The joys of straddling different careers

I HAVE had careers in seven industries, each unrelated to the others. While this might make me sound like someone who does not know what he wants out of his professional life, it all matches a plan I developed while still in my late teens.
When I was in college, I struggled to figure out what I wanted to do with my life. Politics? Academia? Police? Military? Journalism? Each sounded interesting, even exciting, but every time I came close to choosing a career, I would start to feel claustrophobic.

It was then that I made myself a two-part promise: I would go only into a field I could easily exit, and I would stay in that field for only as long as it brought me joy. So, the FBI and the military, with their minimum terms of service, got scratched from the list.

Most people who are unhappy professionally change jobs within their chosen fields or go back to school to become grounded in a new area. I have deliberately made the stakes higher for myself by mostly not doing that.
After starting as an advertising copywriter, I took executive positions in law, marketing, entertainment, mobile communications and financial services. Today, I make my living as a writer and a public speaker.
The scariness of repeatedly walking that metaphorical career high wire without a net has been balanced by the opportunities each move gave me to acquire a new professional vocabulary, new skills and new relationships.
For those of us who wish we could clone ourselves to experience different aspects of life and to grow from it, my career pattern has allowed that, even if sequentially and not simultaneously.

There is little doubt that I have paid a price, both financially and psychologically, because of my career moves. Veterans in law, marketing or finance will almost always earn more than relative newcomers.
Starting anew usually meant starting with a pay cut, a situation I prepared for by saving as much as I could before leaving one position for another. Psychologically, it is not easy to be 20 years older than others at a company meeting and have to quietly ask the meaning of some industry term that the 30-year-old “veterans” were using, but it motivated me to get up to speed.
Oddly enough, despite the anti-establishment nature of my university promise, I was not then a countercultural type nor had I thought of myself as such. But if not a laid-back hippie, I did internalise the carpe diem ethos of that time that the largest part of who we are is what we do. I have always felt that major new challenges and exposure to new ideas are among the greatest things life has to offer.

Coming from a lower-middle-class background, I wondered, at first, if my staccato career outlook would cause my wife (now of 36 years, so this lack of fidelity is strictly tied to career) and children to pay a price for my hopscotch approach to professional life.
But now in hindsight, the career path I have taken looks different to me. While what I have done may at first appear scattershot, I now see that each move has built on the others. Sure, I have a learning curve in each new endeavour, but the time needed to master the field grows shorter and shorter.
Since all business has some common DNA, I am not really starting from scratch with each move. As I change careers, I am able to bring experiences and perspective that allow me to add insights that others long in that field may not have.
My judgement tends to be trusted by new colleagues and clients who might not otherwise value the advice of a newbie. When leaving a career track, I have not burnt my professional relationships, so I get to call on former colleagues and service providers who can also cheer me on or help me spot what I am missing in my new life.

Sometimes former colleagues become new clients. While changing careers has required some “look before you leap” thinking, I will admit that a few choices, in retrospect, were less interesting, challenging or lucrative than expected.
But even if I left those careers after a few years, in each case, I am also wiser for the experience. To cite one case, I did not enjoy the quantitative nature of financial services, but left with enhanced skills that have helped me in other positions.

I have never felt trapped in a job, a mindset that has allowed me a “gee whiz” sense of wonder everywhere I have worked. I am a passionate guy, so as soon as my current work starts to have a sameness about it or as soon as I begin to feel that I am faking interest at meetings, I feel liberated knowing that, if I need it, a pivot can soon provide an escape route.
Just knowing that I have a way out helps make even those inevitable bad days at work more tolerable. Plus, always being on the lookout for my next career helps keep me current with changes in business, society and technology. Who knows what career might come next?

This article was first published in The New York Times