Year-End Planning: Tax-Loss Harvesting

11 snips

Dec 3, 2025

Dive into year-end retirement planning as tax loss harvesting steals the spotlight! Gain insights on minimizing capital gains tax by offsetting gains with realized losses. Understand the difference between short-term and long-term capital gains, plus learn how to navigate the IRS wash sale rule. Roger shares a step-by-step process to optimize your tax strategy before the year's end. Don't miss the smart sprint action item to boost your financial moves and the inspiring retirement pivot from a listener!

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ADVICE

Stepwise Year-End Harvesting Checklist

Estimate your realized short-term and long-term capital gains for the year from account statements.
Then identify taxable (after-tax) positions that are down and consider selling to produce usable losses.

ADVICE

Avoid Wash Sales When Rebuying Positions

Avoid buying back a substantially identical security within 61 days of selling to claim a loss.
If you want exposure, buy a similar but not 'substantially equal' fund or wait 31 days each way.

INSIGHT

Substantially Equal Is A Gray Line

'Substantially equal' is a gray area the IRS interprets, especially for index-tracking funds.
Swapping to a fund that tracks a different index usually reduces wash-sale risk while keeping asset exposure.

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💬 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