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.

Bill McInerney built his career the hard way at Cadwalader, Wickersham & Taft, leading by example, earning loyalty, and doing whatever it took to get the deal done. Sometimes that meant sleeping on the office couch. Then, after nearly four decades riding the waves of New York real estate, he walked away at 65 — burned out and thinking he might simply "do nothing." But that's not what happened. In this episode, Bill shares what it really takes to build a practice — and what he discovered when he finally stepped away.

Noah Hanft was attracted to the legal profession because he wanted to help people. His career started at legal aid and after a brief stint in a law firm, he joined a five person legal department at Mastercard. He then spent three decades helping to build Mastercard, and, as General Counsel he led the way through a complex and hugely successful IPO. His secret to success is something many lawyers miss. In this episode, find out what Noah believes worked for him and what lawyers need to remind themselves to practice.

Larry Weinstein says being the best at what he does made it possible to build his law practice, largely through word-of-mouth. His clients trusted him, and they followed Larry from one firm to another. He left his mark on big law including firms like Proskauer Rose and Davis Polk. In 2022, he left Proskauer and started an arbitration business that he was told it would take years to build. But he left the naysayers in the dust when his strong work ethic and client focus helped him grow quickly. Find out how Larry rose to the top and how he pivoted to a new business and entrepreneurship.

Alexander "Sandy" Thomas began his career as a Federal District Court clerk and as an Assistant U.S. Attorney in Virginia. He then entered the private sector and practiced with his father. When his father's firm merged into Reed Smith, Sandy's career took off. He became the Global Managing Partner where he oversaw the growth of the firm to 31 offices across 10 countries. But, Sandy's story isn't just about reaching the top, it's about what comes after.

In this episode, Sandy offers a candid perspective on the difference between leadership and management, knowing when to step aside, and how he followed his next passion.