The first day of school is the most terrifying, hopeful day of my whole year.

And I’m not even in school.

Every year, the first week of school kicks my ass. Oh heck, let’s be honest: it’s usually the first couple of months.

The year Peanut started a new daycare we got calls every few days about his refusal to do the group activities. The year he started kindergarten it was calls about him running away from class and hiding. The year he started grade 1, at a new school, it was calls about him pushing the furniture to the edge of the classroom or hiding in the cloakroom.

For the past three years I’ve been right there for the action, so instead of calls it was live drama. The fall of homeschooling, when he refused to leave the house. The fall of part-time private school, when he refused to stay for more than an hour. Then last year, the return to full-time school, when it took everything from wrestling matches to midday movie dates to ensure Peanut was at school at the beginning and end of each day — even if what happened in between was all over the place.

Tomorrow, it begins again, and despite seven years of experience with The Fall From Hell, I find myself tempted to hope that this will be the year. The year school just works, the year there are no crises, the year that Peanut starts to feel like life isn’t quite so hard. There are so many reasons to be hopeful: he really did get used to full-time school last year, he is returning with a support worker he already trusts and adores, and he is much more adept at managing his own stress levels than he was a year ago.

And yet, I am afraid to hope. September has kicked my ass far too many times. I find myself trying to prepare for a day of meltdowns, a week of intransigence, a month of drama. I want to insulate myself from the exhaustion, the risk of disappointment, and most of all, the risk of pressuring Peanut.

But if I don’t hope, then what? Do I create a self-fulfilling prophecy? Do I become that mom who is always right there, ready to catch her kid if he falls….and making the fall inevitable?

Ultimately, there’s no decision. Yes, I prepare for school like the mom who has learned from seven years of painful Septembers. I clear my schedule so I’m available for crises; pack a backpack full of distractions in case we run into trouble; distribute a safety plan to the teachers in case Peanut once again takes off.

In my heart, however, I’m like every other parent, the night before school starts. I pack the school supplies, lay out the brand-new first-day-of-school clothes. I picture a child bounding into class, then grinning ear-to-ear after a successful first day.

I don’t know if this is the year that will finally happen. I don’t know if it will ever happen. But here I am, once again, giving into the reckless, dangerous temptation of hope.