Make Failing a Daily Habit

If you’re looking for a rah-rah success read, you’re on the wrong page. However, if you stay, I promise you won’t be sorry.

I love failure. And I am an expert at it.

I fail every single day. Sometimes I do it more than once, which makes me even happier.

So now you may be asking yourself, has DrJ slipped a gear or what?

Nope. You’re getting, as they say on Twitter, #TRUTH.

Because if you are not failing, you are not trying hard enough.

Or, as the poet Robert Browning, suitor of the elusive Elizabeth Barrett, wrote: “Ah, but a man’s reach should exceed his grasp, or what’s a heaven for?” (Spoiler alert: He did marry her despite robust parental interference, and apparently the result was quite heavenly.)

So, what’s your excuse for not failing?

In an informal survey I just completed, I found that the reasons for not failing fall into three bins.

Some people just don’t see their failures. Or shortcomings. Or, for that matter, reality, in its many shapes and forms. Now actually, this is failing, but in such a way that it does no one any good. You can’t learn from something you never noticed, so it doesn’t count in my book. Also, in the long run, it makes for a lonely life. Sharing our frailties is a great way to make friends. How cool is it to have the freedom to share who you are, warts and all, with someone, and to know that they’ll still want to hang out with you?

Then there is the Bizarro World strategy, where everything is opposite. Instead of ‘You can’t win if you don’t try’, they recite ‘You can’t fail if you avoid participating.’ At work, these are the folks who clock in; drink a lot of coffee; grouse about office politics or the weather or any of the million other things that add no value, and over which they have no control. By the end of the day they might have managed to fit in some modestly productive activities. But maybe if they attempted something big, or at least new, and failed at it, and repeated the cycle a few times, eventually they’d discover what really living is about.

The third group is made up of those who do participate, but never bite off more than they can chew. And swallow. And digest. (How is this possible? Maybe it’s genetics, like curly hair or funny shaped toes.) Pristine resumes that show ‘progressive levels of responsibility’ and other things that HR managers love, are carefully cultivated by these folks. They would never, ever get involved in anything so messy as multiple career changes, startup ventures, or traveling to the steppes of Central Asia to study the history and culture of yurt-dwelling Mongolian nomads.

Becoming an entrepreneur is how I discovered that failing isn’t nearly as bad as people think. You can fail and do better next time. You can fail in one area while making huge progress in another. You can fail, and in the process, discover that your true meaning in life is totally not what you’ve been doing for the past X number of years, and be utterly grateful for that life-changing fail. And I’m pretty lucky, because that’s what happened to me, and now I get to work every day with a bunch of awesome people who have no fear of failure.

We accept failure willingly because the heaven we’re reaching for is really, really far from our grasp. And we’re not going to be satisfied by lowering the goalpost. In fact, we’d like to raise it even higher.

The fact is, getting there may only be 10% of the fun. The other 90% is in the striving, the sharing, and the everyday satisfaction of beautiful teamwork.

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