Fear of Falling

Ryan Crispin Heneise
The Longcut
Published in
5 min readApr 20, 2017

There have been some wonderfully raw discussions in my communities lately about failure and the stigma attached to failure. It seems like a lot more people are “coming out” about their failures, or lack of successes, recently. Or maybe the Internet gold rush has peaked and there are a lot more failures going around.

I’m not gonna lie and say I don’t feel a sense of shame for my failures. I’ve contemplated keeping one of my failed apps running just so I don’t have to make any uncomfortable announcements. My own self talk has been absolutely brutal: “well self, now you’re a failure and you’ll never be anything but a failure”. And “this is going to be really hard to explain to potential employers when you’re forced to go get a real job like the failure that you are”. And “how are you going to explain this to potential clients, to whom you are marketing yourself as a success guru, you fraud”.

These inner voices emerge unbidden like demons perched on my shoulder, whispering in my ear that whatever I’m working on the moment is also destined for failure, so why not just give up and go check Facebook or watch YouTube.

It’s easy to let failure define your sense of self. Everyone who has ever failed at something has let that failure define them to some extent. But we shouldn’t.

Have you heard that saying “failure is not failing, but not trying again”?

I say that’s only partly true.

True failure — the kind of failure that we ought to be ashamed of — is not “not trying again”, but refusing to take responsibility for the things that contributed to the failure. Blaming others instead of reflecting on what went wrong.

Don’t say you’ve not done this — I don’t believe you. I’ve done it myself. Whenever it’s someone else’s fault, whenever circumstances were beyond your control, you’re ceding the deeper learning that you could gain from the experience.

It’s hard when everyone around us seems to be succeeding, and here we are struggling day after day.

Maybe we are forgetful. In the public version of our success story we’ll inevitably crop out the “before” segment showing our awkward uncomfortable casting about. Nobody is really interested in hearing about the “long cut” to success; about the failures that we experienced before we succeeded. Joichi Ito, former chairman of Creative Commons, said “we only talk about our successes but there are probably ten times as many failures that I’ve started” (source: BBC News).

Maybe there really are some people who have never experienced failure. But I doubt it. Failure is part of the human condition. Show me someone who has never failed and I’ll show you someone who hasn’t yet lived very long.

Permission to Fail

We startup founders and entrepreneurs worship success and stigmatize failure. We can’t help it, it’s in our DNA. We’re pigheaded and stubborn. We believe the world isn’t quite right and this idea we have will make the world just a little bit better.

Nobody became an entrepreneur in order to fail. We all want to succeed. But if we don’t give ourselves permission to fail, the stakes go up in terms of our mental and spiritual well being and even our ability to perform. We can become so myopically focused on success that we can ignore warning signs and healthy fear.

Healthy Fear

Fear isn’t only a bad thing. Fear of falling can help you make good decisions when you’re in a precarious position. Most people who are able to confidently do a cartwheel still wisely wouldn’t try one on the edge of a cliff. But we shouldn’t let our fear of falling keep us from climbing that mountain in the first place. That’s unhealthy fear.

In the same way, fear of failing can inform our startup decision making. You ought to feel a healthy fear when signing a million-dollar loan that you aren’t sure you can pay back. Or when hiring an employee that you’re just not sure of, or partnering with someone (remember partnerships are like marriage without the sex), or taking on an investor that has a reputation for being a shark.

Fear of failing is as natural and visceral as fear of falling. But it is exactly the possibility of failure that makes the taste of success so much sweeter. If we have given ourselves permission to fail we may open ourselves to options and possibilities that might otherwise be beyond our reach.

Failure is Cheap

The USA is still one of the cheapest and safest places to start a business (though many other countries are catching up and even exceeding). It is possible to start a successful business out of your home with just a few hundred dollars. Everyone can name at least two billion-dollar businesses that have started up and operated literally out of a bedroom or garage. If you start a business and fail, most of the time it’s not going to ruin you. You might lose everything you’ve worked so hard on, but your life won’t be destroyed (unless you’ve ignored your healthy fear of failing and made some very unwise decisions). You won’t be blacklisted, arrested, or imprisoned, and you will get another opportunity to try again.

As Many as it Takes

I heard someone say that the average entrepreneur fails four times before they achieve any appreciable success. (I couldn’t find the source for that number but it sounds right, and the sentiment is what’s important.)

Failure is a core part of the story of entrepreneurship. Each year about 6 million new businesses start up, but they don’t last long. By five years, half are gone. By 20 years, almost all are gone. (source: The Case Foundation)

Should an entrepreneur expect to fail? How many times? As one person quipped on Quora “as many as it takes”

That right there my friends, is the key. That’s the money statement. Write that down and tattoo it on the back of your hand. “As many as it takes”. Because as entrepreneurs we are not cowed by failure. We are pigheaded and bullish, and press forward doing absurd things no matter what society tells us because we know it’s the right thing to do, and everyone else will catch on someday. And if we’re wrong, then well, we were ahead of our time, but let’s try again.

The important thing is not to let yourself be defined by your failures, but instead to own them, integrate them, and learn from them. Keep on innovating, starting, and building.

Speaking of building — lean in close for this — let’s keep building each other up. We all need to hear this from time to time. Failure does not disqualify you from success. Let your successes and failures inform your experience and outlook but do not let yourself be defined by them.

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Ryan Crispin Heneise
The Longcut

Entrepreneur, innovator, homesteader, family man. I help SaaS businesses create new web-based products.