An Inside View of Hoity-Toity East Coast Boarding Schools

A fac brat tours the sausage factory

You haven’t written a post in over a year.

Yes, I took a rather exhausting if very interesting job in Miami as a research chemist doing batteries. However, I’ve had a decent chunk of equity vested and I’m now mostly superfluous, so I’m out at the end of the month to work on other things. More on that anon.

This essay is an expansion of an old 77-tweet thread (with side threads) that I wrote about a year ago, but I kept linking people to it enough that I thought I’d rewrite it as a much-more-easily-linked Substack post. There’s a faint possibility that I’ll go back to boarding-school world in the distant future (ideally to teach a couple sections of Ancient Greek for fun), but it won’t be any time soon, so I feel fairly equanimous spilling the beans.

I am the son of a boarding-school history teacher and lived on the campuses of various boarding schools from the age of two until a few years after college¹; I also taught middle-school Latin at a day school for a year and a half (however, none of the stories that follow are drawn from my stint as a teacher, only as a faculty kid). In other words, I’ve got a lot of insight into how these places work behind the scenes—certainly more than your average boarding-school alumnus.

The original Twitter thread ended up with a number of branches that are a bit difficult to navigate, and I’ve done my best to condense most of the relevant discussion here.

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What is a boarding school, anyways?

First, let’s dispel some misconceptions.

What I mean by ‘boarding-school world’ (BSW) is historically an old-money(ish), WASP phenomenon. It is therefore concentrated in the Northeast and eastern South, with a few outposts in California. Elsewhere in the country “boarding school” usually seems to mean a military academy or reform institution (or the notorious and now thankfully closed Native American residential schools); we’re ignoring those here².

Even with those restrictions, boarding schools are highly variable and the definition is fuzzy, so we’ll consider a prototype. The prototypical boarding school (BSch) is a formerly or nominally Episcopalian institution in a rural or exurban area not far from Interstate 95. It was founded as a boys’ school sometime between 1880 and 1910 and then went co-ed some time in the 1970s³. It has seven-day boarding during the school year, which means that the students live in dorms with faculty serving as dorm parents and legally-required Present Adults, but go back home during the summer and winter/spring break (exceptions are sometimes made for the latter periods, especially for international students).

Outside major cities, there is also a subspecies with five-day boarding where students live in the dorms from Sunday night to Friday afternoon, but go home on the weekends. Almost any boarding school will also have at least a handful of day students who live nearby; in rural areas there are usually only a couple because rural areas can only support so many members of the relevant social strata, but they’re there⁴.

It is something of a common misconception that boarding schools cater only to old money, though there is almost always old money kicking around. BSW emerged—much like the classic WASP class that it incubated—during the Gilded Age when new-money industrialists and financiers suddenly felt the need to get their heirs away from the temptations and dangers of How the Other Half Lives-era urbanization and give them an education that would prepare them to schmooze with the old-money Boston Brahmins and Knickerbockers they were absorbing (to say nothing of European aristocrats). More or less from the beginning there was a philanthropic tradition of financial aid and scholarships for promising middle-class kids⁵, though the usual prewar prejudices against admitting (too many, or simply any) Catholics, Jews, African-Americans, etc. remained at most places until sometime in the postwar era. Today BSch caters to a combination of old money, new money, sharp kids on scholarship and international students paying full-freight tuition.

(Note that private day schools such as D.C.’s Georgetown Prep or L.A.’s Harvard-Westlake draw their students and teachers from the same social class as boarding schools and so, except in the obvious cases where I talk about the reality of living on campus, most of the discussion that follows also applies to them. The other major difference is that they tend to have far fewer international students.)

An important thing to keep in mind is that BSch caters to the rich but is not usually that rich itself. Phillips Andover’s endowment is $1.9B, and it is either the richest or very close to it. Per Form 990—an excellent resource you should always consult before deciding to send your child to or take a job at a boarding school—my alma mater had, in FY2021, total revenue of $47.8M (of which more than two-thirds was tuition) and expenses of $42.8M⁶.

Total assets were about $130M, but that includes $80M of campus. And the problem with a boarding-school campus is that it can’t really be anything other than a boarding-school campus. The endowment stricto sensu, i.e. the stocks and bonds that belong to the school, would cover just over a year of expenses if tuition disappeared⁷.

