Entrepreneurship & the Real Downfall of Failure

Before the very first cohort of Factory45 launched in 2014, I asked each of my 10 participating companies to fill out a “Pre-Program Questionnaire,” so that I could get a better idea of how everyone best navigates challenges, strengths, weaknesses, fears and other by-products of entrepreneurship.

One of the questions I asked was:

What are you most afraid of in starting a business?

7 out of 10 people answered with some variation of “failure.”

“I’m afraid that I will fail, and become another ‘statistic’.”

“Failure … waking up one day and realizing that I truly don’t have what it takes to run a business or launch a successful company.”

“Giving up because I’m too afraid of massively failing.”

I wasn’t surprised, having gone through my own entrepreneurial journey thus far, but it got me thinking about our relationship to failure. I wondered is it the act of failing that’s scary? Or is failing scary because of the external connections we make to it?

Failing — or simply the act of not completing a task — can be disappointing, yes. But isn’t failure just another stepping-stone towards growth if its negative associations are taken away?

Those closest to me know that my ideas are a dime a dozen. It’s hard for me to even go a few days without having some “new, amazing business idea.” I love the creation phase of entrepreneurship, so I tend to easily get kept up at night by light bulbs going off in my head.

I couldn’t begin to count the number of ideas I actively pursued in 2014 alone (in addition to building Factory45). First, there was the idea for the bricks-and-mortar “barter boutique” for used clothing. I wrote a business plan, spent countless hours researching, laid out financial scenarios to present to potential investors, created branding boards, bought a domain, and even contacted a realtor to start looking for a space.

And then there was the idea for High Rise, a women’s mentorship website that would connect young professionals with executives in their industry. I spent three months designing logos, writing blog articles, conducting market research, looking for a CTO, and building the framework for a website. I even had a co-founder.

Despite the time, energy and money I put into both of these ideas (and again, these are just two of them) neither saw the light of day.

For most people, the biggest connection with failure is a loss of money. We envision bankruptcy, losing our homes, spending the rest of our lives under a bridge, or worse…  Our thinking immediately goes to: “Failure = worst case scenario.”

We also fear the ridicule. We are afraid of appearing inferior, foolish, or naive in the eyes of others, the people in our lives who will say, “I told you so.”

More than anything, though, we fear failure because of the way we attach it to our self worth. “If my business/idea/venture fails, then I fail as a person.” When we make a habit of connecting our inner value to something external, then we lose our sense of self worth as soon as that external “thing” goes away.

And that is scary.

If I associated every one of my abandoned ideas with a loss of inner value, then I would probably be curled up in a crawlspace somewhere. As an entrepreneur, I’ve had to learn to see these “failures” as “tried and try agains.”

Is it easier to fail when it isn’t public? Or when you don’t lose lots of money? Sure. But some of the most successful CEOs in the world only found their model of success after failing multiple times and losing everything.

So how do you cut the metaphorical cord that attaches your inner self value to the external act of starting a business?

1.) Feel. Embrace the emotions attached to the failure. Go through the rollercoaster ride (disappointment, sadness, anger, acceptance) so you can come out on the other side.

2.) Learn. Take as much time as you need to observe what worked, what didn’t work, where you went wrong, and what you would do differently the next time.

3.) Reframe. Flip your view of the “failure” into a scenario of growth, self-discovery, progress and acceptance.

4.) Adapt. Where are the opportunities to move forward? What can you adjust? What holes can be filled in a different way?

If failure was just another stepping-stone towards growth, then what risks would you take? What big ideas would you pursue? How would today be different?

Photo credit: YEC.co