Should You Retire at Age 59.5?

Should You Retire at Age 59.5?

September 5, 2025 · 29 min · Episode 85

About this episode

The episode discusses the evolving stages of retirement and financial strategies to navigate them.

Retirement isn’t a date on a calendar; it’s a series of evolving stages. Robert Gilliland & Karen Heider walk through the three phases of retirement (Freedom, Stability, and Legacy) and the financial strategies that keep you confident at every step. They share ways to: Maximize your Freedom Years (late 50s to early 60s) with smart withdrawal strategies, Roth conversions, and healthcare planning before Medicare kicks inNavigate the Stability Stage (mid-60s to mid-70s) by optimizing Social ...

People in this episode

Host: Robert Gilliland

Guest: Karen Heider

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