Chris’s Summary:
Jim, Jake, and I use this Dialogue EDU episode to explore how we approach flexible retirement spending. We respond to listener emails about DIY simplicity, budgeting for irregular expenses, and how we assign assets to spending needs. The conversation highlights why we prioritize adaptability over rigid withdrawal rules.

Jim’s “Pithy” Summary:
Chris, Jake, and I use this Dialogue EDU episode to explore what flexible retirement spending really looks like—beyond the spreadsheets and into the real-life tradeoffs people actually face. A few listener emails set the stage, from a DIYer aiming for simplicity to someone tackling unexpected home repairs, and another asking how we assign dollars to various spending needs across tax categories.

We take those as a jumping-off point to talk about the importance of structure without rigidity, and why having a plan doesn’t mean you need to over-optimize every detail. I share thoughts on safe withdrawal rates (you can guess where I land!), why the best-laid plans always get tested, and how people get in trouble when they assume retirement is just a math problem. Jake weighs in on building plans that bend instead of break, and Chris brings it all back to how our See Through Portfolio and 2-1-0 Tax Ordering Number provide enough order to make decisions—without painting you into a corner.

Along the way, I go on a bit of a tangent about why rules of thumb usually leave people stuck—especially if they’ve been good savers their whole life but have trouble flipping the switch to spending. We get into how why simple doesn’t always mean easy and how people can tie themselves in knots trying to make every move efficient. There’s a reason we keep coming back to flexibility: it’s the only way a plan actually holds up when life starts throwing curveballs!

The post Flexible Retirement Spending: EDU #2522 appeared first on The Retirement and IRA Show.

Jim and Chris answer listener questions on Social Security timing, the Earnings Test, nondeductible IRA basis, and the Roth 5-Year Rule.

(16:15) Georgette asks whether filing retroactively in December, with Social Security payments issued in January, ensures that all income—including the retroactive amount—will be reported on the following year’s tax return.

(28:00) A listener working in a State job who is eligible for a Social Security widow benefit asks whether large pre-tax contributions to 403(b) and 457(b) plans would reduce his earnings under the Earnings Test.

(42:30) The guys address whether IRA basis can be isolated from gains when converting a nondeductible IRA to a Roth.

(1:02:15) Jim and Chris respond to a listener seeking clarification on the 5-Year Rule for Roth IRAs, including how it applies to earnings distributions by original owners and non-spouse beneficiaries.

The post Social Security, IRA Basis, and Roth 5-Year Rule: Q&A #2521 appeared first on The Retirement and IRA Show.

Chris’s Summary:
Jim and I are joined again this week by Kevin Sebesta from the Rock Retirement Club in this EDU episode. We explore what helps retirees start spending confidently—especially when markets are volatile or the saver mindset is hard to shake. Kevin shares how structure, support, and community all play a role, and why building confidence takes more than just having a solid financial plan.

Jim’s “Pithy” Summary:
Chris and I bring Kevin Sebesta back this week for round two, and this time we’re talking about what it really takes to start spending confidently in retirement. Kevin’s been retired for over a decade and now coaches others through the emotional messiness of it all—because let’s face it, knowing you “have enough” and actually feeling comfortable using it are two very different things.

We dig into how savers struggle to flip the switch, how things like the Fun Number and Minimum Dignity Floor can give people the permission they need to enjoy their money, and why building in a simple cash reserve might just be the difference between “Hey, let’s upgrade the cruise cabin” and “Let’s sit in steerage because the market dipped 8%.” We talk about community, support, peer influence (yes, even a little friendly shaming), and how watching other retirees live well can sometimes do more than a spreadsheet ever could.

Kevin shares some great anecdotes—including what happens when frugality runs too deep—and I get into my usual rants about emotional risk, the real cost of inaction, and why deferring fun until your 80s is a plan only a masochist could love. Retirement planning isn’t just about having a secure strategy—it’s about creating a life worth funding!

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With Jim away at a conference, Chris is joined by Jake and Jacob to answer listener questions on child-in-care spousal benefits, the Earnings Test, HSA strategy, reconstructing cost basis, and Social Security timing concerns.

(6:00) A listener asks whether reaching full retirement age makes him ineligible for child-in-care spousal benefits, and what steps he can take to appeal the denial.

(21:30) George questions whether excess earnings prevent payment of family Social Security benefits when the worker’s own benefit is offset

(34:00) The guys address how inheritance and medical spending may influence HSA strategy and if it’s possible to overfund an HSA.

(50:00) “Chris and the Jacobs” respond to a couple trying to reconstruct the cost basis of mutual funds purchased in the 1980s without access to their records.

(1:02:15) Georgette wonders if divorce should be considered while deciding when a lower-earning spouse should claim Social Security, as well as whether pre-tax 401(k) contributions reduce reported earnings for benefit calculations.

The post Social Security, HSA Strategy, and Cost Basis: Q&A #2520 appeared first on The Retirement and IRA Show.

Chris’s Summary:
Jim and I welcome Kevin Sebesta from the Rock Retirement Club in this Dialogue EDU episode to explore the retirement mindset and why preparing for life after work goes beyond just the numbers. Kevin shares lessons from his own journey and the broader retirement community about identity, purpose, and what makes a fulfilling transition.

