The Retirement and IRA Show

If you want to miss all the fun banter about Jim’s Singo (song bingo) night and his trip to Kentucky and Amish country you can skip ahead to (16:00).

Chris’s SummaryJim and I are joined by Jacob Vonloh as we discuss investing for retirees, using a listener email as the starting point for a broader conversation about how investment advice and asset management work in practice. We explain why investing changes once people move from accumulation into distribution, including differences in risk tolerance, liquidity needs, and volatility. Jacob outlines how investment tools are evaluated based on time horizon and downside exposure rather than labels. We also discuss planning for aging and long-term care costs, including liquidity needs, inflation considerations, and the SEAL (Savings for Emergencies, Aging, and Long-Term Care) reserve framework.

Jim’s “Pithy” SummaryChris and I are joined by Jacob Vonloh as we start a new series of conversations inspired by listener emails, and we use those questions as a jumping-off point to talk about what really changes when you’re investing in retirement. A lot of DIY investors successfully built wealth with an accumulation mindset and then try to carry that same approach into retirement, where it doesn’t work. The problem is that accumulation investing and retirement investing are not the same thing, and pretending they are is where people get themselves into trouble. Once withdrawals begin, volatility feels different, timing matters more, and the emotional impact of market swings gets amplified in ways people don’t expect.

We spend time pulling apart how the investment advice industry presents itself, how fee structures are typically layered in, and why we’re very intentional about separating retirement planning from asset management. Jacob walks through how we evaluate investments based on when the money might be needed and how much downside someone can realistically tolerate. Buffered ETFs come up in that context, not as a recommendation, but as a clean example of how downside protection and upside caps reshape risk. The point isn’t the product — it’s that comparing retirement-stage tools to a fully unbuffered equity index without adjusting for risk is fundamentally misleading.

From there, we connect investing back to real planning issues retirees face, especially aging and long-term care. We talk about why insurance isn’t always available or sufficient, how covering one spouse can still protect a household, and why the financially hardest stretch is often when both spouses are alive and care costs begin to show up. That leads into how we think about liquidity, inflation, and time horizon working together inside what we call the SEAL reserve. This isn’t about chasing returns — it’s about structuring money so it can actually support people through retirement without forcing panic decisions at the worst possible time.

The post Investing for Retirees: EDU #2603 appeared first on The Retirement and IRA Show.

Jim and Chris discuss listener questions on Social Security survivor benefits and divorce rules, a listener PSA on spousal benefits, HSA contribution limits, and whether annuities make sense versus Treasury bonds.

(8:45) A listener asks whether someone who is newly widowed can claim survivor Social Security now, keep working part time, and later switch to their own benefit, and also asks whether you still offer a “coffee and second opinion” or an a la carte Social Security review.

(23:00) The guys field a question from someone with two ex-spouses asking if it’s possible to combine their own Social Security with part of either (or both) ex-spouses’ benefits.

(33:30) George shares a PSA on how filing for Social Security online triggered a spousal-benefit eligibility notice for their spouse, and how the follow-up phone appointment worked without needing an in-person visit or marriage certificate.

(45:15) Jim and Chris answer a question about 2026 HSA contribution limits for two spouses on an ACA family plan who each opened their own HSA and want to avoid overfunding.

(54:45) One writer asks why they should consider annuities given fees and insurer risk when they can buy 20-year Treasury bonds, and adds a quick note about simplifying word choice from a prior email discussion.

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Chris’s SummaryJim and I continue last week’s EDU discussion on Roth IRA mistakes from an Investopedia article. We cover direct versus 60-day rollovers, the one-per-365-day IRA-to-IRA limit, and the 401(k) 20% withholding rule with the RMD and NUA exceptions. We revisit backdoor Roth mechanics and the pro rata rule, then shift to beneficiary designation forms and why naming an estate creates probate and creditor issues. We close with inherited Roth withdrawal timing under SECURE Act rules and the 10-year window.

