Tom Rocco

Transitioning to Retirement

Education EN ↓ 5 episodes

Transitioning to Retirement is a thoughtful, real-world conversation about what happens after the career ends—and the next chapter begins. Hosted by Shaun Emerson, the series follows the retirement journey of Tom Rocco, a former marketing executive navigating life two and a half years beyond full-time work. Through candid discussions, the two explore the practical, emotional, and often unexpected realities of retirement. From managing finances and Medicare to redefining purpose and identity, each episode tackles a different aspect of the transition. Along the way, Tom shares how he structures...

Author

Tom Rocco

Episodes

Finding Your Rhythm in Retirement 26.06.2026 23:51

In the final episode of Transitioning to Retirement , Shaun Emerson and Tom Rocco step back and reflect on what it really means to build a fulfilling life after work—two and a half years into Tom’s retirement journey. The conversation centers on how to balance short-term and long-term goals, and why trying to do everything at once often leads to frustration. Tom shares how he learned to pace himse...

Life Stuff: The Hidden Reality of Retirement 12.06.2026 27:15

In Episode 4 of Transitioning to Retirement, Shaun Emerson and Tom Rocco explore a part of retirement that often gets overlooked: the everyday realities of managing your time—and why having “more time” doesn’t always mean getting more done. Building on earlier discussions of internal and external projects, Tom introduces a third category: “life stuff.” These are the essential, recurring activities...

Finding Balance in Retirement: Projects, Purpose, and Time 29.05.2026 23:35

In Episode 3 of Transitioning to Retirement, Shaun Emerson and Tom Rocco take a deeper dive into how to actually structure your time in retirement—and why thinking in terms of “projects” can make all the difference. Tom introduces a simple but powerful framework: dividing retirement activities into internal and external projects. Internal projects are the ones you control—organizing your space, pu...

The Reality of Retirement: Money, Mindset, and Meaning 19.05.2026 27:01

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 qua...

“So… Now What? Starting the Retirement Journey” 11.05.2026 18:20

In this debut episode of Transitioning to Retirement, host Shaun Emerson sits down with Tom Rocco to kick off a thoughtful and practical conversation about what it really means to move from a full working life into retirement. Tom shares his personal story—retiring after a long career as a marketing executive, navigating life two years into retirement, and building a new rhythm that includes famil...