In other words: BSch is not Harvard. It may be a traditional feeder school for Harvard, it may educate a lot of kids whose parents went to Harvard. But Harvard is rich enough that it can live in a reality of its own construction (mostly, modulo current events) and BSch does not get to do this.

Boarding-school world is The Help™, institutionalized, like a well-educated butler. There are some corollaries to this fundamental truth.

The Help by the numbers

Private-school teachers are often assumed to be paid better than public-school teachers. Except at the top schools—Andover, Exeter, St. Paul's, Deerfield—this is rarely the case.

There are exceptions, and my perspective is skewed to a certain degree by being a second-generation humanities teacher. If you're a good physics teacher you can command a pretty good salary and have a decent pick of options. There's no union (the idea strikes me as utterly absurd), so there is no strict pay scale. You have no pension beyond your 401(k), and no tenure, although in practice if your contract is not renewed there will almost always be a reason, and it won’t occur without warning.

A non-STEM teacher will top out around 60K plus housing at the peak of their career. A STEM teacher may hit 75-80K but probably not much beyond that. You'll probably get a fair number of free meals, as well (there's a dining hall), but while edible they are not always guaranteed to be terribly appetizing.

We will, however, assume you get free housing on campus (again, this does not apply at day schools). In exurban schools in places like Long Island or greater Boston, this matters a great deal; in the middle of nowhere not so much. But again, you can't keep the house when you retire, and it may not be the sort of housing you wanted. You generally can’t do any but the most minor repairs if anything breaks (and on-campus maintenance is virtually never as well-funded as it should be), and depending on your family situation it may be inadequate in practice. When I visited my parents’ place after college I was sleeping on the couch in the living room because I no longer counted as a family member and there weren’t any spare bedrooms.

If you have kids, you'll generally get heavily discounted tuition—generally at least half off and in some cases nearly free. If yearly tuition for day students is $35K or more this is considerable, and if you are a boarding-school teacher you are usually the sort of person who values your children’s education highly and would spend a lot of money on it anyways. I have met more than one teacher whose effective salary was well into the six figures because they had multiple kids that they would have worked a less preferable job to send to a good school anyways (the classic case is the former law partner teaching civics and US History).

But the point is: the comp package is certainly decent but not generally something to envy.

Wait, what about growing up on a boarding-school campus?

You’re the last free-range kid in the United States: three hundred acres of completely safe campus where you can wander around, play with sticks in the woods, get your shoes irreversibly soaked in the creek and discover that the horse paddocks are protected by electric fences. If you are nine years old it is absolute paradise and this should be more than a non-factor for some people thinking about teaching at a boarding school.

This is one of a number of intangible perks for teachers that are difficult to render as a dollar-denominated sum and which compensate for what look, at first, like surprisingly low salaries. You can usually decide what you want to teach (within reasonable bounds) and how you want to teach it. Your students may be a bit dimwitted, lazy, or prone to precocious experimentation with substances, but they will rarely be truly disruptive—disruptive students are asked not to return, mid-year if it’s bad enough. You don’t have to worry about standardized tests, except for APs. You are regarded as The Help by parents, but you’re generally of a closer social class to them than public-school teachers are and will generally be treated accordingly.

Boarding-school teachers tend to be smart and interesting people, so their kids are also usually reasonably smart and interesting and therefore do fairly well at their parents’ employer. You can take a class that your parent is teaching, and indeed I did, though this can of course be a bit awkward⁸. Unless both spouses are teaching ~the same grade levels at the school, the inevitable division of parental labor is that the Other Spouse is the one emailing teachers about grades and so on and so forth (if e.g. Mom teaches middle school and Dad high school, they will usually switch roles once Junior is a ninth-grader).

Fac brats are accorded about the same respect as any other student—it is not correct to model boarding-school social dynamics as Mean Girls gone haywire, though that said I was a boy, and an unusually oblivious one at that (most of it innate, some of it trained—see later discussion). There are subcultures (I was a member of the ‘library group’, an eclectic mix of intellectually-leaning oddballs) and at no point was I ever looked down on for not wearing the right designer clothing. Daughters of faculty may have a different verdict and I would love to hear from one in the comments. One major effect of your status as a faculty kid, however, is that you are never invited to the good parties (on the assumption—probably a correct one in my case—that you’ll snitch) and are kept in the dark about various rumors and gossip. I learned more-or-less the day of graduation that a girl in my class had been bullied relentlessly since ninth grade on the basis of rumors about sordid escapades that, of course, were entirely unfounded; I was alone in having not a single inkling that any of this had been going on.

