Slipping designed by Luis Prado from the Noun Project

Slipping designed by Luis Prado from the Noun Project

In his book, A More Beautiful Question, Warren Berger interviews serial entrepreneur and writer Jonathan Fields, who tells us that asking ourselves: “What would I do if I knew I couldn’t fail?” is the type of question that makes us powerless. Instead, Fields says, we should ask these alternate questions. From Fast Company:

What if I fail–how will I recover? Often when we think about failure, Fields says, “we do so in a vague, exaggerated way–we’re afraid to even think about it clearly.” But if before embarking on a high-risk challenge, you visualize what would actually happen if it failed–and what you’d likely have to do to pick up the pieces from that failure–this can help you realize that.

What if I do nothing? The point being, when we take on a major challenge it’s often because we really need to change–and if we don’t go ahead with it, we’re likely to be unhappy staying put. Whatever problem or restlessness already exists may, in fact, get worse. “There is no sideways,” Fields says; if you’re not moving forward, you’re moving back.

The other questions Fields says we should be asking include: What if I succeed? What’s truly worth doing, whether I fail or succeed? And: in this failure, what went right? If you’re faced with a frightening decision today, you need to ask (and answer) these questions.

Get the whole story about why these questions work (and why you shouldn’t always ask “What would I do if I knew I couldn’t fail?”) right here on Fast Company.

  • Sarah Peterson

    Love the one that asks, “What is truly worth doing whether you succeed or fail?” <— right on the money!

    • tannerc

      Completely agree Sarah. It’s one of the more powerful questions to ask for any task or project. Thanks for commenting!

  • Common Man

    This article is taken from life hacker website!! Plagiarism!!!!

    • tannerc

      Actually, you’ll note that Lifehacker links to the original source article highlighted here as well, on Fast Company. They also attribute 99u for being *their* source. Nobody has plagiarized anyone.

      For those curious:

    • Sarah Peterson

      This made me laugh… saying Fast Company plagiarized Lifehacker is like saying The New Yorker plagiarized Buzzfeed. 😉

  • Madeliene Rose

    I think when you fear failure, you just have to ask yourself, What would your 80 year old self think if you gave up on this just because you were afraid of failure, of shame, of being ridiculed, of making the 999th mistake…who cares…the 80 year old you won’t because she’s beyond the things that are not important…

  • Steiner on Failure


    There is much to be gained from studying, understanding, learning from and leveraging failure, a subject I have been researching for almost 20 years now…

    Some of the initiatives I run online include:

    + Twitter: @Stnr_on_Failure – active, dynamic feed updated approx 20 times/daily

    + Linkedin discussion group: The Anatomy of Failure

    + Pinterest Board: The Anatomy of Failure

    + THE BLOG: Steiner on Failure

    Would love to see you all there


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