Aligning The Tax Plan Across the Retirement Income Plan to the Estate Plan

Retirement income planning doesn’t end with generating a sustainable paycheck. For high-net-worth and mass-affluent clients alike, true planning requires synchronizing income strategy, tax strategy, and estate strategy into one cohesive framework. As the sunset of the Tax Cuts & Jobs Act approaches—and as RMD rules, SECURE Act provisions, and state-level taxation continue to evolve—advisors must ensure that their clients’ retirement income decisions support (not undermine) their long-term legacy goals. In this session, Jamie Hopkins walks advisors through an integrated approach to aligning retirement income planning with the estate plan. The presentation explores the interplay between Roth conversions, HSA accumulation for end-of-life medical costs, advanced 529 planning for multigenerational education goals, and charitable strategies that support tax efficiency throughout retirement while preserving wealth for heirs. Advisors will also learn how to structure trusts as IRA beneficiaries in an SECURE Act era—balancing control, stretch limitations, and tax efficiency. Attendees will leave with a more comprehensive framework for designing tax-efficient retirement income distributions that reduce lifetime taxes, support charitable intent, and increase the net amount that ultimately passes to heirs. 0:00–5:00 — Overview & Framing Explain why retirement income planning, tax planning, and estate planning must be coordinated. Introduce the “Tax-Integrated Retirement Life Cycle” framework. 5:00–12:00 — Saving for Retirement: Tax Buckets Compare taxable, tax-deferred, and tax-free savings and their impact on future RMDs and tax brackets. Highlight funding order issues and long-term tax drag on retirement income. 12:00–20:00 — Digital Asset Taxation Review tax treatment, basis tracking, and upcoming IRS reporting for digital assets. Discuss implications for estate planning, valuation, and beneficiary access. 20:00–28:00 — HSAs in Retirement & Estate Planning Outline the triple tax advantage and strategic timing of HSA withdrawals. Note how HSAs transfer at death and tax consequences for beneficiaries. 28:00–35:00 — 529 Plans & Legacy Strategy Explain multi-generational planning and the ability to superfund or shift funds to a Roth. Review estate and gift tax considerations tied to 529 contributions. 35:00–45:00 — Roth Conversions Show how conversions reduce future RMDs and create tax diversification for heirs. Identify ideal conversion windows in early retirement before Social Security and RMDs. 45:00–55:00 — Charitable Remainder Trusts (CRTs) Describe when CRTs are effective for appreciated assets or large IRAs. Explain income tax deduction mechanics and how CRTs can replicate the “stretch” for heirs post-SECURE Act. 55:00–60:00 — Conclusion & Advisor Checklist Provide a unified tax-to-estate checklist: withdrawal order, conversions, digital asset access, 529/ HSA use, and charitable strategies. Final reminder: tax alignment improves income sustainability and estate outcomes.