The Retirement and IRA Show

Chris’s Summary Jim and I examine a recent Social Security claiming strategies debate prompted by articles from Derek Tharp and Laurence Kotlikoff. The episode highlights how opposing valuation frameworks—economic modeling versus purpose-driven income planning—can lead to drastically different conclusions. We explain why assigning Social Security a clear job, such as covering your Minimum Di...

Jim and Chris discuss listener questions on spousal Roth IRA eligibility, backdoor Roth contributions using a solo 401k, Social Security timing, post-tax contributions to an IRA and 401k , and an HSA strategy coordinating withdrawals with Roth conversions. (9:30) George asks whether he can contribute to a spousal Roth IRA after his retirement if his wife continues working and their income meets el...

To skip over Jim and Chris chatting about the government shutdown delaying Social Security and Medicare announcements, and Jim’s upcoming travel plans—including concerns about flight delays and his upcoming elk hunt in Utah you can skip ahead to ( 8:15). Chris’s Summary Jim and I walk through common IRA rollover mistakes and clarify the once-per-year rollover rule, including exceptions for Roth co...

Jim and Chris discuss a listener PSA on estimating early retirement benefits, followed by questions on Social Security benefit calculations and reductions, HSA held annuities, and IRA annuity pro rata rule application. (14:45) George shares a PSA explaining how to input future earnings on the SSA site to better estimate early retirement benefits. (25:15) A listener asks whether their benefit is fu...

Chris’s Summary: Jim and I are joined by Rear Admiral Brian Luther to discuss veterans benefits and military retirement planning. We explore how Navy Mutual supports service members, examine the survivor benefit plan, and talk about the role of annuities in managing longevity risk. Rear Admiral Luther also shares insights on TRICARE, VA health care, and the importance of financial literacy through...

Jim and Chris discuss listener questions on Social Security spousal benefits, a listener PSA on IRMAA repayment silence, IRMAA reduction eligibility and planning considerations, and a PSA on how 60-day rollover Roth conversions affect year-end RMD calculations. (7:45) A listener points out a possible error from a recent episode and looks for clarification whether delaying benefits past full retire...

Chris’s Summary Jim and I return for an EDU dialogue episode focused on a listener’s delay period strategy. His plan includes laddered CDs, equity ETFs, delayed Social Security, and Roth conversions. We use his plan to discuss bracket drift, spending liquidity, and how rising markets can complicate a fixed glidepath. We also cover the tax planning window, crossover risk, and why even strong plans...

Jim and Chris discuss listener questions on Social Security disability, dependent benefits for an adult child, a 60-day rollover nuance, inherited IRA RMD rules, and a deferred income annuity strategy. (15:00) George asks whether his brother, who is on SSDI and will transition to retirement benefits at 67, can suspend and restart his benefit to grow it until age 70. (27:30) The guys address how th...

This week, with Jim away at a conference, Chris is joined by Jake for an EDU episode that takes the shape of a Q&A, focusing on tax planning strategies. The guys cover a series of emails that highlight how different tax rules and opportunities intersect with retirement planning, income management, and financial decisions. (10:30), the first question explores how the new OBBB changes—particular...

Jim and Chris discuss listener questions on IRMAA reductions and Roth-conversion effects, widow filing status and IRMAA, in-kind stock Roth conversions and RMD transfers, annuity RMD interactions, and 60-day rollover mail timing. (7:45) George asks whether an approved SSA Form 44 that reduced 2025 IRMAA will also govern next year, how a large 2026 Roth conversion will be trued up and affect future...

If you would like to skip over Chris and Jim chatting about a recent Colorado hail storm and Jim’s garden while he’s in Ohio, please skip to the 7:45 mark. Article discussed in today’s show: https://www.kiplinger.com/retirement/retirement-planning/the-me-first-rule-of-retirement-spending Chris’s Summary I chat with Jim about a recent article regarding retirement planning an...

Jim and Chris discuss a listener PSA on WEP treatment for foreign pensions, followed by questions on Social Security strategies, benefit calculators, account consolidation, and MYGA selection. (13:00) Georgette shares a PSA on how a lump-sum superannuation payout impacted WEP treatment under the POMs rule and led to a successful Social Security appeal. (21:45) George outlines his family’s si...

