With our nation’s daily record-setting surge of people turning 65, a question asked more frequently than ever is: “Should I enroll in Medicare if I am still working?”
As more people continue working beyond 65, perhaps encouraged by the increased age requirement for receiving Social Security’s full retirement age (FRA) benefits, questions about when and how to claim Medicare are always top of mind.
If you are confused about this, do not feel bad. This question has confounded people irrespective of a person’s household net worth, location, educational background or level of work experience. It’s a question being asked more than ever because, as the Retirement Income Institute at the Alliance of Lifetime Income recently reported, the United States has reached a historic milestone with 11,200 people turning 65 every day through 2027. We have never had so many people reaching 65 all at once, and the Pew Research Center last year reported one in five people over 65 are still working. This translates to 11 million in the workforce, a fourfold increase from 40 years ago.
From just $107.88 $24.99 for Kiplinger Personal Finance
Become a smarter, better informed investor. Subscribe from just $107.88 $24.99, plus get up to 4 Special Issues
Sign up for Kiplinger’s Free Newsletters
Profit and prosper with the best of expert advice on investing, taxes, retirement, personal finance and more - straight to your e-mail.
Profit and prosper with the best of expert advice - straight to your e-mail.
Here are answers on what you can and, more important, should do when applying for Medicare for optimum benefits and how to avoid any penalties, which can be long-term and costly.
What you can do
When you turn 65, you are free to electively cancel your participation in your employer-sponsored plan and enroll in all parts of Medicare (A and B, D or Medicare Advantage). You will need to work with your human resources department to cancel your employer plan. There will be forms to complete, and make sure you allow for a multiweek transition period to get through all the administrative steps.
If you have reached 65 and are remaining on as a full-time or part-time employee who is still eligible for participating in your employer plan, you are not required to apply for Medicare at all. Your employer-sponsored plan, however, must include drug benefits deemed to be creditable coverage, as determined by the CMS (Centers for Medicare & Medicaid Services).
Many people do choose to enroll in Medicare Part A (hospital coverage) only alongside their employer plan. This is a popular approach for those who continue to work since Medicare Part A has no premium and can be coordinated with an employer-sponsored health insurance plan. However, you must have accumulated 40 quarters of coverage as determined by the Social Security Administration. The spouse of a full-time employee can also choose to not enroll in Medicare under these conditions. If you haven’t already, sign up for an ssa.gov account to check your status.
Lastly, special attention is required for those who are enrolled in a high-deductible health plan (HDHP) and are making deposits into a health savings account (HSA). One reason that people may not want to enroll in Medicare Part A while still having coverage from an employer plan is that you are not allowed to be covered by any part of Medicare, from the date that any Medicare coverage begins, while simultaneously making any deposits into an HSA under your name, as doing so would be considered a tax violation. This also means that your employer cannot contribute to your HSA while you are enrolled in any part of Medicare.
What you should do
Avoiding penalties and meeting eligibility requirements when signing up for Medicare or delaying signing up is one thing. Getting the most out of Medicare is another topic entirely and is dependent on individual circumstances.
The first is understanding your own health status and/or condition. If you know or predict you’ll be needing extensive health care services, and depending on which coverage you select, Medicare and its adjacent policies will likely result in lower overall health care costs to you and greater access to your choice of health care providers.
In other words, even if the premiums you pay are the same under both an employer-sponsored plan and Medicare (and its adjacent policies), the cost of deductibles, coinsurance, co-pays and/or out-of-pocket maximums will likely be lower under Medicare compared to almost all employer-sponsored coverage.
However, your income also needs to be taken into consideration. Employers have discretion when it comes to deciding how much you will pay for your health insurance, and your payroll deduction may be less than the cost of Medicare and the adjacent policies (Medigap, Part D, Medicare Advantage). For high-income earners, Medicare IRMAA provisions may increase both Part B and Part D premiums. In addition, you will want to check if you will lose other benefits, such as dental and vision coverage, if you transition to Medicare.
