Culture

Regimentation in Education: Stricter the School, Sneakier the Child

In this piece, the author reflects on the transition from being homeschooled to being a pupil in a British boarding school. These two contrasting experiences demonstrated the unintended and unexpected consequences of regimentation, which harmed students more than helped. Pragmatism, the author concludes, is a much better approach to discipline than intense regimentation.
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Regimentation in Education: Stricter the School, Sneakier the Child

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May 16, 2026 05:26 EDT
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“The Master is having a crackdown on jewelry!”

As soon as our housemistress had made the announcement to us that morning, illicit bracelets were promptly pushed under the sleeves of our tucked-in school shirts. The newly-appointed headmaster (or “the Master” as he was referred to, bizarrely enough), clearly thought the enforcement of the lengthy dress code too lax for his standards. So, he took it upon himself to straighten us up into the prim and proper student body of a school that took its discipline very seriously indeed. 

I had been attracted by the school’s ambitious academic environment. I had enrolled expecting a good education, but I hadn’t fully considered the culture shock I was about to experience after years of enjoying an exceptionally high degree of agency as a homeschooler. 

While ironed blazers and floor-grazing uniform skirts made for excellent marketing material for strict parents, behind this veneer of decorum I observed the rebellious reality of teenagers in an atmosphere of repressive regimentation. They had become experts in the art of subversion rather than the disciplined students the school had expected.

Regimentation can lead to repression, which in turn leads to rebellion

Heavy-handed attempts to control have a tendency to backfire, as if the strictness compels people to act out. In some of my friends, particularly those with stereotypical Tiger parents who demanded obedience to their infallible parental wisdom, I noticed the same pattern: the stricter the parent, the sneakier the child. The parents do not know how their child dresses or how she spends her weekends. She pretends to be out studying, ready with photographs taken beforehand in case the parents need proof. She jumps out the window to meet the boyfriend she is not allowed to have.

Growing up with distinctly non-traditional parents myself, I was used to a dynamic of open communication, so I was often puzzled by their need for secrecy. After I experienced strict regimentation for the first time at boarding school, I began to understand why children of disciplinarians often end up leading a double life. Once autonomy has been denied to you, it’s all you strive for.

It is not necessarily the rules that provoke rebellion, but the absence of any rationale for them. Either the adults provide no justification (after all, students answer to the school and not the other way around!) or no justification really exists, since much of the discipline enforced is a euphemism for conformity. For instance, it seems unlikely that student behaviour or performance would be impacted by wearing black socks (as many dared to) instead of the sanctioned navy. Such rules felt jarring to me after I had become used to spending hours studying in pajamas and bedroom slippers. When the rules seem more like an arbitrary list, it makes it hard to understand them. 

With teachers jumping out of alleyways to exclaim their outrage at your untucked shirt, it becomes difficult to trust that the rule-makers have your best interests and not mere optics in mind. The school administration begins to feel like an annoying adversary. And any rule-breaking that follows only furthers the administration’s hostile attitude towards the students they deem to be irredeemably unruly. That, in turn, leads to more spite among the students, creating a vicious cycle of both sides increasingly alienating the other.

This mutual lack of trust can lead to dangerous consequences. I have seen people whose experimentation with rule-breaking has gone very wrong. A classmate told us about the intensely negative reaction to weed she had when she tried it; she teared up as she recounted the experience. She hadn’t felt comfortable sharing this with either her strict parents or the equally strict housemistress at school, fearing that it would lead to more restrictions. Authority figures that seem solely controlling rather than supportive can end up isolating the ones they’re supposed to be watching out for. Consequently, students may not get the opportunity to properly process harmful experiences and lack the advice needed to make better decisions. 

You cannot balance on your own if you have always ridden with training wheels

The school recently reduced some freedoms exclusive to Sixth Formers (students in their final two years of school), known as Sixth-Form “privileges,” tightening rules to be more similar to those for younger years. The idea was that 17- and 18-year-olds, who would soon be starting university, still require rigid scaffolding to properly manage their time.

