“Any year that passes in which you don’t destroy one of your best loved ideas is a wasted year”


Says Charlie Munger. If only it were that easy. It’s mentally hard to come to a beloved opinion and even harder to give up that attachment and admit that we were wrong.

F. Scott Fitzgerald famously wrote: “The test of a first-rate intelligence is the ability to hold two opposing ideas in mind at the same time and still retain the ability to function. One should, for example, be able to see that things are hopeless yet be determined to make them otherwise.”

The idea is to live in the middle of ideas, believing in them enough to take action but not enough so they become too big of an anchor when something better comes along. More than acknowledging the uncertainty of beliefs you need to embrace it. Keats called this ability “negative capability.” Roger Martin argues that successful thinking involves integrating several different ideas while maintaining the ability to act. It is through the exploration of these opposing ideas, or uncertainty if you will, that we come to better outcomes.

I came across this passage in Sharpio’s “Still Writing” that speaks to the necessity of failure and uncertainty in the creative process:

When writers who are just starting out ask me when it gets easier, my answer is never. It never gets easier. I don’t want to scare them, so I rarely say more than that, but the truth is that, if anything, it gets harder. The writing life isn’t just filled with predictable uncertainties but with the awareness that we are always starting over again. That everything we ever write will be flawed. We may have written a piece, or many, but all we know — if we know anything at all — is how to write the piece we’re writing. All creations are failures. Perfection itself would be a failure. All we can hope is that we will fail better. That we won’t succumb to fear of the unknown. That we will not fall prey to the easy enchantments of repeating what may have worked in the past. I try to remember that the job — as well as the plight, and the unexpected joy — of the artist is to embrace uncertainty, to be sharpened and honed by it. To be birthed by it. Each time we come to the end of a piece of work, we have failed as we have leapt — spectacularly, brazenly — into the unknown.  

Shapiro further highlights the parallels between writing and the broader parallels with the creative life:

The writing life requires courage, patience, persistence, empathy, openness, and the ability to deal with rejection. It requires the willingness to be alone with oneself. To be gentle with oneself. To look at the world without blinders on. To observe and withstand what one sees. To be disciplined, and at the same time, take risks. To be willing to fail—not just once, but again and again, over the course of a lifetime.


The page is your mirror. What happens inside you is reflected back. You come face-to-face with your own resistance, lack of balance, self-loathing, and insatiable ego—and also with your singular vision, guts, and fortitude.No matter what you’ve achieved the day before, you begin each day at the bottom of the mountain. Isn’t this true for most of us?

Well isn’t it? Come on. Go create something today.


7 thoughts to “On The Necessity of Failure and Uncertainty

  • Lyn

    These are some inspiring and thoughtful words about writing. Writing is a process and one needs to be open to failures and have the drive to try again.

    • Prattle

      Absolutely agreed

  • Thanasis Karavasilis

    I love how you champion creativity in this piece, especially writing and the pains that come with birthing something out of words. I would have loved it even more, however, if you had made a connection to the industry (you know, that one with anime and manga and cool robots and many colors) somewhere in the article. It goes well with other things I am sure you agree and you have written about: criticism in anime, the illusion of perfection in anime, the ‘always right’ critic, and more.

    Great piece, nevertheless, and well written.

    • Prattle

      Thank you Thanasis. I’m happy as a critic and writer yourself that you enjoyed the piece!

  • sonicsenryaku

    Way to go using Yozakura Quartet as a thumbnail to this piece; just another instance reminding me of how much i want another season of this fucking awesome series…..sigh

    • Prattle

      Same, I miss it


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