Failing Forward: Dealing with and Learning from Failure

Every quarter Chris Yeh and I convene some friends in the Bay Area to talk about topics that are not usually talked about. We've had conversations about humor, happiness, Americanism, storytelling, death, love, belief systems, and advice. This time the Silicon Valley Junto met to discuss Failing Forward: Dealing with and Learning from Personal and Professional Failure.

In entrepreneurial circles failure is absolutely part of the game. If you haven't failed, you haven't lived, as they say. Probably the most inspiring aspect of Silicon Valley is how many failed entrepreneurs there are who get back on the saddle. Here are some general notes that I took from the Junto conversations:

  • People whose identity is wrapped up in being “successful” tend to take on projects / tasks that are easier to lower their chances of failure.
  • Introspection produces wisdom. Success doesn’t produce introspection.
  • If you’ve "failed" by conventional standards, but you’re happy, it doesn’t matter.
  • People we see as happy usually have a way to measure failure.
  • Repeated failure can be a lifestyle. The importance of lots of little “oops" as opposed to one big "oops."
  • Failure is the intrusion of reality into our perception of ourselves.
  • Successful failure helps you realize personal competencies.
  • Some baseball players go 4 for 10 at bat and they’re still considered some of the greatest hitters of all time. Success is relative. In Latin America, for example, a "successful" company can mean not selling it but rather keeping it and passing it onto your kids for them to run.
  • Be terrified of failure and avoid failure until the moment it arrives, then be able to let go (and ignore sunk costs) and embrace it / learn from it. This is tough: you don't want failure, but you do want to see the silver lining when it happens.
  • What's harder – personal or professional failure? Consensus: personal.
  • One approach is to not believe in failure. If you fail, just change the rules of the game. If you fail, just continue pursuing the larger vision in a different way.
  • A very hard question: when to quit? When to accept failure versus to keep going and keep being persistent?
  • It's possible for something to "fail" but not be a "failure."
  • Book recommendations: Mindset: The New Psychology of Success and Code Named Ginger.

Here are Jackie Danicki's notes from the meeting.

10 comments on “Failing Forward: Dealing with and Learning from Failure
  • Insightful post Ben.

    Another book you may wish to consider with respect to the recomended reading for this post is:”Failing Forward: turning mistakes into stepping stones for success” By John C. Maxwell.

  • My takeaways from past experiences –

    Start early, fail early. That means you’ve got a headstart.

    Never confuse a single defeat with final defeat. The big relief about failure is that it has no finality.

    Just keep doing your best and you’ll have less time to worry about failure.

    Failure is not attributed to the trier, he’s a mere witness to the passing event.

    Never bother figuring out the key to success. There may not be one. But the key to failure is well known – trying to please everybody.

  • Recognize the difference between anticipated experimental failures and catastrophic unplanned failures. All top performers ‘probe and learn’ by setting up small failures in controlled circumstances. Examples include a driver on a skidpad testing handling and learning how to control a skid; or a runner pushing the pace during training until she ‘blows’ and learning her limit; or a football team running into the line or throwing short passes to probe the defense; or a weight lifter pushing the iron until his muscles can’t overcome the weight. In each circumstance the limits are pushed with the expectation of ‘failure’. The key is to do it in controlled circumstances, when the failure won’t cause a long term problem (e.g., crashing the car) and won’t compromise a key event (e.g., blowing during the big race).

    Entrepreneurs especially need to probe and learn, since they are ‘going where no man has gone before’. The key is to find ways to make small ‘bets’ with a plan for learning from each ‘failure’, rather than putting your head down and all your effort into a long-term project and then being devastated if it fails.

  • The issue of personal and business failure is a minefield. Research points out a significant number of issues to be wary of. We smart people can usually rationalize nearly any failure as a success–I’m a genius at rationalizing my failures as success. I learned to do it as a kid. It’s just second nature. And having worked with senior executives in major corporations, I often realize that when it comes to rationalizing failure as success, I regularly meet my match in my clients.

    As a consequence, I’ve learned that the best way to really analyze failure is to lay out your measuring yardstick before you undertake the task. Of course, that implies that how you frame a problem, determines the yardstick.

    Carol Dweck’s book, Mindset is an absolutely masterful work, and she does deal with failure. However, she does not approach failure from the standpoint of measuring stick or research–she has another agenda. My review is on my site. I think her subtitle stinks, because it deters the book from its real agenda. FYI: Carol sent me a personal note, thanking me for my review.

    I think that in dealing with failure, we also have to look at it from the standpoint of the decision process. There are a number of brilliantly researched books growing out of the work on behavioral decision making at the University of Chicago. The older is Decision Traps, by Schoemaker, et al–and the newer is Winning Decisions by Russo and Schoemaker.

    As a result, I’m very wary of intuitive conclusions about success and failure–my own and others also.

  • Ben,
    Having been in business for about 30 years, I’ve had a lot of ‘failures’. Several involved going into debt to pay for marketing efforts which could have been been done better through building relationships. That’s part of the learning process.

    You’ve written a very positive and informative piece. Good job.

    Charles Gupton

    On Twitter @
    “Real people. Really well.”

  • A nitpick — at the time you’re facing the failure, personal is much worse than professional. But in the information/internet age, personal failure could be easier to overcome (or conceal) in the long run, in the sense that professional failures are easily discoverable via Google, unlike personal failures. If you were a jerk to your ex-wife, a future dating prospect probably won’t easily find out about it on the internet.

  • Actually, I recommended one big OOPS rather than lots of little oops – though this is where you’ve got an opportunity for a big OOPS at the start, but stretch it out instead. In general, just say as much oops as possible as fast as possible; don’t stretch a big one out, don’t accumulate little ones.

    Also, my suggestion was that important failures successfully resolve, usually involve realizations of personal incompetence.

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