Working After 65? Managing and Planning Your Retirement Timeline

When it comes to working after 65, you’re not alone. Find out how this growing trend affects your savings, health care costs, and Medicare benefits.

Roll with the Changes

If it seems like the world of retirement planning is growing more complex every day, you’re probably right. One thing is for certain: The economy is going to keep changing, and financial laws and regulations that affect your retirement planning and accounts and your health care options are worth keeping up with.

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Your Retirement Income

Many people find they want to or have to keep working past their planned retirement age. Traditionally, this has been thought of as 65, but the Social Security Administration (SSA) considers the full retirement age to be between 66 and 67 for people born in 1943 or later.*

Depending on when you retire early, at the full retirement age, or later in life and whether you retire and then return to work again, the SSA may recalculate your benefit, and you may be responsible for taxes. For details, see IRS Publication 915, “Social Security and Equivalent Railroad Retirement Benefits.” You should also speak with your tax adviser or financial planner.

Choosing a Health Care Plan

Just as important to a happy, healthy retirement is an approach to health care benefits that works for you. One of the main reasons people keep working past 65 (or return to working after 65) is access to commercial insurance through their employer.

The basics: If you’ve received Social Security benefits for four months before you turn 65, you’ll automatically receive Medicare Part A and Part B for your 65th birthday. You can delay Part B if you have other coverage. Delaying Part B will allow you to use a health savings account (HSA).

Employer-Based Insurance and Medicare

If you are 65 and already enrolled in Medicare, and you are considering returning to work, check with your company’s human resources department to find out how their insurance coverage would function with your Medicare program. Coordination of benefits can be complex, but your human resources department should be able to help. “Medicare and Other Health Benefits: Your Guide to Who Pays First” may also contain the answers you need or give you a place to start.

One guideline that generally holds true is this: If your employer has 20 or more employees, then their plan pays first, and Medicare pays second. If your employer has fewer than 20 employees and isn’t part of a multi-employer or multiple-employer group health plan, then Medicare pays first, and the group health plan pays second.

If your employer has more than 20 employees, you can probably put off signing up for Medicare. Of course, you may already have health care benefits thanks to your spouse’s employer – which can also give you some extra time.

Private Insurance and Medicare

If you have private insurance, compare your existing plan with your new employer’s plan carefully.

Group plans do tend to be less expensive, but if you think you might be going back to your private plan sooner rather than later, it may be wise to stick with your current coverage. Some people also choose to use Medicare plus a private plan as their secondary insurance. Again, consult your financial adviser.

What About Enrollment Periods?

Medicare is fairly strict about offering enrollment only within specific time periods, but there are exceptions, and you will need a calendar (and perhaps an adviser) to time your enrollment.

Many people “age in” to Medicare when they turn 65, and this traditional approach is often satisfactory for those following the typical path to retirement.

You may be able to enroll after age 65 without a penalty if you receive employer coverage for a period of time after you reach age 65. But, after you are enrolled in Medicare, you may no longer contribute to an HSA. Time your enrollment carefully: if you enroll in Medicare after you reach age 65, your enrollment will be backdated by six months (but no earlier than age 65). To avoid an IRS penalty, make sure you stop contributing to your HSA before this cut-off date.

Whatever You Do —

Do it for you! Find a path through retirement that combines healthy activity, planned finances, and meaningful connections. If you’re able to do what you love by working after retirement, or if working after retirement is necessary for financial reasons, find moments to celebrate your involvement in the lives of others and recognize how you’re contributing to the greater good.

Kindness towards yourself is important, and gratitude has been proven to be a pillar of mental health. The right type of health insurance will allow you to take care of yourself so you can enjoy your golden years.

For More Information

The best sources for help in making decisions about your financial future and your health care options may be your financial adviser, your health care provider, and your company’s human resources department.

UPMC Health Plan offers UPMC for Life, UPMC Health Plan’s Medicare Advantage plan, which may meet your needs. Call a UPMC for Life Medicare adviser at 1-844-755-5608 (TTY: 711) or visit to learn more about plan options available in your area.

The Aging Institute of UPMC Senior Services and the University of Pittsburgh can also help with resources and information. You can call the help and referral line at 1-866-430-8742.

*, Rob Williams: “Working in Retirement: How Does It Affect Social Security and Medicare?” (November 16, 2022)

About UPMC

Headquartered in Pittsburgh, UPMC is a world-renowned health care provider and insurer. We operate 40 hospitals and 800 doctors’ offices and outpatient centers, with locations throughout Pennsylvania, Maryland, New York, West Virginia, and internationally. We employ 4,900 physicians, and we are leaders in clinical care, groundbreaking research, and treatment breakthroughs. U.S. News & World Report consistently ranks UPMC Presbyterian Shadyside as one of the nation’s best hospitals in many specialties and ranks UPMC Children’s Hospital of Pittsburgh on its Honor Roll of America’s Best Children’s Hospitals. We are dedicated to providing Life Changing Medicine to our communities.