The Bookend: A Teaching Career Change After 25 Years in the Classroom

Hey, and welcome back to If Teachers Ruled the World. I’m your host, Leah Cleary. And if you’re listening to this right now, I want you to know something before we even get started. You made it. You made it to the last week of school. And I don’t mean that in a cute motivational poster sort of way. I mean that in a very real, very tired, slightly delirious way that only teachers at the end of May actually understand. You’re here. You’re still standing. Give yourself just a moment with that. This week, I want to talk about something that I don’t think we give enough space to at this time of year. And that’s the emotional weight of the end of school. Not just the logistics, not just the checkout lists and the turned in textbooks and the packing up your room, the actual feeling of it. Because here’s what I’ve noticed after twenty five years of doing this. We’re all really good at white knuckling our way through to the last week of school. We put our heads down, we get through the exams, we do the checkout, we wave goodbye, and then we collapse into summer without ever actually processing what just happened over the past ten months. And I do think that costs us something. So today I’m doing something just a little bit vulnerable because this end of the year, well, this end of the year is unlike any end of the year I’ve ever had before. I’m going to invite you into what this particular end of the year looks like for me personally, because it’s my hope that this story might be the mirror for something some of you are already feeling, even if you haven’t found the words for it yet.

I’m going to start today with one word bittersweet. I think bittersweet is actually the most honest word for what this end of the school year feels like. And I’m not sure we let ourselves say that enough. We talk about summer break like it’s this uncomplicated relief, like it’s just sunshine and sleeping in and forgetting about school for a while. And yeah, there’s absolutely some of that. And I know a lot of us have second jobs, so there’s not all it is, but I’m not going to pretend like that’s all it is for any of us. If you’ve spent a year genuinely invested in your students, if you’ve built something real in your classroom, then the end of the year also carries a grief with it. I think we need to call it that, grief, because you are saying goodbye to kids who mattered to you. You’re also closing a chapter that you can’t get back to. And even when you’re exhausted, even when you’re counting down the days, which we all are exhausted and we all are counting down the days, that loss is very real. So if you’re feeling a little bit like that this week, maybe a little hollowed out, even as you’re relieved, I want you to know this. It’s not a weakness. That’s what happens when you actually showed up for your students. That, my friends, is the cost of caring.

Now I’m going to tell you where I am right now, because this end of the year is definitely different for me. I resigned. I turned in my resignation at my current school and I’m making a transition. Next year I’m going to be teaching seventh grade English language arts at a school that is right down the street from my house. And before you say anything, yes, I know what that sounds like on paper. I’ve been a department chair. I’ve been teaching AP world history. I’ve been teaching IB theory of knowledge. I’ve spent the better part of two decades in social studies, and now I’m going to be teaching seventh graders how to write paragraphs and analyze a novel. And here’s what I want to tell you about that. I am genuinely, deeply excited, but I also want to tell you about the other feelings because they’re all true at the same time. I’m really going to miss my school. I love my current school. I love the students I’ve taught there. They’re the best part of the school. When I told my classes I was leaving, they were so sweet. The kind of sweet that makes you wonder, just for a second, if maybe you’re making a huge mistake. They got together. They gave me a card. They gave me a sweet gift that I’m absolutely going to treasure. And I am going to miss those kids so much. I’m going to miss my colleagues in the social studies department. We’ve built something fantastic together. I’m very, very proud of our department, and I’m truly going to miss being department chair. I’m going to miss the work we’ve done in AP and I’m going to miss IB and.

And yet, I know this is the right decision, but all of those other things are completely true. Here’s what I want to be really honest with you about, because I think this is the part that might actually matter for you today. I wish someone had given me permission years ago to think about myself first. And when I think about myself first, that means that I’m also thinking about my family. Not instead of my students, not as some kind of abandonment of my calling, but just as a fact. My family comes first, and for a long time I was not living like that was true. The school where I’ve been teaching is not close to my house. My commute takes time. It takes energy. It takes part of my day that I could be spending differently. My parents are getting older. See, my dad got sick. I’ve written all about that on my blog. I will link to that post in the show notes. Um, but my mom fractured her hip while he was in the hospital. And when I looked at what the next chapter of my life actually needed to look like, I realized I had been making a particular decision with my career by default, not actively choosing to stay. Just never making a move to change it.

