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


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:

  • Listen to the little voice in your head. Turn up its volume. Take in what it’s telling you.
  • Make a plan. Whether on the back of a napkin or across a spreadsheet, begin planning how much money you’ll need to save, the skills you’ll need to hone, the people you’ll need to meet. And start doing those things.
  • Let yourself be lucky. After you’ve solved for everything, welcome the uncertainty about what happens next. When you do, you’ll allow yourself to be lucky and that’s when you’ll collide with beneficial people, opportunities, and experiences that you couldn’t possibly have predicted.
  • Don’t look back. Every journey will change once you start it. Among all the individuals I’ve researched and interviewed who have listened to the little voice, taken the time and effort to plan a thoughtful jump, and then taken the chance and jumped, not one person has regretted the decision, regardless of its outcome.

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. 


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