Illustration: Oscar Ramos Orozco

Screwing Up On Purpose: The Beauty of The Deliberate Mistake

Often when faced with a difficult task we make a set of assumptions that dictate our actions. “I’m not good enough to get that client.” Or “I can’t go to that event, it’s too big-time for me.” We can sabotage ourselves before we even begin, afraid of failure or embarrassment. To tackle hard problems and to really stretch ourselves, sometimes we have to make a “deliberate mistake.”

I’ve been fascinated with deliberate mistakes since Paul Schoemaker and the late Robert Gunther introduced the idea in the Harvard Business Review in 2006. To repeat their definition:

True deliberate mistakes are expected, on the basis of current assumptions, to fail and not be worth the cost of the experiment…. But if such a mistake unexpectedly succeeds… [it] creates opportunities for profitable learning.

In other words: if we fail, we learn something. If we succeed, our long-shot risk actually paid off. By reframing tough tasks as “deliberate mistakes” we can help remove all of the pressure that can keep us frozen, all while learning something along the way.

Consider an example from the sports world. The LPGA Qualifying Tournament is the most difficult women’s golf test each year. Over 250 up-and-coming players and veterans alike endure three elimination tournaments for a mere 15 positions on the women’s professional tour. Golfer Marina Stuetz made a deliberate mistake when she entered this tournament in 2012 as an amateur golfer having never even watched an LPGA event.

Her assumption, was that her game was not good enough to turn pro this soon. Instead of attempting to gather more information or ask around, she tested that assumption quickly and entered the Q-School anyway. She finished eleventh, and qualified for tour playing privileges (and its sponsorship dollars) this year.

Most deliberate mistakes, as expected, don’t work out. Our instinct, therefore, is to avoid them. But what are you missing if you do? Here’s what Schoemaker and Gunther have to say on the topic:

When fundamental assumptions are wrong, companies [or people] can achieve success more quickly by deliberately making errors than by considering only data that support the assumptions.

If Marina Stuetz had acted based in accordance with her assumptions, she would never have reached the LPGA tour this year. But by acting counter to her assumptions that she wasn’t ready, she moved much faster. The downside of failure wasn’t that bad. Even if she hadn’t qualified for the tour, she would have banked crucial knowledge of what her gaps were. Her deliberate mistake allowed her to more quickly address those deficiencies and reach her goal sooner than if she’d used a standard approach.

If you would like to use this tool to advance your own career, how can you manage the process of making deliberate mistakes most effectively?

Scrutinize your assumptions – Our innermost assumptions are the fuel for deliberate mistakes.  What are the rules you follow without thinking? Do you avoid public speaking opportunities or leadership roles? Pick one out and think about something you could do to put it to the test – in which the downside is low and what you will learn is potentially very valuable.  For example, if you tend to avoid public speaking, you could volunteer to do a talk on a favorite subject at your local library or coffee shop, and invite a friendly audience, as opposed to trying a TED talk.

Be prepared to fail Don’t put too much stake in the outcome. You probably won’t succeed. But as long as the cost is low and you are prepared, it won’t hurt a bit.

But do your best – This is the hard part. When you don’t expect to succeed at something, your self-protective instincts can affect your effort. If you don’t do your best, you effectively guarantee that you won’t succeed – and you give yourself a flawed data set to measure against. But, more importantly, you reduce the lessons you learn even if you fail. So, you must, must, must do your very best to succeed.

Compare reality to assumptions – If you fail, if the mistake proceeds as expected, you will have a list of lessons that you gained from the experience. Which of your assumptions were correct, and which didn’t hold up?  What surprised you? Use this list to plan your next development steps, so that the next time you venture into this experience, you will have a much better chance to succeed.

And sometimes, you won’t fail. In spite of your own instincts, your mistake will sometimes work out, as Marina Stuetz’s did. Her mistake landed her on the LPGA tour at least a year ahead of schedule.

Deliberate mistakes are an underutilized tool in our personal growth. They are not natural and don’t arise by default. But, if approached the right way, they can propel us forward and provide us crucial information to guide our future development. To paraphrase Henry Ford, if you believe you can’t do something, you’re always right.

What’s Your Take on Making Mistakes?

When have you “made the leap” and tried something you “knew” would fail? What happened? What did you learn?

More insights on: Failure

John Caddell

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John Caddell is the author of “The Mistake Bank” and contributed to the most recent 99u book. His latest project is 3-Minute Journal. John also organizes the New Tech Meetup of Central PA. You can reach him at or @jmcaddell on Twitter.  
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