4 Questions a Teacher Should Ask Before Retirement

Your answers matter for your future.

Teacher Retirement: 4 Questions to Ask

During your final year of teaching before retirement, it can seem like things are happening very quickly. Not only are you teaching each day for the last time and bringing closure to the working phase of your life, but there is a laundry list of items to cross off in order for you to retire in the very best way. Asking—and answering—these four questions can help you plan your teacher retirement with the least amount of stress and the most amount of money.

Is my pension in good shape?

Communicate early and often with your pension provider, even if you think you have things all figured out. Make sure to ask any relevant questions, even if they seem trivial. Be aware of filing deadlines and verify estimates of your expected benefits and when they will begin. Ask if you are eligible for any refunds from benefits you are not using.

Can my pension be upgraded?

In the year before retirement, look closely at your pension to make sure you’re getting the greatest benefit possible. Make sure you understand how your pension is calculated and if there are any upgrades you can make to increase your pension income.

See if you can take advantage of any optional service credit. Optional service credit may be earned in the following ways: teaching out-of-state, substitute teaching, pregnancy leave, military service, or teaching in a reciprocal pension system. There will be a cost associated with converting optional service credit, so check with your pension administrator to make sure it is financially worthwhile to convert.

How will health insurance work once I retire?

Retirement health benefits vary by state. Some districts provide health insurance at retirement as a benefit after paying into the system over many years. If this is your situation, make sure you understand the coverage and the costs associated with the policy, especially if you have dependents who also need coverage. Be sure to have your coverage selected and notify the provider of your retirement date to ensure that you don’t have any gaps in coverage.


For teachers who retire from districts that do not provide health insurance benefits, there may be a gap in coverage if you retire before you are eligible to receive Medicare. In this case, you’ll either need to find another job that offers health insurance or navigate the private insurance marketplace to find a policy that works for you. For more information, read What to Do About Health Care in the Gap Years.

What do I want my retirement to look like?

Here’s where you start to dream. Retirement is a great time to travel, start a new business, spend more time with family, or even continue to work if that is where you find your joy. The options are endless, as long as you balance your choices with what you need in terms of income to support yourself. If you’re planning to work, start looking into what employment is available. Figure out what it will pay, see what benefits are available, and decide if it’s worth pursuing. If you want to travel, begin the next phase with a bang: Take that big trip you have on your bucket list and start retirement off right!

As you prepare to retire, don’t assume that your district will take care of things for you. They won’t; it’s not their job. Instead, take responsibility and understand the steps you need to take in order have a clear path to the next stage in your life.

What is your plan for teacher retirement? What questions do you have about the process? Please share in the comments, and we’ll address some of your questions in future posts.