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caption: Celeste Headlee talks about how freelancing has given her control over her schedule, insight into her own work habits, and the freedom to take risks.
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Celeste Headlee talks about how freelancing has given her control over her schedule, insight into her own work habits, and the freedom to take risks.
Credit: Courtesy of Tamzin B. Smith Photography

'I'm the best boss I've ever had.' Lessons from Celeste Headlee on freelancing

This week, public radio legend Celeste Headlee tells us how freelancing has allowed her to do deeper, more intentional work and to have control over her schedule and the profits of her labor.

Whether you’re a freelancer (Eula), live with a freelancer (Jeannie), or are freelance-curious, this episode is a must-listen. (And, honestly, since Headlee has so many valuable insights into how humans work best, this episode will resonate with everyone.)

Headlee, who is also the author of "We Need to Talk: How to Have Conversations That Matter" and a popular TED talk on the same subject, told us that freelancing has inspired her to take positive creative risks.

“I’m the best boss I’ve ever had,” Headlee told us. “My boss trusts me implicitly and lets me fail over and over without giving me a bad performance review. Allowing you to fail is what empowers you. I need to know I can try stuff out.”

But Headlee didn’t always have this freedom. And one of her worst workplace experiences was very public.

From 2009-2012, Headlee co-hosted The Takeaway with John Hockenberry. She says he bullied and undermined her. (New York Magazine reported on these allegations in December 2017, Hockenberry wrote a response to the allegations in an essay in Harper's Magazine in October 2018).

“That was three years of my life that was pure hell,” she said. “I was co-hosting with John Hockenberry. He’s a veteran in the business, he’s someone that I had respected and looked up to until I worked with him. And he’s just abusive.

“I was bullied and harassed on a daily basis, and ended up losing my job to John. And both of my friends and very esteemed colleagues Farai Chideya and Adaora Udoji had experienced the same thing.”

“After I left The Takeaway,” she said, “I basically became a freelancer.”

Even now, as her own boss, Headlee still has to deal with sexism and racism. She's on social media, after all, and continues to live in the world. But now she can choose to turn down clients, and she is transparent about her boundaries and what she expects to be paid. And she refuses to be paid less than an equally qualified man in her field.

Headlee told us that freelancing has taught her how to structure her work more effectively, set limits, and ask for help.

Here are a few things that we learned.

Know your strengths

Headlee said that being your own boss requires an intimate knowledge of where you excel — and when to ask for help. As a freelancer, you're responsible for every part of the business, from administrative work to self-promotion to managing your projects.

Headlee told us that one of the most valuable things she learned was how to outsource some of that work so that she could focus on her strengths.

Now, she said, “I have a manager, I have an executive assistant, and I hire a PR firm and a book agent as well. And so I get to actually bring in income that pays other people. They’re all brilliant and talented and fantastic women. And I get to be a part of that engine.”

Find your own definition of success

One of the things we keep talking about this season is how, instead of just “leaning in” to traditional ideas of success, we need to redefine success for ourselves.

So we asked Headlee, how do you know if freelancing is working for you? How can you tell if you’re successful?

She said that first you need to ask if you’re making enough money to cover your expenses and to pay yourself a fair salary.

But one of the most important questions she had to ask herself is, “‘Am I healthy?’ And up until this year,” she said, “the answer was no.”

Headlee noted that figuring out the answer to both of these questions takes time. Just as you have to carefully track your income and expenses over a year or two to see if your business is sustainable, you need to keep checking in with yourself to make sure that you're taking care of your physical and mental health.

It's important to be mindful of your own limits, she said, but at the beginning, “you don’t even know what those limits are yet. It takes a little while to know. I literally had to figure out, ‘How much sleep do I actually need?’”

Find time to sit with others — and yourself

When you’re your own boss, Headlee said, “you have to practice some kind of self care.”

As a practicing Buddhist, Headlee schedules time for meditation. But she also schedules meaningful social time with other people. One of the pitfalls of freelancing, she said, is that you might miss out on the everyday interactions that are such an essential part of being human.

Freelancing can provide a respite from some of the stresses of the traditional workplace, but it shouldn’t drive us away from making meaningful connections.

“I don’t mean social time on your tablet or phone. I mean actual human interaction. Because that heals," she said. “Loneliness degrades your internal organs. It shortens your life.”

Sometimes, it’s important to stay and fight

Despite the success and freedom she has found in freelancing, Headlee still believes that it’s important for people to fight for change within their workplaces.

She noted that, in the situation with Hockenberry, she made the decision to come forward in the hope that it would help others.

"It didn’t benefit me to do that," she said, "but my thought process was, ‘I wish that someone had done that for me. I’m going to do for another generation what I needed from someone then.'"

“If we opt out, there’s no one doing that. There’s nobody protecting the next generation, there’s nobody making those workplaces a better place and forcing them to change. Because they won’t change on their own," Headlee said. “There has to be somebody advocating and fighting and battling, or we will see no change."

Headlee said that she can see herself re-entering the traditional workforce if very specific conditions are met.

"But I don't think that I would come back disempowered," she said. "I would be very careful about where I was in the organizational chart and who I was reporting to and what my measureables were."

"And I will tell you right now that I am not taking a salary that is less than men in my field again," Headlee said. "For the rest of my life."

Produced for the web by Christy Scheuer.