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.  
load comments (23)
  • Casi

    I would add: Detach from the outcome (meaning there other opportunities out there. This helps to put any “failure” into perspective, at least my experience.)

  • Ned Horvath

    This is completely aligned with the Agile / Lean approach, summarized by the dictum, “Try something – quick!” Alternate version: “Fail Early and Often.”

    That doesn’t mean you don’t do the research up front, but when entering unknown territory, limit the research to a survey; then, “taking your best shot” – at relatively low cost – increases knowledge and actually DECREASES risk: the inexpensive attempt may succeed, and if it doesn’t, it will still expose flaws in the approach and build real knowledge about the problem at hand.

    Thanks for sharing this!

  • growthguided

    What about the notion of allowing yourself to fail and not preparing! I know we generally fail our way to success, but preparing for failure might be a discouraging jump off point.

    Thank you for the great post though!

    • jmcaddell

      The attitude should be, “I’m going to try something, that may not work, that probably won’t work, but if I don’t try it, it’ll take me a long time to learn otherwise.” That is, try it out of a spirit of adventure and exploration. Focusing on “preparing for failure” makes it sound like a root canal – something completely unpleasant and painful. These experiences don’t have to be like that. It’s all in the mindset.

      • Rochelle

        This is the attitude I’m moving into this summer, as I look to freelance edit full time. I’ve been at a stable job for 5 years, and it is time for me to branch out and work on my own. I’ll give it a few months, and if I fail exceedingly, I can always get a part-time job. I will definitely be trying my best, though.

  • SirisGraphics

    Nice post. I had the experience you mentioned above. But my failure was weird that I made I succeeded in getting a project in my second attempt by correcting my previous mistakes but unintentionally did another major mistake during my second attempt which I didn’t realize until the last moment. Now I lost confidence in myself but still trying to rise.

    • jmcaddell

      Each mistake is information you can use to press forward. Keep going and don’t lose faith.

      • SirisGraphics

        Yes Caddell, thank you.

      • V1rus

        Each mistake is learning experience – agree, wish everyone understand that. Some justify their mistakes as “my life my choice” and I cant stand it when they bring God in between and say that “God gave the gift of choice”, God also gave us a Brain to think and learn.

      • SirisGraphics

        Exactly. I believe in fate, god, luck etc. But for everything to work we need a base of hardwork. It teaches how to deal with problems. So I think I will learn how to develop eventually.

  • Aaron Morton

    My take on mistakes is at some point in history we made it a separate entity to success. Its like saying you built muscles without resistance exercise, it doesn’t happen!

    Rather than pretending they don’t exist, I think it is time we learn how to individually deal with mistakes that doesn’t send you too off course. And deliberate mistakes, or functional failing as I like to call it, is a great way of practicing that.

    Thanks for the article John

    The Confidence Lounge

  • Beckons Attore

    Upon first reading the title of the article, i was thinking of auto mechanics and realized that that’s not like the auto repair in Las Vegas and was tempted to assume that what I thought what it meant was what it meant. However after forcing myself to reading the article I had a completely different state of mind. This will be useful to me and some of my friends.I have bookmarked this article and will share it. Thank you for your posting.

    • Paul Erna

      Nice. Can you tell me what kind of car? I just bought a new car for sale and I want someone to work on it for me. Thanks

      • Allen Clifford

        I would like that info too

  • jmcaddell

    A question I’ve been pondering, prompted again by the prior comment by B. Attore… does this tactic (embedding commercial links in comments) work? I mean, does it do anything for the business that is buying these? Does it really increase SEO? I see this stuff all the time but I find it hard to believe they work. Of course, I could be wrong…

  • yavvee

    I too had a similar experience but did not realize its impact on me until recently. I gave the interview for the Convener of a technical fest (which is a big thing for a college student like me), with very less experience and zero hope of getting the post. I was more than exhilarated when I got the post, but the work was overwhelming, and I had little experience. But its experiences taught me a lot and helped me get an internship in a coveted company, which was the best learning experience in my whole life. I can only now connect the dots looking backwards!

  • anonymous

    This advice actually has the scientific method in action – 1) state a solution to a problem, 2) test it and 3) reformulate if needed, possibly using insight gained by experiment. It is a method of selecting solutions, with a bias towards the ones that stand out to experiment.

    • jmcaddell

      Thanks for commenting. There is a subtle but important difference between the deliberate mistake and the scientific method as you describe. In the scientific method the hypothesis is something you believe to be true, and the experiment is designed to confirm or disconfirm this hypothesis. A deliberate mistake is an action believed to be wrong – and the experiment, as it were, is expected to confirm that but provide valiuable information in the meanitime. As such, the deliberate mistake should be very exploratory, probing the margins, meandering and perhaps intentionally digressing, instead of aiming right for the heart of the matter. The goal is maximum learning, rather than getting the answer right.

      I’m not completely confident in this as written. Feel free to add to or refute this.

      regards, John

      • Anonymous

        Hypothesis can be either true or false – often a statement is made for the purpose of pushing it over with the experiment itself.
        The scientific method isn’t only for getting answers either, although it plays a big part too. Much of he information gained with the scientific method comes out during the process, not only post-experiment.

  • V1rus

    Sadly I have known people who use their past bad experiences as an excuse to justify their mistakes, they continue making the same mistakes because its nothing other than a low and bad habit. As it says that we learn from our mistakes and not to repeat it again, however, some things dont change, they make mistakes over and over again and they have the audicity to justify their actions to make the wrong look right. They are nothing but weak people – sorry I have gone a bit personal on this one – just my rant for the day.

  • Bry

    Great timing… I entered a song contest… reluctantly (first one) and was picked as a finalist… one of the other finalists is much “better known” so it seems futile to publicize much but I am pushing myself to do so… although their is no real cost to hope for the win, it is a challenge to my ego… with part of me withholding my excitement and willingness to get “all in”… thanks for you post!

  • Carl ToersBijns

    One of the most effective management tools out there – especially if no one in the workforce or constituency questions your methods.

  • Ash

    I was only going to comment that there’s a great Fiona Apple song to this.
    But this is a refreshing way of looking at the usual “I should lower my expectations”. It could be specially be a great way to -get used- to trying and failing, losing fear of it.
    Like what Chuck Jones went through: “in one art school class, the professor gravely informed the students that they each had 100,000 bad drawings in them that they must first get past before they could possibly draw anything worthwhile”. So for something based on practice, or fear of trying, it’s a very useful philosophy.
    I sabotage myself because of
    1.things I haven’t tried before
    2.things I have tried only a couple of times and gave up soon
    3.things I tried and worked on for a long time but eventually gave up on (like learning an intrument or language) which makes me feel the act of giving up invalidated all the work I did get done before it. (“all or nothing” thinking. I recommend looking into cognitive therapy)

    When I was younger I passed on a college entrance exam twice in my country with no preparation and both times I had expected to fail and wasn’t worried about it. It wasn’t something I wanted that much at all, so passing was only a bonus. My driving licence test was similar in I didn’t want to drive that much.
    When I deal with contests I get frustrated because I get hopeful… but at least I’ve done them enough that I know how they work (or mostly don’t work) for me.
    Anyway, thanks for the post, and sorry for the long comment.

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