How to be a creative problem-solver

I get so many books in the mail to review, and the way I evaluate which ones are worth my time is to first read the jacket flap. So I’m not even going to pretend that I have read Tipping Sacred Cows, by Jake Breeden, but I’m going to tell you that it has an amazing jacket flap.

He lists sacred cows in corporate life that we should reconsider:

Balance: Disguising indecision as a bland compromise that attempts to achieve many things but ends up accomplishing nothing

Collaboration: Creating a culture of learned helplessness with little individual empowerment and accountability

Excellence: Spending too much energy producing perfect work instead of developing the quick-and-dirty solution needed now

Fairness: Keeping score and evening the score to make sure no one gets more than their “fair share”

Passion: Racing down a path seeking success only to find burn-out and misbehavior instead

The reason I love this list is because so much of being creative at work is looking for things that are opposite or things that clash. Breeden picks a list of workplace words that we think are intrinsically positive, and he shows us how they’re jargon. The act of looking at things in their opposite light is the best skill to have if you want to be a creative problem-solver.

When I told this to Melissa, she said, “You need to link to Leonardo da Vinci writing backwards.” So here it is. But that’s not that practical for you. So I’m going to tell you four ways I’ve taught myself to think counter-intuitively.

1. Act like you have Aspergers.
Okay, I know it’s a cheat, because people with Asperger’s don’t understand social conventions, but still, the number-one thing to do if you want to be a creative problem-solver is to not let yourself be constrained by social conventions.

The point of social conventions is to get everybody to act in predictable ways. What this means is that people with Asperger’s Syndrome are usually offensive, because they are unpredictable, but they see things in new ways. Try it.

Non-scientific evidence that Aspergers leads to creative problem-solving is that Silicon Valley is a magnet for people with Asperger’s. But also, I was talking to an editor at the New York Times, and he said, “You know how people say that the Jews rule the world? It’s not true. People with Asperger’s rule the world.” (I might argue that it’s a fine line, as I have a hunch based on no documentation that Aspergers is an affliction the Jews have selected for. Think about Shtetl life: whoever memorizes the most Torah gets the best wife.)

2. Practice asking why.
The problem with asking why is that you often get answers that are really inconvenient. For example, why do we give boys a circumcision? I spent nine months arguing this with my ex-husband before my first son was born.

The benefit to asking why over and over again is that eventually you come up with innovative solutions. At the beginning of my adventures in homeschooling, everything seemed terrible. I was scared to put my kids in school, I was scared to teach my kids curriculum, I was scared not to teach my kids curriculum. The trick is to hold two competing things in your head: what you wish to be true, and what looks like the actual truth. The benefit of asking why and sticking with it is that you’ll come to a new and innovative solution to make things clear in your head.

3. Try things you don’t like.
William Falk, the editor of The Week always has a mini-essay on page five. He’s become one of my favorite writers. Last week, he wrote about the research explaining why older people don’t try new things as much as younger people do. It made me realize that the last few big changes I made in my routine came from trying something that was originally repugnant to me.

For example, I was giving a speech at the Natural Foods Expo and this guy came up to me afterward. He said he loved my blog and he brought a sample of his product for me to have. Foosh. That’s the name of the product.

I said, “Oh, I’ll check out your booth on the floor.” And he said, “I don’t have a booth, because this isn’t really a natural product, it’s got other stuff in it.” I was totally grossed out, but I said thank you, and put it in my bag, because that’s what you do to show good social skills.

Two months later, when I was cleaning out that same bag, I found the sample again. I was hungry, and tired, and I thought, why not? So I tried one. They’re caffeine supplements. They’re caffeine pills, but they have other stuff in them (I’m scared to look). I’ve gotten addicted to them, I’ve ordered Foosh boxes from Amazon like I’m Costco, stocking up.

And it made me think, why do people drink coffee? It’s got a lot of calories (because I don’t drink it black) and it just makes me want sugar, and the sugar makes me want more sugar, and if I have a sugary mint instead, it makes everything after it taste yucky. So it’s much better to have caffeine in a mint than coffee with sugar. Also, the last time I complained about having to put sugar in my coffee, someone told me to buy Illy coffee. It has really snappy packaging, but it’s not as good as Illy coffee with sugar.

