Amy LaBelle was assistant general counsel at Fidelity in Boston when a hand-painted sign on a Nova Scotia roadside changed everything. Following it to a "teeny-tiny winery" sparked an epiphany; 4,083 days later, she opened her first winery.

The transition from attorney to entrepreneur was a marathon of balancing a full-time legal career, motherhood, and family life—all while fermenting her first batches in a fourth-floor walk-up. In this episode, LaBelle shares her journey of leaving a secure legal career to forge a unique path toward her dream.

David Miraldi followed in his father's footsteps and joined the family law practice. They specialized in personal injury litigation, initially from the insurance side, and then representing plaintiffs. But at 59, Miraldi had a life event that made him reevaluate what he wanted to do with his future. Without much hesitation, he left the law for a dusty basement full of police files on the hunt for an old case of his father's. He wrote a book about it and won an international book-of-the-year award, and three books later, he sat down to share his story with us. In this episode find out how Miraldi made an easy transition from the law and what he says are important things to consider before other lawyers do the same.

Mark Shaiken wanted to be a writer or a sports photographer when he grew up. When he was in college, he told his father, and the response was less than promising. Not knowing how he would make a living over the long term, Shaiken took jobs as a highway line painter, a septic tank fixer, and a fork lift driver. He also took the law school entrance exam, and through a series of fortunate events, he became a corporate bankruptcy attorney. For decades he grew a successful practice, but he wasn't ready to give up his other career dreams. Eventually deciding "it was now or never", Shaiken took the plunge and left the law for writing. In this episode, Shaiken talks candidly about how he approached his career through the "back end", and how he left a structured, traditional office, and no longer tethered, created a new life as an award-winning writer.