I Thought Healthcare Would Keep Me Working Until 65. I Was Wrong.
- Jenny Blackmon
- Jun 6
- 5 min read
For years, I believed healthcare was the one thing standing between me and retirement.
Turns out, I “thought” I was afraid of healthcare costs. Instead, I learned I simply didn’t have the correct information, and my fear was based on my ignorance.
I Thought Healthcare Would Keep Me Working Until 65. I Was Wrong.
I have a confession.
For years, I used healthcare as my 2nd-favorite excuse, behind not having that million-plus dollars every time I need first.
I didn’t use it intentionally; it was just a runner-up I hadn't fully looked into yet.
Not because I was trying to avoid making a decision.
But every time I started thinking seriously about leaving full-time employment, healthcare would show up like some giant monster hiding in the closet.
"What about insurance?"
"What if something happens?"
"What if one diagnosis wipes us out?"
"What if I retire and discover I made the biggest mistake of my life?"
Sound familiar?
If you're a Gen Xer, especially a woman over 50, you've probably had some version of that conversation with yourself.
I know I have.
Healthcare wasn't just another expense in my mind.
It was THE expense.
The one thing I believed could destroy every retirement plan I'd spent years trying to build.
The funny thing?
I never actually sat down and figured out what it would cost.
I was afraid of a number I didn't even know.
And that's where a lot of us get stuck.
We Have Been Scared By Stories
Every family has one.
A cousin.
A neighbor.
A friend of a friend.
Social Media Doom Scrolling!
Somebody who had a medical event, and suddenly the story turns into a financial horror movie.
We've heard those stories our entire lives.
The problem is we hear the stories.
We don't hear the numbers. We don't hear the details. We don't hear the planning that happened before or after.
We just hear the scary ending.
After enough years of hearing those stories, healthcare becomes this giant mystery that we assume is impossible to manage.
So what do we do? We keep working.
Not because we need to. Not because we've run the numbers. Because we're afraid.
And there's a difference.
The Real Problem Was Ignorance
Now, before anybody gets offended by that word, hear me out.
Ignorance simply means lacking information.
That's it.
It doesn't mean you're stupid. It doesn't mean you're irresponsible.
It means you don't know what you don't know.
And that was me.
I knew enough about healthcare to be scared. I didn't know enough about healthcare to make a decision.
Big difference.
The more I started researching, the more I realized I had allowed fear to fill in all the blanks.
Fear is really good at that. Fear always assumes the worst-case scenario. Fear never runs a spreadsheet. Fear never gets quotes. Fear never compares options.
Fear just keeps you frozen.
Healthcare Is Bigger Than Insurance
One of the biggest surprises for me was realizing healthcare costs aren't just health insurance.
I used to think healthcare costs meant: Insurance premiums. Deductibles. Co-pays.
Done.
That's not the whole picture.
Healthcare includes:
Prescription medications.
Supplements.
Gym memberships.
Exercise programs.
Preventive care.
Dental work.
Vision expenses.
Everything you spend trying to stay healthy.
Once I started looking at the entire category, something interesting happened.
The mystery disappeared. I could actually see where the money was going.
And once you can see it, you can plan for it.
Stop Treating Healthcare Like A Monster
Here's what finally changed my perspective.
Healthcare isn't a monster.
It's a budget category.
That's it.
No different than housing. No different than groceries. No different than transportation.
Do I like paying for it?
No.
Do I wish it was cheaper?
Absolutely.
But wishing doesn't change reality.
Planning does.
When you know approximately what something costs, it stops feeling unpredictable.
The uncertainty is what creates anxiety.
Not the actual number.
The Question That Changed Everything
I stopped asking: "Can I afford healthcare?"
And started asking: "What does healthcare actually cost for me?"
And because I am before Medicare at age 65, my next question was:
“Are the youngest years of the rest of my life worth the money line item in my budget, or do I keep going to work knowing I am trading these years for that exact amount each month?"
That single question changed everything.
Because healthcare isn't one-size-fits-all. Your costs are different from mine. Mine are different from my husband's. Your neighbor's situation is different from yours.
The only numbers that matter are your numbers.
Once I accepted that, the research became easier.
The fear started shrinking.
And I stopped using healthcare as my reason for standing still.
Action Creates Clarity
I wish there was some magical calculator that would instantly tell us exactly what life will cost ten years from now.
There isn't.
But action creates clarity.
Every quote you gather creates clarity.
Every policy you compare creates clarity.
Every prescription you evaluate creates clarity.
Every question you ask creates clarity.
And clarity beats fear every single time.
What I'm Doing Now
Instead of treating healthcare as a giant unknown, I've started treating it like every other financial decision.
Research. Compare.
Budget. Adjust.
Repeat.
That's it.
Nothing glamorous.
Nothing exciting.
Just adulting.
The same thing we've been doing for decades.
The difference is I'm no longer allowing healthcare fears to make decisions for me.
I'm making decisions based on facts.
And facts are a lot less scary than imagination.
The Bottom Line
If healthcare is the reason you're delaying retirement, slowing down, starting a side hustle, or moving into your next chapter, do yourself a favor.
Stop listening to horror stories.
Start gathering information.
Run your numbers.
Price your options.
Ask questions.
Get educated.
You don't need every answer today.
You need enough information to make your next decision.
That's all.
For me, healthcare went from being the giant boogeyman hiding under the bed to something much simpler.
A line item.
An important line item.
But still just a line item.
And once I realized that, I stopped feeling trapped.
Maybe it's time you stop feeling trapped too.
Ready To Get Real Numbers Instead Of Healthcare Horror Stories?
If healthcare costs have been the thing keeping you stuck, you're not alone. I spent years believing healthcare was going to be the reason I couldn't leave full-time work.
Turns out, what I really lacked wasn't money.
I lacked information.
That's why I created two resources to help you stop guessing and start planning.
Start Here: Free Healthcare Planning Checklist
Before you spend another month worrying about healthcare costs, download the Healthcare Planning Checklist.
This free checklist walks you through:
• The questions you need to ask before leaving employer coverage
• The healthcare expenses most people forget to include
• Prescription cost planning
• Insurance research steps
• Healthcare budgeting categories
• Documents and information you need to gather now
The goal is simple: replace uncertainty with a plan.
Watch The Complete 7-Part Healthcare Series
If you're still sorting through the healthcare side of retirement planning, I've documented my own journey through this process in a seven-part video series.
Each video tackles a different piece of the puzzle:
• Why healthcare keeps so many women working longer than they want
• Healthcare myths that create unnecessary fear
• Prescription costs and the questions that can save you money
• Hidden healthcare expenses most people overlook
• Planning for real-life healthcare events
• Creating a healthcare budget you can actually live with
• Turning fear into a workable plan
The more information you gather now, the fewer surprises you'll face later.
Healthcare shouldn't be the reason you stay stuck.
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