Failing to Fall
Newsletter 2025-09-26
Fall break has always struck me as strange. It doesn’t line up with any major holidays—or minor ones, for that matter. If schools scheduled fall break to coincide with Halloween, I’d be fully on board. I need a week to prepare for acquiring all that candy—or to recover from eating it—depending on when Halloween falls. Correction: My children need all that time. I’m merely an uninvolved driver who certainly won’t eat his body weight in Kit-Kats. As long as I’m rescheduling everything, Halloween should be permanently fixed to a Friday or a Saturday. The spirits will adjust. I’ll text them. Sadly, I don’t run the world. Halloween will still be on a random day, and fall break will still land on a random week. This will be the tenth year I’ve been a parent with a kid on fall break. I’m as unprepared as ever. But I’m aware in advance of how unprepared I am, even if I won’t do a single thing to get ready. That feels like progress. Sometimes personal growth is just procrastinating further in advance.
The actual reason for the timing of fall break is that it’s roughly when kids need relief from school—and when their teachers need relief from them. After a month and a half, both sides need some time apart before academic burnout transforms into a full-blown riot. I’m exhausted by school, and I’m not even in class. The problem is that teachers keep me in the loop. Every morning, I get an automated email for each child about missing assignments. I don’t know if you’re aware of this, but I have a lot of kids. The emails go out at 4 a.m., so they’re the first thing I get when I wake up. There’s nothing quite like greeting the day by stressing out that my children might have a zero on something. I say “might” because, most of the time, the emails are wrong. Something was graded early when it wasn’t due yet or wasn’t graded at all. In rare cases, my kids forgot to click submit. Since I don’t know which scenario applies, I have to text my kids every time. If I don’t do it right away, I’ll forget. I read their academic emails when I’m barely awake and message my kids about them while they’re still asleep. I feel like an ineffective middle manager running my family by email. We could all use a break from that. Unfortunately, the emails don’t stop for breaks. Going into last year’s fall break, one of the kids had a missing assignment that wasn’t really missing. I got an email about it every morning until the girls went back to school. I shudder every time I see that email indicator on my phone. I hope that’s not the reaction you have when you see the alert for my emails. I promise to never tell you that you’re failing. I fail enough for all of us.
Needing a break is one thing. Knowing what to do on it is another. Some people take fall break very seriously. A nearby suburb is one of the richest in the state. At the start of fall break, the city empties out. Good luck at the airport. It’s the one time of year the metal detectors here actually have a line. People in my suburb don’t travel as much. It took me years to discover that people disappearing for a week was a cultural event one town over. People in my community mostly just scramble to find childcare for that week. That’s the opposite of a vacation. You have to pay extra to stay in town. I’m grateful my kids are big enough to watch themselves. If you can, I recommend starting out with big kids and skipping the baby and toddler stages when childcare is more expensive. The only downside would be that delivery would be more difficult. Natural birth wouldn’t be an option when pushing out an eighth grader.
The trickiest part about fall break is that no two fall breaks line up. For Christmas break, schools might start on different days, but your kids will be off from Christmas to New Years. If your child’s Christmas break doesn’t include Christmas, you should move. The same thing happens over the summer. Our school year starts earlier and ends earlier than many others in the area, but everyone is off by the first week of June. Eventually, everyone syncs up, making it possible to do things with friends and family members in different districts. That’s not the case with fall break. The schools are conspiring to keep us apart. We had considered going on a short trip with my brother-in-law and sister-in-law Jerry and Alice next month, but their kid is off on a different week than ours. We’ll miss each other entirely. That’s for the best. Instead of driving to Tennessee, I can stay in my own house, which I already paid for. Paying for two beds when I can only sleep in one at a time seems like a waste. Until I learn to bilocate. Then all bets are off.
Aware of the chaos associated with other school breaks, we did our best to squeeze in our family activities over the summer. It was easier then because school activities were paused, if only in theory. In actuality, my fifteen-year-old, Betsy, had cross country practices over the summer. It was technically voluntary, but she was expected to be there every day that she was in town. We’re a step away from having high school coaches attach ankle monitors to athletes. Then again, Betsy already uses far more invasive tracking methods. She shares her location on her phone with me so I can make sure she actually makes it to and from practice. She also wears a watch that tracks her location to precisely calculate how far she runs. Some college coaches have their athletes turn over that data to make sure they don’t cheat on workouts. If that technology existed when I ran in college, our entire team would have been kicked out by week two.
Betsy will also have practice over fall break. Once again, it’s voluntary, unless she’s in town, in which case it’s mandatory in all but name. Betsy would skip practice if we went on a day trip, but she’d feel guilty. Naturally, she’d pass that feeling on to me. There’s nothing easier than making me feel bad about literally anything. I exist in a state of preemptive guilt. I don’t know what’s going to happen, but whatever it is, it will be my fault. We need to stay close to home, which probably means staying home, period. It’s my dream come true.
This calls into question why I took that week off work.