4. Pretend you have unlimited money.
My favorite way to solve a problem is to ask myself, What would Victoria do? There is no way Victoria Beckham puts up with the level of problems I do. If Victoria needs a stamp, she doesn’t think twice, she hands the letter to someone else. I tell myself that for every problem I have.

So, I’m in the car sixteen hours a week, and I start thinking, What would Victoria do?

First, I tried doing coaching calls during my car ride. But I kept losing my concentration and missing my exits. I couldn’t program the GPS, so I bought two iPhones—one for talking to me about directions and the other iPhone for coaching. But I got frustrated only people in Australia want to talk that late at night.

Then, I tried listening to books on tape. But I’m a really fast reader and it just frustrated me how slow it was. Then I tried hiring a driver, but the social demands of being with a driver for sixteen hours a week were too much. Then, I decided to dictate blog posts to Melissa. And look, that’s how I did this one.

53 replies
  1. adam
    adam says:

    i can tell you right now that as a software engineer, losing excellence is a fantastic way to fast track your product to obsolescence. quick and dirty may functionally work, but it is a maintenance nightmare and in the software industry it’s “innovate or die” and you cannot innovate when there’s a fear of breaking anything you touch.

    there are plenty of frameworks out there to allow you to still be quick and not be dirty. like anything else, however, they also give you the rope with which you can hang yourself. you just have to be smart enough not to.

    • Martyn
      Martyn says:

      A director while producing a TV commercial for me once said that there are 3 ways one can be made: Quick, good & cheap, but only 2 can be applied at once!

    • Joseph
      Joseph says:

      I strongly second Adam’s comment. I almost cringed when I read that quick-n-dirty is a preferred choice. Most definitely NOT in software development. Ever. And sure, we could go back later and make it better, but we all know that never happens; because that’s not “productive.”

    • John
      John says:


      His excellence focus is about the process not the outcome. Your comment about “cannot innovate when there’s a fear of breaking anything you touch” is exactly his point. If someone’s ideas or attempts during the process need to be perfect, no one is going to do it.

      • adam
        adam says:

        I think you missed my point John, which probably means I wasn’t completely clear. The fear of breaking something comes from having to maintain and modify fragile code. The code is fragile because it was developed in a quick-and-dirty fashion. IMO, then, the fear is completely rational.

        The outcome is affected by the process. If my team adopts a get-it-done-as-fast-as-possible approach, the code will be riddled with bugs, it won’t be designed well, and it will be impossible to maintain.

        So while I see the point in saying it can’t be perfect, and I believe this is true, in software, you had better make sure the time spent up front is adequate or the time spent afterwards is exponentially longer.

    • Ethan
      Ethan says:

      Boy did you pick the wrong example. Making software is the home of quick and dirty.

      At least that’s true in the startup world, or when you are writing software for yourself, or any other place where results are what matters. If you are working in a large corporate environment with written specs, and where covering your ass is your priority, then by all means, make sure that all the code you write is excellent. But if you are in an startup environment, then 80% of your code will be thrown out pretty soon and you don’t know which 80% it is.

      If you’re interested in startups you’ll need to drop the “I am a craftsman and all my work is high quality” attitude. As we say, if you aren’t embarrassed by your product, you launched too late.

  2. D
    D says:

    “Act like you have Asperger’s.”

    That’s nice, but hard for people to visualize. Here’s one that’s worked for me:

    “What if the opposite were true?”

    Example: Facebook got huge because the social graph is really important.

    What if the opposite were true? What if the social graph is not important at all? What is the antithesis of the social graph?

    Most of the time this kind of thinking is a dead end, but it’s useful to ask the question.

    Here’s a related one I’ve entertained: What if “screwing around on Facebook” was an essential business activity? What would it take to make it your job to be on Facebook all day? What would it mean to complain to your co-workers “jeez, I had to spend 7 hours today on Facebook?”

    • Bike Pretty
      Bike Pretty says:

      That actually used to be my job. Ironically, I hated the way Facebook colors social interactions, so I never had a personal account and bluffed my way through the interview.

      After 2.5 years as a Facebook pro, I still can’t stand it.

