
When I read Dolly Parton’s obituary in the New York Times, I found myself thinking about the final step in my 20 Steps of a Grand Plan: the importance of living with a focus on your legacy.
We tend to think of legacy as something we leave behind, something people get only after we’re dead and gone and flying around free as a bird with the angels. But Dolly’s life offers a much more useful way to think about it. Flying around with the angels sounds nice and all, but legacy is actually something we practice while we’re here flittering around on this earth..
Maybe we need one of those rubber bracelets that says WWDD, what would Dolly do? Maybe that would help us consider ways we can make an impact on others, love big and give authentically in the here and now, to ensure our legacies sparkle.
Dolly was such a beautiful example of this kind of living and legacy-building. Her obituary naturally celebrates the enormous career: the songs, movies, businesses, awards and unmistakable place she carved out in American culture. But threaded through all those accomplishments is something more interesting. You can see the values she practiced again and again: generosity, optimism, humor, creativity, faith, connection to her roots and a desire to make life better for other people.
Perhaps the clearest example is her commitment to organic, authentic philanthropy, particularly toward childhood literacy efforts. Dolly created the Imagination Library in honor of her father, who could not read or write. What began as a program for children in her home county in Tennessee grew into an extraordinary international effort providing free books to children. That choice tells us something about what mattered to her.
And that’s where Dolly’s story connects so beautifully with the idea of having a Grand Plan.
A Grand Plan includes the practical work of preparing for older age: organizing legal documents, understanding finances, thinking about housing and care, communicating wishes, considering who might help us and making decisions before a crisis forces them.
But planning for aging should also ask a bigger question: What do I want my life to have meant?
That question belongs in the planning process because legacy isn’t simply about estates, inheritances, buildings with our names on them or what gets written in an obituary. It’s the accumulation of choices we make over decades.
If you hope people will remember you as generous, well you sure as heck better make generosity a priority in your life today.
If you hope they’ll say you cared deeply about your community, guess what — you need to start participating in your community.
If you want your grandchildren to remember you as curious and interested in their lives, ask the questions now while they know you.
If you hope to be remembered for mentoring others, sharing wisdom, supporting a cause, creating something beautiful or making people laugh, there is seriously no reason to wait.
This is why legacy is the final step of a Grand Plan. After we’ve done all the organizing, planning and preparing, we still have a life to live. And hopefully, quite a lot of it. Dolly Parton’s obituary is powerful because the qualities being celebrated were visible long before anyone sat down to write about them. She had been demonstrating them for decades.
Maybe that gives the rest of us a worthwhile exercise. Imagine someone writing your obituary many years from now. What five words would you hope they use to describe you? What stories would you hope they tell? What would you want people to say mattered most to you? Write those answers down.
Then look at your calendar, your relationships, your priorities and how you spend your time. It’s a very telling exercise, maybe too telling! But I promise it’s also the best gift you can give yourself and the people you love. Hands down one of the most meaningful parts of planning for aging is the simplest: Live today what you want your obituary to preach later.
What would Dolly do? Write a chart-busting song or 100 about it, ones based on her own experiences, and become a model of generosity, kindness, beauty and grit for generations of people to move forward in their own way. I think that’s the exciting part — living with a focus on your legacy helps pay all the good stuff forward and advance your best qualities far into the future, making the world a better place than you found it. Thank you for your example, Dolly!

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