RULE 69: Be Willing to Look Stupid

By | October 10, 2026

[October 10, 2026]  The fool is the humble beginner willing to look stupid, make mistakes, and start anew.  It’s the predecessor to mastery, transformation, and the hero/savior; the opposite of hedonistic avoidance.  Be willing to look stupid.

“[The trickster] is a forerunner of the saviour… He is both subhuman and superhuman, a bestial and divine being, whose chief and most alarming characteristic is his unconsciousness.” – Carl Jung

You have to be willing to look stupid and make mistakes to advance, because when you first move in a new direction, what do you know?  You will begin by being a bumbling idiot, but you won’t be that for long.  And, yes, it’s a very painful thing to do, especially if you’ve been giving it your all, to the degree you were able to.

However, if you stay in your safe space, something will get you sooner or later; you can be sure of that.  But temporarily, you are safe.  In the long run, that’s not helpful.

Sit yourself down and ask yourself, “What am I doing to make things worse in my life?”  You have to ask yourself that question.  What am I doing to make myself weaker and dumber than I have to be?  But you also have to want the answers, and you won’t because the answers are going to hurt.

You will have reasons to be bitter and angry.  You’re going to be searching for the errors that you still make, and discovering your own errors is always extremely painful.  This is particularly true if you are in love with the errors that you’re in bed with.  So, you have to be willing to strip yourself down.  That’s what humility means.

“Why am I weak and stupid?”

So, you may ask, why are you going to all the trouble to take stock of where everything’s broken?  You may also think that there’s nothing you can do about it.  One solution is to aim lower.  Start with something easier and smaller. There’s always something that you could fix today, regardless of how small.

You might think that it’s so trivial that it’s not worth doing.  No, if it’s moving you ahead a little, you’ll be slightly better tomorrow than you were today.  And then maybe you’ll be a little better the next day.  Eventually, doing this will speed you along like crazy.

The advantage of this mindset is that you will find out where you are stupid and where you do things badly and shoddily. This is why it is so important to listen to people, aim properly, and not give up.  Then you can stop being stupid.

You have to be willing to be a fool before you can be a master, and if you’re not willing to be a fool, then you cannot be a master.

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NOTE: Much of this article is drawn from lectures by Prof. Jordan Peterson.

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Please read my books:

  1. “Growing Up Free,” on Amazon (link here)
  2. “55 Rules for a Good Life,” on Amazon (link here).
  3. “Our Longest Year in Iraq,” on Amazon (link here).
Author: Douglas R. Satterfield

Hello. I provide one article every day. My writings are influenced by great thinkers such as Friedrich Nietzsche, Karl Jung, Aleksandr Solzhenitsyn, Jean Piaget, Erich Neumann, and Jordan Peterson, whose insight and brilliance have gotten millions worldwide to think about improving ourselves. Thank you for reading my blog.

13 thoughts on “RULE 69: Be Willing to Look Stupid”

  1. rjsmithers

    Just gotta love all the RULES that General Satterfield has given us. I sent his book to my nephew, who was also in the war with Iraq around the same time, around 2007. He is now a huge fan. And, i get to send him these new RULES. Let us encourage General Satterfield so he can write another book on them. The big question will be, “How many new RULES?”

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  2. Cowboy Bob 🤠

    🫡 “Be willing to look stupid.” 🎯 On target here Gen. Satterfield, so thanks for helping set us all straight. 👍 Too many folks have not learned this important lesson, and might never. 👀 Just look at them and you can see where their life is headed. 🤠

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  3. Bryan Lee

    When you first step outside the familiar territory of what you already understand, you will inevitably behave as a bumbling idiot, and the pain of that recognition is acute precisely because it confronts the gap between the image you maintain of yourself and the reality of your actual capacity. To remain instead within the protective enclosure of what is already known is merely to postpone the encounter with chaos, and while such avoidance may grant temporary safety, it guarantees that whatever lies outside that boundary will eventually arrive unannounced and unprepared for. You must therefore sit with the question of what you are actively doing to make yourself weaker, less competent, and more fragile than necessity demands, and you must desire the answer even though the discovery of your own persistent errors will cut deeply, particularly when those errors have become the companions with which you have long been intimate. Humility, in its proper sense, consists in the voluntary stripping away of the defenses that shield you from this recognition, so that the question “Why am I still weak and stupid here?” can be asked without the protective flinch that keeps the truth at a distance. Begin, then, with what is small and immediately correctable, for the incremental repair of even a trivial defect produces a measurable increase in competence that, once establis

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  4. Nick Lighthouse

    I’m willing to look stupid, but the real question to ask is “Are you?” 😂

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    1. Dale Paul Fox

      Nick, ha ha, good joke. And I believe that our newest generations — like Gen Z — are learning to be full narcissists. Woke parents are helping but teaching kids that they should have it all, while earning nothing, but that the fact they exist is enough for them to deserve all. Sad. 🙏 Pray for them, they will need all the help they can get.

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  5. Tony Cappalo

    Yes, indeed, General Satterfield continues on his proper quest to both understand and advise what makes us better and “good” people. I wish him well, as we all travel with him. This Rule 69 “Be Willing to Look Stupid” hits home. None of us, if we are honest, want to look stupid in any situation and we are going to put on airs to not be “that person” who looks dumb. Sir, please continue with your series, and I’ll be one of the many who read it and hopefully absorb some of those lessons. Er …. RULES.

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  6. LT Mud Flap

    Gen. Satterfield’s Rule 69 makes a straightforward point that real progress begins when a person accepts looking foolish for a while instead of protecting a comfortable image. When someone first tries a new skill, job, or habit, the early results are almost always clumsy, and the only way forward is to keep practicing through that awkward stage. Staying inside a safe routine may feel easier in the short run, but it eventually leaves a person weaker and less prepared when real problems arrive. The useful habit is to sit down and ask what personal actions are making life harder, then face the answers even when they sting. Discovering one’s own mistakes is painful, especially when those mistakes have been defended for a long time, yet that discomfort is what humility actually requires. Starting with one small, fixable problem each day builds momentum, because even tiny improvements compound into larger gains over weeks and months. Listening carefully to others and aiming at clear targets help a person locate the places where work is still sloppy. The person who refuses to be a beginner never becomes skilled, while the person willing to appear stupid for a season gains the chance to master the task. Jordan Peterson’s lectures, which supply much of the material here, simply underline an old truth that every craftsman, soldier, and student has already discovered the hard way. In the end the rule is practical rather than poetic: accept the temporary embarrassment of being a novice so that later competence becomes possible.

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    1. Liz at Home

      Looking forward to the next book too. Thanks SWEENEY. I know we are all fans, but we need to also heed the good advice from Gen. Satterfield. And this one hits home to us all, even if we are scared to admit it.

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