My first day of school is just a week away, so I’m experiencing my last fleeting hours of the Sunday that is August. That is to say, that in teacher world, we consider June to feel like a Friday, July like a Saturday, and August very much like a Sunday where you can’t quite relax and enjoy yourself because that “case of the Mondays” feeling is scratching at your front door. I get a lot of comments from non-teachers about how blissful it must be to have the summers off–and believe me it is blissful–but the week before school starts is filled with bizarre feelings and behaviors. So, for those of you always wanting to know what it’s like to be a teacher at the end of summer break, you now have to wonder no more.
- The “back-to-school”nightmares is a real thing.
The time in which the first nightmare will shoot you straight up in bed varies. For me, it’s usually early August, but I have gotten a random one at the end of June (separation anxiety maybe?). The usual dream is some variation of showing up to school to do some routine “get the classroom back in order action”–in my case usually unshowered and especially unkempt–and I realize as I walk up to my classroom that there is a classroom of eager (and confused) freshmen waiting for their teacher to show up to class. The first sensation when I realize that I mixed up the first day of school date is “PUKE!” And then that feeling settles into that panicked feeling of, “do I run and pretend that I’m sick?” or “do I walk in late with absolutely nothing prepared looking like I’ve come from a week camping in the Outback?”
The strangest back-to-school nightmare I’ve had involved the way I greeted students on the first day. There I was, wrapped from neck to toe in several layers of bubble wrap, chest bumping each student as he or she entered the classroom–all to the tune of the Space Jam theme song.

This is the copy room two weeks before school started. Everyone is already getting their copies made! (PS: that Jessica is not me. I’m not quite that on top of my game).
Thus, most back-to-school nightmares highlight a) our anxiety of not being prepared enough for a new school year b) our worry that in the two months that we got to unkink the tension knots in our backs and be real people that we forgot how to teach, and c) that we will not make the critical good first impression on our students that we need to in order to have a successful school year. Because the research states that most students make judgments on whether or not they will like a teacher and whether or not they feel they will be academically successful and socio-emotionally healthy in the class within the first few minutes of class. And they are usually right in that first impression. No pressure, huh?
So we care a lot about being prepared for that first day and that first impression. I know I’m not alone in spending hours getting my classroom in working order, making copies well in advance, and starting to practice speaking grammatically correct and clean English again.
2. We go a bit nutty over school supplies.
This is a bit of an understatement. There is a knowing look that teachers exchange between each other when we see other teachers at Office Max holding the same coupon clippings in their hands.
Teachers, as you probably already know, spend a lot of their own money on classroom decor, organizational supports, classroom sets of art supplies, and school supplies for low income students. And we only get to write $250 of it off on our taxes. So, we look for deals and free stuff wherever we can, because teachers never feel more broke at the start of the school year after they’ve bought all things needed get the classroom to its effective academic learning environment glory.
My strategy, because I’m especially broke right now, is to obsessively check freecycle.org, the free section of Craiglist, and my community swap and sell page on Facebook. And there are occasional jackpots. Just the other day, I answered a freecycle.org ad for 1,000 FREE PENS. Yes, they have advertising on them, but hey, they work! Every teacher I’ve told about this find has gasped and cheered with me about my good fortune.
Writing utensils, when you teach high school at least, are a hot commodity. I get asked probably 11.7 times a day for a pen. And because I don’t want 2% of my paycheck to go to buying pens due to the low return rate of said pens, I get creative. In the past I’ve:
- Had students give me a shoe in exchange for a pen. But one time I had a student with feet so smelly I had to quickly give him his shoe back and change the policy to “some sort of valuable item” (i.e. their cell phone).
- Spent hours attaching obnoxious fake flowers to the ends of pens and pencils, and “planted” them nicely in a pot, thinking it would cause students to garden each day when they returned the utensils to me on the way out. But what I thought was obnoxious was “cool” to the high schoolers, and those puppies were stolen before I could even get through Of Mice and Men.
- Attached stickers of Barbie and 90s boy bands to my pens and pencils thinking that again, the students would be dismayed at their utensil and want to swiftly return them. But as in above, they started trading them like baseball cards.
I know that it’s good for executive functioning to help students remember to bring a utensil. But I also don’t want to spend any of my precious class time arguing with the one student who forgets a utensil every single day. Because yes, there is always that one student. Instead, I will provide that student with one of 1,000 pens I have in my classroom right now. And yes, teacher friends, I am sharing if you need a hook up.

