01
Claiming Social Security too early while still working
If you claim before full retirement age and continue working, Social Security can reduce your benefit by $1 for every $2 you earn above the annual limit. That money is not lost forever, but most people do not know that, and the short-term cut can catch them completely off guard.
02
Missing your Medicare enrollment window
You have a 7-month window around your 65th birthday to enroll without penalty. Miss it and you pay a 10 percent premium penalty for every 12-month period you were eligible but did not sign up, for life.
03
Not planning for IRMAA before a big income year
A Roth conversion, home sale, or RMD can spike your income and push you into a higher IRMAA bracket two years later. Planning ahead can save hundreds of dollars per month in Medicare premiums.
A Story Worth Reading Before You Turn 65
Janice and Charles did everything right.
Except this one thing.
Janice and Charles had been planning their retirement for years. Charles was 63. Janice was 61. They had built up a solid traditional IRA and a healthy 401(k). Their financial advisor suggested converting some of that money to a Roth IRA before retirement, so they would have tax-free income later. It made sense on paper. So over two years, they converted a combined $180,000.
What nobody told them was that those conversions would show up as ordinary income on their tax returns. Two years later, when Charles enrolled in Medicare at 65, the Social Security Administration looked at his 2024 return and saw household income well above $218,000. The standard Part B premium for 2026 was $202.90 per month. Charles got a letter saying he would be paying $405.80 instead, and that a Part D surcharge would be added on top of that. Between the two of them, they were paying an extra $4,800 a year in Medicare premiums for two years because of a tax move made at age 63.
They were not doing anything wrong. Roth conversions are a legitimate strategy. But the timing created a two-year premium spike neither of them saw coming. By the time the letter arrived, there was nothing to appeal because their income really had been that high.
The two years before you turn 65 are the years that set your Medicare premiums. A large IRA distribution, a Roth conversion, a home sale, or a stock liquidation in that window can push you into an IRMAA tier that costs hundreds of dollars per month once you enroll. Use the calculator above to see where you stand, and call Thomas before you make any big income moves in those years.