Could This Really Be Your Last School Year? Start With These 6 Things

There is a strange difference between saying, “I might retire at the end of this year,” and actually beginning to act like it could happen.

For a long time, retirement can sit comfortably somewhere out in the future. You can talk about it with colleagues, run a pension estimate every so often, maybe even count down the years. But once you begin wondering whether this could really be the last school year, the questions become much more specific.

That is certainly happening for me.

May 26, 2027, is close enough now that I can look at the school calendar and know exactly where it falls. And as that date gets closer, I’m realizing that deciding whether I’m ready to leave education and knowing whether I’m ready for retirement are two different things.

I don’t think any of us has to have the next twenty or thirty years completely figured out before we retire. But there are a few things we probably should understand before we make that decision.

These are six of the things I’m working through right now.

I’ll start with the obvious one because, for many educators, the pension is the foundation of the whole retirement plan.

I’m pretty satisfied with my own pension estimate. After more than three decades in education, it represents a wonderful lifetime benefit, and I’m grateful to have it. But I’d be lying if I said seeing that number made me feel completely comfortable about the next twenty or thirty years.

That is why I think it’s worth looking beyond the big number on the estimate.

Find out what will actually come out of your pension each month. Does your system provide a cost-of-living adjustment? Do different payment or survivor options change the amount? Are there deductions you need to plan for?

For me, the goal isn’t just to know what my pension is. It’s to understand what that pension will realistically allow me to do.

This part isn’t quite as interesting as running a pension estimate, but it may tell you just as much about whether you’re ready.

I’ve been paying more attention to what I actually spend now rather than trying to create some perfect retirement budget from scratch. Housing, utilities, food, transportation, insurance, debt, travel and home repairs aren’t suddenly going to disappear because I retire.

And then there are the expenses that don’t show up every month but still show up eventually—things like a car repair, a higher utility bill, an insurance premium, or something around the house that suddenly needs attention.

Once you have a realistic picture of what you’re spending, compare it with the income you know you’ll have.

That question has helped me think differently about working after retirement. I expect to work at least part-time for a while, not because I necessarily need to replace my teaching salary, but because I’d like to keep building savings, finish some financial goals and give my pension a little more room to breathe.

This is probably the question I hear most often when I tell someone I’m considering retirement:

It’s a fair question, especially for those of us retiring before Medicare.

At this point, I’m planning to continue my school health insurance after I retire. The important difference is that the premium becomes my responsibility. That expense has to be included when I look at what my pension will actually cover each month.

Your options may be very different. You might have retiree coverage through your district, coverage through a spouse, an ACA marketplace plan or another option entirely.

The important part is getting an actual number.

Don’t just know that health insurance will be expensive. Find out what your coverage is likely to cost and put that amount into your retirement plan now.

For me, that cost is also one more reason part-time work after retirement makes sense.

Depending on where you teach, Social Security may already be part of your retirement plan. For other educators, school employment may not be covered by Social Security at all.

I’m in that second group.

I don’t currently have enough Social Security credits on my own record to qualify for a retirement benefit, so this is something I’ve started paying much more attention to. Part-time work after retirement could allow me to earn the credits I’m still missing while also bringing in additional income.

If you’ve worked in a school system that doesn’t participate in Social Security, it may be worth checking your own record instead of assuming you know where you stand.

How many credits do you already have? How many do you still need? Could work after retirement help you qualify?

In 2026, you earn one Social Security credit for each $1,890 in covered earnings, up to four credits for the year.

Social Security isn’t going to replace my pension. But if work I may already be doing could eventually provide another source of retirement income, I think it’s worth understanding.

I’ve started to realize there is a pretty big difference between having to work after retirement and choosing to work because it serves a purpose.

For me, I think there will be a period when working still makes sense. It could help with health insurance, allow me to build savings, finish some financial goals and help me earn the Social Security credits I still need.

That doesn’t mean I want to immediately start another thirty-year career.

It just means work can be part of the retirement plan instead of something that happens because the plan didn’t work.

You may want something completely different. Maybe you want to substitute a couple of days a week. Maybe you want a new full-time career for a while. Maybe you’d like enough extra income to travel without dipping into your normal retirement income.

A useful question might be:

That answer can help determine how much work—and what kind of work—actually makes sense.

Eventually, retirement stops being an idea and becomes paperwork.

Every retirement system and school district handles that process a little differently, so this is one area where it’s worth finding out the specifics for yourself.

When does your pension application need to be submitted? When does your district require notice? What happens to unused sick leave? When does your health insurance change? What happens to your 403(b), 457(b) or other accounts? When will your final school paycheck arrive, and when should you expect your first pension payment?

You may not need to do any of those things yet.

But knowing the timeline means you aren’t trying to figure everything out during the final few weeks of school.

I’ve found that there is something reassuring about taking the very large question—

—and breaking it into questions I can actually answer.

I’m still not going to know exactly what my life will look like twenty years from now. None of us will.

But I can know a lot more about what the first year will look like, and that makes the decision feel much more manageable.

Check Your Pension: Run a current estimate using the retirement date you’re actually considering. Then look past the headline number at deductions, payment choices and cost-of-living provisions.

Price Your Health Insurance: Find out what coverage you could keep after retirement and what the actual monthly premium would be. If you’re retiring before Medicare, this could be one of the biggest numbers in your plan.

Check Your Social Security Record: See how many credits you already have and whether future covered work could help you reach eligibility. In 2026, $1,890 in covered earnings earns one credit, with up to four credits available during the year.

→ Check your Social Security Statement and earnings record

Give Work a Purpose: If you think you’ll work after retirement, decide what you want that income to do. Build savings? Cover health insurance? Pay for travel? Earn Social Security credits? The answer may help you decide what kind of job actually fits.

Know an educator thinking this might be their last school year? Share this with them.

I still don’t know exactly what life will look like after May 26, 2027.

But I’m getting much clearer about what I need to know before I get there. And right now, that feels a lot more useful than trying to predict everything that comes after.