Resources and guidance for people turning 65 and enrolling in Medicare for the first time.
Retirement Hub Ā· Social Security How Social Security and Medicare Interact in 2026 Your income ā even from two years ago ā can quietly raise your Medicare premiums by hundreds of dollars a month. Here’s what you need to know before you retire. Schedule a Free 30-Minute Review The short answer Social Security and Medicare … Read more
Medicare Enrollment · Updated May 2026 · 11 min read C Cindy Kowalski Licensed Independent Medicare Advisor · Eligry LLC · NPN 21601670 If you are leaving your job — whether you are retiring, got laid off, or your employer is ending your coverage — one of the first questions you will face is whether … Read more
If you split your retirement between two states ā whether that’s the Midwest and Florida, the Northeast and Arizona, or anywhere in between ā you’re part of a proud, long-standing tradition. But while your clothes and car transition seamlessly between states, your health insurance might not. The wrong Medicare choice can leave you completely unprotected … Read more
When do you sign up for Medicare? It’s one of the most common questions people ask ā and one of the most confusing to answer. The truth is, there isn’t one single enrollment date. There are at least seven different paths onto Medicare, and which one applies to you depends on your age, your work … Read more
If you’re on a Medicare Advantage plan and thinking about leaving, you’re not alone. Every year, millions of people switch from Medicare Advantage back to Original Medicare ā and many of them pick up a Medicare Supplement plan (also called Medigap) to cover the gaps. But whether you can switch and whether you should switch … Read more
Medicare Plan Selection Ā· February 2026 Ā· 8 min read The Hidden Cost of a Free Medicare Advantage Plan ā One Woman’s $150,000 Mistake Linda chose a zero dollar Medicare Advantage plan when she was healthy. Three years later, a kidney failure diagnosis revealed what that free plan would actually cost her over the next … Read more
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 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
š Last updated: February 2026 ā± 12 min read In This Article What Is the Initial Enrollment Period? The 7-Month IEP Timeline Coverage Start Dates: When Does Medicare Actually Begin? What You Can Enroll In During Your IEP Automatic Enrollment: Are You Already Covered? The Birthday-on-the-1st Exception 6 Common IEP Mistakes (and How to Avoid … Read more