Every year I watch incredibly organized people do something completely irrational.
They'll spend months researching a new car.
Weeks planning a vacation.
Hours reading Amazon reviews for a $30 coffee maker.
Then Medicare and Marketplace Open Enrollment arrives and suddenly their strategy becomes:
"Eh, I'll look at it later."
Three weeks later:
"Wait, when's the deadline again?"
Healthcare planning has somehow become the financial equivalent of Christmas shopping at 8:00 PM on Christmas Eve.
Everyone knows it's coming.
Everyone has plenty of warning.
And somehow, it still sneaks up on people.
The Real Plot Twist
Most people think Open Enrollment is about health insurance.
It isn't.
It's about avoiding surprises.
Because every year something changes.
A plan changes.
A carrier leaves the market.
A prescription costs more.
A doctor moves networks.
A premium shifts.
And suddenly the coverage that worked perfectly this year may not be the best fit next year.
Nobody likes surprises.
Especially the expensive variety.
Why We Start These Conversations Early
One of the biggest misconceptions we see is that healthcare decisions happen separately from financial planning.
They don't.
Healthcare affects retirement income.
It affects cash flow.
It affects spending plans.
It affects tax strategies.
In some cases, it affects whether someone feels comfortable retiring at all.
When someone tells us they're planning to retire before age 65, we immediately start talking about Marketplace coverage.
When someone leaves an employer plan, we discuss COBRA options.
When someone turns 65, Medicare becomes part of the planning conversation.
Because healthcare isn't a side quest.
It's part of the main story.
A Few Dates Worth Putting on Your Calendar
And unlike your gym membership, these deadlines won't let you "start fresh next month."
Marketplace Open Enrollment
- Opens November 1
- Closes December 15
One thing people often find surprising:
Plan details and pricing won't be available until November 1.
Until then, estimates can help provide a general idea of costs, but final pricing isn't released until enrollment begins.
For anyone currently on COBRA, this is an important opportunity to evaluate whether Marketplace coverage makes sense moving forward.
Medicare Open Enrollment
Part D Drug Plan Reviews
- Preview Window: October 1 - October 14
- Enrollment Window: October 15 - December 7
If you've added medications, changed prescriptions, or simply haven't reviewed your drug plan in a while, this is one of the most important reviews of the year.
Medicare Advantage
This is when eligible Medicare beneficiaries can enroll in or switch Medicare Advantage plans.
Medicare Supplement
Many people expect a lengthy annual review for their Medicare Supplement coverage.
In many cases, the review looks something like this:
"Still have the plan?"
"Yep."
"Still paying the premium?"
"Yep."
"Perfect. Let's grab lunch."
It's the least dramatic conversation in healthcare.
And we're all thankful for it.
What People Usually Get Wrong
The biggest mistake isn't choosing the wrong plan.
The biggest mistake is waiting until the deadline is staring back at you.
The earlier someone starts the process, the more questions can be answered thoughtfully.
The later they wait, the more the conversation turns into a game show.
"Let's see what's behind Door Number Three!"
That's rarely the planning strategy we're aiming for.
Final Thought
The best healthcare decisions are usually not made under pressure.
They're made with enough time to review options, ask questions, compare costs, and understand how those decisions fit into the bigger financial picture.
If you're approaching Medicare eligibility, considering retirement, leaving employer coverage, reviewing Marketplace options, or simply wondering whether your current plan still makes sense, now is a great time to start the conversation.
Because when it comes to Open Enrollment, being early may not be exciting.
But it's a lot more fun than explaining on December 10th why we should have talked on October 10th.
Need help sorting through Medicare or Marketplace options?
We help clients coordinate healthcare decisions with retirement, tax, and income planning every year.
Reach out if you'd like a second opinion before enrollment deadlines arrive. Your future self will thank you. And unlike your holiday shopping habits, this is one area where procrastination doesn't usually come with free shipping.