Just a couple of weeks ago, I was climbing into tombs. Now I’m excavating all of my classroom materials out of dusty boxes.
3. Getting our rosters is our equivalent of the NBA draft.
I can’t speak for all teachers on this one, but I can’t wait when our class rosters are released. On August 1 when the new school year officially changed over, I logged into our online grading network as fast as my fingers could press the keys. Every year, I cross my fingers and hope with all of my might that I have repeat students or my student athletes. Now, I know that not all students are that excited to have me again, but I love it. It’s my security blanket on that first day, when I’m nervous and trying to hide my pit stains, that there will be familiar and (hopefully) friendly faces. I can ask them about whether or not they finished that Zombie story, or how their summer camp in Maine was. And for students who weren’t my biggest fan, I see it as a delightful second chance.
We also are anxious about getting our rosters for classroom numbers. It’s a big deal for teachers to see how many blinking eyes will be assessing you that first day. And for a lot of teachers, it’s a unfortunately a matter of, “Will I have enough desks to fit all the students on my roster?” We trade stories of class sizes and issues of equity instead of point guards and forwards.
4. We are suddenly obsessed with Pinterest.
Because, I mean… this!

Creative ways to do exit slips!
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I mean, come on, this vase! What you do to me!
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5. We grab onto summer with our fingernails and try to squeeze as much out of it as possible.
Teaching is ridiculously hard. Although we have get our summers “off,” I’d argue that there is no possible way that the teaching career could sustain itself if we didn’t get this break. For many of us, the summers are the time we actually get to create curriculum productively, without trying to build the plane while its flying. We do our professional development and get several trainings. For example, I’ve already logged 40+ hours of curriculum planning for this next school year.
And besides getting some much needed time to exclusively reflect and plan for the next school year, we do need, for our own mental health and sanity, a time to shrug off teaching. Because teaching clings to you all school year. And I mean c-l-i-n-g-s, so much so that we never really get to take off the teaching cape. While many professions get to rip off the cape of their job when the clock hits 5 p.m., not having to think about putting it on until 8:45 a.m. the next day, teachers have their capes flamboyantly flapping in the wind 24/7.
Because after the bell rings at 3:04 we still have to:
- complete all of the grading, which can take up to two hours a day–and if it’s an essay it can take up your whole week and weekend.
- contact parents to give accolades for great things achieved in class or problem solve if a student isn’t achieving up to potential.
- plan each lesson for the next school day (which for me is 3 complete lessons because I have 3 preps).
- tutor students 1 on 1 who don’t understand a concept taught in class.
- make copies.
- hang out with students who don’t have anywhere to go after school.
- mentor and support students who are having difficult times in their lives.
- clean and organize the classroom so it at least doesn’t reflect your frazzled mental state.
- Plan and reflect with co-teacher and Special Education supports.
- worry, worry, worry–about students, about grades, about how to be a better teacher, about deadlines, about testing, about inequities, about teacher observations, about pensions, about that thing that came off wrong in class, about behavior management, about balancing work/home life balance, about being happy and healthy so you can model that to your students, even though the irony is that teaching (often unhealthily) consumes much of your life.
And that all has to be squeezed into packages that somehow allows time for family, friends, exercise, and eating.
So you can imagine that we actually need this break like oxygen. It’s the lifeblood of the next school year as we’d pass out without it. I think of my teaching friends, about 85% of them are currently on vacations to remote places or somewhere that requires the use of an airplane right now, trying to suck the last few days out of the summer cup. Those that are here are filling their days with lazy afternoons at the beach and long hot summer nights. Because the time will come where we will have to give up on those last fleeting seconds of summer, set our alarms for 5 a.m., and strap on a cape that will stay on until next June.
* * *
And so, these are five little glimpses into how a teacher feels during the last week of summer break. We are anxious hot messes. If you help out a teacher during this time, it would be appreciated as a treasure that will be remembered fondly for the whole year. The best ways are to donate some supplies (kleenex!!) or to help set up classrooms, as it is surprisingly really hard to put up a bulletin board on your own, and it’s also pretty scary standing up on desks alone in your classroom with a staple gun in hand.
And for all you teachers out there, cheers to the happy last days of summer. Even though this is an anxious stressful time, we have to remember that we have the best job on the planet. Time to get those superhero capes ready!
Love the pictures!
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Thanks Nancy!!
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Jessie- You probably don’t want to hear this, but I still have “teacher dreams.” And that’s after being retired for five years!
I hope you have a wonderful school year. I love your writing!
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Congrats, Jessie! You’re a true Rock Star.
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I so feel like this. I love my job but feel very panicky right now and have had one nightmare already. I can relate so well to this, yet it has been a glorious summer.
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I feel you Petra–and I’m right there with you as I toss and turn on the eve of a new school year. We can do this!! Sending you happiness and peace.
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Hello Jessie:
I stumbled on your beautifully written article tonight after announcing to my family, at the dinner table, that I was not going back to work in September. I told them that I know I could have retired 3 years ago and that “enough is enough!”
As I watched my husband in disbelief and my daughter fearing for her future in college, I decided it would be better to get a good night sleep instead of going into all the reasons why we suffer from panic, anxiety and nightmares in August!
Thank you for sharing your observations and feelings with us. If I go back in 21 days I will owe it partly to you and to the loud cheers of encouragement you so generously give out through your writing !
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