... I couldn’t resist asking, “Tommy, why do you keep throwing yourself at this climb? You’ve experienced so much success as a climber, but all this climb seems to do is give you failure upon failure. Why would you go back?”

“I go back because the climb is making me better, it’s making me stronger,” he replied. “I’m not failing, I’m growing.” We got into a long conversation about how to think about failure, arriving at the idea that the opposite side of the coin of success isn’t failure but growth.

“What I find with a lot of people,” he continued, “is that they’re so focused on success that they don’t put themselves in situations where they’re likely to grow through the process of failure. But to truly find your ultimate limit, you have to go on a journey of cumulative failure and hopefully come out the other end someday. Even if I never succeed in free climbing the Dawn Wall, it will make me so much stronger, and so much better, that most other climbs will seem easy by comparison.

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.

Lots of companies try to win and still can’t do it. So imagine, then, the likelihood of winning without explicitly setting out to do so. When a company sets out to participate, rather than win, it will inevitably fail to make the tough choices and the significant investments that would make winning even a remote possibility. A too-modest aspiration is far more dangerous than a too-lofty one. Too many companies eventually die a death of modest aspirations.

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.

It’s easy to underestimate the role ease plays in decision-making. Since behaviour follows the path of least resistance, a surprisingly successful approach is to add friction where you find yourself doing things you don’t want to do.