The one-sentence summary

All of us are fallible, but we can use this fallibility to create a life of never-ending learning.

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  • We used to think of failure as a problem to be avoided at all costs. Now we are often told it is desirable (‘Fail fast, fail often’). But neither approach distinguishes the good failures from the bad, so we miss the opportunity to fail
  • The author is the originator of the term psychological safety – the most successful cultures are those in which you can fail openly, without your mistakes being held against you. Better teams don’t make fewer mistakes, but they are more able to discuss them, which increases learning.
  • Where psychological safety is low, low standards lead to checking out and high standards lead to avoiding risks or covering up failure. Where psychological safety is high, low standards lead to enjoying the status quo and high standards lead to failing well.
  • Most of us go out of our way to avoid experiencing failure, and it is possible to calculate the wasted time and resources created by our failure to learn from failure.
  • Failure is an outcome that deviates from a desired result.
  • Errors (synonymous with mistakes) are unintended deviations from prespecified standards.
  • Violations occur when an individual intentionally deviates from the rules.
  • Learning to fail can teach us to thrive. There are three archetypes of failure: basic, complex, and intelligent:
  • Basic failures are the most preventable, especially by using a checklist. They tend to be in known territory, and single cause, due to inattention, neglect, overconfidence, or faulty assumptions. You can address these by befriending error and vulnerability, putting safety first, catching errors and learning from them.
  • Complex failures have not one but multiple causes and often involve some bad luck. They are multicausal, can consist of many little things, and there’s no point looking for an individual culprit because there probably isn’t one. An external or uncontrollable factor often enters the mix, and they are generally preceded by small warning signs that are missed, ignored, or downplayed.
  • Intelligent failures are good ones that are necessary for progress. They are often the domain of scientists and inventors and are usually hypothesis driven. They usually take place in new territory, are opportunity driven, informed by prior knowledge, and mitigate risk by being as small as possible to start with, leading to learning.
  • The contexts for failure range from consistent (known environment) to variable (different things may occur) to novel (never been tried before).
  • The most common failure types are consistent context = basic failure, variable context = complex failure, and novel context = intelligent failure.
  • Failing well is hard because of aversion, confusion and fear. These reactions can be helped like this: for aversion, reframe to build healthy attributions; for confusion, use a framework to discern failure types; and for fear, pursue psychological safety.
  • A spectrum of cause of failure from blameworthy to praiseworthy looks like this: sabotage > inattention > inability > challenge > uncertainty > experimentation


  • To learn from failure, avoid skipping the analysis (‘I’ll just try harder next time’), superficial analysis (‘It didn’t work. I’ll just try something else.’), or self-serving analysis (‘I was right but someone or something else messed up’).
  • Systems thinking suggests expanding your lens from the here and now to include elsewhere and later. Two questions can help:
  1. Who and what else will be affected by this decision or action?
  2. What additional consequences might this decision or action cause in the future?
  • Diagnose a healthy failure culture by listening to how much you hear about good news, progress, agreement and ‘All’s well’ versus bad news, problems, dissent and ‘I need help.’ The latter is preferable.
  • In conclusion, fail more often, celebrate the pivot, develop persistence, reflect on it, be accountable, and if relevant say sorry. And always resist the quick fix at the expense of proper understanding.
  • “For me, losing a tennis match isn’t failure. It’s research.” Billie Jean King


  • There are a huge number of anecdotes in the book – arguably a greater quantity than are needed to make the points.