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Failure: Is it a Winning or Losing Strategy?

Failure isn’t always preventable. Sometimes truly disastrous things happen. But failing isn’t always the end of the world. For some people, it’s the start of success.

Traditionally, failure had a moral cast. If you failed, you were perceived as irresponsible, as if you should or could have known better. But according to The Art of Failing Upward, an opinion piece in the New York Times, “In the start-up world, failure is in,” particularly when certain entrepreneurs are treated as cool and special because of their failures, as if they operate in some alternate universe.

Can Failure Be a Gift?

When you are part of the very privileged few, failing doesn’t make you a loser. People who are untested by existential reverses, whose success is too easy or swift, may not recognize their own luck, how much others have contributed to their success, or that they’ve benefited from privileged social status.

The preemptively privileged can fall prey to fundamental attribution error, assuming that all their gains are the result of their own efforts, and that others who aren’t as successful just didn’t try as hard. For them, the New York Times piece notes, failure is often a gift: “[I]f we really believe that failure is the path to innovation, we need to fund a more diverse group of innovators.”

But for most of us, failure is decidedly not a gift:

  • It implies a black-and-white, either/or world of total wins or total wipeouts.
  • Only “winning” and “huge wins” count as triumphal successes, not the more typical experiences of small, hard-won bits of progress, or two steps forward and one step back, or giving others a helping hand along the way.
  • It suggests that the end justifies the means.
  • Many people who fail risk it all, and never get the chance — or have the skills or strength — to pick themselves up again.

Let’s Redefine Failure

Here’s a switch: Think of The Magic School Bus. As part of every adventure, Ms. Frizzle, the eccentric, intrepid science teacher, gives her clarion call: “Take chances, make mistakes, get messy!” She is exhorting the kids in her class to experiment, explore, try things, and see what happens. But most of all, she is encouraging learning, empirically, in the real world.

Some lessons can be learned by observing others; sometimes we must undergo the experience ourselves to get the lesson. The lesson of a “failure” might be about what you really wanted or meant. Or it could be about your level of preparation or practicality.

Experimenting with Failure

Perhaps you achieved success only because you had no clue just how unprepared you were, or how much you didn’t understand about real conditions. If you’d actually understood the true circumstances, you might not have pressed forward, gritted it out, and staggered ahead.

Maybe luck was involved too. Some weaknesses become apparent only in retrospect when they’re exposed by empirical challenges, the way secret writing in lemon juice only shows up after you burn the paper a little bit.

Much of life is trial and error, and it takes repeated skillful practice to learn how to choose reasonable trials with significant potential and reasonable risk — and avoid egregious errors.

The important thing is to know what experiment you’re running — and to plan how you’ll handle the result — whatever it is — so that if you experience a business setback, it doesn’t make you a failure.

Onward and upward,


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