The Upside of Uncertainty

Chapter 2

Reverse Insurance

Many of us feel anxiety in the face of uncertainty and so we try to avoid it. But a world with too much certainty becomes a boring, repetitive cycle from which we long to escape. We forget that we actually need uncertainty, and if we don’t have enough of it, we will even pay to introduce more into our lives. As the leader of a major gambling organization explained it to us, “We sell reverse insurance…. Our ideal target customer is the forty-five-year-old person who wakes up in a job they hate, a relationship they hate, and realizes their life is always going to be the same.”1 They gamble to give themselves the chance that something new could happen.

Although most of us spend an immense amount of energy trying to make ...