Second Life

Kerry O'Brien never could have anticipated that her career in public relations would lead her to become an underwear designer, but that's exactly what happened. The entrepreneur started out in corporate PR, quickly making her way up the ranks (she was a vice president at just 25 years old). However, when September 11 happened, she felt like she needed a change. She quit her job without a plan, but it wasn't long before she found her next passion: women's underwear.See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

Carla Hall was always a creative, but before competing on Top Chef, authoring cookbooks, and starring on The Chew, she was auditing at a big accounting firm and pursuing modeling in Europe. When she returned home from Europe—where she'd also taken up cooking—she stumbled into her own lunch delivery service that parlayed itself into catering, culinary school, and her rise to foodie fame. "It was really an adventure," she tells Hillary Kerr on episode 42 of Second Life. See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

Meredith Melling is proof that landing your dream job isn't the end of your career path. In fact, it might even just be the beginning. Melling always wanted to work in fashion, and with a bit of luck, good timing, and the smart decision to dress for the job she wanted, not the job she had, she landed the coveted title of a fashion assistant at Vogue early in her career. But that was only the start of her journey toward creating her own consulting business and co-founding fashion brand La Ligne.See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

Tyler Haney knows activewear. She was raised in Boulder, Colorado—a town known for its outdoor activities—and grew up running track and field. With a few courses in business and design under her belt paired with the desire to create a sporty uniform for recreational activity, Haney eventually became the CEO and founder of her own brand, Outdoor Voices. However, her journey was filled with challenges and missteps that she looks back on as lessons learned.See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

Before Christina Tosi started Milk Bar—the trendy bakery known for its covetable, playful desserts—she was studying math and Italian in college with dreams of becoming a mathematician, a UN translator, or a perhaps a truck driver (yes, really). "I like to be uncomfortable," the entrepreneur tells Hillary Kerr on episode 39 of Second Life. Drawn to restaurant life with a passion for baking, Tosi moved on from her mathematical endeavors to pursue cooking at culinary school and (with a lot of hard work) went on to found her very own wildly successful bakery. Here's how she made it happen.Sign up for Christina Tosi's new Beyond Baking mailer at christinatosi.com.See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

If you've ever visited NYC's trendy new spa-salon-café hybrid, Chillhouse, you can already appreciate the way Cyndi Ramirez-Fulton is cashing in on the wellness industry one adaptogen latte and hangover-curing massage at a time. The "destination for modern self-care," as she describes it, is stylish, relaxing, and affordable—not to mention incredibly Instagram-friendly. But Fulton wasn't always involved in the wellness world, though. In fact, she dropped out of college to work in the nightlife world promoting clubs before ever landing her first desk job.See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

Eva Chen's résumé reads like the front row of a well-stocked magazine stand. She's held jobs at publications like Harper's Bazaar, Elle, Teen Vogue, and Lucky (where she was editor in chief, no less). Although landing a job as editor in chief of a major publication sounds like the peak of one's career, Chen was just getting started. Now, she's catapulted to director of fashion partnerships for Instagram, has written her first book (a children's story called Juno Valentine and the Magical Shoes), and is trying her hand at design with the launch of a capsule collection with Janie and Jack in conjunction with her book.See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

Kerry Diamond, co-founder of Cherry Bombe and owner of Smith Canteen, discusses her journey from the beauty industry to founding a magazine celebrating women in food. She also talks about her experiences in journalism, ghostwriting, and owning a restaurant, and shares insights on building a community in the food industry.

Busy Philipps always knew she would be an actress. In fact, she was studying theater in college when she landed her first major role as Kim Kelly on the coming-of-age hit Freaks and Geeks. While she found success early on at the age of 19, her career hasn't been without setbacks, rejection, and grit. "I never have really fit into a lot of people's molds," she tells Hillary Kerr on episode 35 of Second Life. But Philipps persevered in a male-dominated industry fraught with unrealistic expectations to come out the other side more sure of herself than ever.See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

Interior designer Amber Lewis, the force behind Amber Interiors, is proof that you don't necessarily need a college degree or a straightforward career path to find success. With just a few semesters in an interior design program at UCLA, Lewis found work as an assistant at an interior design firm, and eventually branched out on her own. At the same time, the creative was getting married to a musician, having her first child, and taking every opportunity that came her way. "I was a perfect storm of...luck, talent, and timing," she tells Hillary Kerr on episode 34 of Second Life.See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.