The Association for Consulting Expertise tackles the thorny issue of Medicare costs in retirement.
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Q: Will selling my business affect the cost of my Medicare in retirement?
ACE replies: Yes, it absolutely can — depending on how much you sell it for and when the sale occurs, especially if it’s after age 63.

It’s not uncommon for business owners to fund retirement through the sale of their business. However, large gains can lead to unexpected Medicare costs down the road due to what’s known as the income-related monthly adjustment amount. Medicare looks at your taxable income from two years prior to determine your premiums for Part B (doctor coverage) and Part D (prescription coverage).
This can result in a significant increase. For example, monthly Part B premiums can rise from about $185 to as much as $628.90, and Part D can increase by up to $85.50 — per person, if married.
The good news is Medicare allows for an appeal if a qualifying life event occurs, such as retirement or work reduction. By filing Form SSA-44 with the Social Security Administration, you may request that they base premiums on your current or last year’s income instead of two years ago.
If you sold your business in 2023 for $250,000 and retired, you would face higher premiums in 2025. However, since retirement qualifies as a life-changing event, you could file SSA-44 to have those premiums adjusted based on your potentially lower retirement income.
Important distinction: Selling your business alone is not a qualifying event. Retirement is. If you sell your business while on Medicare and do not retire or have any life-changing events, then you will owe the increased Medicare premiums for that year.
In summary, Medicare premiums are income-based, and large sales can trigger increases. Retiring after the sale may allow for an appeal through proper documentation.
ACE member Brianna Henward is an independent insurance advisor and owner of Tindon Associates. She specializes in Medicare plans and planning, the Affordable Care Act and the Maine Health Insurance Marketplace. She can be reached at brianna@tindon.us or (207) 248-8411.