If you’re nearing retirement and uneasy about the math, you’re not alone. Don and Tom tackle the uncomfortable reality that most near-retirees haven’t actually run the numbers—and many won’t like what they see when they do. Drawing on Vanguard data and real-world client experience, they break down three practical ways to shrink a retirement gap: working longer (but not necessarily full-time), thoughtfully tapping home equity, and spending less before and during retirement.

0:06 Opening and the retirement gap problem

0:52 Podcast platforms, Apple vs Spotify, and Don’s short-story empire

4:08 How TRM ranks among investing podcasts and why that still feels surreal

5:24 Vanguard data: only 40% of near-retirees are on track

6:51 Kids, money, and why retirement math gets uncomfortable fast

7:51 Strategy #1: Working longer (and why part-time can be powerful)

9:41 Purpose, boredom, and the underrated psychology of retirement

10:00 Strategy #2: Home equity as a retirement resource

11:12 Downsizing, renting, HELOCs, and reverse mortgage trade-offs

13:05 Strategy #3: Spending less—before and during retirement

14:29 Reverse mortgage costs, limits, and real-world implications

17:01 Social Security timing and when immediate annuities actually help

18:40 Inflation risk, fixed income streams, and practical trade-offs

19:02 Listener Q: AVGE vs DFAW and understanding underlying holdings

21:48 Listener Q: Aggressive Roth portfolios intended for heirs

25:30 Listener Q: Washington 529 plans and GET vs traditional 529s

27:32 Listener Q: Quantum computing (short answer: no)

28:59 Sector investing, AI hype, and why diversification wins

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