After decades of forcing myself into retirement clichés that felt like wearing someone else's clothes, I discovered that the most rebellious thing you can do at 70 is stop pretending to want the golden years everyone else is selling and start building something so uniquely yours that nobody else would understand it.
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Four years ago, I sat in my favorite armchair with a retirement planning book on my lap, feeling like I was trying to squeeze into a dress that was two sizes too small.
The book promised "golden years" filled with golf, cruises, and leisurely mornings reading the newspaper. But at 66, freshly retired and still grieving my husband's death, I couldn't even pretend to care about any of it. The truth is, I spent the better part of two years trying to force myself into a version of retirement that felt as foreign to me as speaking Mandarin.
What nobody tells you about retirement is how much energy you can waste trying to live someone else's dream. I'd wake up thinking I should be happier, more relaxed, more grateful for all this "freedom." Instead, I felt untethered, like a boat that had slipped its mooring and was drifting toward open sea.
The retirement brochure versus the messy reality
Have you ever noticed how retirement is sold to us like a vacation that never ends?
The imagery is always the same: silver-haired couples walking on beaches, grandparents pushing laughing children on swings, groups of friends toasting with wine at sunset. After 32 years of teaching high school English, I thought I'd earned my place in those pictures. I really did.
But here's what actually happened. I'd retired at 64 when my knees couldn't handle another day of standing in front of a classroom. The first few months were a blur of grief — not just for my husband who'd passed the year before, but for the teacher I'd been, the routine I'd known, the teenagers who'd kept me sharp and laughing even on the hardest days.
I remember standing in the grocery store on a Wednesday afternoon, watching everyone rush past with purpose, and thinking: what am I even doing here?
For six months, I barely left the house. Not because I was planning some grand retirement adventure, but because I couldn't figure out what came next. The retirement I'd imagined — the one from the brochures — felt like trying to wear someone else's life.
When pretending stops working
Virginia Woolf once wrote, "The eyes of others our prisons; their thoughts our cages." I think about that quote often when I remember how hard I tried to perform retirement correctly. I joined a book club because that's what retired English teachers do, right? I volunteered at the library. I took up watercolor painting, which I was spectacularly bad at and didn't enjoy one bit.
Every activity felt like I was checking boxes on someone else's list. Do you know that feeling? When you're going through the motions so convincingly that even you start to believe you're happy, until one day you're sitting in your car after book club, and you realize you can't remember a single thing anyone said because you spent the whole time wondering why you were there?
The turning point came when a friend watched me struggle through another forced hobby and said, "You know, you don't have to do any of this." Such simple words, but they hit me like a lightning bolt. I'd been so busy trying to retire "correctly" that I'd never asked myself what I actually wanted this time to look like.
Building something nobody else would understand
At 66, I started writing. Not because it was on some retirement activity list, but because the stories inside me were demanding to be told. A friend had suggested I share some of my experiences, and suddenly, words that had been trapped for years came pouring out. I wrote about teaching, about loss, about starting over when you thought you were done starting anything.
I've mentioned Jeanette Brown's new guide on thriving in retirement before, but it keeps proving relevant to what I'm discovering. She talks about how retirement is actually an identity shift, not just a career exit, and that it involves real grief alongside the relief and excitement.
Reading that was like having someone finally name what I'd been feeling. It's free, by the way, and Jeanette has this way of making you feel like it's okay to not have it all figured out. For me, understanding that the confusion and grief were part of the process, not signs I was doing it wrong, changed everything.
Writing became my unexpected anchor. Not travel, not golf, not even the grandchildren I don't have. Just me, a laptop, and the stories that had been waiting decades to be told. Some mornings I write for hours, lost in memories of classroom moments that still make me laugh.
Other days, I wrestle with harder truths about love, loss, and what it means to keep becoming when the world expects you to be done.
The freedom in letting go of the script
What would happen if you stopped trying to retire the way you're supposed to? I'm not suggesting you abandon all structure or purpose — quite the opposite. But what if instead of forcing yourself into predetermined molds, you paid attention to what actually energizes you at this exact moment in your life?
For me, that meant accepting that I'm not a cruise person. I don't want to learn mahjong. I have no interest in moving to Florida.
Instead, I've built a life that would mystify the retirement planning books: I write most mornings, I mentor two young teachers who remind me why I loved education, I've learned to make sourdough bread (badly, but with enthusiasm), and I spend evenings reading books I choose purely for pleasure, not because they're "important."
Last week, I submitted an essay to a literary magazine — something I never would have dared as a teacher, too busy with lesson plans and grading to pursue my own creative work. Whether it gets published doesn't even matter as much as the fact that at 70, I'm still becoming someone I haven't been before.
Final thoughts
The retirement I'm living now looks nothing like what I planned. It's quieter, stranger, more creative, and infinitely more mine than anything I could have imagined at 60. Some days are lonely. Some are profound. Most are ordinary in ways that feel like their own kind of treasure.
If you're struggling with retirement, or approaching it with dread, or living it but feeling like you're wearing an ill-fitting costume, maybe it's time to stop pretending. The permission to build something entirely your own — something that makes sense to nobody but you — might be the most radical gift you can give yourself at this stage of life. After all, if not now, when?
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