How did you choose your career path? Or did your career path choose you?

Someday I want to write a book that examines how people end up doing the work they do. It’s a topic that has always fascinated me.

Few people end up in the career they envisioned as a child. Though I was fortunate enough to make my childhood dreams of becoming a writer and a teacher come true, I never envisioned some of the other positions that I have held during my lifetime.

For more than a decade, I managed McDonald’s restaurants. This was a job I fell into back in high school when my friend, Danny, informed me that McDonald’s was one of the only places in the area paying slightly above minimum wage. I started working at the age of 16 and was managing the afternoon and weekend shifts by the time I was 17.


Ten years later, I was still managing McDonald’s restaurants while putting myself through college.

For about five years, I worked in banking, first as a bank teller and then as a customer service representative and assistant manager. I fell into this job after answering an ad in a newspaper for the now-defunct South Shore Bank of southern Massachusetts. Eventually I would work for the also defunct Bank of Boston and the Bank of Hartford before leaving banking entirely and going to college.

bank_boston south shore sb

My career as a wedding DJ began with a phone call in 1997 from my best friend, Bengi, who was looking for a way to make some more money and had recently been disappointed by the DJ that he had hired for his wedding. Having hosted many parties when we lived together following high school, he thought we could do better.

“Do you want to start a DJ company?” he asked. “You know… for weddings?”

“Sure,” I said. “Sounds good. But I’ve got a paper to write for my Econ class, so let’s talk about it later.”

That was all it took.

Three months later, we hosted a company launch party for our friends and family at a local VFW, and three months after that, we were working at our first wedding.


I decided to become a life coach after listening to an acquaintance of my wife describe the life coaching classes that she had just completed in order to become a certified life coach. I was fascinated by the idea that someone with a relatively uneventful life and limited personal success might think that a series of college classes would make him or her an effective life coach.

I realized that if I were to hire a life coach, I wouldn’t want someone merely schooled in the art of life coaching. I would want a coach who had overcome great obstacles in life and achieved significant personal and professional success despite the challenges placed before them.

In that moment, I decided that I wanted to be a life coach.

Three years later, I had my first paying client.

When I meet a person for the first time, I often inquire about the path they choose to the career they have today, and how little choice plays a role. These stories are often filled with chance, coincidence, luck and unexpected twists.

It fascinates me to realize how little control so many people have over their career paths, and how few people fulfill their childhood dreams, not always because those dreams changed, but because a more viable, convenient or profitable opportunity presented itself.

Recently I read about Richard Branson’s path to founding Virgin Airways, and couldn’t help but smile. The man who owns one of the premier airlines in the world and is making strides to become one of the first commercial airlines capable of taking passengers into space began his career thanks to a cancelled flight.

“In ’79, when Joan, my fiancée and I were on a holiday in the British Virgin Islands, we were trying to catch a flight to Puerto Rico; but the local Puerto Rican scheduled flight was cancelled. The airport terminal was full of stranded passengers. I made a few calls to charter companies and agreed to charter a plane for $2000 to Puerto Rico. Cheekily leaving out Joan’s and my name, I divided the price by the remaining number of passengers, borrowed a blackboard and wrote: VIRGIN AIRWAYS: $39 for a single flight to Puerto Rico. I walked around the airport terminal and soon filled every seat on the charter plane. As we landed at Puerto Rico, a passenger turned to me and said: “Virgin Airways isn’t too bad – smarten up the services a little and you could be in business.”

Imagine how different Branson’s life would have been had that flight to Puerto Rico not been cancelled.

What was the path that you took to your career?

Was it fraught with chance, happenstance and dumb luck?

Or was planned and executed with precision?

I want to know.