Dolly Parton and the Art of Ageing Playfully: 7 Lessons To Remember

1. Never Stop Reinventing Yourself

As Sarah Smarsh writes in her book, She Come by It Natural: Dolly Parton and the Women Who Lived Her Songs, the singer is a “universally beloved icon” recognised as a creative genius with a “goddess-sized heart”.

Smarsh highlights how Parton’s songs have, for decades, validated women who go unheard – the poor woman, the pregnant teenager, the struggling mother disparaged as trailer trash.

Parton’s broader career, from singing on the front porch of her family’s cabin in the Great Smoky Mountains to achieving stardom in Nashville and Hollywood, from “girl singer” managed by powerful men to the leader of a self-made business and philanthropy empire, offers a fascinating story of gender, class, culture and reinvention.

And perhaps that’s one of the things Dolly can teach us about getting older: we don’t have to settle into one version of ourselves. We can keep changing, trying things, getting things wrong and surprising ourselves.

Born the fourth of 12 children and raised in Tennessee, Parton grew up in poverty. Yet she went on to sell more than 100 million albums and write an incredible catalogue of songs, including Coat of Many Colors, Jolene and I Will Always Love You.

She didn’t simply have one career, she kept adding new chapters. Dolly never seemed to believe that reinvention came with an age limit. Why should we?

2. Find Out Who You Are—and Do It on Purpose

Dolly was an early master of the soundbite, long before social media made everyone an amateur philosopher. Her many aphorisms and sassy life mottos have spawned their own unofficial language: #Dollyisms.

One of the best?

Find out who you are and do it on purpose

Honestly, what better advice could there be for midlife? After years of being someone’s daughter, wife, mother, boss, employee or carer, perhaps one of the gifts of getting older is finally having the space to ask: Who am I now?

Dolly never seemed afraid of the answer.

Another favourite quote perfectly captures the contradiction that makes her so fascinating:

I think there is a little magic in the fact that I’m so totally real but look so artificial at the same time

And then there’s Dolly’s particular brand of authenticity. It didn’t look like anyone else’s and that was rather the point. The enormous hair, the rhinestones, the eyelashes, the high heels. She enjoyed it all.

Yes, you can be glamorous and genuine. You can have big hair and big dreams. You can wear sequins at 80 if you damn well feel like it.

3. Ageing Doesn’t Mean Becoming Invisible

We midlifers have many reasons for loving Dolly. First of all, she embodied what CrunchyTales means by ageing playfully. Witty, glamorous, honest and confident. Dolly understood that getting older doesn’t mean becoming less curious, less visible or less ambitious. She continued to create and dream well into her later years. Just days before her death, she was still expressing her desire to achieve more.

Getting older, Dolly seemed to say, is not the same thing as being finished. Far from it.

When asked about ageing, Dolly famously said:

I don’t think about my life in terms of numbers

She also said she wanted to “be the best I can be at whatever age.” I rather like that. What about simply being the best 50-, 60-, 70- or 80-year-old we can be?

4. Keep Your Sense of Humour

Dolly’s life was not all lollipops and unicorns. She experienced difficult periods and spoke openly about depression and other struggles. But she also understood the importance of humour.

In her autobiography, Dolly: My Life and Other Unfinished Business, she wrote:

I tried every diet in the book. I tried some that weren’t in the book. I tried eating the book

This is one of the reasons I love her: ageing can sometimes feel like one enormous list of things we’re supposed to fix:. Our skin, our weight, our hair, our bodies, our careers, our wardrobes. Dolly’s approach was rather different: have a laugh and perhaps eat the book.

5. Stop Worrying About Being “Too Much”

Dolly was also remarkably accepting of people who didn’t fit neatly into conventional boxes.

“I love everybody, and I go right through the bullshit to the core of every person because we are all one,” she once told Andy Warhol. “The biggest freaks in the world are my favourite people, like you, like me.”

I love this quote because by midlife, many of us have finally had enough of trying to fit in. Maybe one of the perks of getting older is caring a little less about being “too much”.

Too loud? Too colourful? Too ambitious? Just irrestibly quirky?

Dolly would probably say: so what? For women over 50, that can be a surprisingly liberating way to think about ageing.

6. Leave Something Behind

Dolly’s generosity was never simply an accessory to her fame.

Her Imagination Library was inspired by her father, who was unable to read and write. She launched the programme in 1995 to provide books to children in her home county, and it has since grown into an international literacy programme. In 2025, the programme celebrated gifting more than 300 million books.

She also supported hospitals, disaster relief, medical research and many other causes. Her $1 million donation to Vanderbilt University Medical Center helped support COVID-19 research connected with vaccine development.

And there’s something else in Dolly’s story that feels worth remembering as we get older. What are we going to leave behind? You don’t have to be Dolly Parton to leave something behind. Sometimes it’s a book, a business, a kindness—or simply something you’ve done that makes another person’s life a little better.

7. Keep Dreaming

Perhaps the most beautiful thing about Dolly Parton’s life is that she never stopped imagining what could come next.

She grew up in a tiny cabin in Tennessee and dreamed of becoming a performer. She achieved that dream and then continued dreaming bigger. And even at 80, retirement wasn’t on her horizon. She was still creating, dreaming up new projects—and, true to form, even joking about making a return to the cover of Playboy (well, why not?).

Her Broadway musical, Dolly: A True Original Musical, is scheduled to open in New York in January 2027, in line with plans made before her death.

Maybe that’s what ageing playfully really means: not pretending we’re still 25. Just refusing to believe that all the fun, ideas and adventures belong to the first half of our lives.

Growing Older the Dolly Parton Way

There was so much more to the star beyond her giant sales figures and outsized persona.

There was her humour, her generosity, her determination, her business brain, her ability to reinvent herself, and her refusal to disappear. And perhaps most importantly, her ability to remain unmistakably Dolly. From the girl who grew up in rural Tennessee to the global icon who built an empire, she never stopped carrying her roots with her as she evolved.

She kept dreaming, working, laughing and, thankfully, wearing the glitter. She may be gone, but the permission she gave us to grow older without growing smaller remains.

Thank you, Dolly. We’ll always love you.