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Headwaters Health and Wealth LLC

65 and Employed: What You Need to Know About Medicare

May 15, 20262 min read

Turning 65 once meant retirement, but today, many of us are still working, thriving, and not quite ready to step away from our careers. With that milestone comes an important question: what to do about Medicare. It’s easy to assume you can delay enrollment without consequence, but the reality is more nuanced. Your decision can have financial and healthcare implications, so it’s worth understanding how your current coverage fits into the bigger picture.

If you are self-employed it is likely you need to follow strict enrollment timelines and sign up for Medicare, please call us for guidance.

If you’re covered through your job (or a spouse’s and they currently work), you may be able to postpone Medicare, but only if the employer has 20 or more employees and you are on that group coverage with RX benefits also. In that case, your work plan may remain primary. If your employer is smaller, Medicare typically becomes primary at 65, making enrollment necessary. Missing your enrollment window when required could result in lifelong penalties, so understanding your situation is key.

Turning 65 while still working puts you in a position of choice—but also responsibility. Reviewing your health coverage and your known needs, speaking with your HR department, and understanding Medicare’s rules can help you avoid costly missteps. With the right information, you can keep working confidently while making smart decisions about your healthcare future.

If you have questions, give me a call. There is no obligation and my service is never a cost to you.

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We do not offer every plan available in your area. Currently we represent 10 organizations which offer 106 products in your area.Please contact Medicare.gov, 1-800-MEDICARE, or your local State Health Insurance Program(SHIP) to get information on all of your options.

Mario Waller

Art Director

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Publisher's Letter

Dawa Sherpa, Publisher

The holiday season is upon us. A time to express appreciation for the people, experiences, and opportunities that enrich our lives. As we take a moment to give thanks and celebrate with our families and our communities – let’s not forget the uniquely valuable small, local businesses that are at the heart of our communities.

In today’s fast-paced world, shopping has never been more convenient with online giants and big-box stores offering rapid delivery and low prices. But, unlike mass retailers, small businesses and local shop owners offer personal relationships, leading to better service and customized recommendations. Whether it’s a handmade candle or boutique clothing, these businesses offer a personal touch that can’t be replicated.


The holiday season is a crucial time for small businesses. Events like “Small Business Saturday” remind us to support the shops that keep our communities vibrant. But it’s important to continue that support throughout the year to ensure these businesses thrive.

This holiday season, when shopping for a gift, a service, or just a little treat for yourself, consider visiting our local businesses first. Every purchase makes a meaningful difference, helping build a stronger, more connected community for everyone.

Happy Thanksgiving,

Dawa

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