28 Years in Middle School: The Chaos, The Charm, and The Unexpected Love Story

Twenty-eight years. That’s how long I’ve been teaching middle school.

Let that sink in.

I’ve seen low-rise jeans come and (thankfully) go—along with chokers, gauchos, layered tank tops, feathers in hair, skinny jeans, wide-leg jeans, mom jeans (which used to be an insult and are now somehow trendy?), and more Crocs than a Florida swamp.

I’ve survived every acronym education has thrown at us—NCLB, EOG, SEL, IEP, RTI, PBIS, MTSS, MAP, PBL, PLC, DEI, DEP, 504, AIG, and most recently... IDK. (I don’t know what half of them stand for anymore, I smile and nod at staff meetings.)

I’ve taught through at least six versions of the ELA curriculum, all of which promised to be “the one that changes everything.” I’ve watched books get banned because one character mentioned feelings or, heaven forbid, real life. I’ve seen reading levels become Lexiles, spelling tests become word sorts, and writing become a rubric-riddled mess where the joy went to die.

I’ve witnessed the birth and death of the overhead projector (RIP transparency markers), the rise of Smart Boards that rarely cooperate, and the era of 1:1 Chromebooks, which kids mostly use to Google "what is mitochondria" after I literally just said it.

And don’t get me started on testing. There’s been so much testing, I’m pretty sure we’re one benchmark away from just renaming the school "Assessment Academy."

And through it all? I’ve stayed. Why?

Because I’m either deeply passionate about shaping young minds… or just too stubborn to give up and start over with a normal job—one where people don’t throw pencils like darts, bark in the hallway for no reason, or cry because their AirPod fell in the toilet again. (Yes, again. Different kid. Same toilet.)

It’s definitely not for the paycheck. Or the glamorous lifestyle. I mean, I’ve eaten lunch standing over a trash can while explaining the water cycle to a kid with cheese dust on their face. I’ve had more conversations about puberty than a school nurse and more “Did you REALLY just do that?” moments than a toddler mom.  Or the free weekends (because we all know Sundays are just “grading guilt day”).Or the summers off—because let’s be real, by the time I finish summer PD, redoing my classroom, answering parent emails, and having at least one existential crisis in Target’s school supply aisle… it’s mid-August and I’m laminating again.

No one warns you that this job is part educator, part counselor, part improv comic, and part zookeeper. But here I am—28 years deep and still showing up. Because honestly? There's no place I'd rather be… and no one else I'd trust with my Expo markers.

Year One vs. Year Twenty-Eight

Year One Me showed up with color-coordinated outfits, scented markers, and big dreams of changing lives through literature and group projects.

Year Twenty-Eight Me shows up with orthopedic shoes, dry shampoo in her backpack, and the emotional resilience of a reality show contestant who’s been stuck on a desert island with eighth graders and a Chromebook cart with only two working chargers.

Initially, I believed I had to know it all to be a good teacher.

Now I know: it’s not about knowing it all. It’s about knowing where the Band-Aids are, how to decode a group chat drama from six emojis and a passive-aggressive stare, and when to say, “We’re taking a brain break before someone bursts into tears—me included.”

Things I Never Thought I’d Say (Until I Taught Middle School)

Somewhere along the way, my professional vocabulary took a turn. I have found myself saying sentences I never imagined would come out of my mouth with such calm conviction:

• “Stop humping the air.”

• “No, you can’t trade a Takis bag for a Chromebook.”

• “Why is there glitter on the ceiling?”

• “That’s not what deodorant is for.”

• “Please stop licking your desk.”

• “If your hoodie is pulled any tighter, you’re going to cut off oxygen to your brain.”

• “We do not bark in the hallway.”

• “Yes, I know it’s Friday, but no, we’re not having a movie day.”

The Middle School Species (God Bless 'Em)

Middle schoolers are walking paradoxes. They're both child and adult, confident and self-conscious, hilarious and heartbreaking. One moment, they’re reciting a TikTok dance with absolute confidence, and the next, they’re asking, “Do you think people notice I’m weird?”

(Yes, kid. We all are. That’s what makes this place magic.)

They ask questions like:

• “What happens if you microwave a grape?”

• “Can I be buried with my dog if I die before it?”

• “Is it okay to fart during a test?”

These are not theoretical. These are real-life inquiries I’ve fielded while trying to teach grammar.

But oh—they care. Deeply. Fiercely. And in ways that’ll sneak up on you.

They’ll write you a note that says, “You’re the only adult who listens to me.”They’ll bring you a crushed granola bar and say, “I brought you breakfast!”They’ll email you five years later to say, “You made me feel like I mattered.”

Or if you are lucky like I am, you get a sticky note, hand-written each morning on your desk that says “good morning Shaff Shaff, we love and miss you”...OH the heart strings!!

The Stuff They Don’t Put in the Brochure

Let’s be honest: this is a non-paying career. Yes, we technically get paychecks, but when you calculate the hours, the classroom snacks, the Kleenex budget, and the number of therapy-level conversations we've had over whose turn it is to sit by the window, it’s charity work with a lanyard.

But the feel-good moments? That’s the gold.

It’s the kid who says, “Can I eat lunch in your room? It’s quieter in here.”It’s the camping trips where middle schoolers realize they have to pee in the woods and somehow live to tell the tale.

 It’s coaching volleyball and softball, and watching a kid who was terrified to serve now do it with confidence, then run straight into the net, but still beam with pride. It’s watching them become the kid who high-fives others, cheers on their teammates, and stays behind to help clean up the field because “you looked like you needed help.”

It’s those moments that make this career—this weird, exhausting, beautiful ride—worth every unpaid hour and every gray hair.

What I Know Now

Here’s what 28 years have taught me:

• Always carry gum. It buys you loyalty.

• Don’t underestimate the power of a hallway high five.

• They’re listening—even when they’re pretending not to be.

• The things you say echo. Years later, they’ll remember that moment you showed up, the day you were patient, the time you told them, “You are more than your mistakes.”

And most of all? I’ve learned that teaching isn’t about perfection. It’s about presence. It’s about showing up—day after day, year after year—for kids who don’t always have someone else doing that for them.

So yes, I’m tired. Yes, I have approximately 473 pens in my desk that don’t work. Yes, I occasionally fantasize about a tropical island where no one says, “Do we have to write in complete sentences?”

But I’m also proud. So deeply proud.

Of every kid who dared to be themselves, of every moment of growth I got to witness, of the ridiculous, awkward, unforgettable joy that is middle school.

Here’s to 28 years of laughter, chaos, resilience—and a front-row seat to the best coming-of-age show on earth.

Becky Shaffer

www.liveinconfidence.com