Dianna Cohen: Crown Affair Founder and CEO

Aimee Song's rise to fashion blogger stardom is a lesson in what you can accomplish by following your passions. The fashion guru behind Song of Style got her start working as a receptionist at a construction company right out of high school while saving up money to pay her own college tuition. It was there that she got her first taste for architecture and design and decided to go to school at the Academy of Art in San Francisco. However, one job interview changed everything. "I got the job because of my outfit," she tells Hillary Kerr on episode 46 of Second Life.

7 Tammi 201938min

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.

31 Joulu 201835min

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.

24 Joulu 201832min

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.

17 Joulu 201838min

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.

10 Joulu 201849min

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.

3 Joulu 201845min

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.

26 Marras 201842min

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.

19 Marras 201851min