Retiring Before 65? The Health Insurance Trap Most People Miss

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One of the biggest obstacles to retiring before age 65 isn’t your investments—it’s healthcare. Many people assume health insurance will be unaffordable once they leave an employer plan, so they keep working longer than they need to, even when the rest of their retirement plan is solid.

What most people don’t realize is that health insurance costs before Medicare are driven primarily by income—not net worth. Two retirees with the same savings can pay dramatically different premiums based on how their income is structured. That’s why early retirement healthcare planning is less about cutting spending and more about coordinating withdrawals, taxes, and timing.

I help retirees understand how Affordable Care Act rules, tax-efficient withdrawals, Roth conversions, HSAs, and short-term income planning can work together to keep premiums manageable while protecting long-term financial security. With the right structure, retiring before 65 doesn’t have to mean unpredictable or overwhelming healthcare costs.

If healthcare uncertainty is the only thing holding you back from retirement, this planning framework will help you see what’s actually possible—and how to approach early retirement with clarity instead of fear.









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