Be Willing to Look Stupid


checklist“If you are not willing to look stupid, nothing great is ever going to happen to you.” ~Dr. Gregory House

Are you willing to look stupid?

The only way we improve at something is to push the boundaries of the possible.  We need to build new “connections” in our brain; which means screwing up after reaching for a new skill…and often looking stupid in the process.

When did we become scared of looking silly?

When we were babies, we tried to walk over and over.  We looked silly.  We fell down a lot.  And we got right back up and went at it again without remorse.

In the “Little Book of Talent“, Daniel Coyle writes about Wayne Gretzky skating drills during practice.  During the drills, teammates would watch Gretzky falling all over the place like a grade-schooler.

 “As skilled as he was, Gretzky was determined to improve and push his boundaries…”

Now that we are all a bit older and wiser than our baby selves, looking stupid isn’t fun.  But being willing to risk the emotional pain of making mistakes is one of the most important things we can do to grow.  Somewhere along the line, many of us were taught that making mistakes is the worst thing we can do…and that’s simply not true.  Reaching, falling, and reaching again is the only way toward mastery of a skill.  We cannot be afraid to look silly in the process.

What if you decided to think of mistakes as guideposts you use to get better, instead of…well…mistakes?  Hmmm.

As my trusted readers know, I always bring it back to music:  In my training as a musician, I have spent a ton of time in places and schools that encouraged “productive mistakes”.  I was surrounded by rules that encouraged me to reach beyond my comfort zone (normally a place that feels risky and bad); all the while I was being nudged into a “new” comfort zone beyond my current ability.  What a great way to learn and get better!

What does “looking stupid” look like in other areas of life?

How about the person who drives a crappy looking car with no car payment to pay off debt or accumulate wealth?

Or the dancer who looks awkward in front of everyone while learning a new move?

Or you…making a decision at work that scares you to advance a passionate idea of yours?

Whatever the case, the goal is the same:  reach beyond what you are now capable of, and use mistakes as goal posts to navigate to the correct behavior.  Good luck!

I was featured in the following Carnivals last week.  You’ll find some great other reads here as well:

Finance Carn. for Young Adults at Brick By Brick Investing
Yakezie Carnival at My University Money
Carnival of Retirement at Freeat33
Carnival of MoneyPros at The Happy Homeowner


  1. Some would say that I have no trouble looking stupid :D. I think that Looking silly is part of the learning curve. One other point on “looking stupid”. If you don’t know, ASK! So many people are afraid of asking when they don’t know about something. I view the people that do ask with respect, I definitely would not look down on them for asking!
    Jose recently posted…The Axeman Cometh – Dealing with the Loss of a JobMy Profile

    • My favorite interview answer when I don’t know something: “I don’t know the answer to that, but I know 12 people who do…so I’ll get back to you.”

  2. A fine, fine post, Tony!!! I used to be very bothered by looking stupid. I still get the initial feelings of embarrassment, but they quickly abate and I am now a pro at laughing at myself and allowing others to laugh at/with me. Life is so much more fun this way;)
    cj recently posted…Dart Lessons With Louie The LipMy Profile

  3. I think it all changes during school years when kids start making fun of one another for being different, doing things different, or not doing something as good as other kids. When that level of embarrassment kicks in from what other people are saying, it makes people afraid to look silly or do things incorrectly.
    Money Beagle recently posted…Weekly Roundup: Long Overdue: March 15, 2013My Profile

  4. Like Jose said, some might say I do a great job at looking stupid. 😉 Seriously though, great points. None of us know everything and by never asking a question or ever trying something new life would get awfully boring awfully quickly.
    John S @ Frugal Rules recently posted…Frugal Friday: Blog Posts That Ruled This Week, More Snow EditionMy Profile

  5. Great post and I love your quote from House at the top. I totally agree that you need to be willing to take some risks that might make you look stupid.
    Nick @ recently posted…Apply for Every Job You SeeMy Profile

  6. I honestly look stupid doing what I do 75% of the time, or more! I do try to make myself look more “fluid” in whatever I do, but I find that when worrying about that it really subtracts from the value you provide from your actions.
    Vincent Nguyen recently posted…Can’t Maintain Your Sanity? Take a WalkMy Profile

  7. I’m with Jose and John – I excel at looking stupid, Nice post.
    Marie at Family Money Values recently posted…When is the Cost of a Conference or Seminar Worth the Price?My Profile

  8. It’s true. As young kids, we’re not troubled by the idea of looking stupid, but the older we get – the more rigid we become. Sometimes I get lost in my head, worrying about whether something is right or not, whether it costs too much or not — instead of just doing it whether it works and is a huge success or it fails and I look stupid. I’m going to bookmark your post for time when I feel like this and get stuck. The greater harm is not trying and believing in yourself.
    Shannon @ The Heavy Purse recently posted…Blog Roundup: Week of March 11, 2013My Profile

  9. Really nice post and this one hits close to home!

    I used to worry that people would think I looked stupid with my older clothes or cars. Now, I just don’t care. If they think I look stupid, they are probably caught up in material pursuits and are all the worse for it.

    There was one guy at my work who had some old, really ugly car. The bumper was a piece of wood tied on. Some people made fun of him, but about 10 years later, I learned that “Bad Car Bill” was secretly very wealthy. I like to think that he was laughing on the inside the whole time.
    Mr. 1500 recently posted…Thursday Rant: It’s only a DollarMy Profile

  10. I love this post Tony. And like the others have said, I look stupid all the time. Looking stupid is my default state. I mean, just look at my gravatar — that should tell you everything you need to know about looking stupid.