  3. Carla Golden
    Carla Golden says:

    I’m all for creative multi-tasking, thinking beyond the box that doesn’t exist and intelligent upgrades in lifestyle efficiency however this is pure enervating CRAP: Sorbitol, Caffeine, Natural Peppermint Extract, Other Natural and Artificial Flavors, Proprietary Synergistic Energy Blend: (Taurine, Ginseng, Vitamins: Niacinamide, Pantothenic Acid, Pyridoxine Hydrochloride, Thiamin Mononitrate, Cyanocobalamin), Magnesium Stearate, Salt, Sucrolose, Acesulfame-K, Aspartame*, Blue 1. * Phenylketonurics: contains Phenylalanine. All I can ask is why???

    • Penelope Trunk
      Penelope Trunk says:

      They aren’t online. You should subscribe to the magazine. it’s like expensive candy: So easy to read, but it doesn’t feel like junk.


  4. Greg
    Greg says:

    I’m totally stealing that Victoria Beckham idea and implementing it in my life starting today, because it’s genius. I mean, the whole blog post is great, but seriously. WWVBD? This is going to solve everything, and I mean that.

  5. CL
    CL says:

    I adore Victoria Beckham, but her life will not work for you. You are a celebrity, but she is a gazillionaire.

    Not only that, but I don’t understand why hiring a driver didn’t work. Who said that you had to be there with the driver? You have Asperger’s! While you understandably want to make sure your kids are safe, I think that your kids are old enough to tell when something is wrong and intervene if they need to. This is not like you hiring a Puerto Rican nanny and realizing that he left the baby alone. A lot of kids at my school had drivers and I think that it’s good practice for having a nice, friendly, and professional relationship.

  6. Jake Breeden
    Jake Breeden says:


    Thanks for the post. And I’m glad that you liked the jacket flap. I tried to make the inside as good as the wrapper.

    Given what you’ve said here, I think you might enjoy the opening to the chapter on passion in particular. Take a few Foosh and you can probably make it through a few pages. Or I can call you and read a bit to you while you commute. Don’t worry, I can read very quickly.

    Thanks again for the mention,
    Jake Breeden

    • Kristen
      Kristen says:

      Well played Jake, I’m totally putting your book on my list! Before I dive in, tell me: what points from your book would you recommend me discussing with a small group communication class I teach at a Chicago university?

  7. Ramon
    Ramon says:

    I learned six foreign languages while driving during the last 20 years (mother tongue spanish).

    I can read and understand everything in those languages, even sophisticated text and speech.

    The kind of useless skills Aspergers learn.

  8. Nadia
    Nadia says:

    Love this article! I think its the best of all time! Sigh, act like you have aspergers…I just can’t stop smiling.

  9. Alan
    Alan says:

    I pretty much have to be a perfectionist just to be competent, but if other people can just whip out usable stuff, God bless ’em.

    Love ya

  10. Sydney Jane Baily
    Sydney Jane Baily says:

    Great post. Made me think of my 14-year-old son who this morning, on the way to school, wondered why we don’t have skunk-scented candles for people like me, his dear mom, who likes the smell of skunk spray (not on my dog, but on the road). It made me think, and not for the first time, that my son looks at life a little differently and will do great as a “creative problem solver.”

  11. Joy Phenix
    Joy Phenix says:

    #3 reminds me of a Twyla Tharp idea of not sticking with what you know…

    “If you only do what you know and do it very, very well, chances are that you won’t fail. You’ll just stagnate, and your work will get less and less interesting, and that’s failure by erosion”

  12. todd
    todd says:

    Double the play back speed when listening to books on tape.
    Especially on strung out podcasts, a faster listening speed cuts the listening time in half.

    • doug
      doug says:

      Good suggestion. Could be better if you’d followed up with the name of a device or app that did this along with pitch shifting so you don’t get tired of you books sounding like they are being read by Alvin, Simon or Theodore.

