When is a good time to start your Social Security?
David McKnight reveals why smart retirement planning means waiting until age 70 for reasons that have nothing to do with a bigger check… and everything to do with the years in between being your best window for Roth conversions.
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In this episode, David McKnight addresses one of the most common questions he gets from people approaching retirement: “When should I start taking Social Security?”
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David believes that there’s a compelling reason for having 70 as your default Social Security claiming age – and that isn’t so that you get a bigger Social Security check…
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One of the key reasons to wait until 70 is something that rarely comes up in the traditional Social Security discussion: it has to do with taxes.
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David stresses that the years between retirement and age 70 can be some of the most valuable years of your entire financial life.
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Why? Because they may represent your best opportunity to execute Roth conversions.
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David touches upon the so-called Retirement Income Valley and the benefits it brings about.
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With a wrong approach, you may lock yourself into a permanently smaller Social Security check, and may have caused much of that check to become taxable because you simultaneously do Roth conversions.
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David suggests a different approach: retiring, delaying Social Security, and spending the next several years aggressively repositioning your tax-deductible dollars to tax-free.
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Once all that heavy lifting is done, you can then turn on Social Security.
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By following that strategy you accomplish two things: you lock in a substantially larger Social Security benefit and potentially reduce the other income that could cause that larger benefit to become taxable.
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Remember: delaying Social Security doesn’t automatically make your Social Security tax-free.
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David talks about the IRMAA objection some may make as they hear his recommended strategy, and also touches upon his so-called “rip the band-aid off” approach to Roth conversions.
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David stresses that his interest isn’t in whether a Roth conversion causes you to pay an extra few thousand dollars in Medicare premiums in one particular year.
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What he’s interested in is whether the strategy reduces the total amount you pay in taxes and Medicare premiums over the balance of your retirement.
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“Social Security shouldn’t be thought of as an investment, it’s more like longevity insurance”, says David.
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According to the 2026 Social Security Trustees Report, the Retirement Survivors Trust Fund is projected to exhaust its reserves in 2032 if Congress does nothing.
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However, that doesn’t mean it’s going to disappear, ongoing payroll tax revenue would still be sufficient.
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If higher taxes ultimately become part of the solution, then that only reinforces the importance of getting to tax-free before that happens.
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Your goal shouldn’t simply be to maximize Social Security, it should be to maximize all of your after-tax streams of income.
Mentioned in this episode:
David’s national bestselling book: The Guru Gap: How America’s Financial Gurus Are Leading You Astray, and How to Get Back on Track
PowerOfZero.com (free video series)
@mcknightandco on Twitter
@davidcmcknight on Instagram
David McKnight on YouTube
2026 Social Security Trustees Report

