5 Ways to Be Better at Risk-Taking

You may never tame lions or swim with the sharks, but you still have plenty of opportunities to act courageously every day. Learn the secrets to becoming bolder and braver from five experts (including a poker champion and a stunt coordinator) who smile in the face of fear.


Photo by Dan Winters

1. Be a Quitter

Before any kind of endeavor, whether it’s a new job or a financial investment, come up with some golden rules. Tell yourself what you are unwilling to tolerate or what will cause you to stop the activity. Adhering to strict safety standards has kept me alive in some very dangerous situations. Whatever the issue—maybe I’ve gotten an iffy feeling or just felt that a member of the crew was rubbing me the wrong way—I don’t hesitate to stop. Knowing that I can back out is what gets me in the water in the first place. Only an expert risk taker can swim toward a particular goal and arrive within a hairsbreadth of the treasure, then turn around and go home.

Jill Heinerth is a cave diver and an underwater photographer and filmmaker. She is the author of The Essentials of Cave Diving ($50, amazon.com) and cowrote, produced, and appeared in the PBS documentary series Water’s Journey. She lives in High Springs, Florida.

2. Have a Mental Rehearsal

Before I take a risk—which in my line of work often involves jumping off a building or setting a car on fire—I picture the entire scenario in fine detail, from start to finish, at least 20 times. This can take anywhere from 15 minutes to hours on end, depending on the stunt’s complexity. Each time, I imagine it going perfectly. If negative thoughts creep in, I push them out of my head and start over again. By the time the actual situation rolls around, I’ve imagined it so many times that it feels old hat.

Darrin Prescott has coordinated and performed stunts for dozens of commercials and movies, including 2011’s Moneyball and Drive and the upcoming Gone, scheduled to be in theaters on February 24. He lives in Los Angeles.

3. Don’t Put Everything on the Line

I set aside money for playing poker, and I risk only a small amount of it on each game. You can’t take advantage of big financial opportunities (a passion, a new job, a potential investment) if you’re too stretched. That means you need to maintain a lifestyle that’s more modest than what you can actually afford. Even then, you should never put all your time or cash into one venture. The odds of ruin are just too high.

Annie Duke is a Los Angeles–based professional poker player. She won the World Series of Poker Tournament of Champions in 2004 and the National Heads-Up Poker Championship in 2010.