First, make some noise on your way out.
My regret is that I didn't throw a bigger party. Seriously. Some combination of not wanting to be That Hey Look At Me Guy and survivor's guilt (this hits hard for some folks, because when retiring from teaching is like leaping off a train barreling full speed down the tracks, and you are leaving behind others to continue work that you didn't finish--because teaching is never finished)-- anyway, I should have invited every other teacher in the building and every other person I could think of and made some noise, but I didn't want to be a bother.
Have a project.
Everyone tells you this. Some of us go at it a bit more aggressively than others, but I don't think a teacher brain can shift easily to simply idling. The teacher brain is generally running 147 different threads all at once, and suddenly running 0 can cause the brain to just lock up. You may think you can handle a life of leisure because you went on vacation during the summer that one time, but be honest-- you were lying on the inflatable turtle in the middle of the pool and one little corner of your brain was still figuring out how to tweak that one unit for September and maybe you could rearrange the seating in your room and did you remember to order those posters yet?
Volunteer. Start working through your pile of unread books. Travel. Take a cooking class. Find something for your brain to chew on. It took me a while to get past the feeling that there was something I was supposed to be doing, but wasn't. Being a stay-at-home dad for a couple of small children helped with that, but I don't recommend it as a solution for everyone.
Time is different on the outside.
At some point in retirement, you will think, "How did I get all this done and work full-time, too?" The answer is that teacher time is different than retiree time.
Teacher: I have a two-minute break at 10:03, so I can get some copies made, get another fifty grades in the grade book, and go pee.
Retiree: I volunteered to sit in the booth from 10:00 to 10:30, so I guess my whole morning is filled up.
The rhythms of dealing with people
For decades you have been dealing with other humans on a large scale, working to deliberately engage with dozens (elementary) or hundreds (secondary) of students and family members. They become a major factor of how you go through your days, and then, after nine months or so, they leave.
This is not a natural rhythm for human interactions. I hope your own social and emotional health was anchored outside the classroom, but even so, retirement is a whole new game. If you're an extrovert, you may find yourself craving new sources of human interaction. If you're an introvert, you may find that the part of you that engages with other humans is screaming for a major break. At the beginning of my career, I replaced a guy whose retirement plan was to sit on the porch, read books, drink beer, and talk to nobody.
Weeks full of Fridays
Other retirees may joke about how every day is Saturday, but teachers know that special Friday afternoon feeling, like you've been dragging a loaded semi with a chain for five days, and you just got to set the chain down. For the first year or two, it felt like Friday afternoon a lot.
Have your support system
Another one of my retirement secrets was to be married to an exceptionally excellent woman. So I had that going for me, as well as the many connections that come from being active in many small-town activities like theater and band. A church home can be nice, too.
But you may fine that maintaining your web of humans may take more deliberate work on your part. Being at work put you in natural connection with your web of workplace proximity associates, and you aren't going to have that. If you want to stay connected, you will have to reach out. As far as the school itself goes, you will be a ghost in 3-5 years. Your work friends will be busy in the dailiness of the work, and you will not, so maintaining those relationships will take deliberate effort.
Share
You have a wealth of knowledge and experience, both in terms of content knowledge and educational expertise. You know how to organize large groups of cat-like humans. You know how to manage an undersized budget. You know how to help people understand stuff. You know what life in a classroom is actually like.
There are people and organizations out there that would benefit from what you know. Maybe you can be some sort of activist or communicator about education, or maybe your skills can be put to work in a non-education space. Maybe it is individual humans rather than organizations that can benefit from what you know.
Whatever the case, you still have plenty to contribute to the world. Teachers are too often reluctant to get involved, to push themselves out into the world. The "just" in "I'm just a teacher" keeps a lot of smart, capable people from making as much noise as they could. And I get it-- when you're dealing with the dailiness of your classroom, it's hard to find the bandwidth for wading into other ponds. But you don't have to deal with the dailiness any more, and you are not "just a retired teacher." You are an experienced education professional with a wealth of experience and knowledge. Somebody can use that.
Finally
People still ask if I miss it, and the truth is that, in many ways, I do. The actual teaching parts were, mostly, great, though there is a tendency as a retiree to remember the best parts and not, say, the class that sat there like bumps on a log despite your best efforts. If you've taught more than six months, you have acquired a list of failures, moments when you just didn't get things to fall the way you wanted them to, and I can report that those haunt you a bit less in retirement.
Mostly I miss the actual teaching (when it goes well). I opposite-of-miss the bureaucracy, the stupid paperwork, the stultifying compliance culture, the bosses who were way more worried about stuff that didn't help me do my job, the time wasted on junk like the Big Standardized Test and BS Test prep, the-- well, it's not a short list. But the work itself? That was golden, and I'll never regret a second of it.
That question (do you miss it) is not always asked in good faith; sometimes it's asked in the same way that some people encourage a newly-married couple to smash the wedding cake into each others' faces. They just want to see someone else be miserable, so while the DYMI question is complicated and nuanced, I don't want to cater to anyone who just wants to hear me smash cake in the profession's face. I can tell them truthfully that it was the best job in the world, and if I had it to do over again, I would, and I'm still a tiny bit jealous of my former colleagues who are still in the classroom doing the work.
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