08/31/2026
Here's a retirement surprise nobody warns you about: your Medicare premiums are generally based on your tax return from TWO years ago. π
It's called the two-year lookback β and it's why a Roth conversion, a big capital gain, or an IRA withdrawal today can quietly raise your Medicare costs down the road, long after the decision is made.
By the time the premium increase shows up, the transaction is long finished β and the connection isn't obvious.
The fix? Multi-year planning. Retirement isn't one tax year at a time; it's a series of interconnected years.
If you're approaching Medicare or making decisions about Roth conversions, withdrawals, or Social Security, now is the time for a retirement tax planning conversation.