    But worse than looking stupid is feeling stupid. That’s the real kicker. Nobody likes to look stupid, but when we actually feel stupid . . . that’s when we want to just give up and crawl in a hole.

    So how do you get over feeling stupid?

    I don’t have any good answers, but I can say that, for me anyway, just accepting that it’s going to happen, and happen often, helps me to just get over it. Anytime I try something new I just know I’m going to feel stupid. So I simply admit it to myself and move on.

    Trevor recently posted…The Secret to Achieve Anything You Want . . . and the Surprising Way I Discovered it.My Profile

  11. great post Tony. I don’t really care about what the world thinks and have little fear of failing. Most people who do succeed have tried countless times before it worked.
    Pauline recently posted…Buy-to-let in the UK: a beginner’s guide to becoming a landlordMy Profile

  12. Props for quoting House, dude.

    I definitely used to be afraid of how others might judge me. As I’ve grown older, that fear is gradually dissipating.
    eemusings recently posted…What I value in a jobMy Profile

  13. Tony, thanks for writing an inspirational post about being willing to take creative chances. I’d love to be in a state of mind where I felt completely free to explore without fear. While I might not be there yet, I felt enough inspiration that I wrote a post to provide my own thoughts about the matter. Thanks!
    Dale recently posted…The Fear of Taking Creative RisksMy Profile

  14. Oh my gosh. I know what you mean. Why can’t people just relax?

    “It’s ok to fall, it’s ok to fail, it’s ok to just live!”

    You have no idea how many times I have failed and looked stupid. At the time you feel stupid but then you should be able to laugh about it.

    We are only humans.

    Great post!

    Alexander John
    Alexander John recently posted…Salary of Photography and Photojournalism JobsMy Profile

  15. I’m not afraid to speak up when I have a question, or when I think something doesn’t make sense/is wrong. I’d rather ask a “stupid question”, then not ask and do something wrong. But that being said, some of the best lessons I’ve learned have come from doing something wrong.
    KK @ Student Debt Survivor recently posted…My Spending Life StagesMy Profile

  16. This is a great post! Part of being successful, I think, is being unafraid to fail. That may mean putting yourself out there or looking stupid sometimes!
    Holly@ClubThrifty recently posted…5 Reasons I’m Killing My MortgageMy Profile

  17. Sometimes putting yourself out there is the best thing you can do! When I was still in classes for computer science and starting to look for a job, I went to soooo many interviews, even ones where I would not necessarily be qualified. I looked pretty damn stupid during the first few interviews, but I got better at them and was able to score some quality job offers by the time I was ready to graduate.
    CF recently posted…Updates: March 10 – 16My Profile

  18. Indeed Tony, the fear of looking stupid is one of the key blocks to success; I think probably for many people. For me, I would say that it is my primary Achilles heel, something that prevented me researching my full potential in many areas of my life – music included funnily enough. One of the reasons that was the case for me in particular was the incessant ‘your so able’ messages I was fed as a kid. As the psychologist Carol Deck correctly postulated, telling a kid “you’re so smart” is a recipe for disaster – one that pretty much guarantees they’ll shy away from any potential failure – anything that might tarnish that reputation. Even now in my late thirties there’s a part of me that hates to show any weakness or deficiency – something I constantly fight against. There’s a ‘wise man says’ Chinese proverb to the effect that the wise are never afraid to ask questions, the foolish hide their ignorance. I keep that in mind at all times – it helps me at least, to lessen the fear of making mistakes.
    Gareth | Helpful Habits recently posted…The Art of OptimismMy Profile

  19. Love this post, Tony!!!! We’re just finally gettting to the point where we don’t care what others think in the area of money. We’re finally ridding ourselves of the fear of saying “No, we can’t go out to eat right now” or “No, the kids can’t join you in the community ed class”. It’s somewhat difficult to get there, but SO worth it when you look at the end result: financial peace and freedom!
    Laurie @thefrugalfarmer recently posted…Our Dream GardenMy Profile

  20. Totally just added this to my goal for the week: look stupid at least once per day. It’s so true, those who are not willing to look stupid or fail will not be tasting the success any time soon, for you need at least 9 failures to get 1 success (on average).

    It’s amazing that as young kids we’re more willing to succeed (just to turn it around), but as we grow older we lose that, and the success will start to escape us. Great post!
    Nick Goodall recently posted…Learning To Love FailureMy Profile

  21. This is the problem with a lot of people today. They think that the only way to succeed is to have an impressive-looking resume and a neat and expensive suit.. Maybe they’re right but sometimes, they are missing the fun of life as well. It’s okay to have fun once in a while and make fun of ourselves. Who knows, bigger opportunities can come out of that.
    KC recently posted…Rent A Cow and Save on Taxes, Tax LoopholeMy Profile


  1. […] with debt, to minimalist living…to topics in a similar vein to my own. I particularly enjoyed Be Willing to Look Stupid which nicely highlighted the limitations we place on our own advancement through our irrational […]

  2. […] @ We Only Do This Once writes Be Willing to Look Stupid – The only way we improve at something is to push the boundaries of the possible. We need to […]

  3. […] Tony over at You Only Do This Once talked about the importance of being willing to look stupid. […]

  4. […] with debt, to minimalist living…to topics in a similar vein to my own. I particularly enjoyed Be Willing to Look Stupid which nicely highlighted the limitations we place on our own advancement through our irrational […]

  5. […] @ We Only Do This Once writes Be Willing to Look Stupid – The only way we improve at something is to push the boundaries of the possible. We need to […]

  6. […] @ We Only Do This Once writes Be Willing to Look Stupid – The only way we improve at something is to push the boundaries of the possible. We need to […]

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