MARK KOHLERMain Street Professionals, Main Street Professionals, Main Street Professionals, Main Street Professionals, Main Street Professionals, LLC · Owner at Main Street Professionals, LLC

The Medical Write-Off Strategy Most People Miss

16 Feb 2026 · 1 min

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Mark Kohler shows how people on Medicare can still use HSAs to their advantage. Pay medical bills out of pocket, keep detailed records, then reimburse yourself from the HSA tax-free later, even years down the line. Your money keeps growing in the account while you decide when to withdraw.

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When you reach Medicare age you can no longer put new money in and take a tax deduction. The HSA becomes one of the most powerful and if you're building that account and growing it and keeping receipts of what you might spend with your medical expenses, you can pile those up and reimburse yourself three years from now. It doesn't matter. You just pay for those expenses out of your pocket, keep a ledger of all those medical expenses and reimburse yourself at the end of the year or many years to come and just drain that account tax free whenever you want. That way you can let the investments continue, continue to grow, keep track of your medical expenses and pull out the money when it's most advantageous to you. Now the key there is documentation and timing, not urgency. Try to keep your best records on your medical expenses. Put it in a digital file somewhere and then when that time comes write yourself a check tax free.