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I’ve Been Thinking … 4 Phases To Jumping Into Your Dream Career

When I read the Sunday Paper piece about being “in transition,” I was encouraged by the way Maria’s wisdom supported what I learned from years spent collecting the stories of people who successfully jumped from one career to another.

There was a time in my own life when I had trouble facing a transition. I was a very lucky young man, working in a prestigious corporate job high up in a fancy skyscraper yet wanting instead to pursue a childhood dream of traveling the world on a shoestring and sleeping on people’s couches so I could play on the professional circuit of squash–a racquet sport like tennis but indoors.

I tried to shake that crazy pro squash idea, but I could not. And one frigid winter night in Boston, from my corporate office, I decided to listen to that persistent little voice in my head and began cold-calling anyone I could find who had left one career for something very different. I was searching for how-to’s: how to find the middle ground that comes after you decide to chase a passion but before you achieve it? What are the 10,000 unsexy steps necessary to pursue a dream?

I made the phone calls and the coffee dates and I began collecting stories: of a professional baseball player turned college student; a bartender turned yoga instructor; a PR executive turned church bishop. I called my project “When to Jump.” And as I considered the stories, I heard that a pattern had revealed itself, a reassuring “jump curve,” four phases that, if embraced as they unfold, seemed to lead to a rewarding jump, a satisfying transition.

Here are those steps:

The stories of these career changes and the people behind them ultimately gave me the courage to jump myself. I left my finance job in 2014, planning to play the pro squash tour for a few months. Nearly two years later, I had traveled over 200,000 miles across six continents and nearly 50 countries. I had been ranked the 112th best squash player in the world. I had hit all the goals I had set out to reach, and once I had done so, I felt, for the first time since hearing that little voice, a sense of peace.

Mike Lewis is the author of When to Jump: If the Job You Have Isn’t the Life You Want (Holt, January 2018). He is the founder and CEO of When to Jump, a global community featuring the individuals, stories, and ideas relating to leaving something comfortable in order to pursue a passion. Goldman Sachs named Mike one of the 100 Most Intriguing Entrepreneurs of 2017, and his When to Jump podcast was named a top 10 business podcast by Apple iTunes.