Jim’s “Pithy” SummaryChris and I pick up where last week’s EDU episode left off, using the Investopedia Roth mistakes article as a launching point to correct what they compress or misstate. The rollover section is where people get hurt, because they describe the old IRA rule like it was “once per calendar year,” and it wasn’t. It’s a 365-day framework, and the one-per-365-day limit still matters when you do the “show me the money” version of a rollover. I also keep pushing back on indirect rollovers from a 401(k), because the 20% withholding isn’t optional. There are narrow exceptions—but those aren’t general flexibility, they’re specific rules people routinely misunderstand.

The other item that’s far more important than its position on the list is beneficiary designation forms. These accounts pass by beneficiary form first, not your will, which can create probate delays, attorney fees, and creditor complications for the people left to sort it out. Chris adds the practical version of the same mistake: circumstances change, paperwork doesn’t. Old beneficiaries stay on file, and the form controls the outcome even when it creates an awkward situation.

We also get into inherited Roth timing under the SECURE framework—who qualifies as an eligible designated beneficiary, what the 10-year window actually requires, and why Roths don’t fit the required beginning date logic the way traditional accounts do. That difference matters when you’re thinking about flexibility for heirs and how long the account can sit untouched. If the real goal is the zero in the 2-1-0 Tax Ordering Number, the logic behind leaving a Roth can look very different than what you’d conclude from a short listicle about Roth IRA mistakes.

Show Notes: Article – 11 Mistakes to Avoid With Your Roth IRA

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Jim and Chris are joined by Jake to discuss listener questions on SSA-44 and IRMAA surcharges, inherited IRA spousal rollover rules, long-term care insurance benefit caps, and ACA tax credits.

(4:45) George asks whether an unexpected W-2 stock option payout in 2025 could support filing SSA-44 to reduce 2027 IRMAA surcharges, especially if he stops consulting income afterward.

(12:00) A listener asks whether SSA-44 can be used retroactively to request a refund of 2025 IRMAA surcharges after a job loss pushed MAGI below the threshold.

(18:15) Georgette asks whether she can take withdrawals from her deceased spouse’s inherited IRA without penalty and still later move the remaining balance into her own IRA.

(28:00) The guys address why long-term care insurance policies often have a lifetime benefit cap and whether benefits can run out during an extended care event.

(46:45) Chris and Jake cover whether long-term capital gains count toward the modified adjusted gross income used for ACA tax credits and can affect eligibility.

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If you want to skip over some weather banter you can go to (14:15).

Chris’s SummaryJim and I review Roth IRA mistakes and walk through key rules on earned income eligibility, income limits, spousal contributions, excess contributions, and qualified distributions. We use an Investopedia article as a framework, clarify how MAGI impacts Roth eligibility, explain the October 15 correction deadline, and break down the two-prong test for tax-free Roth earnings withdrawals, including how the five-year rule is measured across tax years.

Jim’s “Pithy” SummaryChris and I kick off the first EDU show of 2026 by taking an Investopedia piece called “11 Mistakes to Avoid with Your Roth IRA” and using it as our launchpad. We’re not reading the article to you—we’re breaking down what they got right, what they explained too loosely, and what they left out that changes the meaning. We start with the basics that still trip people up: you need earned income to contribute, and a lot of income that feels “earned” (like dividends, interest, rental income, or IRA distributions) doesn’t count. Then we pivot to the opposite problem: earning too much and accidentally making an ineligible Roth contribution because your MAGI crossed the line, often after a late bonus or surprise taxable payout.

We get into a category of mistakes that can create problems with the IRS: excess contributions. We walk through how easy it is to overfund a Roth when you have multiple accounts, and why the correction rules matter more than most people realize. We talk about the October 15 deadline, how the custodian won’t stop you, and why “removing the excess” isn’t always the same as removing what you deposited. We also get into the weird but real quirk where, if you miss the correction deadline, you may only need to remove the excess contribution itself, not the growth tied to it.

We also dig into the qualified distribution rules for Roth earnings, because this is where the five-year rule gets misunderstood. The Roth has to be five tax years old, and you need a qualifying condition—59½ is one, but it’s not the only one. That’s where the article oversimplifies, and where people make avoidable mistakes when taking earnings out too early.



Show Notes: Article – 11 Mistakes to Avoid With Your Roth IRA

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