Making Medicare decisions is unfortunately very complicated for people because a lot of work is required to get it right, and some of the choices you make can be permanent. It is understandable that employees are unaccustomed to making choices when it comes to health care coverage. They have historically relied on their employer for health insurance, which limits the menu of plans and enrollment conditions. All of that dramatically changes when it comes to Medicare. The consumer has a far wider set of options from both cost and benefits perspectives.
No doubt, Medicare decisions can be confusing and unsettling, especially if you’re continuing to work after 65. In many cases, it can be helpful to seek advice from a professional Medicare adviser. Regardless, the more you understand the rules and various intricacies of Medicare, the greater your savings and the better your health care outcomes.
Related Content
- What You Must Know About the Different Parts of Medicare
- Medicare and Moving: What You Need to Know
- Seven Things Medicare Doesn’t Cover
- 11 Costly Medicare Mistakes You Should Avoid Making
- Three Medicare Changes in 2024 to Be Aware Of
Profit and prosper with the best of Kiplinger's advice on investing, taxes, retirement, personal finance and much more. Delivered daily. Enter your email in the box and click Sign Me Up.

Jae W. Oh is a Certified Financial Planner (CFP) with over a decade of experience leading GH2 Benefits, based in Ann Arbor, Mich. He is a published author of "Maximize Your Medicare (2024-2025 Edition)" and an education fellow at the Alliance for Lifetime Income, a non-profit organization focused on annuity education. Mr. Oh can frequently be seen/heard on thestreet.com’s Retirement Daily and has been quoted in ThinkAdvisor, USA Today and Marketwatch.com.
-
Is Home Insurance Tax Deductible?With home insurance rates on the rise, you might be hoping to at least claim the cost as a tax deduction. Here's what you need to know ahead of tax season.
-
The December Jobs Report Is Out. Here's What It Means for the Next Fed MeetingThe December jobs report signaled a sluggish labor market, but it's not weak enough for the Fed to cut rates later this month.
-
Trump Signals Plan to Ban Institutional Investors From Buying Single-Family HomesThe president says the move could improve housing affordability. Here’s what the data shows about investor ownership, recent buying trends and what it could mean for homebuyers.
-
4 Simple Money Targets to Aim for in 2026 (And How to Hit Them), From a Financial PlannerWhile January is the perfect time to strengthen your financial well-being, you're more likely to succeed if you set realistic goals and work with a partner.
-
I'm a Wealth Adviser: Everyone Needs an Estate Plan (Seriously, Even You)If you've acquired assets over time, even just a home and some savings, you have an estate. That means you need a plan for that estate for your beneficiaries.
-
How to Be a Smart Insurance Shopper: The Price Might Be Right, But the Coverage Might Not BeChoosing the cheapest policy could cost you when you have a loss. You'll get the best results if you focus on the right coverage with the help of a good agent.
-
7 Reasons Why Your Portfolio Needs Short-Term Bond ETFsMoney market funds are a safe option for your cash, but ultra-short and short-term bond ETFs also deserve consideration. Here are seven reasons why.
-
I'm a Wealth Planner: Forget 2026 Market Forecasts and Focus on These 3 Goals for Financial SuccessWe know the economy is unpredictable and markets will do what they do, no matter who predicts what. Here's how to focus on what you can control.
-
I'm a Financial Adviser: Why In-Person Financial Guidance Remains the Gold StandardFace-to-face conversations between advisers and clients provide the human touch that encourages accountability and a real connection.
-
This Is How You Can Turn Your Home Equity Into a Retirement BufferIf you're one of the many homeowners who has the bulk of your net worth tied up in your home equity, you might consider using that equity as a planning tool.
-
Feeling Too Guilty to Spend in Retirement? You Really Need to Get Over ThatAre you living below your means in retirement because you fear not having enough to leave to your kids? Here's how to get over that.