Year-End Planning: Tax-Loss Harvesting

Retirement Answer Man

Roger Whitney, CFP®, CIMA®, RMA, CPWA®

Education, Investmentmanagement, Saving, Self-improvement, Careerplanning, Retirement, Business, Lifeplanning, Investing, Retirementplanning, Financialplanning, Retirementpodcast

4.6 • 1.2K Ratings

🗓️ 3 December 2025

⏱️ 37 minutes

🔗️ Recording | iTunes | RSS

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Summary

💬 Show Notes

In this episode, Roger Whitney kicks off a month-long series on year-end planning for retirement. He shares insights on tax loss harvesting, a technique that can help you minimize capital gains tax. Listen in as Roger explains the basics of capital gains, the importance of proactive planning, and the potential benefits of offsetting gains with losses. Plus, he introduces a smart sprint action item to help you optimize your tax strategy before the year's end!

OUTLINE OF THIS EPISODE OF THE RETIREMENT ANSWER MAN

(00:00) This podcast is dedicated to helping you rock retirement.
(01:07) Roger shares that he recently finished George Orwell’s 1984, his first in a new hobby of collecting classic authors.

RETIREMENT TOOLKIT

(03:43) Roger breaks down the basics of tax loss harvesting, explaining capital gains, the difference between short-term and long-term gains, and how they impact year-end retirement planning.
(09:17) Roger explains how to implement tax loss harvesting by estimating your realized capital gains, identifying losses in your taxable accounts, selling positions to offset gains, and being mindful of the IRS wash sale rule that prevents repurchasing the same security within 61 days.
(16:50) Using losses in taxable accounts strategically can help reduce capital gains taxes.

ROCKIN’ RETIREMENT IN THE WILD

(18:28) Share your story of rocking retirement at askroger.me to inspire others with your confidence and passion.
(19:30) Mark plans to pivot into business consulting after retiring so he can keep learning, adding value, and connecting with people while enjoying more freedom and purpose.

LISTENER QUESTIONS

(21:54) Richard is preparing for retirement at 67 and asks how he should handle his 401(k) and income to make his plan work best.
(25:00) Kathy asked how a new bill will affect those 65+ with year-end tax planning, and Roger said he’ll provide a checklist to guide Noodle subscribers through the changes.
(25:42) Karen pointed out that annuity payments aren’t inflation-adjusted and emphasized balancing them with other investments.
(30:08) Dan asks: “Where should I keep the cash for living expenses and market downturns?”

SMART SPRINT

(33:59) Smart Sprint: In the next seven days, review your after-tax investment accounts, estimate year-end capital gains or losses, and consider selling positions with unrealized losses to offset gains while avoiding the 31-day wash sale rule.

CLOSING THOUGHTS

(35:18) Over Thanksgiving, Roger continued his childhood tradition of watching the Lions lose, ending up jumping in a pool after a bet with his nephew Graham, a devoted Packers fan.

REFERENCES

Transcript

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0:00.0	Welcome to the show dedicated to helping you not just survive retirement, but to have the confidence to lean in and rock it.
0:09.2	My name is Roger Whitney.
0:11.6	Welcome to the show.
0:13.4	Today we're going to start a month-long series on year-end planning.
0:18.0	Each week, we're going to talk about a planning technique that you might want to consider
0:22.9	in your retirement planning that has to be done before the end of the year. Now, they may not
0:29.0	have a place or not, but they're a good checklist of, okay, maybe I should think about that,
0:32.8	just to see if there's an opportunity that you can take advantage of.
0:40.6	We generally know of these things, but we don't think about them.
0:43.4	So it's always good to get a reminder at the right time.
0:46.8	Today we're going to talk about tax loss harvesting and the rules around that.
0:49.8	Next week, we're going to talk about annual gifting limits,
0:51.5	and each week we'll hit something new.
0:56.7	In addition to that throughout the month, we'll be answering a number of your questions.
1:01.7	We're starting to get more audio questions, so we're putting those in fast pass mode.
1:03.9	So we'll make sure we'll have one of those each week.
1:16.6	Before we get started, I'm excited to say that I finished my first book in this new hobby I have, I guess, of purchasing great authors and buying nicer sets of their books. And I finished one of George Orwell's books, 1984.
1:23.7	Now, you probably read that in high school. I don't know. I didn't.
1:27.9	I've never read a George Orwell book.
1:29.8	I'm going to read his Animal Farm next.
1:32.0	Never read that either.
1:33.5	It was very prophetic.
	...

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