Digital Byte 80: Reflecting On How My Teachers Shaped My Leadership

May 19th, 2026

Last week was Teacher Appreciation Week, so I took the time to reflect on the teachers who stuck with me since. One in particular was one of my high school English teachers, Mr. Lynn.

One day, we walked into class, and he wasn't at his desk. Instead, he was sitting in the corner of the room in a student desk, completely silent. No greeting. No explanation. Just a piece of paper on each of our desks that told us we were running the class for the entirety of our next book, Lord of the Flies. We would create the assignments. We would grade each other. He would not say a word during this part of the syllabus.

If you haven't read the book, I highly recommend it. But in short, it is about a group of boys stranded on an uninhabited island who have to govern themselves.

Contrary to what most of us thought would happen, running things ourselves went surprisingly well. Leaders stepped up, decisions got made, we figured it out. But what it made me realize upon reflection now is how much invisible structure was already woven in from years of being in school. We knew what a class was supposed to look like even without someone telling us. And when things got murky, you could feel the pull toward wanting someone to just make the call. Having hierarchy is human nature.

I think about that classroom assignment now that I'm leading a team.

The processes we build exist for good reasons. Something goes wrong, you learn from it, you put a guardrail in place. That's experience turned into protection. I'm not trying to throw any of that out.

But there's a difference between guardrails and a cage. If every decision has to run through you, if there's only one correct way to do every task, if the people on your team feel like they're just executing a checklist, you're limiting your growth. The people doing the work every day see things you don't. They know where the friction is, what clients are actually saying, which part of the process is slowing everything down. If you've built an environment where surfacing that feels risky, you're cutting yourself off from some of your best information to help your business thrive.

What my teacher understood was that giving people real ownership, even with minor structure underneath it, we gained more experience than him managing our every assignment, and that book was the perfect parallel to do it in. The structure isn't there to control. It's there so people can do their best work without reinventing the wheel every time. Within that, there should be room for someone to try a new approach, push back on the way things have always been done, and occasionally get it wrong in a way that teaches something.

He never said a word that entire unit. But remembering what it was like for a room of teenagers to self-govern with a few invisible guardrails reminded me of the importance of autonomy within my team.

Stay Inspired,

Sydney