Entrepreneurs: Fail Until You Don’t

by / ⠀Startup Advice / November 1, 2012

“Oh man, I can’t do that.  I can’t take that risk.”

I was trying to help my friend–who always talked about his hatred of his corporate job–to jump ship and start his own thing.

Now, if there’s anyone that could succeed at their own thing, this is your guy: an electrical engineer, 3.8 GPA (!), working for one of the most prestigious companies in the city, great social skills…

This guy could outsmart anyone in the room, let alone me (he actually commented to me when we were back in grade school, “you know, I think I’m smarter than you”.  I was pissed, but I knew it was true).

Dismayed, he wondered: “I mean, I have a mortgage, the economy’s not too great, and what if I fail?”

What if you fail?

Ah, the almighty preventer of would-be entrepreneurs.  What am I going to do if I fail?

If you fail?

Of course you’re going to fail.

People that don’t understand entrepreneurship—or more broadly, don’t understand  living an empowered, passionate, interesting life—think that entrepreneurship should be like waiting the stars to suddenly align in one perfect opportunity, sort of like from a really cheesy chick flick.

“But R.C., how can you say that?  I have kids, a new minivan with a 9” TV in the back so the kids can play PS3 on roadtrips…you know, obligations?”

The Failure Factor

Blogger Cal Newport often talks about Steve Martin, the man who redefined comedy from a series of punchlines into something much more dynamic.  To all of the questions of “how did you become such a successful comedian?”, Martin’s response is breathtakingly simple:

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“Be so good they can’t ignore you”.

Newport’s advice dissects and shows the wisdom behind Steve Martin’s approach: all too often, people jump from job to job, from project to project, trying to “find their passion”.  But it doesn’t work, the “passion”  is never found.

Newport argues—and uses extensive interviews with subjects ranging from organic farmers to venture capitalists—that passion for our work comes after working so hard that we become  amazingat it.

So the right approach to a successful career, then, isn’t to hop around aimlessly looking to “find your passion”; it’s to become freakishly good at something, and watch the passion and happiness flow in after.

Trying to “find your passion” is misguided; the exact same way worrying about failure is misguided.

Think of success in entrepreneurship like “finding your passion”.  The only way to get success in entrepreneurship is to “be so good they can’t ignore you”.  And the only way to “be so good they can’t ignore you” is by working really, really hard.

And a huge part of that working really, really hard, is figuring out what works and what doesn’t.  Failure is a necessary part of the equation.  You’re selling yourself a great big barrel of snake oil if you think the key to success in entrepreneurship is to avoid failure.

So stop worrying about failure, because it’s gonna happen.  Instead, fail smart, and fail until you don’t.

The first company I started was a complete flop.  The startup was basically a glorified “the next Yelp”, there was 0 market research, and I had no idea how to work with the web developers on the team.

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Boy, did I try though…until finally after a month, we got tired of working with each other, and the project folded.  We failed.

Our total loss?: $60.  And if we’d been smarter, we wouldn’t have even needed to spend the $60 (curses!)

I mean, it sucked to not be successful.  But I learned a lot: I don’t try to start stupid companies that are basically rebranded photocopies of other companies …lessons people pay thousands of dollars to sit in class to learn, I learned for $50.

And that’s why the “fail until you don’t” philosophy works: it’s basically a given that entrepreneurs (especially inexperienced ones) are going to screw up.

So instead of hiding behind a rock or thinking that you’re so wonderful that “none of this failure crap applies to me”, accept failure, make failure a learning experience, and fail until you don’t.

Stop making excuses, and start with this simple 4 step exercise to overcoming your fears of startup failure.

R.C. Thornton teaches would-be entrepreneurs how to go from excuses to launch at his blog, Decoding Startups.  He is currently working on 2 startups; one for academic research, and the other for the medical field.

About The Author

Matt Wilson

Matt Wilson is Co-Founder of Under30Experiences, a travel company for young people ages 21-35. He is the original Co-founder of Under30CEO (Acquired 2016). Matt is the Host of the Live Different Podcast and has 50+ Five Star iTunes Ratings on Health, Fitness, Business and Travel. He brings a unique, uncensored approach to his interviews and writing. His work is published on Under30CEO.com, Forbes, Inc. Magazine, Huffington Post, Reuters, and many others. Matt hosts yoga and fitness retreats in his free time and buys all his food from an organic farm in the jungle of Costa Rica where he lives. He is a shareholder of the Green Bay Packers.


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