The Retirement and IRA Show

Chris’s Summary Jim and I are joined by Jake as we discuss tax rules and mistakes through two tax-focused PSAs before moving into listener emails. Jake covers a denied non-cash charitable deduction due to an incomplete Form 8283 and missing contemporaneous documentation, then walks through how estimated tax payments and safe harbor rules are calculated from prior-year tax liability. We then...

Jim and Chris discuss listener emails on Social Security claiming strategies, financial education electives for a college student, a listener PSA on podcast word counts, inheritance planning, and SEP IRA conversions. (11:15) A listener planning to delay Social Security to 70 asks whether proposed benefit caps should change that strategy. He also asks Chris for financial education course recommenda...

Chris’s Summary Jim and I share retirement lessons learned from a listener’s account of his mother. Her husband’s survivor pension elections, combined with Social Security, left her a unicorn — secure income covering all expenses — yet she died regretting trips never taken despite a $9 million portfolio. The episode also covers why joint account ownership with adult children can...

Jim and Chris discuss listener emails on Social Security claiming strategies, IRMAA income adjustments, a listener PSA on the Roth five-year rule, conduit trusts for minor IRA beneficiaries and I-Bond tax reporting, and an inherited IRA passing through a trust. (10:30) George asks about the Social Security “January Rule” and whether claiming in December 2027 or January 2028 would captu...

If you would like to skip over the guys’ banter this week about Jim’s experience going to a Cincinnati Reds game, you can go to (7:00). Chris’s Summary Jim and I are joined by Jacob as we revisit buffered ETF mechanics in light of recent market volatility and explain why 100% and 20% buffers can still show interim losses. We also cover how renewals work, why resets are not taxabl...

Jim and Chris discuss listener emails on Social Security timing, whether you can “leave” your Social Security benefit to a spouse who doesn’t independently qualify, having a spendthrift trust purchase an annuity, and using a revocable living trust to manage aging parents’ complex financial affairs. (13:15) A listener born in November asks what their Social Security benefit...

Note : In this episode some information regarding the 5-year rule was misstated – one must get through the fifth, not just be in the fifth year. Jim and Chris clarify on the April 4, 2026 Q&A #2614 episode. If you would like to skip over Jim and Chris’s banter on the weather, that manages to touch on Colorado water rights (an issue many east of the Mississippi probably find bafflin...

Jim and Chris discuss listener emails, opening with listener PSAs on Medicare Advantage HSA reimbursement eligibility, then moving into questions on Social Security beneficiary rules and finishing their look at conduit trusts for IRAs. (7:00) A listener asks whether Social Security benefits can be passed on to a significant other. (28:00) The guys continue from last week with a listener’s mu...

Chris’s Summary Jim and I discuss the Ed Slott quiz questions from his November advisor training, opening with the widow/widower tax penalty and required beginning dates for IRA required minimum distributions before moving into inherited IRA rules — year of death RMDs with multiple beneficiaries and the deadline for satisfying them, spousal rollover options, and spousal RMD timing. Jim&#8217...

Chris is joined by Jake Turner to discuss listener emails on tax filing for mega backdoor Roth contributions, use of HSA funds , I Bonds redemption timing, lowering RMD pressure, and Roth conversions. ( 6: 30) George asks whether leaving a 1099- R off a return after after- tax 401( k) money was immediately converted to Roth means an amended return is needed or whether the IRS will simply follow up...

Chris’s Summary With Jim at the T3 conference in New Orleans, I am joined by Jake Turner to cover how to factor a defined benefit pension into retirement planning, using the situation of a 45-year-old law enforcement officer with a non-covered pension as the backdrop. We walk through evaluating his savings rate against the 15–20% rule of thumb, the lump sum equivalent value of his pension in...

Jim and Chris discuss listener emails on PSAs regarding IRMAA reimbursements, RMD in-kind transfers, and naming a conduit trust as a retirement account beneficiary. (8:15) A listener shares a PSA that an IRMAA reimbursement was applied as a credit balance drawn down over several months rather than a lump sum. (17:00) The guys discuss a listener PSA on SSA-44 filing: when income is underestimated a...

Chris’s Summary Jim and I continue our discussion on 99 Retirement Tips from Fisher Investments, picking up where we left off last week. We cover involving children in financial decisions, the liquidity trade-off of paying off a mortgage early, renting before buying in a new retirement location, lifetime gifts as part of the fun budget, and watching for financial predators including a disput...

Jim and Chris discuss listener emails on Social Security survivor benefits, IRMAA relief and the SSA-44 process, the Social Security earnings test, disclaiming inheritances that are brokerage accounts, and Roth conversion rules for retirees. (6:00) A listener asks whether his wife’s early Social Security claim at 62 would reduce the survivor benefit she’d receive upon his death. (14:00...

Chris’s Summary Jim and I review Fisher Investments’ 99 Retirement Tips and begin working through the list, covering only a handful in this episode. We discuss estate planning basics such as having a will, the importance of reviewing estate documents, and considering living wills and trusts, with emphasis on incapacity planning. We then examine longevity statistics, why life expectancy at bi...

Jim and Chris are joined by Jake Turner to discuss listener emails in this special tax related episode covering Roth conversions after RMD age, balancing Roth versus Traditional IRA contributions, HSA versus Roth contributions, IRA reporting questions, filing deceased tax returns, and a listener PSA on tax planning software. (11:30) A listener asks whether converting to a Roth makes sense at age 7...

If you would rather not listen to the guys’ banter about Jacob’s upcoming move to Iowa, Jim’s garden planning, and a listener correction about the word “imbibe” you can skip ahead to ( 33:30). Chris’s Summary Jim and I are joined by Jacob Vonloh as we discuss using Buffered ETFs prompted by a Morningstar article titled “Buffer ETFs Are Not for Everyone.” We explain how defined outcome...

Jim and Chris discuss listener emails on Medicare Part B decisions for retirees abroad, Social Security survivor benefit surprises, inherited Roth IRA distribution rules, and balancing Treasuries versus annuities when “safety” is more emotional than mathematical. (6:45) A listener asks about situations where it might make sense to skip Medicare Part B, including retirees living abroad with strong...

Chris’s Summary Jim and I are joined by Steve Sansone as we revisit Cash Balance Plans and respond to listener follow-up emails. (8:30) A CPA asks whether cash balance plans could be a fit for farmers with high income near retirement driven by deferred grain and equipment sales. (18:30) A listener with two controlled-group businesses asks how a cash balance plan works with divergent profit cycles,...

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...

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 differe...

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...

If you’d like to skip over the guys chatting about cold weather and football you can to (8:15). Chris’s Summary Jim and I are joined by Jacob as we continue our discussion on asset positioning and explain how we approach managing investment assets within a distribution portfolio. We outline why dollars are assigned based on purpose and timing and how asset positioning functions as a form of...

Jim and Chris discuss listener emails on Social Security survivor benefits and the earnings test, share a listener PSA on Social Security timing and IRMAA, then cover ERISA protections for retirement rollovers and a PSA from Greg on lifetime unlimited long-term care policies. (9:45) Georgette asks whether she must still take her husband’s required minimum distributions if he passes during his RMD...

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 Summary Jim 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 inves...