It’s funny how formative experiences tend to repeat themselves. Being hauled into a Bloomberg HR meeting over my tweets about Martin Shkreli in 2018 didn’t feel that unfamiliar. A template for what the discussion was all about, what would likely be said and unsaid, and how management would try to “deal” with me was already imprinted in my mind — from way back when I was a freshman at St. Teresa’s Academy, an all-girls Catholic prep school in Kansas City, Missouri.

The issue then, 20 years earlier, was a photo I’d taken of two classmates (with their permission) for the local newspaper’s “teen” section. It was published alongside a story about how students at private schools expressed themselves through their appearances despite wearing uniforms. The two girls, who had their arms thrown happily around each other’s shoulders in the photo, were wearing St. Teresa’s signature tartan plaid skirts and white polo shirts…while also sporting hot pink dyed hair and eyebrow piercings.

“They’re…out of uniform!” the principal Mrs. Hoecker, a woman whom you might find on a Venn diagram at the intersection of “church lady” and “aging hippie,” said to me, as she tried to explain my “mistake.” Oddly, she wasn’t talking about the hair and the piercings. Instead she was referring to the girls’ untucked shirts. There were rules against untucked shirts, but no policies against students having pink hair and piercings — merely an unwritten rule against publicizing that fact, so I gathered.

As a skinny, quiet 15-year-old, who was among the top students in my class and not used to being in “trouble,” I found my vocal chords were all but paralyzed as I sat squarely within Mrs. Hoecker’s kind but disappointed gaze. I nodded compliantly along with her. But even though I could not muster the confidence to string together arguments, I still absorbed plenty of information from her that made me think: “Hey, wait a minute…”