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THE YCEO: A Healthy Fear of Failure Makes Entrepreneurs More Likely to Succeed

The business advice and entrepreneurship literature is overflowing with inspiring quotes on how to persevere through failure or how it makes you stronger in the long run.

We've all heard a nugget of wisdom in this vein before. I won't disagree that they are eloquent and insightful (even if, at least sometimes, apocryphal).

However, I wish it had been drilled into me early and often that failure is inevitable. Thinking otherwise can blind you to the reality that you're failing until it's far too late to change course or fix things. Successful people know they will fail (and fail often). They are, therefore, on the lookout for the first inklings of failure so they can change course if need be.

Many novice entrepreneurs and young professionals have these quotes on failure in the back of their minds, but put up a cloud of cognitive dissonance that convinces them failure (at least as far as they’re concerned) is a hypothetical. They embark on the new careers confident in their abilities and certain if they just put their head down and march on, or just listen to their boss, or read the right books/blogs, etc... that they’ll eventually succeed.

I’m not trying to discredit the value of grit, or imply that sometimes success requires soldiering through the tough times. What I am saying is that not expecting failure often blinds you to the very obvious failures that might be obscuring your path to success.

In Seth Godin’s fantastic little book The Dip, he attempts to show that oftentimes a rough patch in a project (or a start-up, or career path) is nothing more than a temporary dip. However, sometimes it is a cul-de-sac, in which case it’s much better to turn back and cut your losses.

This is never easy to do, but entering any new venture with even the slightest bravado makes this very crucial bit of reflection impossible.

Understanding that you might fail, and that this reality doesn’t worsen your prospect of succeeding in the larger scheme of things, alters the context of every decision you make. Coming to terms with the fact that failure is natural and inevitable means that you’ll be more likely to soberly evaluate whether a setback is temporary or insurmountable. You’ll be less likely to view any isolated failure as catastrophic, or to let a failure get you down.

Intellectually acknowledging that failure is unavoidable is one thing. Most of us know it to be true. However, internalizing that this truism applies to you, no matter how safe or how confident you think you are, takes time and constant reminding. One way to drill this fact into your unconscious is try things that might not work, where you don’t feel comfortable and there is clear and apparent risk involved.

Although such projects might not feel safe, they often end up going better than other things you’ve tried, because you know deep down that failures are bound to crop up. This knowledge makes you less likely to miss what isn’t working and continuing down a dead end until it's too late to correct course.

The paradox that every young entrepreneur (and really everyone for that matter) should try and make sense of is that, all too often, expecting to fail might be the very thing that ensures you won’t.


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