In our previous post, Roxanne shared her thoughts about deciding when and how to retire. Now it’s Leslie’s turn to tell you about her very different retirement journey. See if you relate:

I’m a serial retiree. I’ve done it three times.

I started my working years in the mid-1970s, pursuing the career-woman path. Living in Boston, I landed a job in an insurance company, worked full time, went to school in the evenings to earn an MBA, and moved up the ladder to senior management.

But 9½ years in, that path came to an abrupt halt. I met a man whose dream was to sail around the world. Driven by curiosity and learning, I love to say yes to new adventures. So off we went.

Once the sailing adventure (and the relationship) ended, I sought to rejoin the corporate world. My former work associates back in Boston had warned me that I was making a mistake to go cruising, that by leaving I had proved that women weren’t serious about their careers, that I was “no better than women who got pregnant and left their jobs.”

I happily discovered that they were wrong.

Not only did I get another job in the insurance industry after a 6-year hiatus, but I had greater responsibilities and was paid more than if I’d never left. Over the next couple of months I was even featured on a Good Morning America segment and in a Cosmopolitan magazine article about the new trend of “corporate drop-outs.”

Importantly, this experience taught me that I could take a risk—leap into the unknown—and land on my feet. It was a lesson I put to good use when my “real” retirements came along a couple of decades later.

Retirement #1

In 2004 I was living in Rhode Island, working as director of advancement for a university. I was divorced and joined, met a man and—guess what!—he had a dream to sail around the world. So at age 53 came Retirement #1. I gave a one-month notice, he closed his financial planning business, we sold everything, got married and set off. Another leap out of the working world to pursue a dream.

I truly believed that I was retired for good, even when we came back from cruising, sold the boat, and bought a home in New Hampshire. I volunteered locally, started skiing at age 55 (too late—I didn’t bounce well) and took up photography.

Then came the Great Recession and, like everyone else, my husband and I watched our retirement savings tank. Someone had to earn some money and it was easier for me to find work in our small resort town. I got my real estate license and started selling second homes (for which, surprisingly, there was still a market). End of Retirement #1 and back into the workforce, driven by financial needs.

Retirement #2

Two years later, our finances had rebounded sufficiently and I was tired of buyers’ demands and the long hours. Rather than tail off the business over time, I reassigned all my listings and buyers and left. Retirement #2!

I didn’t have a plan, but it didn’t matter. Taking another leap into the unknown was exciting and welcome. I wanted to spend more time with my camera and unearth my long-unexpressed creativity.

Four terrific years passed—making images, graduating from a one-year residency program in photography in Maine, exhibiting in shows, winning awards. Then I came to a crossroads—pursue photography as a full-time business or cherish it as a hobby? The latter won.

We moved to Maine to be closer to the ocean. I loved our new location, but after a year I felt itchy and unsettled. I wanted to go back to work. End of Retirement #2.

Retirement #3

I got a job in 2015, leading a total organizational restructure for a nonprofit, and dove back in for the next two years. It was grueling, challenging, satisfying work and required many more hours than I’d anticipated. The team I led pulled off the herculean reorganization project and the results were better than planned. I was now 65, exhausted and oh-so done with working for other people. I gave a 3-month notice and in the fall of 2017: Retirement #3!

What next? I had no idea but trusted my process and knew that this leap was once again the right step for me. Two months later, my friend Roxanne and I began talking about retirement and why it’s easy for some people and not for others. We decided to learn more, and the concept for Retirement Voices and our book was born.


Some people (like Roxanne) leave their careers by phasing out over time, decreasing their responsibilities in a way that makes sense for them. I used to be envious of “downshifters”—it seems like such a peaceful, reasonable, less-disruptive way to go.

Instead, I’ve repeatedly chosen the hard-stop approach. I’m at work on a Friday, then wake up retired the following Monday. Even when I could have phased out of a job, I chose not to. Lately I’ve been mulling it over—why is this the approach that works best for me?

I realize now that I relish the leap—and that in-between time when I’ve just left the solid footing of a job but haven’t yet landed on the next venture. For me, it’s a time of endless possibilities and few restrictions. Of dreams and hope and freedom. To step into that moment and know that I have absolutely no idea what my life will be like in 6 or 12 months doesn’t create fear—it brings me joy. My history tells me that not only will I land safely but it often turns out better than I anticipate.

Not everyone gets to pick the why, when and how of their retirement. Some are forced out of jobs, or must retire for health reasons or to be a caretaker—and we’ll speak to that in future posts. Roxanne and I are fortunate; we get to choose the approach that resonates for us individually.

She downshifts. I leap—over and over and over.

What about you? If you haven’t yet retired, what approach appeals to you—and why? If you’ve already retired, what approach did you take—and again, why? Please share your thoughts and experience!