What Dolly Taught Us About Leadership, Life and Paving Your Own Road

Yesterday, Dolly Parton passed away at 80 years old.

I wasn’t alive when Elvis died, but as I watched the news spread and saw the reactions pouring in, I found myself wondering if this is what it felt like. One of those moments when someone who has seemingly always been part of our culture is suddenly gone. Someone whose music crossed generations, whose personality was larger than life, and whose influence reached far beyond the thing that originally made her famous.

Dolly was certainly an entertainer. She was an incredible songwriter and performer. But she was also a businesswoman, a philanthropist, an employer, a dreamer and, in so many ways, a leader. She grew up in poverty in the mountains of East Tennessee and went on to build an extraordinary career, an extraordinary business portfolio and an extraordinary legacy. Through her Imagination Library alone, hundreds of millions of books have been given to children around the world.

But I think what made Dolly so special was that she never seemed to apologize for wanting more.

She dreamed big. She worked hard. She became successful. And then she used that success to do good.

There are two Dolly quotes that I have carried with me because they speak to two very different, but equally important, parts of leadership and life.

You Asked for This. Don’t Forget That.

One of my favorite Dolly sentiments has always been about wanting to be famous and rich as a child and deciding that, once she became both, she wasn’t going to complain about it.

I LOVE that.

Not because leadership is about fame or money, but because I think there is an important lesson hiding inside that mindset.

I have always been a natural leader. I have always wanted to lead. I wanted responsibility. I wanted influence. I wanted to build something. I wanted to have a team. I wanted the opportunity to make decisions and create an impact.

And now I do.

That doesn’t mean leadership isn’t hard. It doesn’t mean there aren’t days when the responsibility feels heavy or when the decisions are exhausting. It doesn’t mean we can’t acknowledge that leading people is complicated.

But there are moments when I have to remind myself: Kristie, you asked for this.

How many of us worked incredibly hard to get into the room we are sitting in today, only to spend our time complaining about everything that comes with being in the room?

• We wanted the promotion, but now we complain about the responsibility.
• We wanted a seat at the table, but now we complain about the difficult conversations happening around it.
• We wanted a team, but now we complain about having to lead people.
• We wanted influence, but now we feel frustrated that everyone looks to us for answers.
• We wanted growth, but we don’t always like what growth requires from us.

Dolly’s perspective reminds me that there is a difference between acknowledging that something is hard and resenting the very thing we once prayed, hoped and worked for.

Leadership is a privilege.

There are people trusting us. There are businesses counting on us. There are people whose careers we have an opportunity to influence. There are decisions we get to make today because somewhere along the way we earned the opportunity to make them.

That deserves a little gratitude.

And When the Road Isn’t Right Anymore, Build Another One

Then there is another Dolly quote that has always stopped me:

“If you don’t like the road you’re walking, start paving another one.”

This one isn’t only about leadership. This one is about life.

What I love about it is that Dolly didn’t say find another road.

She said pave one.

There is a big difference.

Sometimes the road we need doesn’t exist yet.

There isn’t always a perfectly paved alternative waiting around the corner with a giant flashing sign that says, “THIS WAY!”

Sometimes we have to create it.

I think women, especially, can spend a lot of time waiting for permission to change roads. We wonder whether we have invested too much time to change direction. We worry about disappointing someone. We convince ourselves that because something once worked for us, it should continue working forever.

We stay in jobs we’ve outgrown. We stay committed to goals that aren’t ours anymore. We keep operating businesses in ways that exhaust us. We remain in roles because we’re good at them, even when they no longer bring us joy. We continue down roads because turning around feels harder than continuing forward.

But what if you don’t have to keep walking simply because you’ve already come this far?

What if you can pave something new?

Dolly’s own life was an example of that. She didn’t stay confined to one definition of what a country singer was supposed to be. She wrote songs. She performed. She acted. She built businesses. She created Dollywood. She invested in her community. She created the Imagination Library. She kept adding roads.

And somehow, every one of them still looked unmistakably like Dolly.

Maybe that’s another lesson worth remembering.

Changing the road doesn’t mean changing who you are.

Sometimes it means becoming even more of who you are.

How to Put These Lessons Into Practice

As we remember Dolly, I think there are two questions worth sitting with.

First, what do you have today that you once asked for?

Maybe it’s your leadership role. Your team. Your company. Your clients. Your influence. Your family. Your home. Your opportunities. Think about the things that occasionally frustrate or overwhelm you and ask yourself whether any of them are connected to something you once desperately wanted.

That doesn’t mean you aren’t allowed to be frustrated. It means remembering to put gratitude next to the frustration.

Then ask yourself a second question: What road are you walking simply because you haven’t given yourself permission to pave another one?

Maybe there is something in your leadership, your business or your life that needs to change. Don’t immediately ask yourself which existing road you should take instead.

Ask a bigger question.

If I could pave the road myself, where would I want it to go?

Then identify one thing you can do to begin paving it.

One conversation. One boundary. One decision. One phone call. One courageous no. One even more courageous yes.

You don’t have to build the entire road today.

You do have to be willing to lay the first piece.

A Legacy Bigger Than Success

There is one more thing I don’t want us to miss when we talk about Dolly Parton’s legacy.

She didn’t only build an extraordinary life for herself.

She used what she built to lift other people.

She created jobs. She invested in the region she came from. She gave children access to books. She supported causes she believed in. She demonstrated that tremendous ambition and tremendous generosity do not have to be opposites.

That may be the leadership lesson I love most.

Build the big thing. Become wildly successful. Take the seat at the table. Make the money. Create the influence. Pave roads nobody has paved before.

And then turn around and use what you built to help somebody else rise.

That feels like a legacy worth aspiring to.

Today, I hope you’ll take a few minutes and answer those two questions for yourself: What do I have today that I once asked for? And what road am I ready to start paving?

Then do something with your answers.

Because if Dolly taught us anything, it’s that you can dream bigger than where you started, build something that looks entirely like you, and leave the world better because you were here.

Rest well, Dolly. Thank you for the music, the laughter, the example and the roads you paved for so many women who came behind you.

We will always love you.

— Kristie Clayton HERverse Founder #HERthoughts