Tomorrow, and Tomorrow, and Tomorrow… and the First Day Back
New school year, fresh save file.
The summer has been good to me. Not the “Instagram highlight reel” kind of good—no perfectly framed sunsets over Amalfi, no humblebrags about hiking the Inca Trail. My summer was good because it was quiet. I had fewer obligations. I gave myself permission to put the to-do list down and walk away. I traded the adrenaline rush of constant motion for the slow burn of intentional rest.
This wasn’t about laziness. It was about recovery. Teaching—and coaching teachers—is a profession of constant giving, of endlessly passing the controller to someone else so they can take the next turn. After a while, you forget what it’s like to have the game in your own hands. This summer, I took it back. I sat with books. I let mornings stretch long enough that the coffee got cold. And I remembered: rest is part of the work.
One of those books was Gabrielle Zevin’s Tomorrow, and Tomorrow, and Tomorrow. It follows three friends—Sam, Sadie, and Marx—over decades of collaboration, conflict, and creativity as they build video games together. It’s not really “about” gaming in the way you might think; the games are just the canvas. At its core, it’s about the messiness of relationships, the risks and rewards of creative work, and the way we keep trying—again and again—to make something meaningful, even when life keeps breaking our hearts.
There’s a line in the book that’s been rattling around in my head since I read it:
“What is a game?” Marx said. “It’s tomorrow, and tomorrow, and tomorrow. It’s the possibility of infinite rebirth, infinite redemption. The idea that if you keep playing, you could win. No loss is permanent, because nothing is permanent, ever.”
If that’s not the school year, I don’t know what is.
Infinite lives in finite time
Every August, the hallways smell faintly of waxed floors and new paper. The whiteboards are pristine. The login screens are empty. You could look at that and see futility—we reset every year, only to wear it all down again by May.
But Marx is right: each year is an infinite rebirth. Every school year is a fresh save file—same console, same mechanics, but a new set of choices ahead.
Jane McGonigal, in Reality is Broken, argues that one reason games are so satisfying is that they give us “the opportunity to start over as many times as it takes to get it right.” They offer a clear goal, immediate feedback, and the knowledge that failure isn’t final. You just respawn and try again.
That’s what school can be. Every failed quiz can be retaken. Every botched experiment can be rerun. Every strained relationship can be repaired. In the classroom, as in games, nothing is permanent—except the choice to keep playing.
The grind, the glitch, and the gallery wall
Zevin writes, “Art doesn’t typically get made by happy people.”
Teaching isn’t art in the gallery sense, but it shares the same blood type: creation, iteration, and an almost unreasonable devotion to something that doesn’t always love you back. You build lessons the way an artist builds canvases—layer by layer, making tiny adjustments no one else will notice. And sometimes, like an artist, you ruin the whole thing with one bad stroke.
That’s the grind. Sometimes it’s exhilarating. Sometimes it’s glitchy—when the tech won’t cooperate, the pacing’s off, or the class energy crashes into the floor.
McGonigal would call these moments “urgent optimism”—that mindset where even if the current challenge is maddening, you believe you can overcome it, and you’re willing to keep trying. Teachers know this better than anyone. The grind produces the work. The grind puts up the gallery wall of moments—students who suddenly get it, classes that click into perfect rhythm, projects that feel like magic.
Knowable. Fixable.
Sam’s grandfather believed two things:
“All things were knowable by anyone, and anything was fixable if you took the time to figure out what was broken.”
That belief feels radical in education. It’s easy to think that some problems are too big, some skills too elusive, some students “just not the type” for success. But if you start from the assumption that everything is knowable and fixable, your posture changes.
It means you approach a struggling student not as a puzzle missing pieces, but as a puzzle that just hasn’t been assembled yet. It means you treat a failed lesson not as proof of your limits, but as an opportunity to debug your own code.
Games give us the same lesson: if you can’t beat the boss, it’s not because you’re permanently incapable—it’s because you haven’t figured out the right strategy yet.
Macbeth and the meaning we choose
Shakespeare’s Macbeth gave us the line Zevin echoes—“Tomorrow, and tomorrow, and tomorrow…”—but the original speech is bleak. Macbeth is mourning the death of his wife, facing the collapse of everything he’s built, and all he sees ahead is “a tale told by an idiot, full of sound and fury, signifying nothing.”
But teaching lets us rewrite that fatalism. Yes, our days are often full of sound and fury—bells ringing, emails pinging, a chorus of “Do we need to write this down?” echoing from the back row. But it doesn’t signify nothing.
We get to choose the meaning. We decide whether this work is a meaningless loop or an infinite rebirth.
That’s the twist. Macbeth saw inevitability; we see possibility.
Playing the long game
There’s another Zevin line I love:
“To allow yourself to play with another person is no small risk… To play requires trust and love.”
This is what teaching is: an act of play in the most serious sense. You design the level. You set the boundaries. You hand the controller to your students and hope they don’t just run straight into the lava pit.
And sometimes, they do. They fail. They push boundaries. They surprise you in ways both delightful and infuriating. But the act of playing—of giving them that trust—is the work.
McGonigal points out that games connect us because they create “shared fiero”—the Italian word for pride after a hard-won victory. The joy is amplified because we went through the struggle together. In schools, that’s every group project, every shared aha moment, every day we make it through the final bell as a team.
The teacher’s respawn
If you’ve been teaching long enough, you’ve experienced the teacher’s version of a respawn: the moment you walk into a new year with the weight of last year’s mistakes still on your back, and realize you don’t have to carry them anymore.
That’s the beauty of “tomorrow.” The Earth continues to spin upon its axis. The sun rises. Joy cometh in the morning.
We get another chance.
This year, I hope you take that chance. I hope you build the levels you wish someone had built for you. I hope you play the long game. I hope you keep showing up to make the art, even on the days when you’d rather throw the whole project in the trash.
Because no loss is permanent. Nothing is permanent. And if we keep playing together, we can win.
Want more like this?
Starting this week, the newsletter is leveling up. You’ll still get my free weekly “10 Things” every Friday—quick hits of ideas, tools, and inspiration to take into your classroom. But on Tuesdays, I’ll be sending long-form pieces like the one you’ve just read: deeper dives into the intersections of teaching, creativity, and the messy, hopeful business of learning.
These Tuesday essays will be for paid subscribers, and because it’s the start of a new school year, I’m offering 20% off all new paid subscriptions through August.
If this piece lit a spark for you, or you want more stories, strategies, and reflections to keep you going all year long, I’d love for you to join me. Think of it as your weekly respawn point: a place to recharge, reframe, and head back into the game with fresh ideas.