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Start retirement tax planning in your 50s to manage Medicare premiums

Financial advisor Sean Bailey advises early planning to optimize retirement savings and Medicare costs.

Oct 26, 2026, 4:38 PM By the Genius Eye newsroom (Finance Reporter) · Fact-checkedHow we report
Photo: Ajay Suresh / CC BY 4.0, via Wikimedia Commons

Sean Bailey of Bailey Wealth Services emphasizes the importance of beginning retirement tax planning in your 50s to help families retain more of their savings, according to heraldnet.com.

Medicare premiums are influenced by income from two years prior due to a two-year lookback rule, which can result in an income-related surcharge called IRMAA for some retirees.

Bailey, with over 35 years of experience, highlights that many people only start considering Roth conversions around age 63, but starting these conversions earlier, ideally in their 50s, allows for better tax management and potentially lower Medicare premiums.

A Roth conversion involves moving funds from a traditional IRA to a Roth IRA, with the converted amount taxed as income in the year of conversion. Spreading conversions over several years can help keep annual tax bills manageable and avoid increasing Medicare premiums.

Bailey’s work with educators, aerospace, and engineering professionals in Snohomish County has shown that early and informed planning can significantly impact retirement outcomes and costs.

He also notes that required minimum distributions add complexity to retirement tax planning, reinforcing the need to start conversations and strategies well before retirement age.

Sources
  1. heraldnet.com: Why your 50s are a smart time to plan for retirement taxes
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