What a Boarding School Does

BSch's job is not fundamentally to give kids the most rigorous academic education it is possible to give them, though there are boarding schools that see this as a major part of their mission. The job of a boarding school is to incubate members of the upper class.

Nota bene: speaking as someone who has had a decently wide-ranging view of the American class system, in my experience the difference between the upper-middle class (UMC) and the upper class (UC) is not terribly wide and mostly about money, not culture⁹.

Not all rich people are the same and so, of course, not all BSch's will be the same. If your child is going to be the next Terry Tao, Andover is not a bad place to send them. If they want to become a trust-fund social worker, you can send them to Northfield Mount Hermon.

They'll get a lot of the U(M)C socialization from their classmates, of course. But teenagers tend to be poor role models, so they need to be getting course-correction from their teachers.

This raises a conundrum: how do you hire culturally U(M)C people who will work for MC wages? Solid MC, for sure—UMC by the time they're in their 50s as part of a two-income household—but it isn’t law-partner money.

Option A

Find UMC-UC kids and hire them young when nobody expects them to be making six figures anyways. A teacher who's 27 years old and unmarried is cheaper to house (you can make them a dorm parent). They also don't have kids of their own yet and won't be drawing the cheap-tuition benny.

Many of them find they hate it or can't hack it and go somewhere else. At one school my dad taught at there was a 9th-grade geography teacher who was found by a student in her bathtub, high on LSD, pretending (believing?) that she was a turtle.

Both had dirt on each other (student had been sneaking booze); neither got caught by admin. Teacher was not fired, but decided to pursue other options (her contract was presumably not renewed) and she moved to Vegas to bartend. (Probably a better option anyways if you’re 27; that school was in the absolute middle of nowhere, so if you want to date, you need to either find another faculty member in the same position or be relatively close to a big city.)

Option B

Hire a teaching couple. This is extremely common and usually mutually beneficial. Teaching couples very often stick around for well over a decade and tend to have well-loved families.

You are also hiring well-educated sophisticates. They'll marry other well-educated sophisticates, and if you're in the middle of nowhere, there aren't that many jobs for people with grad degrees. (My parents were not a teaching couple; this was not great for my mom's career.) They'll also only need one housing unit instead of two, and you halve the number of tuition discounts you need to give out for the kids compared to two teachers whose spouses work off-campus.

There is a major downside: family dysfunction can get EXTREMELY nasty. There was a scandal at one school where a (married) admin left her husband and ran off with another (female) admin. This school was quite progressive, so the 'the dean is living with Sandra from Development now' twist wasn't an issue. However, there were three children involved, and all parties lived within a quarter-mile of each other on campus. AFAIK nobody decided to move elsewhere.

This is the fundamental issue with teaching at a boarding school: the line between your public and private life is very, very fuzzy. And if it's a full boarding school rather than one with five-day boarding, your social life can end up pretty curtailed.

Someone's gotta watch the kids on a Friday night and if you are a dorm parent, that person is you.

Option C

Hire an academic who couldn't find a tenure-track job. Boarding schools like having PhDs on the faculty; that's one of the things that sets them apart from publics (and no, an EdD is not a real doctorate—not in BSW, at least not ten or fifteen years ago, and if you do get a postgrad degree in education you should probably have a postgrad degree in your subject as well, or at least a BA from a respectably selective college).

In the ‘70s and ‘80s you could pretty much waltz right into a good boarding school with a PhD in history or classics to teach social studies or Latin. There are now so many humanities PhDs that it's no longer a sure thing, but they get hired—and they get hired especially if they themselves went to a nice private school. This is how I ended up teaching Latin at a nice day school despite having flunked out of grad school during COVID: I had my high school at the top of my résumé.

This is the dirty little secret of private schools, just like every other elite institution: it might be diverse among any number of other lines, but it's still going to be quite classist.

