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.

REFERENCES

• Submit a Question for Roger
• Sign up for The Noodle
• The Retirement Answer Man
  
  

In this episode, Roger Whitney walks listeners through the complexities of inherited IRAs, highlighting the impact of the SECURE Act of 2019 and clarifying the distinctions between eligible and non-eligible designated beneficiaries. He explains how these classifications affect withdrawals and tax planning, making the rules easy to understand. Roger also answers listener questions on topics like retirement team selection and funding health insurance with HSA accounts. Beyond the numbers, he shares practical strategies for creating more meaningful holiday conversations, drawing on real-life examples to show how curiosity and intentionality can help you connect more deeply with the people you care about.

OUTLINE OF THIS EPISODE OF THE RETIREMENT ANSWER MAN

• (00:00) This show is dedicated to helping you rock retirement.
• (00:30) In today’s episode, Roger Whitney covers the rules around inherited IRAs, explores ways to foster deeper and more meaningful conversations during the holidays and beyond, and answers listener questions.

RETIREMENT TOOLKIT

• (01:00) Today ​in ​the ​Retirement ​Toolkit ​we're ​going ​to ​talk ​about ​the ​rules ​around ​inherited ​IRAs.
• (02:40) Differences between eligible and non-eligible designated beneficiaries for inherited IRAs are explained.
• (14:32) Roger talks about ROTH IRAs and how they work.

RETIREMENT LIFE LAB

• (16:04) Roger explains how approaching conversations with curiosity and intentionality, especially with older family members or those with different interests, can create more meaningful and enriching interactions.

LISTENER QUESTIONS

• (25:37) Ira asks what to ask a financial advisor’s team to understand their retirement planning services and team longevity.
• (37:02) Mary Jane asks if she can use Health Savings Account funds tax-free to pay for private health insurance premiums before Medicare eligibility.

SMART SPRINT

• (38:42) In the next week, approach holiday or New Year’s gatherings with curiosity by asking questions and engaging with people you don’t see often to create more meaningful interactions.

REFERENCES

• 
  Submit a Question for Roger
• Sign up for The Noodle
• The Retirement Answer Man
  
  

In this episode, Roger Whitney, a retirement planner with 30 years of experience, breaks down annual gifting limits and year-end planning. He shares practical strategies for giving that make a real impact and create meaningful experiences for loved ones. Roger also answers listener questions, providing clear guidance to help you navigate your retirement with confidence.

OUTLINE OF THIS EPISODE OF THE RETIREMENT ANSWER MAN

• (00:00) This podcast is dedicated to helping you rock retirement.
• (00:57) Today Roger talks about annual gifting limits.

RETIREMENT TOOLKIT

• (01:45) In today’s Retirement Toolkit, Roger explores year-end planning by breaking down the 2025 annual gift exclusion.
• (04:05) Roger discusses giving money during your lifetime and shares the reasons why it can be beneficial.
• (12:05) Roger shares his observations on giving money, noting that gifts can feel most meaningful when attached to a specific purpose rather than given with expectations.
• (14:21) Strategies for impactful gifting are explored, including transferring appreciated assets, paying medical expenses, and covering tuition directly, showing ways to help others while maximizing meaning and efficiency.

LISTENER QUESTIONS

• (19:00) Mary shares feedback on qualified charitable distributions (QCDs).
• (21:27) Lee describes his “shoulder bonus” strategy to spend excess retirement funds while staying within a safe withdrawal rate.
• (30:10) John asks when to switch from a general financial advisor to a retirement planner
• (34:19) Rick asks about gifting appreciated stocks to adult children.
• (35:17) Steve asks about building a resilient retirement plan at age 80.

SMART SPRINT

• (38:13) In the next seven days: Do you want to give? Can you? How much and to whom? Can it have a purpose? Even small gifts can make a big impact.

CLOSING THOUGHTS

• (40:00) Giving money can bring profound joy, often the greatest gift is the one you give yourself by helping others.

REFERENCES

• Submit a Question for Roger
• Sign up for The Noodle
• The Retirement Answer Man