That’s a difficult title for me to write.
Growing up with two brothers, competition was a way of life. We raced to the dinner table, battled over board games, and kept score of everything. But in education, constantly trying to come out on top can quietly erode the very relationships we’re meant to protect.
As a kid, I hated the final scene in A League of Their Own. I rooted for Dottie (Geena Davis) the entire movie. I found Kit (Lori Petty) overly whiny and frustrating. So when Dottie drops the ball in the championship game—allowing Kit to win the title for Racine—I was devastated.
Why would she do that?
As I’ve grown older and rewatched the film, I see that moment differently. I don’t believe the ball simply slipped out. I believe Dottie made a decision.
She did it for Kit.
But she also did it for herself.
Throughout the film, Kit is fragile, anxious, and deeply insecure. Without Dottie, she likely never would have had the opportunity to play in the All-American Girls Professional Baseball League. Her lack of confidence stems from living in the long shadow of her older sister. Dottie sees it in Kit’s face. Kit even says it outright—she is tired of being second.
And what does Dottie really gain by holding onto that ball? A championship trophy? A moment of personal glory? Perhaps.
But she risks losing something far more important: her relationship with her sister.
When Dottie sees her husband return safely from the war, it becomes clear that she already has what matters most. A championship ring would not add to that. In that moment, she chooses relationship over recognition.
When faced with winning or doing the right thing, Dottie chooses the right thing—and in doing so, she wins in a way that lasts.
Schools face this same tension every year.
Stress builds. Deadlines approach. Policies are signed. At some point, students and parents can begin to feel like teachers’ adversaries instead of partners.
Every teacher has a late-work policy—whether it’s a school-wide expectation, a grade-level agreement, or a classroom rule. Students (and often parents) sign contracts at the beginning of the year acknowledging that they understand those policies.
Then, inevitably, a situation arises. A student has a legitimate reason for not completing an assignment. The teacher has a signed agreement clearly stating the consequences.
So what should the teacher do?
If the student is viewed as the opponent, it becomes tempting to dig in and “win.” After all, the contract supports the teacher’s position.
But if the moment is viewed as an opportunity to strengthen the relationship, the response changes. Working with the student to create a plan for completion becomes a shared victory. The assignment gets done. The standard remains intact. And the relationship grows stronger.
That’s a real win.
As administrators, we face similar decisions with parents. Perhaps a family misses the deadline to apply for Student Council. Maybe they forget to pay a deposit for a field trip. Maybe they miss the window to request placement in an advanced math course.
You likely sent reminders. You posted information on the website. You shared it through social media and the PTA. You did everything right.
So now what?
Do you hold the line because “a deadline is a deadline”? Or do you pause and ask what is best for the child?
Some argue that once a deadline passes, nothing can be done. In my experience, that is rarely true. With creativity, flexibility, and a willingness to collaborate, most missed opportunities can be recovered.
And when parents know they’ve made a mistake, extending grace can be a powerful way to build unity between home and school.
Dottie chose her sister over a championship.
In education, we will be given countless chances to choose between being right and being relational. Between enforcing a rule and strengthening trust. Between winning an argument and investing in a child.
I hope we choose students over “winning.”
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