Why Retire?

Don and Tom tackle the idea that retirement isn’t what it used to be—and maybe shouldn’t be at all. From historical retirement ages (when most people never made it) to today’s longer, healthier lives, they explore why many people aren’t eager to stop working. The conversation shifts to purpose, identity, and the growing trend of “phased retirement,” where people scale back instead of quitting outright. They also answer listener questions on using the TSP’s G Fund as a stable anchor in a portfolio and the smartest way to time withdrawals from 529 plans for future medical school costs. Along the way, there’s the usual banter, skepticism of industry nonsense, and a firm reminder: retirement is no longer a finish line—it’s a design problem.0:05 Don’s “retirement strategy”: Don’t1:13 Should anyone actually retire anymore?2:06 Financial vs. psychological reasons people keep working3:15 History of retirement ages and why they were set4:39 Longevity trends and aging populations5:04 Why modern retirees want purpose and engagement6:14 Companies encouraging phased retirement (Microsoft example)7:48 Planning the “what will I do?” side of retirement8:28 Why experience makes you better (especially in media)10:12 Retirement identity and self-awareness11:01 Real-world example: professionals scaling back instead of quitting12:34 Don’s evolving “never retire” plan14:55 The importance of knowing yourself before retiring16:22 Retirement today vs. historical necessity17:14 Rethinking retirement as continued contribution17:58 Listener question: Using TSP G Fund in retirement allocation20:19 Risks and logistics of split-account rebalancing21:26 Listener question: When to use 529 funds for med school23:17 Why delaying 529 withdrawals maximizes tax advantages24:52 How to submit listener questions26:19 Free advisor meetings and fiduciary pitch (without the noogie)Questions? Comments? Click!