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I’m someone who tends to like to play things safe. Predictable and stable are two of my favorite adjectives, and I always prefer to stick to the beaten path, rather than opting for the road less traveled. And, regardless of what route I’m walking on, you can bet I make my best effort to avoid any of those pesky sidewalk cracks—for fear of causing any careless injuries to my dear mother’s back.

So, needless to say, when I decided to up and quit my full-time job in favor of pursuing a career as a freelance writer, it was a little (ahem, well, a lot) out of character for me.

After I finally put in my two weeks notice with my supervisor, news of my pending career jump began to spread like wildfire. Numerous people approached me with what they said were their “well wishes”—which, in all honesty, were really just harsh criticisms and warnings with a half-hearted “good luck” tacked onto the end.

“Are you sure you want to do this?” they’d ask, with a skeptical look on their faces, like I had just told them I was running away to join the circus, ”It seems like a pretty big risk—wouldn’t you just rather play it safe?”

There they were. The words that had reverberated in my own brain for months before finally gathering my courage and running from my standard 9-to-5: Play it safe.

It’s advice you hear echoed time and time again. And, it’s well meaning, really. After all, many of us operate with this understanding that there’s a step-by-step guide that will eventually lead us to a fulfilling and rewarding career—that there’s some sort of paint-by-numbers approach that will finally give us the lives we want, as long as we play our cards right.

In all honesty, it’s a sentiment that you could easily let dictate your entire career, particularly if you’re someone who tends to thrive on the certain rather than the unknown (I’m raising my hand over here).

As I’m sure you can imagine, those three small words taunted me over and over again as I was preparing to take one of the scariest career risks of my life. Who was I to make this jump? I was still young and green—why would I opt for this less traditional path, when I was already safe and secure in my own full-time job? What made me think I deserved to stray from the norm and do something different?

But, somehow I managed to push all of those criticisms, naysayers, and nuggets of self-doubt aside, and instead took a running leap and hurled myself off of that ledge that—most of the time—seemed totally foolish and unreasonable.

And, you know what? I’m glad I did it. Not only has it led me to a career that I absolutely adore, but it also taught me something valuable about the way I was approaching my entire career—and even other decisions outside of my work life.

It’s all too easy to think that success resides with the predictable. With all the talk of climbing the ladder and paying your dues, anyone can understand why you’d think that there’s a certain rigid structure you need to obey—that if you follow the steps clearly laid out in front of you, you’re bound to eventually wrap your greedy hands around what you really want.

However, it’s important to recognize that there’s always more than one way to do anything. And, safe doesn’t always equal successful. In fact, sometimes sticking with the tried and true is a surefire way to land yourself in a career rut. There are countless stories of people who did things exactly as they were supposed to, and still remain unsatisfied with where they ended up.

So, where am I going with this long-winded tale? Well, if you take one thing from this article, it should be this: Playing it safe isn’t always the best route.

As a matter of fact, some of the biggest career successes and achievements have been attained by those people who disregarded the inclination to stick with the predictable and instead decided to do something that seemed just a little crazy. Bill Gates dropped out of Harvard. Apple got its start in a garage. The initial premise of Harry Potter was drafted on a napkin. You know the stories.

Believe me, I know how tempting it can be to stick to that well-mapped and well-trodden path—it’s comforting. But, while taking a well-informed risk might not always seem as reassuring, it can definitely be more rewarding.

And, take it from me—the view from the road less traveled? Well, it can be pretty amazing.


Photo of happy person courtesy of Hero Images/Getty Images.