In Episode 2 of Transitioning to Retirement, Shaun Emerson and Tom Rocco move from the “why” of retirement into the real-world details of preparing for it—and living it.

Tom walks through the practical side of the transition, including how he approached finances without getting overwhelmed. Rather than obsessing over daily market swings, he shares a more grounded strategy: tracking investments quarterly, monitoring expenses monthly, and staying aware without becoming consumed. The conversation also dives into navigating Medicare, emphasizing the importance of doing your homework and talking to real people—not just relying on online tools—before making decisions.

Beyond logistics, the episode explores the emotional and psychological shifts that come with retirement. Tom reflects on how unemployment unexpectedly became a period of self- ...