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’t
1:13 Should anyone actually retire anymore?
2:06 Financial vs. psychological reasons people keep working
3:15 History of retirement ages and why they were set
4:39 Longevity trends and aging populations
5:04 Why modern retirees want purpose and engagement
6:14 Companies encouraging phased retirement (Microsoft example)
7:48 Planning the “what will I do?” side of retirement
8:28 Why experience makes you better (especially in media)
10:12 Retirement identity and self-awareness
11:01 Real-world example: professionals scaling back instead of quitting
12:34 Don’s evolving “never retire” plan
14:55 The importance of knowing yourself before retiring
16:22 Retirement today vs. historical necessity
17:14 Rethinking retirement as continued contribution
17:58 Listener question: Using TSP G Fund in retirement allocation
20:19 Risks and logistics of split-account rebalancing
21:26 Listener question: When to use 529 funds for med school
23:17 Why delaying 529 withdrawals maximizes tax advantages
24:52 How to submit listener questions
26:19 Free advisor meetings and fiduciary pitch (without the noogie)

Questions? Comments? Click!