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Can Your Side Gig Become Your Dream Job?

Deborah Lippmann wanted to be a singer, but was uncommonly talented as a manicurist. Here’s how she succeeded at both careers.

Right after New York Fashion Week, Deborah Lippmann was finally able to catch a breath. As one of America’s best known celebrity manicurists, her week involved scurrying between shows–from Badgley Mischka to Narciso Rodriguez to Donna Karan–where she led teams of manicurists who prepared models’ nails. She’s also been carefully eying the runways to find inspiration for her own luxury nail polish brand. To any beauty entrepreneur, Lippmann is living the dream, so it might come as a surprise that this glamorous life began as a side gig–one that Lippmann wasn’t particularly proud of at first.

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Deborah Lippmann

In the ’70s, Lippmann moved to New York with ambitions of becoming a Broadway and jazz singer, but like so many aspiring artists, she struggled to make ends meet. After some terrible experiences in the food-service industry (“I was the most untalented waiter of all time,” she says), she picked a different side gig: cosmetology. “I was performing at these clubs where I practically had to pay them to let me sing,” she recalls. “I chose the nail track at beauty school because I didn’t want to stand to cut people’s hair after long nights of singing in high heels.”

She found herself doing manicures at a Frederic Fekkai salon between auditions. Then, suddenly, something bizarre happened: Lippmann discovered she was uncommonly talented at doing nails. Allure magazine listed her in their manicure directory and celebrities’ assistants started calling her in droves to schedule appointments. Timothy Priano, an agent who represents makeup artists, wanted to work with her. She started rubbing shoulders with beauty brand founders like Laura Mercier and Bobbi Brown. Vogue tapped her for commentary about upcoming nail trends. “It was a huge moment in my life, but I was a so conflicted,” she says. “They called me a nail expert, but I wanted to be a singer. It was really a mental struggle for me when I saw my star rising as a manicurist.”

Lippmann eventually came to the conclusion that she did not have to pick one career or one identity. “Part of my story needs to be about encouraging others to think outside the box, to keep your blinders open and to tell yourself that you don’t have to be defined by just one of your passions,” she says. “Everyone is able to do more than one thing.” At parties, she describes herself as a singer or a beauty maven depending on the context and her mood. She says she constantly runs into others who have followed similarly bifurcated paths: One of her close friends is a fashion journalist who started her career as a ballerina for the American Ballet Company and continues to dance when she can.

Over the years, Lippmann has actively pursued both singing and beauty, finding unique ways to bring the two together. Fifteen years ago, with the encouragement of magazine editors and celebrity clients, she started her own nail polish brand, but to stay connected to music, she decided to name each color after a song she loves. This makes her very happy, but it has also been a smart marketing move. “I wanted to give the colors names that evoke a feeling,” she tells me. “These names have resonated in a way that is quite extraordinary: They are fun, kitschy, and if the song has a place in your life, it fosters an emotional connection.”

As a bonus, when she does a personal appearance at a store, customers often ask her to perform a song, and she’s always more than happy to fulfill their requests. In a collaboration with Bath and Body Works, Lippmann recorded an album of songs connected to the nail polish colors she created. “Nail polish was my ticket to singing,” she says. “It allows me to still have my dream.”

Lippmann says that part of the reason her beauty career took off is that she felt like she had no choice but to make it work in order to support her singing. “I couldn’t make the living I wanted to make singing the kind of music I wanted to sing,” she says. “It was hard for me to say no to a manicuring job. I did not have family to fall back on and I had to make my dream happen on my own.”

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But also she thinks she has thrived as a beauty entrepreneur because she did not overthink the process. “Being really naive gave me the courage to enter this incredibly competitive field,” she says. “If I knew then what I know now about the business, I would have talked myself out of it.” Lippmann took the plunge, handling each marketing or product challenge as it came along. For instance, when she was trying to design her nail polish bottles, she didn’t hire a design company. Instead, she invited Cher, a celebrity client and friend, to help her inspect a range of generic bottles on the market. The two ultimately picked a design they thought was pretty, and this has turned out to be one of the brand’s defining characteristics.

For 15th anniversary of her brand, Lippmann has developed a special collection of colors with names that include “I Will Survive,” “A Hard Day’s Night,” and “Daydream Believer.” As she performs these songs at a celebration later this year, audience members might wonder whether the lyrics refer to her music career or her business endeavors. She’ll tell you that the two are inseparable. “I used to wonder whether other people would get how I’ve brought these two worlds together,” she says. “It turns out, they don’t need to get it in the way that I get it. It has worked out extraordinarily well, regardless of what they think.”

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About the author

Elizabeth Segran, Ph.D., is a staff writer at Fast Company. She lives in Cambridge, Massachusetts

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