Health Insurance for Early Retirees (Bridging to Medicare)
Challenges of Retiring Before 65
Many Americans are retiring before they’re eligible for Medicare, but losing employer health coverage creates a gap that can be costly and stressful. COBRA or retiree plans from your last job might be available, but these are usually expensive and only last 18-36 months. Without a plan, you could face high premiums on the individual market, or even risk going uninsured. Navigating this period requires careful planning to avoid surprises and coverage lapses. Understanding all your options is key to enjoying your early retirement with confidence.
Controlling Costs in Early Retirement
We believe in a holistic approach—helping you lower premiums without exposing you to big risks. You might be able to use HSA funds saved from your working years, or pair a high-deductible plan with cash reserves to keep monthly costs down. We discuss the pros and cons of part-time work with benefits, but our main focus is on building an insurance plan that fits your unique goals. We’ll also help you adjust coverage as your income, health, or state laws change. Our aim is to give you peace of mind and more control over your retirement budget.
Coverage Options for Ages 60–64
COBRA or Employer Retiree Plans
If you’re eligible, these plans let you continue the coverage you had at work. They’re usually easy to set up and provide comprehensive benefits, but costs can be significantly higher than what you paid as an employee and coverage doesn’t last until 65 for most people.
ACA Marketplace Plans
Health plans through the Affordable Care Act (ACA) marketplace are available to all, regardless of health status. They’re comprehensive, but premiums can be steep for early retirees who don’t qualify for income-based subsidies—assets and part-time income may affect eligibility for savings.
Alternative Plans (Indemnity/Short-Term)
True North Associates often helps early retirees explore short-term health insurance or indemnity plans. These options can offer much lower monthly costs, flexible enrollment, and coverage tailored to your situation. Combining these with supplemental policies can help you stay covered until Medicare begins.
How True North Associates Can Help
Our process starts by evaluating your health needs, medications, travel, and budget to find the right mix of coverage. We explain every option in plain English, from short-term medical to pairing indemnity plans with accident or critical illness insurance for extra protection. For many clients, we sequence several short-term plans to create a “bridge” right up to Medicare eligibility. As your needs or the insurance landscape changes, we adjust your strategy and manage transitions for you. When you approach 65, we seamlessly move you into the best Medicare solution.


Frequently Asked Questions About Early Retiree Health Insurance
Can I get a policy now that will automatically carry me until Medicare?
There isn’t one single “bridge” policy that lasts until age 65, but we can build a strategy that connects several options for seamless coverage. Typically, this means using a series of short-term or indemnity plans, renewing as needed. When you reach Medicare age, we help you switch to the best Medicare plan with no lapse in protection. You’ll always know what’s next with our guidance.
What if I develop a health condition before 65? Will these plans cover me?
Short-term and indemnity plans generally don’t cover pre-existing conditions at renewal, but the ACA marketplace is always an option during Open Enrollment or with a qualifying event. If your health changes, we help you transition to the plan that offers the best protection for your new needs. You’ll never be left without a path to coverage. Our job is to adapt your plan as life changes.
How much should I budget for health insurance between retirement and Medicare?
Costs vary widely depending on your age, state, and health status, but early retirees can expect premiums anywhere from a few hundred to over a thousand dollars per month. We help you compare every option and look for strategies—like using HSA funds or picking the right deductible—to lower your out-of-pocket spending. Our approach is always focused on your long-term financial security. You’ll have a realistic plan for every stage.
Secure Your Health Coverage—Enjoy Your Retirement
Bridging the gap to Medicare doesn’t have to be overwhelming. True North Associates simplifies the process, helping you avoid coverage gaps and unnecessary costs. With the right insurance plan, you can relax and make the most of your early retirement years. Let us guide you every step of the way.
Ready to Build Your Bridge to Medicare?
If you’re retiring before 65 and want expert help with your health insurance options, schedule a conversation with True North Associates. We’ll find the best strategy to carry you confidently to Medicare—so you can focus on living well.
