The Early Retirement Secret: How to Quit Your Job and Find Affordable Health Insurance Outside of Your Employer

For years, I’ve worked with people who were ready to retire, but felt like they couldn’t.

Not because they lacked savings.

Not because they didn’t know what came next.

But because they were stuck on one question:

“What happens to my health insurance if I leave my job?”

For millions of Americans between 55 and 64, that’s the biggest unknown in their retirement plan. And that’s exactly why I call this the Early Retirement Secret.

Once you solve the healthcare piece, everything else starts to fall into place.

The Real Reason People Delay Retirement

If you’re in the pre-Medicare window, you’re not alone.

Nearly 40 million Americans are currently between the ages of 55 and 64, according to U.S. Census data, many of them financially prepared to retire, but unsure how to handle health insurance once they leave their job.

They’re not staying for the work, they’re staying for the coverage.

And it’s no wonder. Health insurance for early retirees can be shockingly expensive. Without an employer plan or strategy in place, premiums can easily climb into the thousands per month. Most people can’t afford to cover that out of pocket, at least, not for long.

But with the right healthcare strategy, you can make your exit with confidence. You don’t have to wait until 65 to start living the life you’ve planned for.

Why Healthcare Planning Trips People Up

Healthcare isn’t like other expenses. It’s complex, variable, and deeply personal. What you pay depends on where you live, how much you earn, your age, and the type of coverage you choose.

Here’s what complicates things for early retirees:

• You’re not old enough for Medicare.
• You may lose your employer plan suddenly.
• And you don’t want to gamble with bad coverage.

What most people don’t realize is how income can be strategically managed in retirement to lower premiums. Through the Affordable Care Act, many people qualify for Advanced Premium Tax Credits (APTC). These subsidies scale with your income, and they can dramatically reduce monthly costs.

We’ve worked with clients who expected to pay $1,200/month for a private plan. After running the numbers, they qualified for a high-quality marketplace plan at under $300. 

Same doctors. Same hospital network. Just a smarter approach.

How We’re Making It Easier to Retire

I’ve had this same conversation with hundreds of people, smart, financially prepared, ready to move on, but stuck because health insurance felt like a black hole. 

And I saw advisors struggling too, trying to help but lacking the tools to give clear answers.

That’s the problem we set out to solve when we built Move Health.

After nearly two decades in the healthcare and Medicare world, and training thousands of agents along the way, I knew there had to be a better way.

So we created a platform that helps financial advisors and their clients estimate healthcare costs quickly and accurately in early retirement. With just three key data points, our system delivers tailored plan options, real-time pricing, and actionable strategy in seconds.

That means no guesswork.

No waiting until 65.

And no staying in a job just to keep your insurance.

What to Consider Before You Leave Your Job

If you’re thinking about retiring soon, here are a few key healthcare decisions you’ll want to plan for:

• First, COBRA can be a helpful short-term bridge, but it’s usually more expensive than individual coverage. It may make sense if you’re mid-treatment or want to keep your current doctors, but many people find better value through ACA plans or off-market options.
• Second, pre-existing conditions aren’t a barrier. Under the ACA, insurers can’t deny you or raise your rates because of your medical history. You’ll be covered from day one.
• Third, if your income fluctuates through consulting work, capital gains, or retirement withdrawals, you’ll want to be strategic. Subsidies are based on taxable income, so how and when you draw funds can significantly affect your premiums.
• And finally, be sure to avoid coverage gaps. Timing matters. That’s why we work closely with advisors to line up enrollment dates and make sure your transition is seamless.

Early Retirement Is Closer Than You Think

If you’re between 55 and 64 and dreaming of what’s next, travel, starting a business, or just more time with family, you’re not alone.

You’ve put in the work. You’ve done the planning. And you shouldn’t have to stay in a job just to keep your insurance.

At Move Health, we help individuals and their financial advisors create personalized healthcare strategies, so people can retire earlier, with clarity and confidence. We’ve seen firsthand how the right plan can turn hesitation into momentum.

To be honest, the early retirement secret is just a conversation most people aren’t having.

But we are. And we’d love to have it with you.