By Melissa Nicolas Hernandez

If you’re turning 65 and still covered by an employer plan—or spouse’s plan—you’re entering a Medicare gray zone. The rules are different. The timelines change. And one wrong move could leave you with lifetime penalties, tax problems, or coverage gaps that cost thousands.

This must-have reference guide from longtime Medicare industry insider Matt Feret gives you the step-by-step framework you need to coordinate Medicare with employer insurance, avoid mistakes, and protect your health, income, and retirement plans. With over 20 years of experience building Medicare plans, training agents, and guiding thousands of people through enrollment, Feret reveals the insider playbook you won’t find in HR handouts or on government websites.

Inside, you’ll discover:

• The 3 Medicare decision paths for people still working past 65 – and how to choose the right one

• How the 20-employee rule really works – and why HR often gives incomplete or incorrect guidance

• When to delay Medicare safely – and when it could cost you thousands

• How to avoid lifetime late-enrollment penalties for Part B and Part D

• What happens to your HSA when you enroll in Medicare – and how to avoid retroactive IRS penalties.

• Options for spousal coverage when you leave employer insurance (COBRA, ACA marketplace, retiree coverage)

• How to compare employer coverage vs. Medicare so you can make an informed, cost-effective decision

• IRMAA explained – what high-income earners need to know about Medicare surcharges and how to appeal

• The key forms, deadlines and action steps for a smooth transition without coverage gaps

Who should read this book:

• Employees working past 65 who want to keep their employer health insurance but avoid Medicare mistakes

• Spouses, caregivers and family members helping someone navigate Medicare while still working

• High-income earners who need to understand IRMAA surcharges and appeals

• HR and benefits professionals supporting employees turning 65

• Anyone planning for Medicare who wants an insider’s perspective without sales pressure

Unlike generic retirement books or one-page HR fliers, this comprehensive, desk-friendly guide is designed for people who need clarity – fast. Use it as a ready reference you can highlight, tab, and revisit as you prepare for this critical life transition.

Medicare and employer coverage don’t automatically work together—you need to know the rules.

Whether you’re planning for yourself or helping a spouse, parent or employee, this guide gives you the knowledge, confidence, and tools to coordinate Medicare with employer coverage – without stress, confusion, or costly mistakes.

You don’t have to become a Medicare expert. You just need to understand how the system really works when you’re still working at 65.

Take control of your Medicare decisions today—and make smarter choices for your health, finances, and future.

Reviews

“I enjoyed reading Working Past 65 by Matt Feret and found it to be both informative and practical. The book does an excellent job of explaining the complexities that individuals face when working beyond age 65, particularly when navigating Medicare and employer-sponsored benefits. My biggest takeaway was the importance of understanding how Medicare coordinates with group health plans and the potential pitfalls of making the wrong coverage decisions. I would highly recommend this book to Medicare agents, group benefits brokers, HR professionals, and anyone approaching Medicare eligibility while still employed. It provides clear, actionable guidance that can help readers make more informed healthcare and retirement decisions.”

– Joseph Park

“I found Matt Feret’s ‘Working Past 65’ to be a quick, practical read and an excellent reference guide. As an insurance agent, I frequently work with individuals who are still employed when they become eligible for Medicare. With the overwhelming amount of Medicare-related emails, advertisements, mail, phone calls and warnings about potential penalties, it’s no surprise they have many questions.

One of the most common concerns is whether to stay on an employer-sponsored health plan or enroll in Medicare. As Feret explains, the answer depends on each person’s unique circumstances. The thoughtful questions outlined in the book help readers evaluate their options and make informed decisions based on their individual needs.

Feret’s guide does an excellent job of helping readers navigate these often-complex decisions. I especially appreciated his disclaimer: ‘Use your best judgment, ask good questions, and don’t be afraid to get help.’ Picking up this book is a great first step toward asking those important questions and making confident healthcare decisions.”

-Kelsey Calhoun

From the back cover

If you’re working past 65, Medicare isn’t as simple as just enrolling. Whether you stay on your employer’s plan, delay Medicare, or switch to a new option, every decision impacts your healthcare costs, coverage, and retirement goals.

In this clear, straightforward guide, Medicare insider Matt Feret walks you through the complexities of working past 65 and how it intersects with Medicare. You’ll learn:

• Why working past 65 changes your Medicare timeline and how to avoid costly mistakes

• How your employer plan interacts with Medicare (and why many HR departments get it wrong)

• What the 20-employee rule and delaying Part B really mean for your coverage

• How Medicare enrollment affects your Health Savings Account (HSA)

• Why choosing the right path now could save you thousands later

• BONUS: Learn how to make the smartest decisions with your employer plan and Medicare using Step 2 of the Prepare for Medicare Insider Method ™.

Whether you’re planning to work past 65, helping a spouse or parent, or advising others, this book gives you the insights and strategies you need to make informed, confident decisions.

You don’t have to guess. You just need a roadmap. This book is that roadmap.