I’m sure someone must have said this to me at some point in my life because reinventing myself is something I have done many times. Of course, I didn’t think of it that way at the time. I felt no philosophical imperative to change direction or master a new set of skills every few years. But life had a way of forcing me to step outside of my comfort zone when what I was doing was no longer working or meeting the needs of my target audience.

I have been a writer for more than sixty-five years. “Reinvention” never meant abandoning the writing life for a different profession. To me, it meant broadening my capabilities. I began my career as a feature writer for magazines. I freelanced for magazines; I was a staff writer and editor for magazines; and I loved magazines. I couldn’t imagine doing anything else. But for practical reasons, I changed jobs at the same time many of the publications I was writing for were disappearing from the scene.

It was time for a change, which was to become a corporate writer. Nothing could have been further from what I had been doing for eight years. Overnight, I began writing annual reports, employee newsletters, press releases, internet and intranet copy, speeches for CEOs, and even strategic plans. This was reinvention with a capital R: different media, different messages, different audiences, and different challenges.

Two more job changes, and I found myself with a private office and a new title: marketing manager. More OTJ education, new messages, constituencies, media, and more challenges. By 1989, I was burned out by the corporate world. I was fifty-two, which seemed ancient to me. I couldn’t imagine anyone hiring someone over fifty. Nonetheless, I started calling old contacts, expecting rejection. What I got instead, was encouragement and insight into the local employment situation. I was overqualified for entry-level and middle-management jobs, and jobs at my level were not likely to become available. What remained was “consulting” —another name for freelancing.

Both sounded risky, but people I knew were not only doing them but also making a living. While I was checking out the employment scene I landed my first freelance assignment. It was for Citibank—not a bad place to begin. I was stunned at how well it paid. That first job led to a second and then the third; and by that time, I was hooked. No full-time positions came my way, and after a while, I gave up the whole idea of being an employed writer. It was time to stop thinking of freelancing as a stopgap measure and begin to see it as a full-time occupation. I was officially an entrepreneur—a small business owner who knew nothing about what I was doing.

I found a good accountant and set up a few systems for billing and collections. I also kept track of making phone calls, appointments, and results. It was a heady time—exciting and energizing. I was working harder than ever and loving every minute. I was also getting an education in working on multiple projects for multiple clientss and multiple audiences. To my amazement, I was also making money. Why didn’t I know about this sooner? It seemed too good to be true, which, of course, it was. You can’t run a business, no matter how small, on a wing and a prayer.

I had no idea what I was doing but continued to stumble along pretending (to myself) that I did. There were so many things I should have done to educate myself and improve my chances of succeeding. The most obvious and important one was to take a course on how to run a small business. Now, in hindsight, that seems like such a no-brainer, I’m embarrassed to admit that I didn’t do it.

My little venture changed many times over the years. What began as writing for publications and small businesses morphed into training programs, websites, corporate communications, executive speechwriting, consulting, editing, ghostwriting, book coaching, teaching, and publishing my own books—twenty-nine in all. Some years were good, others, not so much. Often, it cost me more to run the business than I took in, but I kept on going for thirty years, an astonishing amount of time for a freelance writer to survive in an ever-changing market,

It ended in late 2019 with a shrinking client list and a corresponding lack of desire to continue. Shutting down a business is relatively easy when the business is languishing. All it took was closing the bank account and taking down the website. Suddenly, I was retired, something I didn’t want to be. Then, out of the blue, COVID hit, and the world flipped on its head. Certainly, my world did. For the first two years of a worldwide pandemic, most people stayed home and tried to adjust to our new reality. I wasn’t ready to stop working, so I did what came naturally: I wrote a book on a subject I was getting to know well—aging.

I was eighty-five when I turned the page and reinvented myself one more time. I moved to Saint Augustine, Florida, a city known for its art community. This was a chance to return to my roots as an artist, and I embraced it. I must have missed that part of my life because I have brought all the energy and enthusiasm to painting I had given to my writing life for more than sixty years. Where I have thought of myself as a writer for so many years, I now see myself as an artist.

It is a picture I can live with…until the next reinvention, whatever that may turn out to be.