Second Life

When Linda Wells landed her first job as an editorial assistant in the beauty department of Vogue, she didn't have so much as a five-year-plan. She admits she could never have planned how her professional life—beauty editor turned editor in chief of a new magazine (a little publication called Allure) turned chief creative officer of Revlon and creator of the cosmetics line Flesh—would have turned out. On episode 24 of Second Life, Wells dishes about how she leaned into challenges and major changes to build the impressive career she has today.

Former broadcast journalist Whitney Casey and model-turned-actress Brooklyn Decker know something you don't. You spend years of your life—10 to be exact—picking out clothes to wear and to pack for all of life's many occasions. After identifying a massive white space in clothing and tech space, Casey and Decker figured out a way to give that precious time back to people with a seriously smart app called Finery. On episode 23 of Second Life, the two share how they turned one brilliant idea into a thriving company (without any formal business school or training).

People with curly and straight hair alike know the power of a good blowout. It was this simple idea that catapulted Alli Webb from former hairstylist and stay-at-home mom to the haircare maven behind Drybar, the blow-dry bar that specializes in blowouts. Before discovering this untapped market in L.A., Webb honed her craft at beauty school on the East Coast, pivoted to a career in PR, and eventually found her way back to hair, where it all began. "It was just a whim and a hunch," Webb tells Hillary Kerr on episode 22 of Second Life.

Andrea Lieberman knew that she was meant to work in fashion ever since she moved to Manhattan at age 13. "I realized at a very early age that I just found what I was meant to do," she tells Hillary Kerr in episode 21 of Second Life. Lieberman parlayed her passion for the fashion industry, an education from Parson's School of Design, and over 10 years experience as a celebrity stylist to eventually launch her own line A.L.C. 

Not everyone is lucky enough to stumble upon a career they're passionate about early in life. For April Gargiulo, the founder of skincare company Vinter's Daughter, it took three college degrees, stints in the design world, and time spent working for the family wine business for her to truly find her calling, and she's just getting started. Despite her untraditional path, she tells Hillary Kerr on episode 20 of Second Life, "There's nothing I would have done differently."