How to Take the Right Risks

I have this job because I took a risk in 2007.

I was a small-town newspaper reporter in Massachusetts then, writing about minor crimes and mayoral races, and the road ahead depressed me. That gig would only lead to a similar one at a slightly larger paper, in another random town. And then another. And another. What I really wanted was to be a magazine editor in a big city, a role nobody in the industry would consider me qualified for. So I started pitching freelance stories to magazines, hoping to prove myself. Whenever one was accepted, I’d stay up late after my day job to meet the deadline. Eventually I got some steady work in Boston magazine, met some of the staff and saw that an editor was leaving and they’d be hiring a replacement. I wanted it to be me.

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So I quit my newspaper job. I moved to Boston, renting an apartment far out of my budget. And I told the editor at Boston that I was ready to be hired. A few months later, that’s what happened. It was the risk that changed my career -- and, frankly, I don’t know where I’d be now if it hadn’t worked out.

Every entrepreneur has a story like this, if not many of them. When we take a risk, we separate ourselves from the safe and steady path. We shift more burden onto our shoulders -- willing to bet that some combination of skill and instinct will lead to greater rewards. In taking a risk to achieve a vision, we can change the rules and create lives of our own making. Risks don’t always work out, but they do always remind us of the vast possibilities awaiting us. And that’s why we at Entrepreneur created this issue, our first annual list celebrating 50 daring entrepreneurs who took inspiring risks within the past year. You’ll know some of their names; others will be new. All are motivating. We want to celebrate the many ways that people can go their own way. 

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From the outset, this could seem reckless: Nobody should celebrate risk only for the sake of risk. In fact, just as we were closing this issue in September, The New York Times captured exactly that problem. Pharma-bro Martin Shkreli had just been sent to prison for violating the terms of his bail, and, to contextualize it, the paper explored research from two economists: They’d found that entrepreneurs are more likely than others to have broken the law in their teens and 20s. “The problem,” says the story, “is that the psychological forces that drive teenagers to break rules may not be so easily channeled later on.” As adults, the impulse can turn into careless business decisions.

It’s an interesting theory, and a reminder of the difference between daring and dangerous. It’s healthy to think of ourselves as risk takers, but what we should do is make bold, calculated decisions that look like risks. The truly smart risk isn’t made like a roulette bet; it’s in seeing an opportunity that others don’t, and summoning the courage to seize it. Consider this: Richard Branson, whom I spoke to for this issue, is famous for his line “Screw it, let’s do it” -- but he doesn’t bust that out every time someone pitches him. He considers the odds of success. He thinks big picture. He’s really saying, “This is a properly assessed risk; let’s do it.” It’s not as catchy, but it’s good logic.

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So with this in mind, let me admit something about that personal story I told you above. When I tell it in public, I do so like a swashbuckler -- I just called up that magazine editor and told him to hire me! In reality, the editor and I had a series of conversations over many weeks while I still had my newspaper job. He hadn’t promised to hire me, but I could tell it was a possibility. So when I quit my job and moved to Boston, it wasn’t done recklessly. It was calculated. I wanted to show him I was serious. And it worked, just like the best risks do.