"This is my son Steven. He's going to be a lawyer someday," was the introduction Steve Harper grew accustomed to whenever his Dad met someone new. Although his father wasn't a lawyer, Harper took his encouragement to heart, built a substantial practice, and became a leading litigator. Early on, however, one of his mentors gave him the chance to enter a courtroom just eighteen months into his first job. That experience taught Harper that a secret to success is delegating to capable younger lawyers, trusting them, and refusing to let the practice of law consume his life. The rest is history.

In this episode, hear how Harper balanced red-eye flights with coaching 25 kids' sports teams, building a thriving practice, and eventually navigating a smooth transition out of the firm and into pursuing new interests.

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.