The Retirement and IRA Show

Chris’s Summary

Jim and I continue our discussion on the Fun Number, this time tackling what comes out first and how we plan for covering retirement income gaps. We look at funding both the delay period and post-delay period, including how a SPIA quote helps determine how much to set aside today to close a future gap. We also address aging and long-term care, and the smaller, less common carve-out for a guaranteed inheritance tied to a special needs dependent.

Jim’s “Pithy” Summary

Chris and I pick up the Fun Number conversation right where we left off, and this time we’re finally cracking open the toy box to show you what has to come out before anything gets set aside for fun. I still say it best with the seesaw: younger you on one side, older you on the other, and every dollar you carve out first is a promise you’re making across that fulcrum.

We walk through the delay period, those years before your Social Security or pension is fully turned on, and why we don’t discount those dollars down the way you might expect. Then Chris shifts to the post-delay period, pulling a real annuity quote to price out a future income gap and translating that future need into a present-day number using our See Through Portfolio thinking, so you can actually see which assets are spoken for and which ones aren’t. We talk through how to close retirement income gaps step by step, and I even work in my usual gripe about the crystal ball nobody’s built yet.

From there we get into the harder, more emotional carve-outs, the ones tied to aging, long-term care, and in some cases a guaranteed inheritance, before circling back to what’s actually left over for you to enjoy. There’s a reason people tend to want to spend now rather than reserve for later, and we talk about why that instinct is so hard to fight. Next week Jacob joins us to talk through how we actually invest each of these positions, so consider this the setup for that conversation.

The post Covering Retirement Income Gaps: EDU #2630 appeared first on The Retirement and IRA Show.

Jim and Chris discuss listener emails on Social Security survivor benefit strategies, a Roth 401(k) catch-up rule loophole, HSA reimbursement for Medicare premiums, pension options including a lump sum rollover, and trust titling versus individual beneficiaries.

(13:00) — George asks whether his brother can claim his own Social Security benefit at 62 and switch to the higher survivor benefit at full retirement age.

(22:45) — A listener asks whether starting a new job in 2026 could exempt him from the new mandatory Roth 401(k) catch-up rule.

(28:45) — The guys field a question about using HSA funds to reimburse Medicare Part A premiums paid for a spouse before age 65.

(40:00) — Jim and Chris review a listener’s decision to take a pension lump sum and roll it into an IRA over the annuity options.

(1:13:00) — Georgette asks which accounts should be retitled into her trust versus left as individual beneficiary designations.

The post Social Security, Roth 401k, HSA Reimbursement, Pension Options, Trust Planning: Q&A #2630 appeared first on The Retirement and IRA Show.

Chris’s Summary

“Jim and I begin a multi-part discussion on the Fun Number, a retirement budgeting concept for how much someone can spend on what they want rather than what they need once other obligations are covered. Jim traces how the idea originated from a client hesitant to follow through with his retirement dreams despite having more than enough saved to do so. In response, a single undifferentiated portfolio evolved over time into separately identified reserve positions.

Jim’s “Pithy” Summary

Chris and I are kicking off a series on the Fun Number, the concept, along with the Minimum Dignity Floor, that I’ve built my whole approach to retirement budgeting on. This first episode lays the groundwork for a multi-part discussion, since arriving at that number means first identifying everything else that needs to be sorted out first.

To get into where the idea actually came from, I tell the story of a client who had more than enough saved but still couldn’t bring himself to buy the camper trailer he’d been dreaming about for years. Watching that play out taught me something I just couldn’t shake: money sitting inside one big portfolio, all lumped together, is money many don’t feel safe spending, no matter what the math says.

That realization led me to start pulling pieces out of a portfolio. It started with handwritten notes and a three-bucket approach that never quite solved the problem. I kept pulling pieces out, the way a kid digs through a toy box, separating out what’s needed for security and reserves so what’s left becomes visible and spendable, for whatever someone wants to do with it. That thinking eventually grew into what’s now called the See Through Portfolio.

The post Retirement Budgeting – The Fun Number: EDU #2629 appeared first on The Retirement and IRA Show.

Jim and Chris discuss the new PROMISE Act’s potential impact on Social Security before covering listener emails on pension RMD timing, interest taxation versus capital gains indexing, and portfolio strategy around Social Security survivor benefits and multi-account allocation.

(5:30) — Chris discusses the new PROMISE Act and how it may impact Social Security.

(17:15) — George asks how long he can delay pension distributions without violating RMD rules, given his 73rd birthday falls in February 2027.

(29:45) — A listener asks whether interest income should be inflation-indexed the same way some propose indexing capital gains for wealthier taxpayers.

(43:00) — The guys field a two-part question on how a surviving spouse’s Social Security loss factors into MDF portfolio and annuity design, and how to allocate a portfolio strategy across different account types.

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Chris’s Summary

Jim and I dig into two beneficiary disputes as part of what we’re calling a “potpourri” EDU show: the 1930s Goodman Triangle life insurance gift tax dispute and a recent Montana Supreme Court ruling on an uncashed cashier’s check. We also discuss a bipartisan proposal to raise the home sale capital gains exclusion and a separate proposal to index capital gains for inflation more broadly.

Jim’s “Pithy” Summary

Chris and I dig into a variety of topics, starting with a court fight that traces back nearly a hundred years, something folks in the industry call the Goodman Triangle. Picture three people tied to one policy: an owner, an insured, and a separate beneficiary. Mrs. Goodman took out five life insurance policies on her husband, moved them into a revocable trust, and thought she was fine, until he died and the IRS said she’d made a taxable gift. She fought it and the court’s decision on the case still gets cited whenever a policy or an annuity has three different people sitting in those three roles.

From there we get into a couple of proposals sitting in Congress right now. One would finally raise the exclusion on gains from selling your primary home, something that hasn’t budged since the late nineties even as home prices have doubled and tripled around the country. The House and Senate versions land in slightly different places, but both would roughly double the current numbers and index them for inflation going forward. The other proposal is a longer shot, backed by senators who don’t have much bipartisan goodwill behind them, and it would apply an inflation multiplier to stocks, real estate, and other capital assets so you’d only owe tax on the growth that’s actually real.

We close with one of our beneficiary disputes out of the Montana Supreme Court: a husband pulls eighty thousand dollars out as a cashier’s check made out to himself, hides it in the house, and dies without a will. His wife cashes it, his son sues, and the ruling comes down to whether a gift was ever actually completed.

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