... the truth is that large success is the aggregation of small successes, and that therefore improvement consists of finding out, in each trial, what works, seizing hold of it, and figuring out how to make more of it. Failure by itself doesn’t teach us anything about success, just as our deficits by themselves don’t teach us anything about our strengths. And the moment we begin to get better is the moment when something actually works, not when it doesn’t.

The better, more subtle interpretation is that failure is a manifestation of learning and exploration. If you aren’t experiencing failure, then you are making a far worse mistake: You are being driven by the desire to avoid it. And, for leaders especially, this strategy - trying to avoid failure by out-thinking it - dooms you to fail. As Andrew puts it, “Moving things forward allows the team you are leading to feel like, ‘Oh, I’m on a boat that is actually going towards land.’ As opposed to having a leader who says, ‘I’m still not sure. I’m going to look at the map a little bit more, and we’re just going to float here, and all of you stop rowing until I figure this out.’ And then weeks go by, and morale plummets, and failure becomes self-fulfilling. People begin to treat the captain with doubt and trepidation. Even if their doubts aren’t fully justified, you’ve become what they see you as because of your inability to move.

A strategy is a way through a difficulty, an approach to overcoming an obstacle, a response to a challenge. If the challenge is not defined, it is difficult or impossible to assess the quality of the strategy. And if you cannot assess a strategy’s quality, you cannot reject a bad strategy or improve a good one.

Athletes in general possess a relatively enlightened understanding of failure’s relationship to success. As Canadian ice hockey superstar Wayne Gretzky famously said, “You miss one hundred percent of the shots you don’t take.

The instinct to exhort people to do their best work in challenging times is understandable. It’s tempting to believe that if we just hunker down, we can avoid failure altogether. It’s also wrong. The relationship between effort and success is imperfect. The world around us changes constantly and keeps presenting us with new situations. The best-laid plans encounter problems in an uncertain context. Even when people work hard and are committed to doing the right thing, failure is always possible in a new situation. Sure, sometimes failures are caused by people who are careless or don’t work hard, but even hard work can end in failure when a situation is new and different or some unexpected event happens. Finally, and most perversely, sometimes sheer luck allows you to mail it in and succeed anyway.