My family moved to Oak Park in 2015, just before our youngest was set to start kindergarten. Our “why we moved to Oak Park” story is charmingly unoriginal — one I’ve heard from countless neighbors. It usually goes something like this: a young couple living in a great Chicago neighborhood, never seriously considering the suburbs, suddenly finds themselves driving out to Oak Park “just to look” at a house. Fast forward 10 years, and that same couple is deep in a debate over leaf-collection policies. We are that couple.
As someone who has spent most of my professional life as a teacher, assistant principal, and principal, I’ll use this column to share thoughts on education, though I’ve got opinions on plenty of other things too.
This spring, I ran for a seat on the District 97 school board. I came in fourth, and while that meant I didn’t win, I was genuinely excited for the three candidates who did. Running gave me the chance to meet so many incredible people (I’m a huge extrovert) and hear firsthand about the wide range of experiences families are having in our schools. My consolation prize? A chance to share my reflections here in Wednesday Journal.
A question I was recently asked stuck with me: “What’s one thing you’d change in District 97 to improve the student and family experience that wouldn’t cost any money?”
Here’s my answer: Create clear, district-wide expectations for how often middle-school teachers update grades and how they handle late work.
One of the most noticeable shifts my family felt moving from elementary to middle school was the lack of clarity around grading. In elementary school, you get regular updates every trimester — Excels (E), Meets (M), and Progressing (P) — and teachers often reach out if your child is excelling or struggling. Middle school, however, feels much less consistent. Some classes update grades weekly; others might have only three grades posted across a 13-week trimester.
Grading practices are complex, and I won’t pretend that one column can untangle the debate over what grades really mean. But at the most basic level, grades are a tool for communicating progress. Without regular updates, families are left guessing how their child is doing. That uncertainty doesn’t help anyone.
So here’s a simple proposal: require middle-school teachers to enter at least two grades per student per month and create a consistent policy across grade levels for submitting late work.
This isn’t about blaming individual teachers or schools. In fact, I think most teachers are already doing this. But for the sake of families and students, we need to make these expectations explicit and consistent. This is a no-cost, high-impact improvement that would bring more clarity, reduce frustration, and help everyone stay on the same page.
It’s a small change, but in education, sometimes the small things make the biggest difference.
Vince Gay has over 20 years of experience in education, ranging from classroom teacher to building administrator. The proud parent of two school-aged children, he has been an active member of the Oak Park community for more than a decade.