What Dolly Parton Can Teach Freelancers
Like many of you, I was deeply saddened by the news of Dolly Parton’s passing. Looking back at the legacy she has left behind, I realized how much we all can learn from the example she set—in life and in her career. I realized that Dolly left us freelancers a surprisingly practical playbook for building careers on our own terms. These eight career tips for freelancers draw on Dolly’s choices and convictions—and invite us to think differently about the careers we’re creating.
1. Do what you love.
One of my favorite Dolly quotes (and there are many) is, “Find out who you are and do it on purpose.” This speaks to the importance of knowing yourself and living with intentionality.
A lot of instructional designers wear multiple hats by necessity. One person might be responsible for everything from learning needs analysis and course design, to graphic design and eLearning development, to facilitation, LMS administration, accessibility testing, and more. It’s a lot to be expected from one person.
But if you are a freelancer, you have the power to choose projects that let you do the type of work that plays to your strengths and interests.
A useful exercise is to list all the things you’re good at. (You can limit this to work activities if you like, but you don’t have to.) Then go back through your list and highlight all the things you love doing—the things that light you up inside. Cross out the things you hate doing. This will help you find focus areas for your work.
Then, in your portfolio, showcase the type of work you want more of. For example, I don’t enjoy creating software training. I’ve done it before, and I’m reasonably good at it, but it’s not the type of project I actively seek. Knowing that, I don’t highlight those projects in my portfolio.
I am most drawn to content that helps make the world a better place—kinder, more inclusive, healthier, safer. So, I lean into projects related to health and wellness, leadership, safety, and self-improvement.
2. Don't be afraid to branch out.
Especially in the early days of Dolly Parton’s career, people liked to try to put her into a box. She was often underestimated because of how she looked and the way she dressed. But Dolly was smarter than a lot of folks gave her credit for, and she was so much more than a country music singer. She was a prolific songwriter, talented actress, generous philanthropist, brilliant businessperson, and—let’s face it—an absolute legend and national treasure.
"I'm not going to limit myself just because people won't accept the fact that I can do something else."
We’re often told we need to find our niche—and if that works well for you, great. (See #1.) But if you’re passionate about multiple types of work, there’s no rule that says you have to stick to only one thing.
This also means that if you have interests and ambitions outside of learning and development, you should give yourself permission to explore those. We are whole human beings, and we don’t have to compress every single ambition into a single identity. For example, I’m currently writing a novel. Spending time outside of work doing something I’m excited about is revitalizing me in a way that’s improving my energy at work too.
3. Recognize your worth.
One of the best examples of Dolly Parton’s business savvy is when she turned down Elvis Presley’s offer to sing “I Will Always Love You.” She was excited about him covering her song and had even told all her family about it. But Elvis’s manager demanded half the publishing rights to the song. Dolly understood that song’s long-term value, and she refused to surrender her rights. The incredible courage of that decision is inspiring to me—and of course, it paid off in a big way when Whitney Houston later covered the song.
As freelancers, it’s important that we recognize the value of our work. Otherwise, it’s easy to find ourselves in a “barely getting’ by, it’s all takin’ and no givin’” situation—especially when clients ask us to lower our rates, absorb scope changes, or blur boundaries around our time.
When we consistently treat our expertise as valuable, our clients and prospective clients will likely do the same.
4. Prioritize people.
One of the biggest reasons I’ve always loved Dolly Parton (and why so many others do too) is her huge heart. She clearly cared deeply about others and was an outspoken advocate for communities that society and politics often marginalize. Her commitment to inclusion was evident at her Dollywood theme park, which has accessibility passes, calming rooms for neurodivergent guests, and other support resources.
That attention to making sure everyone can participate is a trait I hope all of us in learning and development possess. When we develop onboarding and orientation programs, compliance training, and other learning experiences, we are in a unique position to foster a culture of belonging—even from the outside of the organization as freelancers.
From everything I’ve read, Dolly put people above profit and processes. For example, according to several online sources, when Porter Wagoner was having financial difficulties, she purchased the rights to his song catalog. Later, when he asked to buy his songs back, she simply gave them to him free of charge, as a sign of respect for him and their history.
I’m not suggesting freelancers start giving away our services. But we can be generous with our knowledge, gracious when problems arise, and intentional about treating others well. A project may end, but the trust we build can lead to referrals, repeat work, and relationships that last far beyond a single contract.