  13. Carla Golden
    Carla Golden says:

    Please don’t do this to your beautiful brain. Ingredients: Sorbitol, Caffeine, Natural Peppermint Extract, Other Natural and Artificial Flavors, Proprietary Synergistic Energy Blend: (Taurine, Ginseng, Vitamins: Niacinamide, Pantothenic Acid, Pyridoxine Hydrochloride, Thiamin Mononitrate, Cyanocobalamin), Magnesium Stearate, Salt, Sucrolose, Acesulfame-K, Aspartame*, Blue 1. * Phenylketonurics: contains Phenylalanine

    • Liobov
      Liobov says:

      What’s wrong with it? The ingredients list looks totally harmless to me. Caffeine, various vitamin B, and few harmless fillers (to make the physical candy). Unless you are specifically allergic to Aspartame or Phenylalanine it shouldn’t post any danger to your health. It doesn’t do much for your health either, but it’s certainly not harmful.

      • Carla Golden
        Carla Golden says:

        Sorbitol is a sugar alcohol and can cause diarrhea if threshold levels are crossed (not a good thing on a road trip). Artificial flavors: chemical cocktails with often undesirable affects. Sucrolose/Sucralose (brand name Splenda) – a new artificial sweetener with yet unknown affects. Acesulfame potassium: artificial sweetener. Aspartame: artificial sweetener with already proven detrimental brain affects. Blue #1: artificial petroleum based coloring with often negative reactions. Sugar alcohol, 2 artificial sweeteners, mystery chemical flavors and artificial color: recipe for headache, migraine, dementia, Alzheimer’s, ADD, ADHD and other disorders.

  14. Jen
    Jen says:

    This is why you’re one of my favorite writers/thinkers: “I might argue that it’s a fine line, as I have a hunch based on no documentation that Aspergers is an affliction the Jews have selected for. Think about Shtetl life: whoever memorizes the most Torah gets the best wife.”

  15. Colleen
    Colleen says:

    I love this post! When I first encountered the list of the five sacred cow words, I felt immediate boredom and I couldn’t even read that section. I skipped it and only forced myself to go back and read it after I got your explanation. When I got to your list, it was incredibly easy to read and focus on. Because it’s interesting and even if not everybody agrees, it stimulates thought and discussion and makes people take a stand. I just love how internally consistent the post is–how you demonstrate the exact tenets you write about.

  16. Razwana
    Razwana says:

    I’m definitely one for trying to non-conformist route, but it’s relative. What is non-conformist in one area (banking) is the norm in another (the arts, marketing).

    Take the office surroundings as an example – I work in IT, where the walls are blank, or have the odd network diagram on them. Walk into marketing and you see an explosion of colour.

    So with that in mind, I’d like to add to your list is things we can do to be creative – take lead/inspiration from another industry.

    – Razwana

    • Penelope Trunk
      Penelope Trunk says:

      That’s a good point – that what’s off-beat in one industry is mainstream in another. It’s really a question of skill sets. So having the skill to be a creative director and also wanting to wear green pants is not that rare. But having the skill to be a quantitative analyst and also wanting to wear green pants is rare. So it’s a mixture of stuff that makes something non-comformist. I’m not sure anything is intrinsically non-comformist on it’s own.


  17. Peter Holgate
    Peter Holgate says:

    Here is a “why” question for you; why not listen to audio at faster speeds? I find using the iPhone app I can listen to books at 3X speed. Forces me to concentrate and doesn’t sound like chipmunks!

  18. Karolina
    Karolina says:

    I love this article. It’s just what I needed. I’m starting a new company at the intersection of limited edition lifestyle goods and charity and I feel like everything about it is so unconventional. So point #1 “Act like you have Aspergers” makes so much sense to me. I can’t be reactive to conventional responses and rejections by brand managers in light of the novelty that I am proposing. Which then plays into #2 “Practice Asking Why” so I can better understand their hesitation and get them to commit.

    You have just made my day!

  19. Ann-Marie
    Ann-Marie says:

    Penelope, You have been on a roll with amazing posts the last few weeks! I adore your unique perspective on life and will keep coming back for it.

  20. Mike
    Mike says:

    Um, Victoria would fly the cello teacher to her.

    BTW, you still haven’t posted video of your son playing. You need to do that.

