Your Money Guide on the Side 4 Tax Moves That Can Save You 6 Figures - Part 2 of 2
Oct 20, 2025
In this insightful discussion, discover why HSAs are a hidden gem for retirement savings with triple tax benefits. Learn how the timing of claiming Social Security can dramatically impact what you owe the IRS. Explore the flexibility of donor-advised funds for generous giving, and how charitable strategies can lower your tax bracket. Uncover gifting techniques that help move wealth to the younger generation while minimizing taxes. This comprehensive toolkit empowers you to keep more of your hard-earned money as you navigate your 50s.
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Turn Your HSA Into A Stealth Retirement Fund
- Max out an HSA and invest the balance instead of spending it on routine medical costs.
- Keep receipts so you can reimburse yourself tax-free decades later and treat the HSA like a stealth retirement account.
HSA Becomes IRA-Like After 65
- After 65 HSA withdrawals for non-medical uses are taxed like IRA withdrawals but carry no penalty.
- That makes the HSA behave as either a turbocharged Roth or an IRA in retirement depending on usage.
Model Social Security Timing With Taxes
- Model Social Security claiming ages and include tax effects using the SSA calculator and tax projections.
- Use pre-Social Security years for Roth conversions or IRA drawdowns to reduce future provisional income and taxes on benefits.