Episode 233: Should You Worry About Social Security Running Out? episode artwork

EPISODE · Jun 16, 2026 · 30 MIN

Episode 233: Should You Worry About Social Security Running Out?

from Retire With Style · host Wade Pfau & Alex Murguia

In Part 2 of this Live listener Q&A episode, Wade Pfau and Alex Murguia tackle several retirement planning topics, including Social Security claiming strategies for spouses with age differences, how younger workers should think about Social Security's long-term solvency, whether to assume future benefit cuts in retirement projections, the impact of the "widow's penalty" on tax planning and Roth conversions, evaluating an older variable annuity with high fees, tax considerations when selling investments in a taxable account, and how to think about maintaining portfolio discipline during retirement. Throughout the discussion, they emphasize balancing planning conservatism with practicality, avoiding unnecessary forecasting, and making decisions that support long-term retirement goals rather than reacting to headlines or uncertainty.   Takeaways When spouses have similar Social Security benefits, but one spouse is significantly older, the older spouse often has the strongest case for delaying benefits until age 70 because that higher benefit is more likely to become the survivor benefit. Younger workers may not need to heavily discount future Social Security estimates because projected wage growth could offset a significant portion of any future benefit reductions. For retirees already near claiming age, assuming a 25% reduction in future Social Security benefits can be a reasonably conservative planning assumption. The eventual Social Security reform package is unlikely to rely solely on benefit cuts and will more likely include a combination of tax increases and benefit adjustments. The "widow's penalty" can significantly increase taxes for a surviving spouse because income often remains similar while tax brackets and Medicare thresholds become less favorable. Potential future tax increases and the widow's penalty are both compelling reasons to consider Roth conversions even when current projections suggest little immediate tax benefit. High-fee variable annuities should be evaluated carefully, especially to determine whether valuable income guarantees justify the ongoing costs. If guaranteed income sources such as pensions and Social Security already cover essential expenses, a variable annuity can potentially serve as a bridge strategy to delay Social Security benefits. When selling investments from a taxable account, maintaining the portfolio's target asset allocation is generally more important than trying to predict which investments will perform best or worst next. Tax-efficient selling decisions often come down to managing capital gains by choosing whether to realize gains from low-basis or high-basis shares depending on the investor's broader tax situation.   Chapters 00:00 Social Security Strategies for Couples 06:28 Concerns About Social Security Reliability 10:16 Planning for Future Social Security Benefits 13:20 Roth Conversions and Tax Planning 18:18 Evaluating Variable Annuities 22:24 Taxable Account Management Strategies 25:05 Maintaining Asset Allocation Discipline 27:53 Tax Considerations in Asset Sales   Links 📘 New Release: The Retirement Planning Guidebook (3rd Edition) Wade Pfau’s must-read Retirement Planning Guidebook just got even better. The 3rd Edition is now available and packed with the latest updates to help you design your retirement strategy with confidence. Grab your copy on Amazon or your favorite book retailer: https://books2read.com/Retirement This episode is sponsored by McLean Asset Management. Visit https://www.mcleanam.com/retirement-income-planning-llm/ to download McLean’s free eBook, “Retirement Income Planning”

In Part 2 of this Live listener Q&A episode, Wade Pfau and Alex Murguia tackle several retirement planning topics, including Social Security claiming strategies for spouses with age differences, how younger workers should think about Social Security’s long-term solvency, whether to assume future benefit cuts in retirement projections, the impact of the ”widow’s penalty” on tax planning and Roth conversions, evaluating an older variable annuity with high fees, tax considerations when selling investments in a taxable account, and how to think about maintaining portfolio discipline during retirement. Throughout the discussion, they emphasize balancing planning conservatism with practicality, avoiding unnecessary forecasting, and making decisions that support long-term retirement goals rather than reacting to headlines or uncertainty. Takeaways When spouses have similar Social Security benefits, but one spouse is significantly older, the older spouse often has the strongest case for delaying benefits until age 70 because that higher benefit is more likely to become the survivor benefit. Younger workers may not need to heavily discount future Social Security estimates because projected wage growth could offset a significant portion of any future benefit reductions. For retirees already near claiming age, assuming a 25% reduction in future Social Security benefits can be a reasonably conservative planning assumption. The eventual Social Security reform package is unlikely to rely solely on benefit cuts and will more likely include a combination of tax increases and benefit adjustments. The ”widow’s penalty” can significantly increase taxes for a surviving spouse because income often remains similar while tax brackets and Medicare thresholds become less favorable. Potential future tax increases and the widow’s penalty are both compelling reasons to consider Roth conversions even when current projections suggest little immediate tax benefit. High-fee variable annuities should be evaluated carefully, especially to determine whether valuable income guarantees justify the ongoing costs. If guaranteed income sources such as pensions and Social Security already cover essential expenses, a variable annuity can potentially serve as a bridge strategy to delay Social Security benefits. When selling investments from a taxable account, maintaining the portfolio’s target asset allocation is generally more important than trying to predict which investments will perform best or worst next. Tax-efficient selling decisions often come down to managing capital gains by choosing whether to realize gains from low-basis or high-basis shares depending on the investor’s broader tax situation. Chapters 00:00 Social Security Strategies for Couples 06:28 Concerns About Social Security Reliability 10:16 Planning for Future Social Security Benefits 13:20 Roth Conversions and Tax Planning 18:18 Evaluating Variable Annuities 22:24 Taxable Account Management Strategies 25:05 Maintaining Asset Allocation Discipline 27:53 Tax Considerations in Asset Sales Links 📘 New Release: The Retirement Planning Guidebook (3rd Edition) Wade Pfau’s must-read Retirement Planning Guidebook just got even better. The 3rd Edition is now available and packed with the latest updates to help you design your retirement strategy with confidence. Grab your copy on Amazon or your favorite book retailer: https://books2read.com/Retirement This episode is sponsored by McLean Asset Management. Visit https://www.mcleanam.com/retirement-income-planning-llm/ to download McLean’s free eBook, “Retirement Income Planning”

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How long is this episode of Retire With Style?

This episode is 30 minutes long.

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This episode was published on June 16, 2026.

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In Part 2 of this Live listener Q&A episode, Wade Pfau and Alex Murguia tackle several retirement planning topics, including Social Security claiming strategies for spouses with age differences, how younger workers should think about Social...

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