Is Our Education System Broken? Two Educators Debate the Truth
Is America's education system broken? Assistant principal Cashius Jackson joins me for a candid conversation about student behavior, parenting, social media, consequences, charter schools, and teacher burnout. We don't agree on everything—but we do agree that strong teachers still have the power to change what happens inside their classrooms.
8/29/2026
There was a point during my conversation with Cashius Jackson when I realized we were looking at the same problems but coming to two very different conclusions.
Cashius sees an education system in serious trouble.
I see many of the same problems.
But I still have hope.
Cashius is an assistant principal, former teacher, comedian, and content creator. He also has a fascinating background. Before becoming an educator, he was expelled from school five years in a row.
He described himself as the kid teachers had given up on.
Eventually, changing environments changed his life. He went from Louisiana to Maryland, discovered a completely different world, earned his education, became a teacher, and eventually moved into administration.
That experience shapes how he sees schools today.
And he has some strong opinions.
📱 Social media has changed students.
👨👩👧 Parenting has changed.
⚠️ Consequences have disappeared.
🎓 Students are sometimes being moved through the system without mastering basic skills.
Cashius believes we've reached a point where education may not recover anytime soon.
That's where we disagree.
Don't misunderstand me. I've been teaching for over 20 years, and I've watched many of these changes myself. Student behavior is difficult. Teachers are overwhelmed. Administrators have limitations. And sometimes a tiny percentage of students can completely change the learning environment for everybody else.
But I keep coming back to something I've seen firsthand:
The teacher still matters.
Several years ago, another educator was standing in the back of my classroom watching my students work.
He looked at me and basically said, “What are you doing here?”
These were students who could be difficult in other classrooms. Yet they were sitting down, working, and engaged in mine.
That wasn't because they magically became different students when they walked through my door.
The environment changed.
That experience eventually became one of the reasons I started The Classroom Management Guy.
We may not be able to change state laws tomorrow. We can't immediately change social media. We can't control what happens in every student's home. And we certainly can't rebuild the entire education system ourselves.
But we can get better at teaching.
We can build stronger classroom-management systems.
We can create better routines.
We can become better at handling difficult behavior.
And we can create classrooms where students who struggle somewhere else can succeed.
That's where my optimism comes from.
Cashius and I may disagree about where education is headed, but toward the end of our conversation, something interesting happened.
He talked about former students approaching him years later.
They remember him.
They thank him.
They tell him how he helped them.
And suddenly, underneath all his frustration with education, there it was:
Hope.
Maybe neither of us knows exactly how to fix education.
But I know this.
If you can change the experience of one student, you've changed something.
And if we can help thousands of teachers do that, maybe that's where fixing education actually starts.
👉 Watch the full conversation here:
https://www.youtube.com/watch?v=Zq6fbQb4UXM&list=UULFQOIbqNhb_gseSVU6bE3uUA