The Medicare Questions People Don’t Ask Until It’s Too Late

Introduction by Jimmy Zollo, Co-Founder, Joe & Bella

Medicare insights from Jeff Goldman, President, GM Goldman & Associates

Medicare is one of the most important decisions an older adult will ever make — and one of the most confusing. We hear about it constantly from our customers and their families: the deadlines, the plan options, the fear of making a costly mistake.

That's why we asked Jeff Goldman, President of GM Goldman & Associates, to answer the questions we hear most. His agency has been helping people navigate Medicare for decades — not with pressure or jargon, but with patience and plain English. That felt exactly right for our community.

Whether you're approaching 65, leaving employer coverage, or simply wondering if you're on the right plan, we think you'll find his answers genuinely useful.

– Jimmy Zollo, Co-Founder, Joe & Bella

I am turning 65. When can I sign up for Medicare?

Jeff Goldman: Your first opportunity to enroll in Medicare is called your Initial Enrollment Period (IEP). This is a seven-month window that begins three months before the month you turn 65, includes your birthday month, and continues for three months after.

Do I need to sign up for Medicare if I plan to keep working after age 65?

Jeff Goldman: It depends on your employer coverage.

If you work for a company with 20 or more employees and will continue to be covered by that employer's health plan, you do not need to enroll in Medicare Part B. Your employer plan remains primary and Medicare is secondary.

Many people choose to enroll in Medicare Part A since there is no premium for most people. However, if you contribute to a Health Savings Account (HSA), you should be aware that enrolling in Medicare will affect your ability to continue making HSA contributions.

What is Medicare Part A?

Jeff Goldman: Medicare Part A is your hospital insurance. It helps cover inpatient hospital stays, skilled nursing care, hospice care, and some home health services. Part A includes a hospital deductible, which is adjusted periodically by Medicare. Most Medicare Supplement plans pay this deductible on your behalf.

What is Medicare Part B?

Jeff Goldman: Medicare Part B is your medical insurance. It helps cover doctor visits, outpatient services, lab work, preventive care, and many other medical expenses.After the annual Part B deductible is met, Medicare pays 80% of approved charges, and a Medicare Supplement plan may cover some or all of the remaining 20%, depending on the plan selected.

Do I need to purchase a prescription drug plan?

Jeff Goldman: You are not required to enroll in a Medicare Part D prescription drug plan. However, if you do not have creditable prescription drug coverage, you may face a late enrollment penalty if you decide to enroll later.

Many prescription drug plans are available at very low monthly premiums, and some may even have a $0 premium depending on your area and eligibility.

Is one Medicare Supplement company better than another?

Jeff Goldman: If you're comparing the same Medicare Supplement plan letter—for example, a Plan G, the benefits are identical regardless of which insurance company offers it.

Medicare Supplement plans are standardized by the federal government. A Plan G from one company provides the same medical benefits as a Plan G from any other company. The differences are premium, rate history, customer service, and financial strength.

Does my doctor have to accept my Medicare Supplement?

Jeff Goldman: Doctors do not decide whether to accept a Medicare Supplement company.

The important question is whether your doctor accepts Medicare. If your provider participates in Medicare, Medicare processes the claim first and then automatically forwards it to your Medicare Supplement company for payment of eligible benefits.

In other words, your doctor does not care which Medicare Supplement company you have. All that matters is whether the provider accepts Medicare.

When can I change my Medicare Supplement?

Jeff Goldman: Unlike Medicare Advantage and Part D drug plans, Medicare Supplement plans do not have a specific annual enrollment period.

You can apply to change your supplement at any time during the year. In most cases, you will need to answer health questions and qualify medically unless you have a guaranteed issue right.

What is the difference between Original Medicare and Medicare Advantage?

Jeff Goldman: Original Medicare consists of Medicare Parts A and B. Many people also choose a Medicare Supplement and a Part D prescription drug plan. This option provides broad access to providers that accept Medicare.

Medicare Advantage plans are offered by private insurance companies and typically include provider networks, copayments, and other cost-sharing requirements.

Both options provide Medicare coverage but work very differently. The best choice depends on your individual needs and preferences.

What is the Annual Enrollment Period?

Jeff Goldman: The Medicare Annual Enrollment Period runs from October 15 through December 7 each year. During this time, Medicare beneficiaries can review and change their Part D prescription drug plan or enroll in, switch, or leave a Medicare Advantage plan.

This enrollment period does not apply to Medicare Supplement plans.

What does Medicare not cover?

Jeff Goldman: While Medicare covers many healthcare expenses, there are important services it does not cover, including: most routine dental care; routine vision care and eyeglasses; hearing aids and routine hearing exams; long-term custodial care

For a complete list, you can refer to the “Medicare & You” handbook.

Does Medicare cover in-home care, assisted living, or memory care?

Jeff Goldman: Medicare does not cover long-term custodial care, whether that care is provided at home, in an assisted living facility, or in a memory care community.

Medicare may cover certain short-term skilled home health services, but it does not pay for ongoing assistance with activities of daily living.

This is one of the biggest misconceptions about Medicare and one of the most important planning considerations for retirees.

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About the Author:

Jeff Goldman is President of GM Goldman & Associates, an independent insurance agency founded in 1968 and specializing in Medicare guidance and healthcare coverage planning. Over nearly two decades leading the agency's Medicare practice, Jeff has helped thousands of individuals understand their options, avoid costly enrollment mistakes, and make confident decisions about their coverage.

Jeff is an independent broker licensed in Illinois, which means his recommendations are based entirely on what's right for each client — not on quotas or carrier relationships. His approach is built on plain-English explanations, long-term relationships, and a belief that Medicare decisions should be driven by education, not pressure.

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A note from Joe & Bella: Our content is for general informational purposes only. Jeff Goldman and other experts who contribute to our newsletter are not your healthcare provider — nothing here is medical advice, diagnosis, or treatment. Medicare rules can vary based on your individual circumstances. Before making any enrollment decision, please consult with a licensed Medicare professional to review your specific situation. Every person's situation is different. Please consult your own physician or healthcare professional before making any health decisions.