On the other hand: this is, I’d argue, less hypocritical than it looks—or, at least, for all its hypocrisy it’s on some level necessary. If you are a boarding-school teacher you are educating and socializing elites; you need to know how to do that. And one of the best ways to know if someone's likely to know how to do that, regardless of how much of a hotshot as a calculus teacher they are, is to check if they're also a product of the elite factory. Fac brats end up boarding-school teachers at wildly disproportionate rates; they know the culture but won't consider the pay beneath them.

Money and how to spend it

The Help by the numbers, part two.

Boarding-school world, as you can probably guess, sets a lot of money on fire, and yet boarding schools don’t close anywhere near as much as you’d guess from their Form 990s (see More and more and more on money for more on this). We will consider some examples.

Fixing the wrong housing problem

$School has a requirement that all teachers must live on campus. However, $School doesn't actually have enough housing for all of them, so in practice, all teachers must live on campus except for the ones who don't.

Admin looks at the details of the problem (one hopes): there isn't enough housing for single teachers or young couples who haven't yet had a kid or who only have a toddler. The best remedy is probably to build a few duplexes of two-bedroom or small three-bedroom apartments.

Admin, of course, responds by spending $4.2 million (early/mid-2010s price levels) to build six massive four-bedrooms on land the school already owns, then proceeds to go on a massive capital campaign calling up the alums for cash.

How not to do a layoff

$School was founded in the Gilded Age as two campuses on two sides of a river: one for boys, one for girls. They go co-ed and merge in the 1970s.

$School has always had a very progressive reputation. This is great until it's churning out social workers and nonprofit directors who are writing $500 checks to the Annual Fund while the bankers and white-shoe partners who went to Exeter are coughing up twenty times as much.

So sometime in the mid-2000s someone looks at the numbers and realizes that they're dropping $600K a year—and this was 20 years ago!—just running the buses between campuses because kids in a dorm on campus A are taking environmental science on campus B, and vice versa.

Verdict: we have to close one of the campuses. They survey the alums and keep campus A by a thin margin (it has a working toy farm with cows and the alums want to be able to visit the cows at Homecoming).

So they start sunsetting campus B¹⁰.

This means cutting the student intake. It also means cutting the number of faculty. Admin does this in what is possibly the worst possible way: they tell everyone to be in the living room, next to their landlines (remember, it’s 2006), on a Saturday night, and wait for a call.

And they call the ones they'll have to let go. Everyone else sits there in cold sweat until 1 AM before concluding that they almost certainly get to stay on come fall.

Ouch.

Admin is very rarely evil. Faculty sometimes get it into their heads that they are (a fatal turn usually—once you do, you’ll start seeing it everywhere). Admin is, admittedly, often incompetent or a bit clueless in the way that the top brass of any large, intricate organization tends to be.

The real problem with admin

The reality with admin is that their job is to force compromises. You have to triage legal requirements, budgetary constraints, parent demands, faculty, alums, and students, in about that order. And the budgetary constraints are, as we've seen, not inconsiderable. Admin is not the boss; admin is middle management. To the extent that The Boss exists, it’s the board of trustees, who tend to be a collection of well-heeled alumni and parents—but, because they’re usually running their law firm or the emerging-markets department of an investment bank, they can’t keep an eye on things full time. (Nor should they; if you ever end up there you need to fire the head.)

A much bigger problem these days is that admin are trying to move up the chain. Everyone (and I really do mean everyone, or at least a critical mass of everyone) wants to be head at Exeter. It is very, very rare these days to get a head who started out as a math teacher and was with the school for 45 years¹¹. These days, as in most sectors of the white-collar economy, there is a standard cursus honorum for aspiring prep-school heads, courtesy of the Klingenstein Center for Independent School Leadership at Columbia’s school of education. After a few years teaching one of the regular subjects, you’ll convince your school’s admin that you’d make a good dean and persuade them to foot the bill for an MA in Private School Leadership over a couple of summers¹². Naturally, there are also additional degree and certificate programs for heads who didn’t have the good sense to get their MA at Columbia on their way up the chain and would like another credential before applying to their next posting. As if to complete the process, there is now a program whereby ed-school students at Columbia—ideally already with at least a BA in their subject—do an MA in independent-school teaching where they become ‘teaching fellows’ at one of the top schools, TA for an existing teacher and perhaps teach one or two preps themselves. This is now the best route to getting a teaching position at a top school, as this way they can try you out before deciding that they’d like to hire you for the next three and a half decades.