5. Stick to your values.
One of the reasons Dolly Parton was widely beloved is that she held true to her core values—family, faith, love, and servant leadership. When she became a huge success, she invested in the community she came from, through the jobs and tourism created by her theme park, as well as charitable activities of the Dollywood Foundation. Her Imagination Library put more than 300 million books in the hands of children, and she gave back in countless other ways as well.
"My daddy was the smartest man I have ever known, but I knew his inability to read probably kept him from seeing all of his dreams come true. Inspiring kids to read became my mission."
Now, unless you’re doing freelancing very differently than I am, you probably don’t have millions of dollars for charitable giving. But even if you can’t donate to causes you love, you can live out your values in other ways. For me, it means taking on projects that make the world a better place (and sometimes turning down work for organizations I can’t ethically support). It means treating my clients fairly, following through on commitments, and prioritizing accessibility and inclusion. And it means contributing in ways like blogging, in hopes that my words are helpful to someone.
6. Believe in yourself.
Born into extreme poverty, Dolly Parton could have had every reason to doubt her ability to make it big. But she worked relentlessly and used her challenges as fuel—penning enduring songs like “Coat of Many Colors” that helped solidify her stardom.
Before I started my company, I had all sorts of doubts about whether I could manage a business or get enough work to pay the bills. But a good friend and one of my biggest cheerleaders encouraged me, reminding me of my strengths and past successes. I won’t pretend I haven’t had some hard times, but it’s six years later and I’m still here. And 100% of my current clients are repeat clients—which means I must be doing something right.
What have you been putting off because you’re unsure of yourself? Who can you rely on to remind you what you’re capable of? (If you don’t have anyone, hit me up. I’ll cheer you on.)
Take a moment and jot down some affirmations. Then write down one concrete next step. What can you do today to begin moving in the direction you want to go?
7. Remember your impact.
A quote usually attributed to Dolly is that “if your actions create a legacy that inspires others to dream more, learn more, do more and become more, then you are an excellent leader.”
What I love so much about this quote is that this is exactly what we in learning and development do! We create experiences that expand what learners can imagine, understand, and accomplish.
And if that sense of impact feels distant, consider what kind of role or project might help you reconnect with it. As for me, I began to experience much more fulfillment in my work once I got clear on the type of work I wanted to do (see #1 and #2) and cultivated my business culture around those projects.
8. Turn self-doubt into action.
It’s hard to imagine Dolly Parton struggling with impostor syndrome. But when she was nominated for the Rock & Roll Hall of Fame in 2022, she initially tried to withdraw because she didn’t think she’d earned the honor as a rock artist. After learning that the Hall recognized artists beyond a narrow definition of rock, she said she would accept if elected—and later recorded Rockstar partly in response to her induction. (If you haven’t heard the album, I encourage you to check it out. Her cover of “Purple Rain” gives me goosebumps.)
Freelancers, of course, wrestle with self-doubt all the time: Am I experienced enough to pitch this client? Skilled enough to raise my rates? Established enough to call myself an expert? Dolly’s response offers a useful alternative to either shrinking from an opportunity or pretending we have nothing left to learn. Accept the invitation, then rise to meet it. It’s the “yes, and” approach I learned from the first CEO I worked for in my L&D career. Her answer was usually, “Yes, we can do that.” Then she always figured it out!
To be clear, I’m not advocating you misrepresent your capabilities—or suggesting that my former boss did. The “yes, and” approach gives you room to grow into new capabilities. While you probably shouldn’t take on work you have no idea how to do, accepting opportunities that stretch you is good for your personal and professional growth.
To succeed with those stretch assignments, identify what you need to learn, who can help, and how you’ll deliver responsibly. Let your uncertainty guide you to the skills you want to strengthen—not convince you that you don’t belong in the room.
Takeaways: Build Your Freelance Career on Purpose
These career tips for freelancers ultimately come down to building a career that reflects who you are and the impact you want to make.
Most of us won’t become global icons or open a theme park. But we can choose work that feels meaningful. We can treat people well, keep growing, and leave something useful behind. That feels like a legacy worth carrying forward—on purpose.
If you would like to continue Dolly’s legacy of promoting literacy, consider making a donation to her Imagination Library.
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