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Senior professional planning Medicare transition after age 65

Working Past 65 in Vancouver? Your Guide to Medicare and Employer Coverage

By Timothy Jones••10 min read

One of the most frequent questions I get from seniors in Vancouver and Clark County isn't just about which plan to pick. It's more fundamental: "I'm still working and I'm past 65. What do I do before I quit?"

If you're one of the thousands of Americans choosing to stay in the workforce longer, the "Traditional Medicare" timeline doesn't always apply to you. Navigating the transition from employer group coverage to Medicare requires precision. A single missed form or delayed application can lead to lifetime penalties and gaps in coverage.

Step 1: Size Matters (Employer Group Size)

The first thing we look at is how many people work at your company. This determines who pays first—your insurance or Medicare.

20+ Employees

Your employer insurance is "Primary." You can usually delay Medicare Part B without penalty as long as your coverage is considered "creditable."

Fewer than 20 Employees

Medicare is "Primary." You must sign up for Medicare when you turn 65, or your group plan may refuse to pay its portion of your medical bills.

The "Must-Have" Form: CMS-L564

When you finally decide to hang up the hat and retire, Social Security needs proof that you had "creditable coverage" since you turned 65. This is where Form CMS-L564 comes in.

Tim's Advice: Don't wait until your last day to get this form signed. Have your HR department complete their section 2-3 months before your planned retirement date.

The 8-Month Window (The SEP)

Once your employment ends (or your group coverage ends—whichever happens first), you have an 8-month Special Enrollment Period (SEP) to sign up for Medicare Part B without a late enrollment penalty.

⚠️ WARNING: COBRA coverage does NOT count as creditable coverage for Part B enrollment. If you take COBRA and wait more than 8 months to get Part B, you will likely face a lifetime penalty.

Your Retirement Checklist

  • 01
    3 Months Out: Contact the Social Security Administration or call me to verify your "Initial" vs "Special" status.
  • 02
    2 Months Out: Get your employer to sign CMS-L564 and submit your Part B application (Form CMS-40B).
  • 03
    1 Month Out: Finalize your plan choice—Medicare Advantage or Medicare Supplement (Medigap).

Let's Plan Your Exit Strategy Together

Transitioning off a company plan is complex. I specialize in helping Vancouver professionals move from work coverage to Medicare without the stress.

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