By the time winter break arrives, many educators aren’t just tired, but they’re carrying things. Heavy decisions. Hard conversations. Students we can’t stop worrying about, colleagues we want to reach but don’t quite know how.
This season invites rest, but it also invites remembering.
Stories matter because they reconnect us to purpose without pretending the work is easy. They remind us that meaning is often found not in the outcomes we measure, but in the people we continue to show up for. Here are three stories that continue to remind me why teaching and leading in schools still matter deeply, even in the hardest seasons.
Story One: “Every Kid Needs a Champion”
Years ago, I watched Rita Pierson deliver her now-iconic TED Talk, Every Kid Needs a Champion. I’ve revisited it many times since, and it still tugs at my heart.
Her message wasn’t about instructional strategies or school improvement plans. It was about belief. About adults choosing to stand in the gap for students, even when those students push back, shut down, or test every boundary. Her talk reminded me of a student I met in his freshman year of high school.
About twenty-three years ago, a young man stopped by my office and was pretty distraught. I was his ninth-grade Global Studies teacher, and then I became his assistant principal. I had a strong relationship with him and his family. His mom also called me to let me know he might stop by because “things are pretty bad.” So, I wasn’t surprised by his visit, but I was surprised by what he shared.
He was done: done with school, done with home, done with everything. We talked for about half an hour, and he seemed to feel better, but when he left my office, he didn’t return to class; he left the building…
I called his mom to let her know how our conversation went, and she told me she’d let me know if he shows up. A few minutes later, she called to let me know he was home.
Thankfully, he returned to school the next day and finished the year. Before summer break, he gave me a handwritten note thanking me for taking the time to listen. In that note, he shared that he had considered harming himself and that our conversation helped him see things just a little differently.
Stories like this remind me that we may never fully understand the impact of a single conversation, but students remember who showed up when it mattered most.
Years later, on April 6, 2024, I ran into his parents at Home Depot. They shared incredible news: their son was thriving and nearly finished with his doctoral studies. We shared a long hug and a few tears!
Story Two: The Student Who Didn’t Give Up
A couple of years ago, I watched a student in one of our Career-Technical Education programs struggle academically, behaviorally, and emotionally. The CTE lab instructor tried everything to help this young man: tough love, coaching, peer mentoring, parental involvement, you name it. To say he was frustrated with this student is an understatement.
However, instead of labeling the student, he chose persistence.
He didn’t lower expectations; he increased support. He created notecards to help him learn parts. He asked the student to come to the lab during study hall for additional help. He allowed a couple of test retakes after some further review sessions, and he partnered with an Intervention Specialist to learn about other accommodations.
The young man drove a beater of a car that needed a lot of work. The instructor helped him fix his car, which reinforced the skills he was trying to teach him, and he helped him land a job in his chosen industry. Months later, he graduated from his school and earned an industry credential, which helped him get a promotion.
What stood out most wasn’t just the outcome, but the educator’s refusal to separate skill-building from dignity.
Story Three: Choosing Connection When Convenience Would Be Easier
This story isn’t about students, it’s about adults.
One of my executive team leaders consistently chooses conversation over avoidance, growth over comfort, and trust over tension. Whether addressing curriculum concerns, procedural challenges, or personnel issues, her approach is steady: listen to learn, seek the back story, and collaborate toward solutions.
When she first arrived in our district, she heard many negative comments about our application process, which was pretty new. Since it fell under her supervision, she met with those who had concerns, met with members of our Business Advisory Council, and gathered feedback from our building leaders. After months of information gathering, we created a new application process that was much more widely accepted and, most importantly, better for students.
Because of her approach, difficult conversations that could have fractured trust instead became opportunities for alignment and growth.
As you head into break, give yourself permission to rest. Disconnect where you can. Refill what the semester has drained. When you return, recommit to one student or one colleague you’ve been struggling to reach.
Rest now. Then carry one name with you, and begin again.
Wishing you and your family a Merry Christmas, Happy Holidays, and a Happy New Year.
Be Great,
Dwight




