Your Money, Your Wealth

When Should You Take Social Security? (Don't Screw This Up) - 574

Mar 24, 2026
They debate when to claim Social Security for several couples with different ages, pensions, and savings. They tackle tradeoffs like lump-sum versus monthly pensions, Roth moves and tax timing. They clarify break-even misconceptions and stress recalculating claiming strategies as circumstances change.
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ADVICE

Delay Social Security For The Bigger Spouse Benefit

  • Do delay claiming Social Security for the higher-earning spouse when possible.
  • Big Al recommends husband wait to full retirement age while wife works to Medicare to maximize family benefit and reduce portfolio drain.
ADVICE

Use Side Gig Income To Bridge Retirement Gaps

  • Do consider working part-time or keeping a side gig to bridge income gaps before full Social Security and Medicare.
  • Joe and Big Al suggest husband keep his $50k side work to cover early shortfalls and make work optional.
ADVICE

Switch Retirement Contributions To Roth While In Lower Bracket

  • Do prioritize Roth contributions when in a low-to-moderate current tax bracket.
  • Big Al and Joe recommend converting or shifting future solo-401k and contributions to Roth while they're in ~12% bracket to lock tax-free growth.
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