Compensation packages, like ambitions, have ballooned somewhat since the Dead Poets Society era. For example, $School had a head who was pulling a salary of $350K (this was nearly 15 years ago) along with a house, a car and free membership at at least one of the two adjoining country clubs. Now, to be fair, you're schmoozing with multi-millionaire alums; you gotta look the part.

$Head_name stuck around for several years and was somewhat notorious for sticking his terror of a child in the classes of teachers he didn’t like very much. There were, I believe, other issues under his tenure (including a fight between a teacher and a parent that got at least somewhat physical in a parking lot somewhere off campus), but I don’t know the details that well.

One day $Head_name starts nattering on in an all-school meeting with all the faculty in attendance. Member of the Board of Trustees stands up and says “I think that’s enough, $Head_name.”

He left for some other posting shortly afterwards. It's difficult to truly flunk out as a head unless you do something truly beyond the pale; you just sort of bounce within the system, and if you’re simply incompetent rather than a magnet for scandal you can always go back to teaching (you may want to squirrel away some of your inflated salary for this possibility)¹³. Remember, BSW is small: nobody is more than two degrees of separation away from everyone else.

"Oh, you taught at $School_A before moving here. Who was head?"
"Bill Q. Admin."
"Oh yeah, Bill! He was in my precalc class 30 years ago when I was teaching at $School_B. ...yeah, I remember Bill!" (Delivered with a knowing nod, unsurprised that Bill is now a rather unremarkable head.)

As far as I recall, Bill was...fine, really?

Bill ran senior-year seminars on Malcolm Gladwell books. This isn't exactly a tour de force through Gibbon or Braudel, but so what? Bill's job is to talk to alums, and alums are the sort of people who love Malcolm Gladwell.

At core, of course, Bill is a teacher first and foremost (never mind that he may have applied to Columbia’s admin program after three years teaching AP US History). It’s therefore ideal to have Bill also teaching a class of some sort so he knows at least some of the kids and looks like he’s primus inter pares among the faculty. It can't be a huge class or a really rigorous one; he doesn't have time for that. Who cares if it’s not a PhD comp course?

And another anecdote on triaging compromises

Sometime around 2013 or 2014, $School faced a crisis: despite a longstanding tradition of being the most prominent source of Ivy League admits in its metro area, none of the graduating class had gotten into Harvard or Yale. The parents throw a fit; admin responds by firing the college counselor and sending him back to the English department. Something must be done, and this is something.

Looking back at the incident with over a decade of hindsight, it’s difficult to say what, if anything, should have been done differently. $School was not very large, with a yearly graduating class of about 125 students, and 2013/2014 was just at the beginning of the point where Ivy-League admissions games began to give less weight to being from the right prep school. Admissions rates had been dropping for years, of course, but up until this point $School had, effectively, an earmark for at least half a slot at Yale and half a slot at Harvard. Now it’s, maybe, a third of a slot at each and so the lottery comes up short.

But it’s also early in that process—remember, this is still the mid-to-late Obama years—so Dad hasn’t really figured out that he got into Yale with a similar, or even weaker, application than Johnny had when he got rejected from Yale and waitlisted at Amherst. You’re the head; remember, you are fundamentally middle management. You need to show your bosses (the board of trustees and the parents) that you are a proactive agent who can be trusted to make good decisions autonomously, but you also need to act in good faith with regards to your underlings.

And so you demote the college counselor back to the English department. I do not know the details of the conversation, but I imagine that it was friendly, though of course uncomfortable, and that he took no paycut or only a nominal one. He was not fired from the school and as far as I know is still there today. I would be very unsurprised to learn that college counselor has a fairly high turnover rate relative to normal faculty.

The secret to being happy as a boarding-school teacher is to understand that sometimes Something Must Be Done and you are on the receiving end of Something, and you will probably be OK in the end. Good admin will care about what you need and want, but you are not the top priority and simply cannot be. The budget, legal requirements, parent demands, the academic needs of the kids and in many cases (though nobody wants to put it this baldly) pure optics simply have to take priority.

