The Art of Being Unreasonable: Lessons in Unconventional Thinking

Chapter 8

Risk

When you try something new or different, it may or may not work. That’s how I define risk.

The earlier you start taking risks, the more comfortable you will become with them. When you’re young, you don’t have a lot to lose, and you have a lot of time to recover when things don’t work out.

My first school of risk was the racetrack. You can’t win if you don’t bet, but you quickly learn not to wager more than you can afford to lose. There’s an old saying among savvy horseplayers: never bet scared money.

I’m lucky that my wife, Edye, always understood and never shied away from risk. Like me, she’s an optimist. When we went on our honeymoon in Florida, she didn’t want to return home to snowy Detroit. I remember her saying, “Why don’t we stay here? We’re just starting out. We can start here.”

She was not kidding. And she was right—we had very little to lose, so taking the risk of moving suddenly to a new place could have paid off big. Although we didn’t move to Florida, her words rang in my head the next year, when I decided to start our homebuilding company.

To some extent, taking risks is a matter of temperament, the willingness to dare big. But everyone can train themselves to try it.

The first risk is exhilarating, not because it’s big but because you have nowhere to go but up. Legendary entrepreneurs from Andrew Carnegie to Bill Gates all made one starting gamble and won a lifetime of reward.

From the moment you take your first risk—starting a business, embarking ...