  21. Jaclyn
    Jaclyn says:

    I strongly disagree with that final point. If you really want to solve a problem creatively, you should approach it under the assumption that you have a fraction of the money you actually do — that will really light a fire under you ass. There are numerous examples of crazy, low-cost innovation from resource-poor countries. Why? Because the people innovating didn’t have lots of money or infrastructure at their disposal. Some of our most basic and effective health care interventions, such as “kangaroo care,” originated in the developing world where all sorts of resources tend to be more sparse than they are, here in the US.

    When people think they have infinite cash at their disposal, they often get lazy and end up trying to outsource the problem to someone else. They think the right answer is out there as long as they spend enough cash and / or involve the right product or person. Unlimited fund usually just makes you inefficient.

  22. Mark W.
    Mark W. says:

    “The act of looking at things in their opposite light is the best skill to have if you want to be a creative problem-solver.”

    I think sometimes that “opposite light” is another person. Maybe even a person that you can’t really identify with or don’t like but none-the-less is solving a problem. Watching and taking note how other people are approaching and solving problems in ways that are directly or indirectly applicable to your problem.

  23. niko
    niko says:

    More, more, more. Aspie makes me amazing at my job as I track trends and can detect a deviation and know something is wrong even if I can’t explain it. My obsessiveness to understand logic means ppl want to kill me for 6 months after ever project until 6 mos 1 day when they realize I know the entire project top down and right left. I agree with the comment about looking out to other industries, I have great ideas becaus every problem has been encountered in some iteration in another arena and your solution is just adapting that to create your own analog.
    I hope you keep posting frequently. Also for literary buffs, I think of you as the The Great Brain, who made me realize life was just a whole lot of entrepreneurial opportunities waiting for The Great Brains to monopolize on them. I think we need you to find the creative solution for becoming Sandberg with children. I’m buying your theme that expectations and realizing you can’t have it all. But then you write this, and either you have it all and you don’t realize it or you’re one of the few people who could figure out how to have our cake and eat it too (which I think has to do with picking up the fork, eating faster using your hands, or finding someone to feed you the cake while you blog, or read up). You managed to write a dope post about your son neon a stylist that was on point for career ladies everywhere, but allowed you to spend the day with the kiddo. You might have surpassed Sandberg…

  24. Joyce
    Joyce says:

    Great post! I always ask why and sometimes do things I don’t like when asked. I’ll do the tips on Aspergers and Victoria Beckham. In a developing country, asking how a smart person with no money is going to solve a problem would be more effective. My problem might not be a problem after all. No worries!

  25. Darnell Jackson
    Darnell Jackson says:

    I think the best way to deal with these issues is to stop accepting all these diagnosis.

    It’s hilarious Americans are the most unhealthy people on earth but we have the most doctors diagnosing us with everything from restless legs to “social behavior” syndrome.

    It’s amazing NO one in Haiti has any of these horrid conditions.

  26. Lindsey
    Lindsey says:

    I love this, particularly: “The trick is to hold two competing things in your head: what you wish to be true, and what looks like the actual truth.”

    I want to know how to practice these things–how to be creative problem-solver at work–when others are unnerved by it.

  27. Jacky
    Jacky says:

    I agree it. Especially try things you don’t like. Most of older people don’t like to try newest things like me. I might be scare something happen with unable to control. Thanks for sharing.

  28. TK OHearn
    TK OHearn says:

    My new bumper sticker “Act Like You Have Aspergers!” I was reading back to the 2009 column on gold digging when everyone was saying you were unprofessional and would lose your bloggership-ha! You rule. I read you all of the time:)

  29. Claudia Gomez
    Claudia Gomez says:

    I really liked the point about practicing to ask why. I think it shows inquisitiveness, which is valuable as a trait in anyone. Many people don’t ask why because they are scared of the answer or much rather not fully comprehend the situation. This is specially seen between managers and subordinates, where subordinates many times refrain from asking why because they don’t want to seem as incompetent to their boss. This eventually leads to problems and frustrations. I remember something one of my professors at Emporia State University once told me “if you never ask why, you will we too often settle for ideas and for leaders who don’t really make sense.”

  30. Kalander
    Kalander says:

    Marty forgot to mention, that choosing two out of three exclude the last one:

    quick & good = definetly not cheap
    quick & cheap = definetly not good
    good & cheap = definetly not quick

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