Health Insurance for Early Retirees (Ages 60–64)

Retiring before Medicare starts is exciting—but the coverage gap can be daunting. At True North Associates, we specialize in helping early retirees design a “bridge to Medicare” strategy, so you can leave work on your timeline without losing health protection. We compare COBRA, Marketplace, and alternative options to find the safest, most cost-effective path until you turn 65.

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Building Your Bridge: Timeline View

Your insurance needs will change between your retirement date and when you’re eligible for Medicare. We create a clear, step-by-step timeline: when current coverage ends, when to enroll in temporary or private plans, and how to transition seamlessly to Medicare. This personalized approach ensures you never risk a gap or overpay for coverage you don’t need.

Comparing COBRA, Marketplace, and Alternatives

Marketplace plans and COBRA are common choices, but they aren’t your only options. We’ll walk you through all available alternatives, including short-term medical and fixed indemnity plans, weighing each for cost, coverage limits, and what happens if your health changes before age 65. You’ll get a plan that matches your risk level, budget, and need for flexibility.

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Planning for What-Ifs

What if you develop a health condition before you’re eligible for Medicare? Our bridge strategy always includes backup routes—like enrollment rules for ACA plans and renewal details for private coverage. This way, you’re prepared for both the expected and the unexpected, no matter how your situation changes.

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Your Questions, Answered

  • What health insurance can I get if I retire before 65?

    Options include COBRA from your former employer, Marketplace coverage, and private plans like short-term or indemnity insurance. We’ll help you compare costs, coverage, and eligibility for each.

  • COBRA vs Marketplace—what’s better for early retirement?

    COBRA is usually more expensive but keeps your existing coverage; Marketplace plans may be cheaper with subsidies, but networks and coverage can differ. We break down the details and help you choose based on your specific needs and risk.

  • How do I cover the gap until Medicare starts?

    We build a timeline and coverage plan so you’re protected the entire way—from last day of employer coverage to your first day on Medicare, with no gaps in between.

  • What if I develop a condition before 65?

    If your health changes, we explain how and when you can transition to a new plan or use special enrollment periods. We make sure you always have a fallback route.

Retire Early Without the Coverage Guesswork

Enjoy the freedom of early retirement—without worrying about your health insurance. Book your “bridge to Medicare” review, and get a strategy that’s built for both your current life and whatever comes next.