Jim and Chris discuss listener emails on IRMAA appeals using Form SSA-44, avoiding the 10% early withdrawal penalty, and whether a 403(b) distribution can be rolled into an IRA. Jim also manages to turn a discussion on Superbowl food to a conversation on retirement planning for the Go-Go phase of life (with a few other stops in between). So, if you typically skip the banter you may want to tune in around (10:10) for that discussion.

(16:30) George shares his experience repeatedly filing Form SSA-44 to correct IRMAA determinations and explains how Social Security processed and applied his updated income information.

(35:00) A listener asks whether a qualified annuity can be used instead of a 72(t) series of substantially equal periodic payments to avoid the 10% early withdrawal penalty.

(1:04:45) The guys discuss whether 403(b) distributions can be completed as 60-day rollovers into Traditional and Roth IRAs, and whether a custodian could refuse to accept the rollover.

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Chris’s Summary
Jim and I discuss spending anxiety in retirement using a Washington Post article written by a personal finance columnist describing her fear of spending after her husband retires. We look at why the shift from saving to spending can feel destabilizing even when pensions and Social Security are in place, and why fear can persist despite adequate planning. We also address the difference between spending income and spending savings, and how that distinction often affects behavior once retirement begins.

Jim’s “Pithy” Summary
Chris and I use a Washington Post article as a jumping-off point to talk about the moment retirement stops being theoretical and the fear around spending often shows up. The part that stuck with me in this situation is that nothing went wrong. One spouse retires. The other is still working. Pensions are there. Social Security is there. The house is paid off. And the fear shows up anyway. That’s what made me save the article in the first place. She writes about personal finance for a living, and she’s still cutting small expenses, feeling better for five minutes, and then right back to worrying. I’ve said it before, and I’ll say it again—I don’t expect to be immune to that when it’s my turn.

What keeps coming up for me is how differently people react to where the money comes from. Most people are comfortable spending a pension check or a Social Security deposit. It’s like a bottomless cup of coffee—you don’t think about the last sip because another one’s coming. But savings? That’s different. Even when the math works, even when the plan says you’re fine, drawing from something you’ve built for decades feels heavier. That’s where the spending anxiety shows up. Spending slows down. Decisions get second-guessed. Things get pushed out a year at a time. Not because people can’t afford them, but because the shift from saving to spending is uncomfortable.

Show Notes: Article: My husband just retired. I’m scared of running out of money.

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Jim and Chris discuss listener emails on Social Security timing for HSA contributions, investing in a SPIA vs buffered ETFs, and using SEPP 72(t) income to manage ACA credits.
(7:00) A listener describes delaying a Social Security filing to avoid Medicare Part A backdating that would have reduced prior-year HSA contributions, while still receiving full retroactive benefits.
(28:00) Georgette asks what to do with money originally set aside for a condo purchase, weighing ETFs against buying a single premium immediate annuity (SPIA), given an existing fixed indexed annuity (FIA), and pension income that cover living expenses.
(55:45) The guys address whether a SPIA purchased inside a rollover IRA can be used to satisfy SEPP 72(t) rules while keeping income low enough to preserve max ACA credits.

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