I would argue that freedom is not just a “privilege.” It is also responsibility — a responsibility for yourself, which is a defining part of life as an adult. Does a school that dictates and keeps track of what students wear, when they wake up, when they eat, when they study, how they study, when they exercise adequately prepare them for life at university? While a regimented schedule would certainly help younger students instill a healthy routine, spoonfeeding structure to pre-university students does not seem conducive to developing the independence they will very soon require.

External discipline also does not automatically translate into long-term internal discipline. From my vantage point as a former homeschooler, I realized it may even be demotivating. Used to managing my own academic progress, I pride myself on my drive to achieve my goals. I imagined I would easily adapt to the school’s scheduled study sessions. However, with timely knocks on my door every day to check up on me, my self-motivated decisions to honor the responsibility for my own education turned into a mandated, monitored chore.

Finding a balance

Instances of rebellion like dress-code violations or underage drinking seem inevitable in an environment like this. But if too much control tends to authoritarianism, absolute freedom leads to anarchy. The solution is obviously not a laissez-faire approach to managing a large group of teenagers. 

Instead, I am advocating for creating an incentive structure that is more sensitive to teenagers’ penchant for defiance. I have attended another British boarding school that has a contrasting, more unconventional philosophy on disciplinary action. 

At this school, the rules were liberal: no uniform, freedom to spend time outside of school hours anywhere in the city (as long as they disclosed their location periodically), and 10:30 PM curfews to be in your room, but sleep whenever you see fit. This was as close to a university experience as you could get, and that was the point. Students were given a high degree of freedom. Restrictions were implemented only in cases where that freedom was abused. If you had unauthorized absences from or late arrivals to class, you risked losing the ability to go out on the weekends. The school was observant, not ambivalent, to how students used the freedom given to them. This created an obvious incentive to better manage the flexibility we had. People responsible with the liberties could continue to enjoy them.

Compare this with the Master’s school philosophy: maintaining order with an iron hand, and deeming the slightest relaxation of restrictions a great “privilege.” When the sanctions for rule-breaking do not feel significantly worse compared to the regimentation already in place, what is the reward for being good?

Gedogen: pragmatic, not preachy

The difference in attitude between the two schools was never as apparent as in the way they conducted assemblies. 

In the large hall, a teacher declared, “Please stand,” as the Master walked in — dressed in robes. I remember my disbelief the first time I watched this caricature of a British boarding school experience unfold before me. The assemblies created a spectacle out of the school’s discipline and authority hierarchies. Antiquated practices were continued without any of the lightheartedness that would have turned them into endearing traditions. Once, all students were lectured about how, as young people, we suffered from a kind of “temporal illiteracy” and had “no grasp of our own mortality.” One can argue about how accurate the sentiment is, but I wonder if sermonizing is the most effective way of communicating with said temporally illiterate people. 

In the other school, what assemblies lacked in ceremony, they made up for in substance. One of the deputy principals, with whom students were on a first-name basis, spoke to us about cigarette packets found littered near the school campus. After reminding students again of the risks of smoking and school rules, she acknowledged that some students would still smoke anyway. She emphasized that while these students were choosing to make a harmful personal choice by smoking, because of the littering their poor decision was also an unacceptable nuisance to others. We were spoken to as capable young people in charge of our choices and their consequences, which encouraged students to react with more maturity.

Rather than a school that dealt with older students through proscriptions and prescriptions, the second school used responsible pragmatism. By trusting them to have a high degree of freedom and stepping in when that was genuinely mishandled, rule-breaking seemed less glamorous and more like a poor decision. The school’s philosophy reminded me of “Gedogen,” the Dutch policy of tolerating the violation of certain laws where strict enforcement may be more disruptive. While telling us about this, my tour guide in Amsterdam had also shared the anecdote of his parents smoking weed with him before he left for university to remove any tempting sheen of forbiddenness the activity might have had. While this is a shockingly lax approach, it captures what I observed across these two boarding schools: although regimentation does provide the appearance of discipline, a liberal approach can be more effective in achieving its reality. Interestingly, that was the tour guide’s first and only time smoking weed.

[Cheyenne Torres edited this piece.]

The views expressed in this article are the author’s own and do not necessarily reflect Fair Observer’s editorial policy.

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