And I think a lot of teachers live our lives like that. Not burned out exactly. Maybe burned out at times because that does happen. Not broken. Just in a default setting. Showing up, doing good work, telling yourself this is all fine. This is what the job is. This is what commitment looks like. And you never stop to ask, is this actually working for my life? I probably would have stayed put indefinitely if my circumstances hadn’t forced me to look up and actually examine my choices. And that realization. Well, that realization was just a little bit uncomfortable because I’d been teaching other people’s kids to think critically, to question assumptions, to examine evidence, to draw conclusions. And I was not doing that about my own life and my own career.

So I want to ask you something, and I want you to sit with it for a second, not answer it right now. Just sit with it. Are you actively choosing where you are? Or are you just there because you’ve always been there? It took my parents getting sick for me to realize that. But you don’t need a major life event to to look at that. Here’s what I keep coming back to, and it’s the thing that actually gives me peace about this transition. I started my career teaching middle school English language arts. And now, twenty five years later, after two decades in social studies, after AP and IB and department chair and all of it, I’m going back to middle school English language arts, a bookend. On paper, that looks like going backwards. That looks like stepping down. That looks like giving something up. The professional culture of teaching, but really of anything is obsessed with the idea of constantly moving forward, moving up more responsibility, more leadership, more AP, more of whatever signals you’re progressing, advancing, growing.

But here’s what I’ve come to believe. Up and forward is not always the right direction. Sometimes the right move is the one that gives you your life back. Sometimes it’s smaller, sometimes it’s closer to home. Sometimes it’s the thing that lets you be there for the people who need you most and lets you put together a jigsaw puzzle on a Sunday afternoon without feeling guilty about the stack of essays waiting on your desk. I chose that, and I’m at peace with it. And I’ll tell you something else. I’m one of those people who genuinely and perhaps strangely, really likes the middle school age. I know, I know. You either get it or you don’t. But there is something about that age the weird and sometimes wonderful chaos of it. The kids who are still kids but also starting to really become themselves. That I find genuinely compelling. I spent this past year teaching freshmen for the first time in years, and I loved it, partly because they still have that quality, that almost middle school quality. And next year I get to lean all the way into it. I get to teach writing, I get to teach grammar, go back and listen to the episode Not Your Granny’s Grammar, that I interviewed Patty McGee, the author of that book with. I’ll link to that in the show notes because I’m definitely going to be using that book this year. We’re going to read novels together and I can’t wait. This is not a consolation prize. This is not a step backwards. This is a choice I made for my whole life. Not just my professional life. And I think there’s a real difference. So here’s what I want to leave you with as you navigate the last week of school. Whether you’re packing up a classroom or grading final exams, or are just trying to survive until the last bell rings on the last day, I want to invite you to spend a little time this summer, not immediately. Give yourself some real rest first if you can, but at some point this summer, asking yourself three questions.

First, where are you and why are you there? Not in a critical way. Just honestly, are you at the school in this role, in this subject area because you actively chose it, or because it’s where you landed and you’ve never stopped to examine whether or not it still fits your life. Second. What would it look like to choose your life on purpose? What would change? What would you keep? What would you let go of? What would a career that works for your whole life actually look like? Not just your professional life, but your actual life? You. Your family. Third, what are you treating as a constraint that might actually be a choice? Because sometimes we are stuck and sometimes we just think we are. And sometimes the thing we believe we have to do is actually just something we’ve never questioned. We need to understand the difference and look at our lives honestly. I’m going to repeat those questions. All right. The first question is where are you and why are you there? The second question is what would it look like to choose your life on purpose? And the third question is, what are you treating as a constraint that might actually be a choice? You don’t have to answer these questions. You don’t have to make any decisions. And you don’t have to do anything except let yourself think about them. But I really hope you will, because you deserve a career that works with your life, not just a life that works around your career.

I started my teaching career in middle school English, and I’m going back twenty five years, a whole career. And what I can tell you is this: the most important thing I’ve learned in all of that time is not a strategy or a framework or a best practice. It’s that teaching. Teaching is a gift. And like any gift, it’s meant to be given freely, not wrung out of you until there’s nothing left. And if you have found yourself in that position, ask yourself the three questions we talked about. So take care of yourself this summer. Rest. Actually rest. Read something that has nothing to do with education. Spend time with the people you love and give yourself permission. Maybe for the first time in a long time to think about what you actually want. Because we need sustainable teachers in our classrooms far more than we need perfect ones. And a teacher who’s chosen her life on purpose. That’s a teacher who has something real to give. We don’t want to keep moving forward. Sometimes the best and bravest thing we can do for ourselves and our family is to choose what’s right, even even if that looks like we’re going backwards on paper, even if it means leaving something we actually do love and people we love, even if it’s a little bittersweet. Thanks for being here. This podcast, this community, this work. It matters to me so much. And I’ll see you next week.