The Season That Asks Bigger Questions

So what are you doing for the holidays? Are you hosting this year? And when are you finally going to retire?

Everyone has a question for you this time of year. The neighbor with the leaf blower. The cousin who texts in early October to lock down Thanksgiving. The coworker who has started counting your birthdays out loud. And you answer them, pleasantly, while a completely different set of questions runs underneath. Am I still happy doing this? What would I even do with myself if I stopped? Who am I when I'm not the one holding all of this together?

If that second set of questions has been getting louder, you are far from alone. We are living through what retirement researchers call Peak 65. Over 4.1 million Americans are turning 65 every year through 2027, which works out to more than 11,200 people a day. That's a lot of women standing at a kitchen counter in the fall, stirring something, wondering the same thing you are.

The holidays don't just bring celebration. They bring clarity.

Where I live, the aspens turn gold and then drop every last leaf in what feels like a week. Nobody accuses them of giving up. Nobody asks them if they've thought this through. They just know the season changed before the calendar said so. I've started to think women are a lot like that. Something shifts inside us in the fall, long before we have a plan, a date or a speech ready for the family.

The holiday season is a mirror. It takes whatever is already true in your life and holds it up to the light. If you're content, you feel it more. If you're grieving, you feel it more. And if you're quietly outgrowing the life you built, the twinkle lights have a funny way of showing you exactly where the seams are.

The numbers back this up. In the American Psychiatric Association's most recent holiday poll, 41% of adults said they expected more holiday stress than the year before, a sharp jump from 28% in 2024. Nearly half said they were worried about missing someone or carrying grief. Almost one in three said they were worried about being lonely. Here's the part that caught my attention. Only 27% of adults 65 and older expected more stress, compared with nearly half of younger adults. So we've gotten good at the logistics. We know how to make the gravy and survive the seating chart. What we haven't been given is language for the other thing, the one that has nothing to do with the menu.

That other thing usually shows up as a quiet question. Is it time for something new?

It rarely announces itself. Maybe you feel out of sync with routines that used to fit like a favorite sweater. Maybe you're tired in a different way than you used to be, a tiredness that a long weekend doesn't touch. Maybe you catch yourself feeling hopeful and unsettled at the same time, which is a confusing combination when you're also trying to remember who's allergic to walnuts. Maybe you've just noticed that the things you used to look forward to now feel like obligations with a bow on top.

None of that means something is wrong with you. Uncertainty is often the first sign of reinvention.

The work that sits underneath everything I build at Rising Joy comes from a Polish psychiatrist named Kazimierz Dąbrowski. He spent his career arguing that inner unrest is often the beginning of growth, the moment an old way of living starts to come apart so a truer one has room to form. He was writing about a very different population than women in their fifties and sixties, and I'm upfront that carrying his ideas into midlife is my own move. But every time I read him, I think of the women I know who feel restless in October and can't say why.

The hard part is that restlessness rarely comes with an answer attached. We want the clarity first and the feeling second. Life tends to hand them to us the other way around. And the stakes feel high. A 2023 Transamerica Center for Retirement Studies survey found that 56% of retirees left work earlier than they had planned, and fewer than four in ten retired on their own timeline. In a separate survey of financial planners, only 11% said their clients were prepared for the mental side of retiring. So many of us are planning the money and leaving the self to sort itself out later. Later has a way of showing up during the holidays.

For some of us, the quiet question has another layer.

I grew up being asked what I was. Which one of your parents is Black? Where are you really from? Can I touch your hair? When you spend your childhood fielding questions like that, you learn early that identity is something other people feel entitled to define for you. And you learn to answer politely while a deeper conversation runs underneath. Sound familiar? It's the same skill we use at the holiday table.

There are more of us carrying more than one story than ever before. The 2020 Census counted 33.8 million people who identify with two or more races, up from 9 million in 2010. In Pew Research Center's landmark survey of multiracial adults, about three in ten said they had changed how they viewed their own racial identity over the course of their lives. Identity moves. It always has. So when a multicultural woman asks herself what's next, the question is rarely just about a job or a calendar. It sounds more like this. Who am I becoming across all my cultures? Which traditions do I carry forward, and which ones was I only holding because someone handed them to me?

You don't have to be biracial to know that feeling. Maybe your parents immigrated and you've spent your life translating between two worlds. Maybe you married into a family whose holidays look nothing like the ones you grew up with. Maybe your faith changed, or your politics, or your idea of what a good life looks like. Anyone who has lived between stories knows that reinvention is never just a career question. It's a belonging question.

So here is what I'm asking of you this October. Nothing big. I'm not asking you to decide anything, announce anything or update your LinkedIn. I'm asking you to notice.

Notice which invitations make your shoulders rise toward your ears. Notice which conversations leave you more like yourself, and which ones leave you feeling like you've been wearing someone else's coat. Notice what you'd do with a free Tuesday if nobody needed anything from you. Write it down somewhere private. A notebook, the back of a receipt, the notes app you swear you'll organize someday. These small noticings are data. They are your inner self clearing her throat.

Redirection starts long before you make a decision.

This is the first of three letters I'm writing to you this season. In November, we'll talk honestly about the weight we carry into the holidays, especially those of us who've been the cultural bridge in our families for as long as we can remember. In December, we'll talk about what it means to walk into a new year without a plan and still feel at peace. Come sit with me through all three. Bring your questions. You don't need answers yet. You just need to stop pretending you aren't asking.