Episodes

  • Social Security, HSA Held Annuities, IRA Annuities: Q&A #2541
    Oct 11 2025

    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 […]

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    1 hr and 23 mins
  • Military Retirement Planning: EDU #2541
    Oct 8 2025

    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 […]

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    1 hr and 13 mins
  • Social Security, Roth Conversions, RMD Calculations: Q&A #2540
    Oct 4 2025

    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 […]

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    1 hr and 20 mins
  • Delay Period Strategy: EDU #2540
    Oct 1 2025

    Chris’s SummaryJim 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 […]

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    1 hr and 10 mins
  • Social Security, 60-Day Rollover, Inherited IRA, and Deferred Income Annuity: Q&A #2539
    Sep 27 2025

    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 […]

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    1 hr and 48 mins
  • Tax Planning Strategies: EDU #2539
    Sep 24 2025

    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 […]

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    1 hr and 19 mins
  • IRMAA, Widow Status, Roth Conversions, Annuity RMDs, and Rollovers: Q&A #2538
    Sep 20 2025

    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 […]

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    1 hr and 15 mins
  • Discussing An Article On Retirement Planning: EDU #2538
    Sep 17 2025

    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 and compare how the article approaches […]

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    1 hr and 11 mins