Taking a risk is scary when you focus on what can go wrong and exciting when you consider the benefits if all goes well. The trick is to think about risk in the right way and use it to your advantage. Most people see taking risks as opening themselves up to unnecessary, even dangerous, chance. But the truth is, avoiding risk won't keep you safe, nor will it guarantee a smooth ride.
In fact, the opposite is often true. It's like the monkey parable: A monkey sees a nut in a hole and reaches in to grab it. Once he's closed his fist around it, he can't get his hand back out of the narrow opening. He can't free himself unless he lets go of the nut, but because he's afraid to lose it, he won't let go.
Trying to avoid risk is like clinging to that nut. You may think you're playing it safe by holding on to what you have, but in reality you're just hindering your own progress.
Rule 1: Take Risks That Are Calculated, Not Crazy
So how can you make risk work for you? The first rule: Take risks that are calculated, not crazy. There's a big difference between rafting in white water with a helmet and an experienced guide and jumping on an inner tube to soar over a waterfall on a whim. When you're considering taking a risk, ask yourself: How can you maximize your chances of success while minimizing the potential downside?
About a year into my first job, as a sales assistant at Holiday magazine, my boss quit. As soon as I heard she was leaving, I wanted her job. I made an appointment with Holiday's publisher, a top executive who'd been in the magazine business about as long as I'd been alive. "I want to talk to you about Phyllis's job," I told him. And although I had a grand total of one year of experience in advertising sales, something about my demeanor, and my aggressive pursuit of the job, must have convinced him I was ready. "Okay," he said after a short interview. "We'll give you a chance. We'll also bump up your salary $3,000 to reflect your new position."
Success! I was thrilled to be moving up—yet there was already a sticking point. I knew how much money Phyllis had been making, and it was considerably more than they were offering me. I could have just thanked the publisher and taken his offer, but I decided to risk asking for more.
"I know what Phyllis was earning," I said. "And I think I ought to be paid the same salary, as I'll be doing the same work with the same responsibilities."
The publisher's face turned the color of a beet. How dare an inexperienced 24-year-old ask for a bigger salary just minutes after getting her first-ever promotion? Didn't I know that moving into a higher position didn't guarantee I'd make the same salary as the person leaving?
Well, no, I didn't. But even if I had known, I probably would have asked for the raise anyway. The upside was obvious: making more money. The downside was...what? That the publisher would think less of me, or even rescind the job offer? Perhaps there was a chance of that, but it was unlikely. Besides, if I didn't take the risk and ask for a higher salary, there was zero chance I'd get it. As ice hockey legend Wayne Gretzky once said, "You miss 100 percent of the shots you never take."
In the end, I didn't get as much money as I asked for, but the publisher did increase my salary above what he'd initially offered. Nothing lost, something gained—it was the ideal outcome for taking a risk.
Which brings us to the second rule for making risk work for you. When assessing the downside of any risk, remember: The worst-case scenario is rarely as bad as you think.
In 1975, after nearly a decade in New York City, I decided to pursue new adventures out West. The draw: a San Francisco–based magazine being published by film director Francis Ford Coppola. It was certainly risky at that point in my career to leave New York, the epicenter of the magazine and advertising businesses, for the West Coast. It was risky to leave Ms. magazine, where I had been the advertising manager for three years and was starting to make a name for myself. And it was risky to leave my friends and colleagues for something unknown, thousands of miles away. But not only was I ready for a change, I fully expected the magazine to take off, and my new life in San Francisco to continue the same upward career trajectory I'd experienced in New York.