. Well-meaning people will discourage you, say the market is too crowded, tell you to wait until the economy is better … a thousand different ways to say “no.”

The comments that cause embarrassment, that hurt, and make you question your plans are usually about you, not your business.

People will object to your risk-taking for many different reasons. You’re late and disorganized. You don’t have the energy or motivation. You’re more about ideas than execution.

Well, it’s time to flip the script.

Is that a personal failing?—or is it a feature?

Okay, sure, people who are punctual, hard-working, detail-oriented perfectionists are likely to have great success — as an employee somewhere. Those are all great skills for people who punch a clock, selling their time to build someone else’s dream.

If you want to create something, start something, or build something of your own, you might be surprised which qualities are actually assets.

Instead, learn to harness the upside of the shortcomings people harp about. This list of “flaws-become-features” will provide famous examples of people and businesses flipping the script on criticism.

And maybe it will help you to do the same!

“Feel embarrassment? Him? He’s shameless!”

When’s the last time you really embraced embarrassment?

I’d be willing to bet the most successful creators can readily tell you about their last humiliation.

After all, Richard Branson cross-dressed to raise money for a charity.

Doja Cat made a video about being a cow before her breakout.

Mark Cuban got schooled by Randy Orton in the WWE ring.

Independent creators learn to stifle their pride because often opportunities exist behind the barrier of social disapproval. When others wouldn’t dare, an entrepreneur stands up, takes the mic, and belts out the lyrics to the theme from Lion King.

entrepreneurial secret weapon

Preparing for embarrassment takes resolve, but that skill might also take you to the [big] top

Sending out your first marketing proposal or writing the copy for your social media services page on your new website opens your dream/life work/baby/purpose to criticism and scorn. The fear of failure or rejection is always an adversary, but it’s one we must conquer. Reid Hoffman, founder of LinkedIn, said:

“If you’re not embarrassed by the first version of your product, you’ve launched too late.”

So shout your URL from the rooftop. Wear your company’s tee to weddings. Beg talent on bended knee to join your team, if that’s what it takes to get things done.

Being shameless opens access to opportunities your competitor is too timid or too polite to seek.

“He’d argue with a fence post!”

Being pegged as a contrarian might not be a bad thing for a creator.

If the status quo remains unquestioned —i f no one at a company wonders if a process could be improved or made more efficient — then that company becomes a slow-moving Kmart-of-a-brontosaurus, food for faster, smarter, and more innovative Wal-Mart-velociraptors.

Of course, there are many real-world cautionary tales of an industry’s refusal to change, even when faced with one of Christiansen’s disruptive innovations. Examples of entire industries, wiped out by better technology from smaller, faster companies abound.

Of course, the more entertaining stories play out on a more individual level. My favorite disruption story will probably always be how Sam Walton took on Kmart, even though Walmart began as the distant underdog.

Over time, Everyday Savings in ‘one horse towns’ became the apex predator of the Blue Light Special. Nom nom.

Sam Walton wasn’t going to shy from a fight. The odds against him were only hurdles, ones that thorough research would help him leap. A 1992 Fortune article quoted him:

“Kmart had interested me ever since the first store went up in 1962. I was in their stores constantly because they were the laboratory, and better than we were. I spent a heck of a lot of time wandering through their stores talking to their people and trying to figure out how they did things. I’ve probably been in more Kmarts than anybody in the country. For a long time I had been itching to try our luck against them…”

While Walton’s adversarial nature was … intense… even curiosity with pure intentions can annoy leaders or peers who prefer their authority unquestioned.

When I worked retail during college, my manager dinged my annual review score because I was prone to “asking too many questions.”

“You don’t always have to know why something is done, you just have to do it.” He said.

The irony was that, in the same review, I was praised for always finding a creative solution to our most challenging customer satisfaction issues. “You know the return system better than anyone.”

My manager didn’t understand that trying to understand every facet of a system and the ability to find new paths to a solution are cause and effect.

I didn’t get a raise that year.

But I did co-found a company.

So while always questioning the status quo might not win you friends, it can win you market share.

Of course, there’s another route to finding new solutions.

“Could she be more lazy?”

In 1947 the Chrysler Corporation testified in Congress. In the public record, you can read that Senator Ellender (D-LA) followed up on something odd that Mr. Bleicher, the Chrysler executive, had said:

Senator: “You say you would put a lazy man on a job to find an easy way to do it. Why would you say a lazy man rather than a hard worker?”

Mr. Bleicher: “Because the lazy man will find an easy way to do it. He may not do much, but he will find an easy way to do it.”

[the record reflects that Congress laughed]

Since that time the quote has been made pithier and is falsely attributed to Henry Ford or Bill Gates: “I will always choose a lazy man to do a hard job because a lazy man will find an easy way to do it.”

entrepreneurial secret weapon

“This just in?—?it seems the first place winner of the 2022 Coca-cola 600 race, Clown Car Motorsports, might be disqualified for cheating. Their driver was heard shouting ‘I’m thinking outside of the box–shortcuts are just innovation!’”