More and more and more on money

Many schools, like many universities, have admitted a lot of international students. This is one thing when you're a university with a large endowment. Remember: that’s not the case here.

International students tend to come in waves, particularly from East Asia. In the late ‘70s, it was Japanese kids; in the ‘80s and ‘90s, Koreans and Taiwanese. Around the turn of the century of course you get a huge number of mainland Chinese kids.

The spigots haven't turned off yet (we will…have to see how the current state of affairs plays out), but this gets riskier and riskier for several reasons.

In almost all cases, international students pay full freight. This is fine in and of itself. Schools want to be able to admit poor, sharp Americans, especially black and Hispanic ones. Except at about the top ten or twelve schools, the endowment can't pay for them so their classmates have to.

Despite their reputation at American universities, cheating isn't, as far as I know, actually all that rampant among that crowd (and my father is not the sort of person to ignore cheating, nor to make it easy).

The trouble is what this means for the longer-term finances. There's, of course, the geopolitical risk. If Chinese students stop coming one day, there is ~nobody to replace them. Maybe kids from India, but this seems unlikely for some reason (maybe things have changed in the last decade). There aren't enough rich Latin Americans, Indonesians or Middle Easterners.

Moreover, schools are reliant on alumni donations as well as tuition. The culture of 'oh of course I'll cut you a check' that you get with American alumni doesn't exist yet with most international students (though I’m told this is starting to change with Chinese alums).

I do not presume to forecast how this will shake out in the wash, but it’s safe to say the consequences will vary by school. Remember that although BSW is small, it's not so small that it doesn’t have niches and tiers.

Andover and Exeter are never, ever going to go under. The worst-case scenario is that they'll have to trim a bit of fat—maybe cut the Arabic program and admit Leverett Tackwater V over a middle-class math whiz—but they will stay in business, and remain recognizably the same institutions they always were. The real trouble is further down.

There are, of course, two ways of balancing your books: you can cut expenses or you can increase revenue.

Scenario: it's 2009; $French_teacher at $School has trouble getting $Student to learn the days of the week in order. They do flashcards. He asks her to recite them in English.

She can't.

$Student’s parents were paying full freight for her, and it was 2009 so the endowment had just taken a once-in-a-lifetime beating. In 2005 or 2018 $Student gets rejected; in 2009 she gets admitted.

This doesn't necessarily put a huge dent in the school's reputation unless it becomes a pattern (particularly in a scenario like the Great Recession when everybody is in the same boat). Unfortunately at $School it did. $School now costs over $60K a year and doesn't offer AP classes. A more diplomatic way of putting it (this is a boarding school, we’re learning to be diplomatic) is that $School ended up in a different market niche.

But more broadly: is it bad for a school that used to be decent at academics to end up educating >50% mainland Chinese students with subpar English or kids with serious learning disabilities?

It's disappointing if you're an academically-minded faculty member, no question. (My father is.)

But remember, these schools are The Help. And those are niches in the market. Someone's going to fill them, and students who can hack multivariable calc have a lot of options; you cannot count on them forever. Like any business, boarding schools are fundamentally exposed to risk.

A note on bookkeeping

The school with the French student with the severe learning disability also played host to the only case of financial malfeasance I’ve ever heard of at a boarding school. A few years later they got an eight-figure gift from an alum that they put into a separate fund to fund full-ride scholarships. It later came out that they were spending money from the fund’s principal on the scholarships and not just the interest. Whoops!

What’s surprising about this story, looking back on it from over a decade of increasingly tenuous ties to the system, is that I know of no others—and that, as far as cases of fiscal improbity go, it’s pretty mild: the money was spent on additional scholarships for kids who wouldn’t otherwise get to attend, not on enriching members of the admin.

But if you’ve read enough stories about non-profit organizations, then you know that embezzlement and run-of-the-mill setting money on fire is fairly common. Non-profits aren’t disciplined by the need to produce profits for shareholders and, because their job is to Do Good in the world, they get the benefit of the doubt. They do fill out Form 990 for the IRS, but Form 990 is very short given their organizational complexity: my alma mater’s was only 48 pages long for FY2022.

