I was thinking the other day about how much time we spend trying to figure out whether we’re ready to retire.

We run the numbers. Then we run them again because apparently the first six times weren’t enough. We think about insurance, pensions, Social Security, whether we should stay another year, and whether “one more year” is actually going to become three more years.

And all of that matters. I’m certainly doing plenty of it myself.

But somewhere along the way, I think the question starts to change.

It’s less Can I retire? and more What am I actually going to do when I do?

That one feels a little different.

I can picture not setting an alarm quite so early. I can definitely picture not checking email on Sunday night. But beyond that? Would I still want to work? Would I miss having a routine? Would I suddenly become someone who takes a trip in October just because Tuesday looked like a good day to leave?

I don’t know that we can plan all of that ahead of time.

Maybe we’re not supposed to.

Maybe part of getting ready for retirement is simply giving ourselves permission to wonder about it for a while.

So let me ask you the question I’ve been asking myself lately:

When you picture retirement, what’s the first ordinary thing you can’t wait to be able to do differently?

For a long time, retirement seemed to come with a pretty simple picture. You worked for 30 or 35 years, had the retirement party, turned in your keys, and that was that.

I’m not sure that picture fits nearly as many people anymore.

Some educators will absolutely be ready to walk away from work altogether, and I completely understand that. But I suspect plenty of others are somewhere in the middle. They’re ready to leave the meetings, deadlines, paperwork, early mornings and the strange ability school has to follow you home long after you’ve left the building.

That doesn’t necessarily mean they’re ready to stop doing something useful.

There’s a pretty big difference between being ready to retire from your job and being ready to retire from work.

That may be a better place to start than immediately searching job boards.

Think about the parts of your career you still enjoy. Maybe you like working directly with students but would be perfectly happy never attending another committee meeting. Maybe you enjoy mentoring younger teachers, creating curriculum, helping families or solving problems. Maybe you’ve spent years doing something well that isn’t even technically part of your job title.

Educators pick up an incredible number of skills over a career. We explain complicated things, work with every kind of personality, manage groups, organize programs, communicate with families, keep records, learn new systems and somehow adjust when the perfectly good plan we made yesterday falls apart before 9:30 this morning.

Those skills travel pretty well.

They can translate into tutoring, assessment, training, mentoring, consulting, nonprofit work, college support services, educational companies, community programs or part-time administrative work. And maybe your next job has absolutely nothing to do with education. After decades in schools, trying something completely different might be the whole point.

Before looking at openings, it may help to ask why you want to work in the first place.

Maybe you want to work full-time for a couple of years and use the extra money to pay off debt or build savings. Maybe you need health insurance until Medicare. Maybe Social Security-covered employment is part of the plan. Or maybe you simply like the idea of having somewhere to go two or three mornings a week.

For some people, the money won’t even be the main reason. Work can give you structure, interaction and a sense of usefulness that can be hard to replace overnight after spending decades in a school.

Someone trying to maximize income for two years is going to look at post-retirement work very differently from someone who wants a flexible part-time job that pays for a couple of trips each year. Neither one is better. They’re just trying to get different things from the job.

Knowing which one you are can save you from saying yes to something that doesn’t really fit.

This is the less interesting part of the conversation, but it matters.

If you’ll be receiving a pension, don’t assume every post-retirement job works the same way. Retirement systems can have rules about waiting periods, hours, earnings and returning to an employer covered by the same system. A job with your former district may be treated very differently from one with a private company, nonprofit, another state or an employer covered by Social Security.

Before accepting something, I’d want answers to a few basic questions:

That last question may be the easiest one to underestimate.

A position can begin as “just a couple of days a week” and slowly turn into meetings, evening emails and someone asking if you can take care of one more thing.

You already know what that feels like.

There’s no reason your next job has to become another version of the one you just left.

One thing I like about the idea of working after retirement is that the stakes can be different.

You could work full-time for a year and then cut back. You could tutor for a semester, substitute once or twice a week, try consulting or take a seasonal position. If something isn’t what you expected, you can change direction.

After spending so many years building a career, it may feel strange to approach work that way. But perhaps that’s one of the advantages of this stage.

The question no longer has to be, “What should I do for the rest of my working life?”

It can simply be, “What sounds right for now?”

Before You Say Yes to the Next Job → Know what you want the job to give you — and make sure you understand what it could take away from your time, pension or flexibility.

This is not the most exciting retirement advice I’ll ever give you, but it might save you a headache later.

Before you leave your district, take some time to save the records you may want in the future.

