How do you know when it's time to go?

Thinking about retirement ... or not.

I heard yet another story this week about a friend who had planned a retirement strategy, but keeps postponing it. It’s understandable — he has built his firm through the decades and it’s been wildly successful. But I can’t help but think about the people who are waiting for him to go so they can begin leading the firm into its next era of success.

I have deep sympathy for anyone trying to reinvent themselves at the end of a successful career in which your work becomes your identity.

Then there’s my friend who started her own nonprofit with a vision and a credit card, and who has taught herself how to fund great work as well as do that work herself, adding employees along the way. Nearly a decade later, she’s taking a well-earned sabbatical and is thinking about what comes next, realizing that it may not look at all like what came before. She’s not retiring, per se, but she doesn’t want to work the way she’s worked in the past.

Even my friends who are coming to the end of their corporate careers are hanging on longer than I ever imagined they would. Some of them love their work and are finally getting the opportunities they’ve longed for based on their experience and success. They are healthy and engaged and still able to work at the level they want to.

So how do you know when it’s time to step away?

For women, retirement is not an easy decision, for the reason we rarely discuss: Money. As the Association of University Women reports, “Women encounter a pay gap at every stage of life, but nowhere is it more pronounced than during the retirement years. On all three components of the ‘three-legged stool’ of retirement security — Social Security, pension and savings — women fall short.  As a result, they have 70% of the income that men have during retirement.”

As infuriating as confronting the larger question of a women’s pay gap still is — didn’t we wear those 59-cent buttons back in the 70s for a reason? — if you’re a Black or Latina woman, your retirement choices get even more scary.

So add another reason to the list of why some women might not look forward to retirement. Or even have much of a plan for it.

I probably fall into this category, the group that doesn’t really have a plan. As a solo entrepreneur with a custom creative business (and a husband who’s an entrepreneur, too), thinking about retiring hasn’t really been on my radar screen, aside from (thankfully) being able to make some decisions about money, Medicare and Social Security.

I love my work, and have been lucky enough to have come to the place where my clients are all doing work I admire and letting me use every ounce of my creativity and ability to help them along the way. Every day I have new ideas to share and think of possible next steps for my work. I still see new projects and new clients everywhere I look, though I’ve been doing this long enough to know that even this kind of energy is seasonal. My work is invigorating, satisfying and sometime terrifying, which I have come to realize is how I thrive.

The retirement question for me: What would I do if I didn’t do this?

So I ask again: How do you know when it’s time to stop, if you are lucky enough to have a choice? How are you thinking about life after retirement, if that’s what you’re calling it? If you’ve already retired, what are some of the things you know now that you wish you’d known before?

I’d love to hear from this amazing, engaged community about some of your learning, the resources you’ve used and how it’s going.

Thanks for being willing to help a girl out.