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.

There’s a quick way to determine if your company has embraced the negative definition of failure. Ask yourself what happens when an error is discovered. Do people shut down and turn inward, instead of coming together to untangle the causes of problems that might be avoided going forward? Is the question being asked: Whose fault was this? If so, your culture is one that vilifies failure. Failure is difficult enough without it being compounded by the search for a scapegoat.

In a fear-based, failure-averse culture, people will consciously or unconsciously avoid risk. They will seek instead to repeat something safe that’s been good enough in the past. Their work will be derivative, not innovative. But if you can foster a positive understanding of failure, the opposite will happen.

Perversely, the desire to avoid risk often magnifies it. Dumping money into big me-too projects with modest upside is a lot more perilous than seeding lots of early-stage ideas that are further out on the fringe. In the age of upheaval, incrementalism is the riskiest bet of all. What’s needed is a radical shift in how we think about experimentation. The goal isn’t simply to reduce the uncertainty around new products or get them to market faster, but to build an organization where everyone is working to extend the boundaries of what’s possible. That’s how an organization buys insurance against irrelevance.

The dilemma is that when the challenges facing an organization are not about repeatable execution, but about innovation or responding to complexity, the idea of breaking things down into well-understood parts is not only unhelpful, it can also be a dangerous trap.

The pain of hating our own creation is a consequence of our investing too much of our sense of being into the company, the product, the creation. When we hang our sense of self on the whisper of an idea; when we unwittingly insist that our love, safety, and belonging depend on what we do and, most important, how others feel about our feelings, our actions, and our work; then we leave little space for anything other than bitter, existential suffering.