We tend to assume we can always call HR and get whatever we need. Most of the time, we probably can. But finding something yourself in a folder takes 30 seconds. Tracking down an old record through a district office several years after you retire may not.

I’d make sure I had personal copies of important employment and salary records, years-of-service information, retirement-system documents, insurance and benefit information, licenses and certifications, continuing-education records and any evaluations you might want if you decide to work somewhere else later.

You certainly don’t need to keep everything. Nobody needs an archive of every staff meeting agenda since 1998.

A simple rule might be this: if a document shows where you worked, how long you worked there, what you earned, what you were qualified to do or what benefits you had, it’s probably worth saving.

And make sure those files aren’t stored only in your district Google Drive or attached to your school email. Once you lose access to those accounts, knowing the document existed somewhere in there isn’t going to help much.

Worth Doing this Week → Create one personal retirement folder and start dropping important employment records into it now. Future you may be very glad you did.

There are people at work we see almost every day for years.

Sometimes we see them more often than we see members of our own family. We know what they order for lunch, which meetings they dread, what kind of day they’re having before they even say anything, and exactly who to find when we need to vent for five minutes.

Then retirement happens, and that built-in contact can disappear almost overnight.

I don’t think we talk about that part very much.

Some work friendships will easily continue. You’ll text, meet for lunch, go to dinner, travel together or keep showing up in each other’s lives because the friendship was always bigger than the workplace.

Others may fade, not because anything went wrong, but because school was the thing that kept you connected. When you stop seeing each other in the hallway, at meetings or during the five minutes before students arrive, maintaining the relationship suddenly takes effort.

And that can feel strange.

Maybe it’s worth thinking about before retirement rather than after.

Who are the people you would actually call when you no longer work together? Who would you still want to meet for coffee or lunch? Which friendships matter enough that you’d make a point of maintaining them once the school calendar stops doing that work for you?

There’s no need to turn this into another retirement checklist. Relationships don’t work that way.

But it may be helpful to recognize that the social side of work is real. Even people who are very ready to retire can miss the everyday conversations, inside jokes and familiar faces that have been part of their routine for decades.

That doesn’t mean you should stay in a job because you’ll miss your coworkers.

It just means that leaving work may also mean rebuilding parts of your social life in ways you haven’t had to think about before.

Retirement can change old relationships, but it can also create room for new ones.

Maybe you reconnect with people you haven’t had time to see. Maybe volunteering, part-time work, a hobby, travel or simply being available during the day brings new people into your life.

Your social circle after retirement doesn’t have to look exactly like the one you had while working.

But the relationships that matter probably deserve a little attention.

Because when the daily schedule disappears, the people you want to keep seeing won’t automatically appear in the staff lounge at 7:45 tomorrow morning.

Worth Doing this Week → Before you retire, think about which relationships you want to carry with you — and don’t assume they’ll maintain themselves automatically.

Save This: Keep a personal copy of your most important employment records before you retire, including salary history, years-of-service information, retirement documents, licenses, certifications, and anything else you may need later.

Check This: Look at which important accounts are still connected to your school email address. Professional organizations, licensing sites, benefit portals, retirement accounts, and training platforms are all worth reviewing before that email account eventually disappears.

Ask This: If you’re considering working after retirement, ask your retirement system exactly how post-retirement employment could affect your pension, including any waiting periods, hour limits, earnings rules, or restrictions on returning to a covered employer.

Keep in Mind: Your next job does not have to become another full career. It can be temporary, part-time, seasonal, or simply something that fits the life you want at that point.

Beginning next week, After the Bell will move to Substack, and the newsletter will have a new rhythm too.

Tuesday, September 29 will be the first article in the new format. Tuesdays will focus on the practical side of retirement: pensions, Social Security, Medicare, 403(b)s and 457(b)s, estate planning, and the financial questions educators face as they prepare to leave the classroom.

Then, beginning Thursday, October 1, Thursdays will give us more room for the other side of retirement: second careers, health, travel, routines, relationships, identity, and what life actually looks like once the school calendar is no longer running the show.

So instead of one longer weekly magazine-style issue, you’ll begin hearing from me twice a week with shorter, more focused articles.

If you’re already subscribed, there’s nothing you need to do. After the Bell will continue arriving in your inbox.

I’m looking forward to the change because it gives us a little more room to focus on one idea at a time but also preserving the wide variety of information for you from a financial and lifestyle point of view.

Next week, we start the next chapter.

And I’m glad you’ll be there for it!

Until next Tuesday,
C.T.

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