Jamie Kantrowitz co-founded Countertop with Nicole Rice based on the goal of helping people focus on wellness through simple and delicious home cooking. Today, the duo sells a variety of products from seasonings to honey, all meant to enhance both the flavor and nutritiousness of your food. But before all this, Kantrowitz was following a very different career path. She spent her twenties working in politics and digital media at companies like Rock the Vote and Myspace. "Even though I've jumped industries, there are common threads that go through it," the entrepreneur tells Hillary Kerr on episode 45 of Second Life.

Everybody knows that before Jennifer Lopez was the multihyphenate superstar she is today, she was Jenny from the block. But most people don’t know how she made the leap from a dancer to an actor to a singer to an icon. “I always knew from a very young age that I loved performing,” Lopez tells Hillary Kerr on episode 44 of Second Life. With the help of Elaine Goldsmith-Thomas (then her agent, now a producer), who’s had a few career swaps of her own, J.Lo catapulted herself to international success. Lopez’s philosophy for mastering the pivot? “If you feel like you need to move, move.” Find out how both women paved their own paths.

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.

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. 

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.

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.

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.

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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.

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.