Bespoke Future
This episode dismantles the myth of “one-size-fits-all retirement,” arguing that retirement isn’t a date, an age, or a lifestyle—it’s a personal transition that demands both an income plan and a purpose plan. Don and Tom explore the growing trend of “un-retiring,” why fear and economic anxiety are lousy motivators for going back to work, and how a lack of planning fuels unnecessary worry later in life. Listener questions cover smart uses of 529-to-Roth conversions, parking large sums of cash, Roth strategies for young investors, rebuilding emergency funds without sabotaging retirement, and why converting Vanguard mutual funds to ETFs in taxable accounts is often a no-brainer. The through-line is clear: stop predicting the future, stop reacting emotionally, and build flexible plans that let your money support the life you actually want.
0:04 Retirement isn’t a script, a date, or a finish line
0:56 The myth of “retire at 65 and stop living”
1:20 The rise of “un-retiring” and why Disney hires retirees
3:22 Fear-based reasons people go back to work
4:28 Why retirees often worry more, not less
5:10 Studies showing how many retirees expect to work again
6:38 Income plans vs. purpose plans in retirement
7:16 The Dalai Lama, retirement, and dark humor
8:16 Using leftover 529 money for a future Roth IRA
10:31 Anton Chekhov’s The Bet and money as a moral test
12:08 Parking $3.5M: T-bills vs. high-yield savings
14:30 Why holding massive cash piles is usually a mistake
16:21 Interest-rate predictions and the illusion of certainty
19:17 How (and where) people actually listen to podcasts
21:02 Mortgage rates under 6% and why context matters
23:15 Roth IRAs for young investors and compounding reality
25:12 VT vs. AVGE vs. AVGV for long-term simplicity
27:51 Disney’s $60B expansion and what it says about costs
31:07 Rebuilding emergency funds without derailing retirement
33:32 Converting Vanguard mutual funds to ETFs in taxable accounts
35:20 Why small tax efficiencies matter over decades