If you would like to skip over Chris and Jake chatting about Jake’s recent trip to Ireland you can go to 7:00. Chris’s Summary I am joined by Jake today, while Jim is traveling, to examine taxes in retirement. We look at why not all taxes belong in the Minimum Dignity Floor . We also consider the trade-offs between Roth conversions and IRMAA, and the role of a cash reserve during the delay p...

Jim and Chris discuss listener questions on surviving spouse Social Security benefits and Roth conversions, SSDI and pensions, the Social Security Fairness Act, managing large HSA reimbursements, and choosing between MYGAs and the TSP G Fund. (7:45) George asks whether Roth conversions count toward the earnings test when planning to claim his surviving spouse Social Security benefits. (26:30) A li...

Chris’s Summary Jim and I look at behavioral finance in retirement planning, noting that spending from secure income feels safer while drawing from assets feels like a loss. People resist balances going down after decades of saving, even though the money was built to be spent. We highlight how framing savings as deferred spending and covering the Minimum Dignity Floor with income addresses uncerta...

Jim and Chris discuss listener questions on Social Security timing rules, retroactive benefits for an ex-spouse, investment strategy philosophy, fraternal benefit societies, and Roth conversions. (6:30) The guys address a listener’s question about whether applying for Social Security at 70 requires enrolling in Part B or if retroactive filing is an option without losing payments. (16:00) A listene...

If you are not in the mood for Jim and Chris’s delightful banter, you can skip ahead to (5:45). It should be noted that of all the episodes to start sharing that information, it’s the one in which Jim said “we didn’t even banter!”. But, from now on, right here before the guys’ summaries you can find the timestamp to jump ahead to if you want to get to the meat o...

Jim and Chris discuss listener questions on Social Security retroactive payments and delayed retirement credit timing, share a listener PSA on horse speed, and answer questions on fixed indexed annuity default credits, a living benefit rider with a proprietary index, and RMD rules for an inherited account. (15:45) A listener asks if the lack of a prior formal application affects eligibility for re...

Chris’s Summary Jim and I review catch up contributions across IRAs and workplace plans using questions from the Ed Slott training quiz. We clarify the $1,000 IRA catch up (now indexed), explain the age 60–63 super catch up in 401(k)/403(b) plans, and outline the Roth mandate that will require high earners’ catch ups to go to the Roth side. I focus on what’s actually changing and where these rules...

Jim and Chris discuss listener questions on Social Security spousal benefits, filing logistics and spousal eligibility with a disabled child, an inherited Roth IRA, and IRMAA concerns. (14:30) A listener asks why his spouse’s Social Security spousal benefit is less than half of his primary benefit amount. (21:45) George asks about the process and documentation needed when filing for Social Securit...

Chris’s Summary Jim and I continue discussing funding discretionary spending in Robert Merton’s three bucket retirement income framework from last week’s article, focusing on how his flexible and aspirational spending categories compare with our philosophy. We explore why annuities are insurance products, where TIPS fit into income planning, and why funding Go-Go years demands liquidity and princi...

Jim and Chris discuss listener questions on Social Security timing strategies, Roth conversions in an RMD year, annuity return calculations, account sourcing for SPIA purchases, and Rule of 55 withdrawal rules. (12:30) A listener asks whether his brother should delay claiming Social Security to age 70 for better longevity protection despite a narrow breakeven. (35:15) George asks if he can complet...

Chris’s Summary Jim and I review a recent article featuring Robert Merton’s views on retirement income versus savings, using it as a springboard to unpack income planning fundamentals and annuity projections. While we agree with many of Merton’s framing points—especially the focus on secure income—we also note several key areas where academic theory diverges from real-world retirement dynamics. Ji...

Jim and Chris discuss Jim’s relocation experience to Ohio, a listener PSA on Medicare, questions about Social Security payment timing and divorce eligibility, Roth 401k withdrawals under the rule of 55, and close with an annuity comparison answer so long it practically qualifies as a mini EDU. (17:00) A listener PSA reminds others that Medicare Part A only covers hospital costs and that Parts B, C...

Chris’s Summary Jim and I are joined by Matt Kaufman, Senior Vice President and Head of ETFs at Calamos Investments, to discuss buffered ETFs vs stocks and cash, focusing on AQR’s recent critiques. We examine the flaws in AQR’s methodology, the broader history of buffered products, and why these tools can offer certainty in retirement planning. Matt explains how buffered ETFs differ from accumulat...