When Should You Start Medicare? 

Welcome to the "New to Medicare" Bootcamp!

If you’re feeling overwhelmed by Medicare like it’s a whole new language, you’re in the right place.

This blog series is part of my New-to-Medicare Bootcamp, a step-by-step guide I created to help you finally make sense of Medicare without the stress, confusion, or late-night Googling.  It’s designed especially for people who are brand new to Medicare,  and trying to plan ahead the easiest way possible.

Each post walks you through key piece(s) of the Medicare puzzle, in the right order, so you can understand how it all works and make confident choices for your health coverage.

Today’s post (Day 1) is all about figuring out when you should actually sign up for Medicare. Spoiler alert: it’s not the same for everyone.

Let’s Clear Up the Confusion Around Turning 65

Turning 65 is a big milestone, but it doesn’t automatically mean you need to sign up for Medicare right away.

Here’s when you do need to sign up at 65:

• You’re not working anymore (or your're not on your spouses work insurance).
• Your employer has fewer than 20 employees.
• You don’t have other current job-based insurance.

Here’s when you might be able to wait:

• You (or your spouse) are still working and have health insurance through a current employer with 20+ employees (or your spouse's).

But here’s the kicker… it has to be active job-based insurance.

 Other types of insurance such as COBRA, retiree insurance, or Marketplace plans (like Obamacare) don’t count. These won’t protect you from late penalties if you delay Medicare.

Why Your Medicare Timeline Is Personal

When it comes to Medicare, everyone’s situation is a little different.

That means your timeline might look totally different from your friend, neighbor, or spouse.

A few things that affect when you should enroll:

• Are you still working?
• Is your spouse still working and you are enrolled in their employer plan?
• Are you already collecting Social Security?
• How big is the company providing your health insurance?

All of these factor into when and how you sign up. If you get the timing wrong, you could end up with late penalties or gaps in coverage.

What About Social Security?

People often assume that if they’re already collecting Social Security, Medicare will just start automatically and that’s actually true!

• If you’re already collecting Social Security before 65, your Medicare card will show up in the mail a few months before your birthday. You’re all set unless you want to delay Part B (more on that below).

• If you’re not collecting Social Security yet, you have to actively enroll. Nothing will happen automatically.

You’ll go to ssa.gov and click “Sign Up for Medicare” on the homepage.

Easy peasy once you know what to do.

Two Real-Life Examples

Let’s walk through two scenarios to show how personal your timeline really is:

🧑‍💼 Example 1: Jane, Turning 65 in September

She’s not collecting Social Security yet and doesn’t have job-based insurance.

• Jane can apply for Medicare starting June 1  (3 months before her birthday month).  Her coverage would start September 1.

👩‍❤️‍👨 Example 2: Susan, Also Turning 65 in September

But Susan has health insurance through her husband’s employer.

• She can choose to delay Medicare Part B, sign up for free Part A now, and then enroll in Part B when her husband retires. She’ll need to fill out a few forms to prove she had job-based coverage.

The Pitfalls You Really Need to Avoid

If you take anything away from today, make it this:

Not all insurance is created equal when it comes to delaying Medicare.

Here’s what doesn’t count as safe coverage if you’re trying to delay Medicare:

• COBRA – It’s not considered active job-based insurance.
• Retiree Insurance – Same issue. It’s not tied to current employment.
• Marketplace Plans (ACA) – As soon as you’re eligible for Medicare, you lose the subsidy.  If you keep it, you could be forced to pay it back or your plan could cancel.

Even if those plans seem “good enough,” Medicare sees it differently, and the penalty for getting it wrong can follow you for life.

Need Help Figuring Out Your Timeline?

That’s what I’m here for.

If you’re unsure when to sign up or what kind of coverage you can keep, I offer free one-on-one calls where we map out your personal Medicare timeline together.  I’ll help you avoid the traps and get everything done in the right order.

And if you're the DIY type, I created a full Medicare Roadmap Workbook that walks you through this first step in more detail:

What’s Next: Day 2 Is Ready for You!

If you’ve got a better handle on your Medicare timeline now - yay! That’s a huge first step. 🥳

Ready to keep going?

👉 Click here to dive into Day 2 of the Bootcamp

In that post, we’ll talk about what Medicare actually costs, (such as how much you’ll pay each month for Parts A and B), what drug plans run, and what to expect if you choose a Medigap or Advantage plan. We’ll also talk about the penalties you want to steer clear of (because yep, they’re real).

See you over there!