Episode Details

From your 20s to your 60s, the priorities change—but the basic job doesn’t. Don and Tom walk through emergency savings, Roth IRAs, 401(k) matches, rebalancing, retirement planning, Social Security, Medicare, and estate planning, decade by decade.

Then Mary calls with a smart Roth-conversion puzzle. They weigh whose IRA to convert, how much to move without wasting a low tax bracket, the age-59½ penalty, and why a household’s accounts should be managed as one portfolio—even when the spouses have very different tolerances for risk.

Finally: whether retirees still need emergency cash, how much umbrella insurance is enough, when a family office begins to make sense, and three near-identical retirement portfolios from a listener in Wagner, South Dakota—whose hometown briefly steals the show.

00:25 Tom’s brassy choice
01:36 Financial priorities, decade by decade
02:58 Start early with a Roth IRA
04:02 Your 30s: emergency cash and the 401(k) match
06:02 Your 40s: fixed obligations and retirement planning
09:13 Your 50s: risk, HSAs, and getting on track
10:45 Your 60s: Social Security, Medicare, and estate planning
14:48 Roth conversions and household asset allocation
24:12 Emergency funds in retirement
27:01 Umbrella coverage and family offices
30:16 Three retirement portfolios from Wagner

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