I sometimes feel like I’ve had about 10 careers. My wide-ranging work life has spanned journalism, Microsoft and teaching. I’ve also earned money performing music, wrangling kids at camp, and probably other ways I’m forgetting now.

Reinventing oneself as many times as I have comes with costs and benefits. I’m glad to have worked across such a broad spectrum: I consider myself skilled in a large number of different areas, and I’ve had the opportunity both to indulge multiple interests and to work with all sorts of people. It’s been an interesting life so far, and sometimes even a lucrative one.

At the same time, I feel a certain amount of regret at not having amassed the clout, prestige and authority that staying in one field might have allowed. Changing careers often means starting over at or near the bottom, which takes a toll on your psyche, especially as you get older. More than once (particularly after I started teaching middle school), I found myself thinking, “I really miss being good at my job.”

Furthermore, there are always those who will interpret your career changes to mean you simply couldn’t hack it in your earlier positions — and sometimes they’re not shy about sharing these opinions publicly.

All too often workers don’t have a choice about whether to change careers. If you don’t need to leave your current field, though, is it worth indulging a wish to?

That’s a question only you can answer for yourself, but here’s another possibility raised by Kabir Sehgal in a career-planning column in Harvard Business Review called “Why You Should Have (at Least) Two Careers”:  Why not work in two or more fields simultaneously?


In the column, Sehgal — a veteran of Wall Street and the military, a Grammy-winning record producer, and a bestselling author — says his vastly different careers complement each other. Knowing people in different areas can broaden your perspective and help you avoid groupthink, he notes, while familiarity with different fields can help you figure out where their ideas intersect and thus where opportunities lie. Plus, Sehgal says, following your interests will help you bring passion and energy to your work and leave you more fulfilled.

Adding a second career takes time and money, and no matter how much you might want to do it, sometimes it’s just not feasible. But if you’d like to give it a try, start slowly — as they say, “Don’t quit your day job” — and make sure to build up a financial cushion first so that any bumps are minimized. Invest in knowledge: Skills are your lifeblood, so do whatever it takes to learn the skills required for your new field. Meanwhile, if you already have skills that transfer well to your second act, such as writing or business acumen, use them for all they’re worth.

Done smartly, changing careers — or adding a new one — can reinvigorate you, revitalize your first career or other areas of your life, help you branch out, and leave you better situated to weather the vagaries of the modern workplace.