Jim’s “Pithy” Summary:

Kevin shares lessons from his own early retirement and what he’s learned working with hundreds of other retirees—plus a few gems that made even me and Chris stop and think. We get into why so many savers have a hard time flipping the switch to spending, the tension between saving and spending, and how tools like the Fun Number can help reframe your mindset around using money for more than just security.

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Jim and Chris respond to listener emails on Social Security record accuracy, IRMAA repayment options, naming a Trust as an IRA beneficiary, and the Roth 5-year Rule.

The post Social Security, IRMAA, IRA Beneficiary, and the Roth 5-Year Rule: Q&A #2519 appeared first on The Retirement and IRA Show.

Chris’s Summary:
Jim and I take a step back in this Dialogue EDU episode to explore how we design retirement plans for again. We talk through common misunderstandings around projections, explain how our See Through Portfolio helps people navigate retirement with more confidence, and clarify how simplicity is built into the process.

Jim’s “Pithy” Summary:

Along the way, I dig into why every projection is technically wrong (but why that doesn’t mean you shouldn’t do one!), how we use the law of large numbers to find planning value, and why the first few years of retirement are the hardest. I rant a bit about outdated bond assumptions, explain how our forward-looking returns are built, and revisit my old fog and boat analogies (yes, again). We talk about how retirement should get easier over time, how to protect your future self from cognitive decline, and why someday—even for all you hardcore DIYers—it might be worth hiring a firm like ours, as long as they’re not charging AUM fees. I even manage to tie it all together with a story about firewood. You’ve been warned!

The post Retirement Plans for Aging: EDU #2519 appeared first on The Retirement and IRA Show.

Jim and Chris are joined by Jake and Paul to discuss tax-related listener questions on IRA contributions from self-employment income, special needs trusts, year-of-death Roth conversions, Cost Basis, and IRMAA.

(9:00) George asks how QBI and self-employed health insurance deductions affect how much he can contribute to a traditional IRA.
(20:00) Jim, Chris, Jake, and Paul respond to a question about whether creating multiple special needs trusts can multiply the $5,000 federal tax deduction.
(28:00) The guys weigh in on a year-of-death strategy involving large Roth conversions and other planning considerations for a surviving spouse.
(49:45) A listener wants to know how Form 8606 helps during retirement and when its tracking of after-tax basis becomes useful.
(57:00) George asks what documentation the IRS will accept to establish a 2001 cost basis for inherited land now worth significantly more.
(1:07:45) The team evaluates whether Roth conversions make sense for a retiree already in the third IRMAA tier.

The post IRA Contributions, Special Needs Trusts, Roth Conversions, and Cost Basis: Q&A #2518 appeared first on The Retirement and IRA Show.

Chris’s Summary:
Jim and I are joined once again by Jacob for the third and final part of our series on transition period strategy. This time, we focus on the practical side of asset positioning: how near-retirees can begin structuring spending reserves without overreacting to short-term volatility. We use an example case study to explain how to segment early retirement needs into time-based chunks, identify dollars that require principal protection, and distinguish between your Minimum Dignity Floor and Fun Number spending.

Jim’s “Pithy” Summary:
Chris, Jacob, and I finish up our series on positioning assets during what we call the Venn diagram years or transition period. That’s that murky overlap between accumulation and decumulation, where you’re not retired yet, but you’re gearing up to live off your savings. This week, we dig into a listener’s question—he’s five years out from retirement and feeling nervous about market drops. He doesn’t know when or how to start making changes.

So, we build a hypothetical case to show what this might actually look like on paper. I walk through how to start allocating dollars across time without trying to do everything at once (because that’s how people freeze up or make bad calls). Jacob jumps in to explain why we don’t just ladder investments, we build what we call a liquidity timeline—an approach that gives you structure and flexibility. I dig into recency bias, the emotional hang-ups that stop people from spending even when they can—and should. We talk through which dollars need principal protection, which don’t, and why timing matters. And then I get into buffered strategies, laterals, the illusion of statement dollars, and, of course, my ongoing beef with growth-focused asset managers who don’t understand the first thing about distribution planning.

The post Transition Period Strategy Part 3 – A Case Study: EDU #2518 appeared first on The Retirement and IRA Show.

Jim and Chris discuss listener questions relating to Social Security spousal benefits, IRMAA relief, suspending Social Security for tax planning, and QCD timing with RMDs.

(3:00) A listener enquires whether her 85-year-old mother, who recently remarried, must remain on her ex-spouse’s record for one year before switching to spousal benefits on her new husband’s record.
(12:15) The guys address what happens if you file form SSA-44 for IRMAA relief but end up in a higher income tier than estimated.
(23:30) George asks to revisit a previous question about if suspending Social Security could allow for more Roth conversions and tax savings.
(34:30) Jim and Chris respond to a listener who challenges whether QCDs must be taken before RMDs.

Show Notes: QCD Timing Article by Lord Abbet

The post Social Security Benefits, IRMAA, and QCD Timing: Q&A #2517 appeared first on The Retirement and IRA Show.