Reflections on Choosing a High School

I recently caught up with an old friend who runs a left-handed and progressive bookstore here in Portland. During my visit, he mentioned that his son would be starting high school next year. “He’s keen on attending Central Catholicism,” he said, clearly surprised. “His mother and I didn’t expect that. Since you went to Catholic High School, what do you think sparked his interest?”

This took me a moment, but I quickly grasped what was probably going on. His son leans conservative, at least regarding his school choice.

Public schools in Portland are generally very progressive, often leaning toward more activist ideals, sometimes bordering on the absurd, reminiscent of “Portlandia”.

It seems my friend’s son believes that attending Central Catholicism might provide him with a more traditional high school experience.

I found myself hesitant to break the news directly to my friend, so I tweeted about how Catholic schools often provide more structure and can enhance a student’s college application.

Still, I could sense that my views might disappoint him. But I completely understood where his son was coming from—after all, I had similar thoughts at that age.

My School Experience

I attended a public middle school in Portland ages ago, and honestly, it wasn’t too different from what it is now.

My family lived in an affluent neighborhood, meaning my school was filled with bright, well-mannered, middle-class kids. The school was well-respected and even drew students from other areas who wanted to share in its resources.

I enjoyed my time there. I had good friends, a supportive teacher, and participated in various sports. We even had a ski bus!

That said, I was also a small, energetic child with a tendency to be a bit of a class clown. I had already been held back in elementary school due to class disruptions.

Initially, my new middle school teachers were patient with me. That was their approach: a comprehensive and advanced educational philosophy that prioritized individual needs. We were seen not just as students, but as unique individuals.

How did I respond to that level of acceptance? Well—let’s just say I became an even bigger class clown, leading to more mischief and trouble.

Reflections on the Student Experience

Unbeknownst to me, I was on the radar as a “problem” student. I liked my classes, did well academically, and seemed to be popular, yet by eighth grade, I found myself in a parental meeting due to my behavior.

All the teachers elaborated on my rule-breaking antics: running in the hallways, tossing pencils out the window, and jokingly attempting to drag a girl to the boys’ bathroom.

I was genuinely surprised by their reactions. I never thought I was causing that much chaos; I assumed they liked me!

The High School Dilemma

That summer, as high school loomed ahead, my parents and I explored potential schools.

We could opt for a public high school, where I would likely encounter more trouble, or settle on the Jesuit Catholic High School nearby. All I knew was that it had a reputation for strictness and was all-boys.

My family wasn’t particularly religious, and I wasn’t either, but at some point, the decision fell on the Jesuits.

Years later, I asked my mother, “When did you decide to send me to Jesuit school?”

She replied, “We didn’t decide. I wanted you to go.”

The Atmosphere of Hierarchy

I can still vividly recall my first day at the Jesuit school. The energy in the hallways was intense, and there was an undeniable sense of male energy and an unspoken hierarchy.

As a freshman, you were at the bottom of that hierarchy, but interestingly enough, this seemingly unfair structure created a sense of calm. Everyone had to endure the same initiation.

We shared our various humiliations together, which echoed the classic American high school experience. It felt timeless, and weirdly enough, I embraced it.

Transitioning into Manhood

One thing that impressed me during those first few days was the apparent seriousness with which the school operated.

There were rules to follow, and the authority figures were predominantly male: teachers, administrators, even our principal.

This was in stark contrast to my previous public school, where respect felt more like a requirement; at the Jesuit school, it felt earned. These people commanded respect.

Among our coaches and educators were remarkable individuals; one had played as a San Francisco 49er, another had flown helicopters in Vietnam.

The Social Landscape

My social life had its difficulties in my first year at the Jesuit school, especially as we tried to navigate interactions with girls from a nearby all-girls Catholic school.

These dances and events had a certain awkwardness. The girls didn’t seem as prim and polished as those from public schools; some felt almost rustic.

It was all innocent and, frankly, often amusing. The nuns ensured that a respectful distance was maintained while we danced in the dimly lit hall.

Above all, if you faced embarrassment from a girl on a Friday evening, you certainly wouldn’t want to see her the following Monday at school.

A Focused Education

Despite the challenges, my studies at the Jesuit school were grounded and foundational, particularly at the new student level. The teachers didn’t bombard you with advanced material; instead, they taught you how to focus and manage your time.

This was the school’s brilliance—it recognized the reality of a teenage boy’s life. A lot of energy, difficulty sitting still, and emotions to manage.

Thus, sports were emphasized—there was soccer, a weight room, and less concern about emotionality. Their method aimed to redirect that teenage energy productively.

Finding My Place

Catholic school turned out to be just right for kids like me. Sure, I remained a troublemaker and a class clown, but there was understanding surrounding that behavior.

In those four years, I never found myself in serious trouble—no fights or parental meetings, and, thankfully, no drama with any girls.

A Different Landscape

So, I hope my friend’s son thrives at Central Catholicism. Unlike my all-boys Jesuit experience, it’s now coed. Those all-boys institutions seem to be fading away.

Still, I suspect he will enjoy it much more than a public school where traditional boyish energy is often viewed as toxic. It’s almost hard to imagine returning to an all-boys setup these days.

If they were reinstated, though, many boys might seriously consider it—perhaps even needing to chat with their parents about it.