Retirement
Retirement Planning Before Medicare
Retiring before 65 adds two constraints that later retirees never deal with: health insurance you have to buy yourself, and limited access to your own retirement accounts.
Get the income planning right in these years and you can pick up ACA subsidies and cheap Roth conversions at the same time. Get it wrong and you can lose thousands to a subsidy cliff you never saw.
What the article covers
- The two big constraints before 65: health coverage and account access
- Understanding your health insurance options and the ACA subsidy structure
- Withdrawal order before 65, including what unlocks at 55 and at 59 and a half
- Why age 63 is when IRMAA starts to matter
- Managing income around the ACA cliff in practice
- Social Security timing decisions
- Roth conversions during the early retirement window
- The key planning numbers for 2026 and what changes at 65
Key takeaways
- 1The years between your last paycheck and 65 are usually the best Roth conversion window you will ever get.
- 2ACA subsidies make your taxable income a health insurance decision, not just a tax decision.
- 3Withdrawal order before 65 is constrained by age rules, so plan the sequence in advance.
Who this is for: Anyone planning to stop working before age 65.
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