The Smart CEO’s Medicare Checklist: Stay Covered Without Missing a Beat

May 4

If you’re a business owner approaching 65, Medicare probably isn’t at the top of your to-do list. But here’s the reality: ignoring Medicare can lead to costly penalties, gaps in coverage, and unnecessary stress—none of which a smart CEO has time for.

Running a business means you're juggling payroll, operations, marketing, and growth. But as you transition into Medicare eligibility, it’s essential to understand your options and plan ahead, especially if you’re still working or providing coverage through your company.

This is where a smart CEO’s Medicare checklist comes in. With the right information and expert guidance, you can make confident, cost-effective decisions without disrupting your business or your life.

In this guide, we’ll walk through:

What every CEO needs to know about enrolling in Medicare
Key decisions to make around timing and coverage
How to stay insured without missing a beat

Ready? Let’s check off your Medicare to-do list.

1. Know When You’re Eligible—and Why Timing Matters

The first step in the smart CEO’s Medicare checklist is understanding your eligibility window. For most people, Medicare eligibility begins three months before your 65th birthday and continues for three months after (a 7-month Initial Enrollment Period).

But here’s where it gets tricky for business owners:
If you're still working and have coverage through your company—especially if your company has more than 20 employees—you may not need to enroll right away. But that doesn't mean you can ignore it entirely.

Failing to enroll in Medicare Part B on time could lead to:

Lifetime late enrollment penalties
Gaps in coverage
Claim denials if your employer plan doesn’t coordinate well with Medicare

🗸 Checklist Tip:
Talk to your benefits coordinator or insurance advisor to determine whether your employer plan qualifies you to delay enrollment. Or connect with Medicare and Money’s team for a personalized consultation.

2. Decide Which Medicare Parts You Actually Need

One of the biggest misconceptions is that Medicare is a single program. In reality, it's made up of multiple parts:

Part A (Hospital Insurance): Usually free if you’ve paid taxes for 10+ years.
Part B (Medical Insurance): Covers doctor visits, outpatient care, etc.
Part C (Medicare Advantage): Private plans that bundle Parts A, B, and often D.
Part D (Prescription Drug Coverage): Optional, but highly recommended.
Medigap (Supplemental Insurance): Helps pay what Original Medicare doesn’t.

As a CEO or entrepreneur, you’ll need to evaluate:

What coverage you already have through your business.
Whether you travel often or live in multiple states.
How often you use healthcare services.
If you want predictable out-of-pocket costs.

🗸 Checklist Tip:
Visit our Medicare 101 page to understand how each part works, or schedule a strategy session to get help customizing your plan.

3. Coordinate Medicare with Your Business Strategy

The smartest CEOs know how to align personal planning with business strategy. Your Medicare choices can directly affect your company’s operations, finances, and even your employees.

Key Considerations:

Will you stay on your company’s group plan?
If your company has fewer than 20 employees, Medicare may become your primary insurance—even if you keep your group plan.
Are you planning to retire, scale back, or sell the business?
Timing your Medicare enrollment with your exit strategy can save you thousands.
Do you offer health benefits to spouses or dependents?
Switching to Medicare might affect your family's coverage if they’re on your plan.
What tax and financial planning moves do you need to consider?
Medicare premiums can be based on income. High earners may face IRMAA surcharges.

🗸 Checklist Tip:
Consult your CPA, benefits broker, and a licensed Medicare advisor together. Or simplify the process by letting the Medicare and Money team walk you through it.

Bonus: Why CEOs Choose Professional Help

Let’s face it—navigating Medicare is a completely different world than group insurance, and the stakes are high. You’ve built your business by making informed, strategic decisions. Medicare should be no different.

Working with a Medicare specialist saves you:

Time (no more Googling Part B vs. Advantage plans at midnight)
Money (avoid penalties and pick plans that actually fit your budget)
Stress (get personalized support every step of the way)

At Medicare and Money, we’ve helped countless entrepreneurs make confident decisions so they can keep doing what they do best—running their businesses.

Your Smart CEO’s Medicare Checklist

Here’s a recap of what you need to keep in mind:

✅ Mark your Initial Enrollment Period
✅ Decide if you’ll delay or enroll in Part B
✅ Review your group insurance and how it interacts with Medicare
✅ Explore whether Original Medicare, Advantage, or Medigap works best
✅ Account for income, dependents, and travel needs
✅ Get expert help to avoid costly mistakes

Secure Your Health, Protect Your Business

Medicare isn’t just another box to check. For CEOs, it’s a strategic move that affects your health, wealth, and future plans. And just like any big decision in business, the more informed you are, the better the outcome.

You don’t have to navigate this alone. Let Medicare and Money be your trusted partner—so you stay covered, stress-free, and focused on your business.

🗓️ Ready to make Medicare make sense?
Schedule your consultation now and take the first step toward smarter coverage.

Carol Kaye