Jim Wolfensohn: don't ask if you will succeed, ask if trying is worth the risk

From Peter Bregman's blog post on Jim Wolfensohn, former president of the World Bank, concerning Wolfensohn's acceptance of a university friend's request to join their fencing team for the national championships, knowing he had no chance of winning. That experience propelled a love of fencing, and eventually a spot on the Australian fencing team in the 1956 Olympics.

Most people, when they explore an opportunity, next step, or decision, ask: "Will I succeed?"

But Jim asks a different question: "Is it worth the risk?"

The difference in those questions is the difference between never fencing at all and fencing in the Olympics. When Rupert asked Jim to fence in the championships, there's no chance he could have succeeded. Failure was the inevitable outcome. But was it worth the risk? For Jim, it certainly was.

Jim's approach to life is to take a risk, learn from it, and take his new knowledge and understanding to the next risk. Failure is an essential part of his strategy.

Really taking risks requires failing. You have to fear failure enough to work hard to make the risks pan out successfully, but not so much that you don't take the risks in the first place. Viewed through the lens of learning, failure is at least as beneficial as success. Working only on things you're pretty sure will work significantly limits what you can achieve. Instead, take risks. And then see what happens.