Enrolling in Medicare While Working

Turning 65 doesn't mean you have to retire, and it doesn't necessarily mean you have to enroll in Medicare right away. If you are still working and have health insurance through your employer, you have options. But making the wrong move can lead to lifetime penalties or gaps in coverage. We are here to give you straight answers, no surprises, so you can protect what you've earned.

The most important factor in deciding whether to enroll in Medicare while working is the size of your employer. The rules change depending on whether your company has 20 or more employees, or fewer than 20 employees.

If your employer has 20 or more employees, your group health plan pays first. Medicare pays second. In this situation, you can usually delay enrolling in Medicare Part A and Part B without facing a late enrollment penalty later. Many people choose to enroll in Part A (hospital insurance) because it is premium-free for most people who have worked at least 10 years and paid Medicare taxes. However, if you have a High Deductible Health Plan (HDHP) and want to continue contributing to a Health Savings Account (HSA), you should not enroll in any part of Medicare, including Part A. Once you enroll in Medicare, you can no longer contribute to an HSA.

If your employer has fewer than 20 employees, Medicare pays first. Your employer's group health plan pays second. In this case, you generally need to enroll in both Medicare Part A and Part B when you turn 65. If you don't, your employer plan might not pay for services that Medicare would have covered, leaving you with the bill.

When you eventually retire or lose your employer coverage, you will be granted a Special Enrollment Period (SEP). This period lasts for eight months, starting the month after your employment ends or your group health plan insurance ends, whichever happens first. During this SEP, you can enroll in Medicare Part A and Part B without a late enrollment penalty.

Remember, the Medicare decision is fundamentally about choosing between two paths, not two products. You are deciding between Traditional Medicare (Parts A and B) and Medicare Advantage (Part C). If you choose the Traditional path, you will likely want to add a Medicare Supplement (Medigap) plan to fill the gaps, and a standalone Part D plan for prescription drugs. If you choose Medicare Advantage, you are opting for a private plan that replaces your Traditional Medicare benefits and usually includes drug coverage. The supplement decision comes AFTER you choose Traditional Medicare - it's a component of the Traditional path, not an alternative to Advantage.

Navigating Medicare while working can be complex, but you don't have to do it alone. We are on your side of the table, ready to walk you through every option.