Welcome to Second Life, a podcast spotlighting successful people who’ve made major career changes—and fearlessly mastered the pivot. Hosted by Hillary Kerr, co-founder and chief content officer at Who What Wear, each episode gives you a direct line to people who are game changers in their fields. Subscribe to Second Life on Apple Podcasts, Spotify, or anywhere you get your podcasts to stay tuned.

There’s nothing quite like a good pair of loafers, and right now, there is one woman completely dominating the loafer game: Jamie Haller with her namesake brand. Specifically, the Jamie Haller penny loafer (which we recently styled for the ultimate holiday look). These shoes are sleek, slightly oversize, and rendered in buttery leather or unexpected suede. They’ve become the “if you know, you know” shoes among editors, stylists, and creators. Yet Haller’s path to becoming a minimalist footwear—and now apparel—darling was anything but linear.