Oct. 8, 2026

Life at 88 Is Still Worth Writing About

What happens when you combine 88 years of living, a wicked sense of humor, a lifelong love of writing, a healthy dose of satire and absolutely no interest in disappearing quietly into the background?

You get Elaine Soloway.

Elaine is a writer, author, writing coach, tech tutor, former PR and marketing consultant, former Chicago political press aide, former Apple Store specialist, memoirist, novelist, blogger, Substack writer and, as I discovered during our conversation, apparently a character in a hit television show. 😂

Yes. That Transparent.

Elaine's children created the Amazon series, and Judith Light played a character based on Elaine. I had NO idea before we started talking. And naturally, Elaine mentioned it almost as casually as she might mention what she had for breakfast. (You'll want to hear the story.)

But Transparent isn't the only fascinating chapter in Elaine's life.

She has written three memoirs and a novel. She's lived through marriage, motherhood, caregiving, widowhood, moving, reinvention and all the messy bits in between. She has written about those experiences with humor, honesty and a satirist's eye for the absurd.

Today, she writes two Substack posts a week, and they're terrific because Elaine isn't writing from some polished mountaintop about how to “age successfully.” She's writing about life as it actually happens.

At 88.

She's curious about technology and AI. She journals. She reads. She writes. She learns. She lives in an intergenerational building and enjoys her younger neighbors. She got tattoos at 80. She learned to swim at 80. She's working on Spanish and playing Rodgers and Hart on the piano. She gets up ridiculously early because she likes the quiet for writing.

And she has a dog named Doris who has a very important role in the household.

Our conversation wandered through money, aging, family, creativity, curiosity, technology, caregiving, loss, writing, reinvention and what it means to keep participating in your own life rather than quietly stepping aside from it.

Elaine also has a terrific answer for anyone who thinks they're “too old” to try something new: imagine how empty life would be if you stopped being curious, stopped being friendly and stopped being active.

Exactly.

And there's one more thing I love about Elaine: she doesn't seem particularly interested in becoming an inspiration.

She's interested in being Elaine.

Writing. Observing. Laughing. Learning. Creating. Telling the truth about what she sees.

Which brings me back to that wonderfully improbable number: 88.

Eight looks like infinity when you turn it sideways. So perhaps 88 is a little bit of double infinity.

And maybe that's a pretty good way to think about a life that is still unfolding.

Because at 88, Elaine Soloway isn't finished.

She's still writing about what happens next.

If you found inspiration from this conversation, please rate, review and share this episode.

I’d love to hear your thoughts, so be sure to hop on over to Don’t Be Caged By Your Age on LinkedIn or Instagram. Or leave a message on the website here.

Looking for a few simple ways to age well? Here are two products I use and genuinely recommend:

🚶‍♀️ Favorite Walking Pad – I use it almost every day while watching my favorite shows. It's quiet, easy to store, and makes getting more steps simple and enjoyable.

🥤 Favorite Protein Powder – Getting enough protein becomes even more important as we age. This is my go-to because it's easy to digest, delivers 25g of protein per serving, and supports healthy muscles and bones.

Waving from Boston – cheers!

Ande ♥

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