So Get Going Already and Start Stumbling!

If you do much reading of books on business or leadership, you’ll soon be encouraged to fail. Popular books and the gurus who write them are always touting failure: “We should be free to fail.” “We should celebrate failure.” “Success only comes through much failure.” Etc. etc. etc.

Still, much of our world hasn’t learned this less. Not our business. Not our schools. Not even ourselves, if you’re anything like me. My inclination towards perfectionism, one might almost say my obsession with perfectionism, makes it extremely difficult for me to be willing to fail. I don’t like to do it. I don’t like to admit it. And I’m not at all inclined to celebrate it.

Peter Sims' latest book: Little Bets

So I was struck once again by my need to be open to failure by an article in yesterday’s New York Times. Peter Sims, best-selling author, entrepreneur, and collaborator with the faculty at the Stanford Institute of Design, has much to say about the benefit of failure in “Daring to Stumble on the Road to Discovery.” He begins:

Jobs, careers, valued skills and industries are transforming at an unheard-of rate. And all of the change and uncertainty can make us risk-averse and prone to getting stuck.

Despite these realities, our education system emphasizes teaching and testing us about facts that are already known. There is much less focus on our ability to discover, create and reinvent.

The same often holds true in the workplace. Perfection is rewarded, while making mistakes is penalized. It’s no wonder that “failure” has taken on a deeply personal meaning, something to be avoided at nearly all cost.

The skills we’re taught work well for familiar situations, yet we’re trained to perfect our ideas and use the past to predict the future with linear plans in a nonlinear world. As such, we need a completely new mind-set. Linear thinking is a death knell for creativity.

This new mind-set is willing to experiment extensively, with plenty of failures along the way. You find this sort of approach to creativity, not only among business leaders, but also among artists and entertainers. As Sims explains:

Even the most successful stand-up comedians, like Chris Rock, try thousands of new ideas in front of small club audiences in order to develop a one-hour act. Some jokes fail, but Mr. Rock is willing to be imperfect; he persists night after night because every small bet takes him closer to a brilliant act on the big stage.

This is how comedians and entrepreneurs must work — by making countless small bets to discover what works. The real genius is in the approach.

The same holds true for leaders, managers and collaborators. They must to be willing to learn from mistakes. Affordable risks should be encouraged, and small failures celebrated — these are the mark of learning organizations. Otherwise, risk aversion will lead to stagnation and decline.

Notice that Sims is not encouraging us to make mistakes about the big things that really matter. He’s not suggesting, for example, that you can make mistakes as a parent when it comes to learning how to keep your toddler from running into the street. And I don’t expect Sims would applaud major mistakes by the federal government. His point is not that all errors are equally valuable. The best ones are relatively minor, yet afford maximum learning.

So if you want to be creative and successful, get about the business of trying and failing. According to Sims:

Invention and discovery emanate from the ability to try seemingly wild possibilities; to feel comfortable being wrong before being right; to live in the world as a careful observer, open to different experiences; to play with ideas without prematurely judging oneself or others; to persist through difficulties; and to have a willingness to be misunderstood, sometimes for long periods, despite the conventional wisdom.

All these abilities can be learned and developed, but doing so requires us to unlearn many of our tendencies toward linear planning and perfectionism.

So, fellow perfectionists, let us be encouraged to try some wild possibilities, even if they fail!

P.S. Some of the material for this article in the Times comes from Peter Sims’ latest book: Little Bets: How Breakthrough Ideas Emerge from Small Discoveries. I have purchased and scanned this book. It seems well worth reading. You can buy it from Amazon, where you can also find an interview with Sims about his book and its main ideas.

P.P.S. I find it interesting that Christians, who supposedly live their whole lives on the basis of God’s grace, are sometimes the most perfectionistic and the least open to failure. Why do we live with such fear, rather than in the freedom of God’s grace?

  • Guest

    Great post. Loved your PPS. If we indeed have a BIG GOD – why do we fear such a ‘small thing’ as ‘failure’?

  • Clearlycrystal

    You are only allowed to fail on your own time and on your own dollar. As you mentioned you cannot consistently fail on your job.  You cannot consistently fail in classes and move forward. There are some things you must do on your own.  Obviously failure is that kind of learning experience.


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