Second Life

Erin and Sara Foster are nothing if not honest. In the newest episode of Second Life, the sisters get real about feeling in over their heads, pursuing careers that paid the bills but weren't fulfilling, and regretting not going to college. Whether you know the Fosters from their parody-reality show on VH1, Barely Famous, or from their current positions as the heads of creative at Bumble, you'll learn a whole new side to the sisters.

Shiona Turini has the résumé that anyone with a dream of working in fashion envies. In episode 50 of Second Life, she shares what she learned cutting her teeth at the industry's major print magazines before fearlessly moving into freelance styling and finally transitioning into costume design for HBO's acclaimed tv series Insecure.

Everyone has interests outside of work, but not everyone knows how to turn their side hustle into a successful business. But it's safe to say that Sierra Tishgart, co-founder of cookware brand Great Jones, knows a thing or two about the transition. In the newest episode of Second Life, Tishgart tells Hillary Kerr how she went from being a Teen Vogue intern to becoming an entrepreneur in home cookware.

How do you go from being a hat maker to running a billion-dollar jewelry brand? In episode 48 of Second Life, Kendra Scott tells Hillary Kerr about the embarrassment of dropping out of college, learning retail "the hardest way possible," and how she transitioned from running a hat store to creating one of the most successful jewelry brands on the market.

Like many of us, Hannah Bronfman's most valuable college experience came from outside the classroom. Bronfman successfully pivoted from being a sculpture major to becoming fashion's favorite DJ and wellness master. In episode 47 of Second Life, Bronfman tells Hillary Kerr how she's learned to cope with the failure of a business venture, understand her worth, and inspire fans to lead a healthier, happier life.

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.

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.