Guidance for people turning 65 and enrolling in Medicare for the first time. Learn about eligibility, enrollment periods, plan options, costs, and how to avoid common mistakes.
Turning 65 + Still Working The right answer depends on your employer size, your coverage, and whether you contribute to an HSA. Hereās how to avoid costly mistakes and permanent penalties. Quick navigation Do I have to enroll in Medicare at 65 if Iām still working? Medicare doesnāt automatically know youāre working The 20-employee rule … Read more
The One Medicare Decision You Can’t Undo Later | Eligry LLC C Cindy Licensed Independent Medicare Advisor Ā· Eligry LLC Ā· February 2026 7 min read “What happens if your health changes?” That was the question my older sister asked me when I was turning 65. It’s the question most people never ask ā and … Read more
Medicare Plan Selection Ā· February 2026 Ā· 7 min read Can You Switch from Medicare Advantage to a Supplement Later? The honest answer is: sometimes. But not always. And that “not always” is where people get stuck ā often permanently. C Cindy Kowalski Licensed Independent Medicare Advisor What You Must Know Before You Decide When … Read more
Medicare Planning Why Your First Medicare Decision May Be the Most Important One You Make You pick your Medicare plan when you’re healthy. But you live with it when you’re not ā and that first decision may shape every option available to you for the next 20 years. C Cindy Kowalski Licensed Independent Medicare Advisor … Read more
If there is one Medicare decision that causes more permanent financial damage than any other, it’s delaying Medicare Part B enrollment without understanding the rules. Unlike many insurance deadlines, Medicare penalties don’t go away. Some last for life. Here’s exactly when you should enroll, when you can delay safely, and how to avoid costly mistakes. … Read more