Year-End Planning: The Basics of Charitable Giving
Dec 24, 2025
This engaging discussion delves into the essentials of charitable giving, emphasizing the importance of timing and documentation for year-end donations. Listeners learn about maximizing tax benefits through strategic contributions. A touching story of a listener's adventurous retirement highlights the value of purposeful living. Additional insights include the risks of high-yield bonds and the significance of clear communication after leaving corporate culture. The episode wraps up with reflections on generosity and crafting a meaningful retirement.
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volunteer_activism ADVICE
Batch Gifts To Maximize Deductions
Batch charitable gifts if you normally take the standard deduction to create an itemizable year.
Use a donor-advised fund or bunch multiple years into one tax year to maximize deduction benefits.
volunteer_activism ADVICE
Give Appreciated Securities, Not Cash Only
Give appreciated securities held over a year to avoid capital gains and deduct at fair market value.
Non-cash gifts over $5,000 need appraisals and vehicles/boats are deducted at actual sale value.
volunteer_activism ADVICE
Mind The Year‑End Timing Rules
Time donations carefully: credit card charges deduct when charged and checks when mailed or delivered.
Move stock transfers early and be mindful custodians are busy at year-end to ensure the charity receives assets in time.
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In this Christmas Eve episode, Roger Whitney explores the basics of charitable giving as part of an intentional retirement plan, with a timely focus on year-end decisions. He explains how charitable deductions work, common planning mistakes to avoid, and why generosity is most effective when paired with a resilient financial plan. Roger also shares a Rocking Retirement in the Wild story from a listener who is actively living a purpose-filled retirement, reflects on the corporate language we can leave behind when we retire, and answers listener questions on retirement readiness, gifting inheritance early, and the risks of relying on high-yield bonds for retirement income. He closes the episode with personal reflections on lessons learned, reminding listeners how to keep retirement simple, resilient, and meaningful while making a positive impact on others.
OUTLINE OF THIS EPISODE OF THE RETIREMENT ANSWER MAN
(00:00) This show is dedicated to helping you not just survive retirement, but confidently lean in and rock it.
(00:20) Roger introduces a Christmas Eve episode focused on charitable giving, listener stories, answering questions, and reflecting on intentional retirement living.
RETIREMENT TOOLKIT
(03:45) Roger walks through the basics of charitable giving, including qualified charities, documentation requirements, and how deductions work with standard versus itemized returns.
(07:55) Year-end timing rules for checks, credit cards, stock transfers, and donor-advised funds.
ROCKIN’ RETIREMENT IN THE WILD
(09:30) A listener shares how, at 67, he backpacked 121 miles through Maine’s 100-Mile Wilderness, reconnecting with longtime friends and staying physically engaged in retirement.
(12:28) Roger reflects on why rocking retirement doesn’t have to be impressive—only meaningful to the person living it.
RETIREMENT LIFE LAB
(13:03) Roger explores the idea of “retiring” corporate jargon in retirement and how simplifying language can help us reconnect and speak more human again.
(18:21) Listeners are invited to share the words and phrases they are most looking forward to leaving behind.
LISTENER QUESTIONS
(19:50) Don asks why most people enter retirement with relatively little savings and what that reality means for financial and social stability.
(29:25) A listener asks how to give inheritance before death without triggering taxes.
(33:46) James asks whether using high-yield corporate bonds as the foundation for retirement income is a safe strategy.
SMART SPRINT
(42:08) In the next seven days, Roger challenges listeners to choose a single word for 2026 to serve as a guiding focus for the year ahead.
CLOSING THOUGHTS
(43:59) Roger shares final reflections on the lessons of the episode, emphasizing elegant simplicity, financial resilience, and showing up to help others in meaningful ways.
Retirement Answer Man