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Retiring After 65? Medicare Checklist When Leaving Employer Coverage

by Joseph DeAngelis | Jun 2, 2026 | Medicare

Many people do not retire exactly at age 65. Some continue working until 66, 67, 68, or even later. Others remain covered under a spouse’s employer health plan. When retirement finally approaches, Medicare suddenly becomes a major decision. One of the most common...

Can I Contribute to an HSA After Enrolling in Medicare?

by Joseph DeAngelis | Jun 2, 2026 | Medicare, Medicare Blog

Can I Contribute to an HSA After Enrolling in Medicare? One of the most common surprises for people approaching Medicare eligibility is discovering that Medicare enrollment can affect their Health Savings Account (HSA). Many people continue working after age 65 and...

Leaving Employer Coverage for Medicare: A Step-by-Step Guide

by Joseph DeAngelis | Jun 1, 2026 | Medicare

One of the most common calls I receive is from someone who says: “I’m retiring soon. What do I need to do about Medicare?” Whether you’re retiring at age 65, 67, 68, or beyond, transitioning from employer coverage to Medicare is one of the most...

10 Medicare Mistakes I See Every Year

by Joseph DeAngelis | Jun 1, 2026 | Medicare, Medicare Advantage, Medicare Supplement

After helping Medicare beneficiaries for more than 42 years, I’ve noticed something interesting. The same Medicare mistakes happen year after year. Most people don’t make these mistakes because they’re careless. Medicare can be confusing, and many...

Medicare Part B Late Enrollment Penalty Explained

by Joseph DeAngelis | May 30, 2026 | Medicare, Medicare Blog

One of the most expensive Medicare mistakes a person can make is delaying Medicare Part B enrollment when they are required to enroll. Many Medicare beneficiaries assume they can sign up whenever they want. Unfortunately, that’s not always the case. If you miss...
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