Common Questions – Week of March 23rd, 2026

We hear a lot of the same questions over and over. It tends to happen when you’ve been in business as long as we have and you’ve helped as many retirees and soon-to-be-retirees with their planning as we have. We thought it would be a good idea to answer a couple of these questions every week.

Please note this very important fact. Our answers do not take into account your particular investment objectives, financial situation, or risk tolerance and may not be suitable for all investors. Our answers are not financial advice and should not be taken as advice. This material is provided for educational purposes only.

Can I take Social Security and keep working?

Plenty of retirees have a plan where they will take Social Security and keep a part-time job and supplement their retirement that way. So “Can I take Social Security and keep working?” is a common question that we hear a lot.

The short answer is yes, but if you take Social Security early, you can lose your benefit if you earn too much.

The long answer to figuring out if you can file for Social Security and continue working involves a lot of math, so hang on. You first need to know your Full Retirement Age (FRA)… that is, the age in which you can file and receive 100% of your Social Security benefit. Remember, you can file anytime from age 62 to your FRA, but earlier than FRA comes with a permanent penalty to your Social Security benefit. Your FRA is determined by your birth year, as illustrated by this chart:

Birth YearFull Retirement Age
1943-195466
195566 & 2 months
195666 & 4 months
195766 & 6 months
195866 & 8 months
195966 & 10 months
1960 or later67

If you are at Full Retirement Age, you can earn whatever you want without penalty while collecting Social Security. If you are under your FRA, however, the Social Security Administration (SSA) will apply an “Earnings Test” to your benefits. If you earn too much, the SSA will pull back a portion of your benefits. Don’t worry, they give it back… just later.

For 2026, if you are under FRA for the entire year, the earnings limit is $24,480. For every $2 you earn above that, $1 is withheld from your benefits. If you reach FRA during the year, your limit is $65,160 and you can earn $3 before they withhold $1. Once you hit the month of your FRA birthday, the training wheels come off entirely. You can earn whatever you want, collect your full benefit, and any money withheld is paid back to you through higher payments. Happy birthday to you!

What should you consider before filing for Social Security if you plan to keep working?:

  • Check Your FRA: Know your exact date so you know when the limits vanish. You can get this information from ssa.gov.
  • Calculate Your Earnings: Only “earned income” counts; in most cases your investment income and pension income is not factored in.
  • Plan for Recalculation: Remember, that withheld money isn’t gone forever. At FRA, your benefit is recalculated to give you credit for those withheld months and your benefit payments are higher.

So now you know what you can expect if you file for Social Security and continue working.

Do I get Medicare when I file for Social Security?

Two things every working person anticipates are Medicare and Social Security. While some politicians may frame them as some sort of welfare, they are both entitlement programs. Workers pay into them at every paycheck, and in return, they can claim them once they reach a certain age. But are Medicare and Social Security filings tied together in any way? When you file for Social Security, do you get Medicare? When you file for Medicare, do you get Social Security?

Most American workers are eligible for Medicare when they turn 65 years old. Most Americans are eligible for Social Security when they turn 62 years old. Their Social Security benefit is penalized/reduced if they file before Full Retirement Age (see the chart above), but they can file for Social Security as early as 62. So what happens if you’re already enrolled in Social Security when you become eligible for Medicare? If you are taking Social Security when you near the age of 65 (aka Medicare eligibility) you will automatically be enrolled in parts A and B.

Quick sidebar on the parts & coverages of Medicare:

Medicare PartSummary of What Is Covered
Part AHospital Insurance – covers inpatient care in hospitals, skilled nursing facilities, hospice care, and home health care.
Part BMedical Insurance – services from doctors and other health care providers, outpatient care, home health care, durable medical equipment, and preventative services.
Part DDrug Coverage – pharmacy drug coverage, will vary by plan
MedigapExtra insurance you can buy from private companies that helps pay your share of Medicare and fill in gaps.
Part C
Medicare Advantage
Private insurance acting much like an employer-provided PPO plan.

If you have not already filed for Social Security when you reach the age of 65, you will not be automatically enrolled and instead have seven months to enroll in Medicare Parts A, B, and D. You have the three months prior to turning 65, the month you turn 65, and the three months following your turning 65. After that period of time ends, you will be subject to penalties when you file for Medicare unless you can show similar coverage (usually through an employer plan, a spouse’s employer plan, or an existing ACA plan).

But relevant to the question asked, you do not get Medicare when you file for Social Security unless you have filed to receive Social Security before the age of 65.

Where does the confusion come from? Prior to 2002, the age in which you could file for Social Security and receive your full benefit (your Full Retirement Age… or FRA) was 65. So if you held out to FRA, you filed for Social Security at the same time you filed for Medicare. Since 2002, however, FRA has increased incrementally until today, where anyone filing at FRA will be filing at 67. Furthering the confusion, while the two agencies are independent of one another, the Social Security Administration handles the administrative processes for Medicare.

But again, to answer the question “Do I get Medicare when I file for Social Security?”… not unless you time it just right.

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