When I look back at almost a decade of experience at my middle school, I see thousands of decisions I rushed into without thinking about, actions I took without examining the consequences. There were plenty of times I said things I shouldn’t have, didn’t prepare enough for an exam or missed out on an opportunity. Out of all of that, only one day stands out.

It was like most advisory meetings before, except instead of the controlling Mrs. Gigounas, who was on sick leave, we were meeting with her substitute, the beloved Mr. Penn. His steel-rimmed glasses, jackets, vests, and slacks made him look like a college professor, and he always ready with a story from when he was our age at boarding school, nearly everyone in the class held him in the highest regard — he was safe from the ridicule that most teachers were subjected to every time a group of students was out in the halls. But that being said, he was still a substitute, and they never knew the rules; that’s why when Conner, a friend of mine who always seemed to be ahead of the coolness-curve, told me about the extra popsicles in the teacher’s lounge freezer, I figured it was an easy way to earn some low-risk street cred.

I got us some popsicles and easily deflected the little suspicion that Mr. Penn cast on me. We always get a snack, and he didn’t seem to pay much attention. We had been a well-behaved advisory, attentive and enthusiastic. He trusted us.

Everything was going according to plan, we just had to finish and dispose of the evidence. Just as I was enjoying the bites, it all came crashing down around me. Mr. Lee, a teacher battle-hardened from other schools and constantly on the lookout for plots such as mine, had decided now would be the perfect time to check in on Mr. Penn about something. He noticed instantly.

“Where did you get that Will?”

“Uhhh. My locker.”

This exact moment is where it all went wrong. I am sure that up to that sentence, there were dozens of escapes. If I had eaten a little faster, or maybe even sat in a different seat, I would have gotten away scot-free. Of course, confession would be an easy out as well. But such a feeble attempt to deny the deed had completely sentenced me to my fate. What kid would keep popsicles in a locker?

The rest of the conversation turned trail was a blur.

I confessed to Mr. Lee almost instantly and he quickly delivered my sentence. Friday detention, in which I would write a letter of apology. Completely standard. But the real punishment was when he left the room. Mr. Penn stared at me for an instant. It was more than enough. Suddenly, as though it had been building up, a wave of emotions hit. I felt shame I had attempted to sneak by a man I had so much respect for, I was furious at myself for violating his trust, and I was filled with regret that I had violated the trust of a man whose opinions I deeply valued and whose ideals I admired. I was borderline whiplashed from the speed of it all.

It felt a whole lot for a stupid popsicle.