And while that might sound silly at first, it cuts to the heart of innovation: find a solution to a real problem, even if no one realizes they have a problem at all.

In the academic discussion of innovation and entrepreneurship, Eric Von Hippel of MIT was one of the first to directly address how tacit knowledge—the things people within a situation simply know and might not think to convey, like that speeding up a little might help you balance a bike around a curve—can reveal a sticky problem: a problem that few can see, because it relies on first-hand knowledge to even identify that there might be a better solution.

The wonderful thing about using your tacit knowledge to cut corners is that it’s not just lazy—it’s also innovation.

In reality, successful creative entrepreneurs are the opposite of lazy. But they still can be perceived that way, since they’re always asking: “is there an easier way to do this?”

What corners could you cut in your regular work without sacrificing quality?

“They’re just a screw-up!”

Failure can seem like the end of the world. And when you start stringing failure after failure together, it makes you want to roll into a blanket-burrito of embarrassment with your favorite ice cream and never take another chance again.

But failure–or more accurately, being able to quickly bounce back from failure–is also a skill.

Jack Ma, the founder of the now-maybe-in-limbo Ant Group, often talks about his failures prior to founding Alibaba.

He once applied for an hourly job at KFC. 24 people interviewed and KFC hired them all—except for Ma.

However, Ma is more famous for his persistence. His application to Harvard was rejected 10 different semesters. Maybe he’d still be applying today if his company hadn’t taken off.

Risky business

When FedEx was pushed to the verge of bankruptcy during the 1970’s energy crisis, founder Fred Smith knew he had $5,000 left in the bank and no way to meet the next month’s payroll.

So he took a risky, foolhardy, and likely outright stupid gamble—quite literally. On the way back from a failed pitch for more financing, Smith stopped in Vegas, withdrew that last $5,000, and hit the blackjack tables.***

When he stopped playing, Smith was able to put $27,000 back in the bank. It wasn’t enough to run FedEx for long—but it allowed him to pay everyone until he raised another $11 million dollars. The company went public two years later and remains a powerhouse.

***Don’t try this at home, my friends.

Still, if Smith had been unlucky that night, he would have faced serious repercussions. For most people, it would have been an irrational decision. But to Smith?

“I was very committed to the people that had signed on with me, and if we were going to go down, we were going to go down with a fight.”

— Smith on his gamble.

Entrepreneurs have to take rejection in stride and learn to use failure as a lesson.

Move on from embarrassment quickly

Countless entrepreneurs have cited one Japanese kotozawa as inspiration: fall seven times, get back up eight.

That is certainly a good motto, but I think Khosla’s advice is most comforting when you’re feeling embarrassment.

Vinod Khosla, founder of Sun Microsystems, has asked audiences if they’ve ever heard of The Data Dump.

His question is usually met with the sound of crickets chirping. But when he asks who’s heard of Sun Microsystems, nearly everyone in the room puts their hand in the air.

The Data Dump was Khosla’s previous (and failed) startup. He now says:

“Nobody remembers failures.

Success matters. Failure is inconsequential.

Yet what I hear most people do is not do things because they fear failure.

Most people are limited by what they think they can do, not what they can do.”

So stop fearing rejection.

Okay, that’s easier said than done. And Mark has warned us in the past about the dangers of making failure a fetish.

But if you can’t make yourself apply for a job despite meeting 95% of the qualifications, or you keep doing quizzes to diagnose your imposter syndrome, you likely would benefit from failing more often. So what steps can you take to work toward overcoming the fear and embarrassment of rejection?

One way is to begin pursuing it.

Collecting rejection to overcome the embarrassment

I, like Jia Jiang and many others, once undertook a Rejection Challenge. My remixed goal was to receive 100 official journal article, job, or opportunity rejections in 2018. And to my delight, I failed. By mid-year I was too busy with new and exciting opportunities to actually complete my challenge. #goodproblems

If you’d like to read more, this is my summation, but the tl;dr is: push yourself to do things you think are just beyond your capability, and you’ll be surprised at how much you grow.

So while it’s still a good idea to do a little soul-searching when called a lazy, argumentative, attention-seeking reject, there is a chance that you’re just on the wrong career path. Your annual review might be punishing you for the very traits that will make you a great creative.

So remember the mic drop from Steve Jobs’ Standford address:

“Stay hungry. Stay foolish.”

KikiSchirrKiki Schirr is a freelance marketer, writer, and former founder who enjoys new technologies. She believes success is a product of luck, tenacity, and chutzpah. You can email Kiki Schirr at her full name without spaces at Gmail. Just remember that she responds faster on Twitter.

Illustrations by the author. 

Top photo is from a North Face video called “Question Madness.”

All posts

The Marketing Companion Podcast

Why not tune into the world’s most entertaining marketing podcast!

View details

Let's plot a strategy together

Want to solve big marketing problems for a little bit of money? Sign up for an hour of Mark’s time and put your business on the fast-track.

View details