In this Retirement Voices blog post, we thought it made sense to explore some of the factors that go into making the decision to retire—starting with the “when.” Roxanne’s going to take the lead on this post since she’s currently sorting that out:

I’ve been working for (gulp!) 50 years, the last 25 as a freelance medical writer. I’m fortunate to have developed a stable of clients who give me regular work. To keep my sanity, I sometimes even have to turn down projects. It’s a good problem to have.

But juggling constant multiple deadlines is getting old. I’m 66, and the “life is short” refrain is getting louder and more insistent. Do I really want to spend this chapter of my life tethered to my computer, letting other folks’ needs and expectations dictate how I spend my time.


On the other hand, am I ready to cut the cord and step away from my career completely?

Nope again.

While on crazy-busy workdays I fantasize about how luxurious it would feel to have nothing to do but read a book and nap, I also realize that a steady diet of that would bore me to tears. I want to keep my brain more actively engaged—and writing does that.

Conversely, on days when I have no commitments and try to think of something fun to do, I feel like the proverbial deer in the headlights—frozen in place, my mind a blank. Yet I’m too antsy to sit and read a book—I feel like I should be doing something. Which is probably why I have both work and weekend to-do lists—I love the sense of achievement I get from crossing items off! But it’s made me realize that I need to cultivate more interests outside of work (I’ll start a list!), as well as hone the skill of being instead of always doing.

I’ve also pondered the issues of relevance and connection in retirement. I recently I left the board of directors of a professional organization that I’d been part of for over a decade. This was my professional tribe, a group in which I’m recognized for my professional skills and the source of a steady stream of new clients over the years. I didn’t have to step down, but it felt like the right time to let go of those responsibilities, open up space for the next generation of leadership, and focus my time and attention elsewhere if I’m serious about transitioning to retirement. It was a real gut check—but having one less claim on my time ultimately has felt great. It was a bittersweet reckoning, nonetheless.

Then there’s the matter of identity. I admit, a lot of my sense of self has always been tied to my career. As I’ve gotten older, however, I realize that work is only a piece of who I am. Relating to people based on shared values and interests matters more than what I do for a living. So at this stage of life, letting go of my “day job” feels less like a loss and more of an opportunity to make space to (re)discover other pursuits and passions. What’s more, chances are I’ll always be a writer, just on different topics—so I’m not “losing” anything in that regard (and my ego is assuaged!).

All that said, when it came to deciding when to retire, I had an epiphany last year: Retirement doesn’t have to be an all-or-nothing proposition (duh!). There’s no “rule” that I must come to a full stop on a specific date. I can downshift, gradually resigning clients (and not taking on new ones) until I achieve a level of busy-ness that feels right (and can change over time).

This realization has relieved a ton of (self-imposed) pressure to carve a retirement date in stone. Plus, since I could start taking my full retirement amount from Social Security last year without penalty for earning other money, I did so, which gives me a financial cushion as I scale back on paying clients—and I can delay dipping into my retirement savings.

This flexibility is particularly important since Leslie and I have undertaken this Retirement Voices initiative, and writing our book and this blog are claiming a growing chunk of time (without financial remuneration—at least yet!). But this project also fulfills a great deal of my retirement must-haves, like engaging my brain via writing and staying connected. And what could be more relevant than exploring what retirement feels like with a community of women in the same boat?

I realize my gradual “glidepath” approach to retirement is a luxury I have as a self-employed person. It doesn’t necessarily apply if your employer won’t allow you to downshift to part-time work (although it doesn’t hurt to ask!), you face mandatory retirement due to age, health issues force you to retire, or you get downsized due to corporate changes (or this current COVID-19 pandemic). It’s also likely not an option if you need a full-time paycheck, or if you simply have no desire to retire.

But I hope that my experience and some of the issues I’ve touched on give you some food for thought. The bottom line is that retirement is a uniquely personal journey for each of us, and there’s no one “right” way to make the transition—despite what the self-anointed retirement police may say (a topic we’ll tackle in a future blog!).

Also, please be sure to read Leslie’s post about her very different approach to retirement!

What do you think? If you’re retired, when did you stop working—and why? If you haven’t yet left the working world, when and how do you plan to do so? Please share your thoughts in the comments below.