In this episode of Bare With Us, we explore a side of retirement planning that rarely gets the attention it deserves—everything beyond the financial projections. Today’s retirees are navigating a new reality, often spending 10 to 30 years in retirement, and many are discovering that it’s not the money that’s the hardest part…it’s finding purpose.

Drawing from their firsthand experience helping dozens of clients transition into retirement, Scott and Mike share what they’ve observed over the years—where retirees tend to thrive, where they struggle, and the patterns that consistently show up among those who enjoy the most successful retirements. Along with Finn McKay, they discuss the hidden losses people face when they leave the workforce, including the loss of structure, community, identity, and daily purpose.

We also explore how physical and mental health play a crucial role in keeping your financial plan meaningful—and how maintaining well-being can help ensure the retirement you planned for is one you can actually enjoy.
This thoughtful conversation goes far beyond spreadsheets and savings projections. It’s about designing a retirement that’s rich in purpose, connection, and quality of life.