“I’d love to retire… but I’m not 65 yet. I need my employer’s health insurance.”
Have you ever said that?
On the surface, it sounds responsible.
Practical. Mature.
But here’s the uncomfortable truth:
That belief is keeping a lot of people working five, ten, even fifteen years longer than they actually need to.
Let’s be clear.
Health insurance absolutely matters.
The lie isn’t that insurance is important.
The lie is that you can only get it through your employer — and that Medicare is the gatekeeper to your retirement.
It’s not.
Why This Fear Feels So Real
Employer coverage feels safe.
You know the premium.
HR handles the details.
You don’t have to shop for plans or compare options.
And yes — health insurance is expensive. A bad year without proper coverage can derail a budget quickly.
But here’s the key shift:
Health insurance is an expense.
It’s not a retirement blocker.
A Real Example: Carl and Sally
Carl is 58. Sally is 59.
They’ve saved well.
They’ve invested consistently.
They even downsized their home to free up more liquid assets.
On paper, they’re in a strong position.
But they feel stuck.
Why?
Because they believe they need to work until 65 for Medicare.
When we ran their plan assuming they worked until 65, their portfolio grew significantly. In fact, they’d likely end up with far more than they’d ever realistically spend.
But that wasn’t their goal.
Their goal was freedom.
So we tested something different.
What Happens If They Retire Now?
We modeled retirement immediately — six to seven years earlier than planned “The Biggest Retirement Lie_ ‘I….
The result?
Their probability of success barely changed.
Yes, they’d have slightly fewer dollars at the end of life. But their plan was still extremely strong.
Then we added the missing piece:
$40,000 per year for private health insurance coverage until Medicare kicks in “The Biggest Retirement Lie_ ‘I….
That’s not a small expense.
But even with that included, their plan still worked.
Health insurance wasn’t the dealbreaker.
It was just another line item.
The Real Cost of Waiting
If health insurance costs $40,000 per year, that’s a visible cost.
But what’s the invisible cost?
Six to seven years of:
- Energy
- Mobility
- Flexibility
- Time
Those pre-65 years are often the healthiest and most active years of retirement.
When people say they “can’t retire,” what they often mean is they haven’t run the numbers correctly.
So What Are Your Options Before 65?
If you leave your employer before Medicare eligibility, you still have coverage options.
Here are a few common paths:
1. COBRA
You can temporarily continue your employer’s coverage — just without the employer subsidy.
It’s more expensive.
But it’s straightforward.
2. ACA Marketplace Plans
Depending on your income and state, marketplace plans can be surprisingly viable.
This is where coordination between tax planning and insurance planning really matters.
3. Private or Cost-Sharing Plans
In certain situations, private plans or cost-sharing networks may make sense.
Each option has trade-offs. None are “perfect.” But they exist.
And that changes the conversation.
A Bonus Option: Shift, Don’t Quit
Not everyone needs to go from full-time to fully retired overnight.
Another option?
Move to part-time work.
Take a lower-stress role.
Consult.
If that preserves coverage and reduces pressure, that might be the right bridge.
Retirement doesn’t have to be binary.
Medicare Isn’t the Requirement. A Plan Is.
This is the real takeaway.
Medicare isn’t what allows retirement.
A plan does.
A plan that factors in:
- Investment strategy
- Withdrawal timing
- Tax coordination
- Healthcare costs
- Contingencies
When health insurance is modeled correctly, it becomes manageable.
When it’s feared abstractly, it becomes paralyzing.
Money Is a Tool. Use It.
You worked hard to build your assets.
Don’t let a misunderstanding about health coverage delay the life you want to live.
If your plan works — even after accounting for insurance — the question shifts from:
“Can I afford to retire?”
To:
“Why am I waiting?”
Want to Know If This Applies to You?
Every situation is different.
Your assets.
Your state.
Your income.
Your health history.
If you’re wondering whether Medicare is truly the gatekeeper — or just a mental barrier — let’s run the numbers properly.
At Root, we build plans that integrate healthcare planning with your full retirement picture.
If you’d like clarity on whether you can step away before 65 — without putting your future at risk — you can schedule a call with our team.
No pressure.
Just a conversation.
👉 Schedule a call and see what retirement on your terms actually looks like.works harder for your life, not the IRS.
The information presented is for educational and informational purposes only and should not be construed as personalized investment or financial advice. The content discusses general retirement planning strategies and is not intended to recommend any specific course of action for any individual.
Social Security claiming strategies involve a number of variables, including life expectancy, portfolio returns, tax considerations, and personal circumstances. Decisions regarding Social Security benefits should be made in consultation with your financial advisor, taking into account your full financial picture.
Examples provided are hypothetical and for illustrative purposes only. They do not reflect any specific client situation and should not be relied upon for investment decision-making. Past performance of investments is not indicative of future results. All investing involves risk, including the potential loss of principal.
Root Financial Partners, LLC provides tax planning as part of its financial planning services. However, we do not provide tax preparation services, represent clients before the IRS, or offer legal advice.
Clients should consult their CPA or attorney before implementing any tax or legal strategies discussed. Nothing in this video should be interpreted as a recommendation to take a specific tax position or legal action.
This content may include discussions around advanced financial planning strategies such as Roth conversions, backdoor Roth IRAs, tax loss harvesting, charitable giving, estate planning tactics, or Social Security claiming strategies. These concepts are general in nature and are not personalized advice. Actions related to these strategies may trigger tax consequences or legal implications. Always consult with your CPA or attorney to assess suitability based on your personal financial circumstances.
Suitability for these strategies depends on your individual tax situation, income, age, investment profile, estate plan, and other factors. Actions related to these strategies may trigger tax consequences or legal implications. Always consult with your CPA or attorney to assess suitability based on your personal financial circumstances.