The apparent impeccability is therefore all the more remarkable because if I were brainstorming organizations to embezzle money from, I would put boarding schools near the top of the list. Their endowments are small relative to those of universities, but they are absolutely loaded by the standards of individuals. And while the head (as CEO-equivalent) ultimately makes the top-level decisions on how to spend money, that is not her¹⁴ main job. Her day is taken up with talking angry parents out of lawsuits, giving stern lectures to sophomores who were caught smoking weed behind the gym, calling Carney Sandoe to start looking for a replacement for the biology teacher who just got offered a position for next year at the Hill School, reminding the 24-year-old art teacher that she is supposed to act in loco parentis and not in loco amicae for the students on her dorm hall, reviewing proposed changes to next year’s class schedule and making appropriately pompous and circumstantial arrangements for graduation.

In other words, the head does not want to think about the budget; that’s the CFO’s job. The head will review the books at the scheduled monthly meeting with the CFO and give them a more thorough look a couple times a year or so, but she is not trained as an accountant, she is trained as a teacher, and she trusts the CFO implicitly—if she didn’t, she and the board of trustees wouldn’t have hired him. The board will have an in-depth meeting with the CFO, again, probably twice a year, maybe quarterly. At least a couple trustees will have some knowledge of accounting because they run businesses¹⁵, and they will check reasonably carefully, but they are not really looking for problems in the budget. They are looking for reassurance that all is well, that the school is in the black or very close to it, and that they hired the right head and the right CFO. (But they already knew that, of course).

The CFO, meanwhile, must oversee the budget of what is very nearly an entire city-state. Jack Smith’s air conditioning has just broken down, in July, in rural North Carolina, and here is a $6,000 invoice for fixing it. The art department needs an extra $25K for supplies just to cope with inflation and would really like an extra $35K. Can you get a rundown of how many freshmen we can admit on full scholarship this fall, given that about a quarter will go somewhere else before senior year? We have just signed a $100,000 contract with the online quiz platform KaWow!, please wire the payment. By the way, the dining hall needs a new industrial dishwasher…

Given all this—and given that these are extremely respectable institutions in the business of educating children with well-connected parents, run by very charismatic members of the UC and high UMC—it is probably not hard at all for administrators with a school credit card to skim a little bit here and a little bit there. If you think the mere fact that it would look like a waste of money or that the school overpaid for something might on its own raise eyebrows, dear reader, you are in the education sector, and the commanding heights of the education sector at that. Everybody is primed to treat everyone else with kid gloves.

My shot in the dark—and I would love to hear some anecdotes—is that embezzlement at boarding schools happens with decent frequency at low volume; low four to mid-five figures a year, depending on your position and how checked out the high command is. I would also hazard a guess that a big reason that I can find so few stories of it occurring from Google—mainly in Florida, and I’m guessing not only because I’m searching from Miami—is that unless the amount is truly obscene, the hit to the school’s reputation and therefore the financial hit from publicizing the incident is less than just quietly firing the culprit and pretending nothing happened¹⁶. Indeed, if it’s medium-scale the perp probably won’t even be fired; do you know how difficult it is to replace these people mid-year? They will simply be told to be much more careful with school money for the rest of the school year, please, and that we will be happy to only say good things about you when Carney Sandoe comes knocking for a letter of rec this spring.

Mistakes, in boarding-school world, are commonplace¹⁷. Bad faith is rare.

And another note on mistakes (or: really, why spend $4.2M on six of the wrong houses on land you already own?)

It is notoriously tricky to measure outcomes in education, as everyone knows, and we are a preparatory academy. We do not make the kids sit standardized tests like the public schools do; we’re not taking public money, and then we’d have to make our teachers teach to those tests, as if they aren’t professionals. (And they would rightly revolt if we tried). We do have APs, of course, but if the kids for whatever reason don’t do well on them then we will, as we have seen, simply stop offering APs¹⁸.

College admits are a carefully-watched metric, as I’ve illustrated, if only because parents with options are going to pay close attention to them, but you generally don’t admit a student body if you don’t think enough of them will cut the mustard (the unfortunate college counselor above was, again, the victim of a sea change in higher ed and not in the student body’s ability or the teachers’ competence). But everybody knows, at the end of the day, that college admits are kind of a gamble and that even there, the real metric is not whether or not you got one kid into Yale but whether or not you got the majority of them into Bowdoin/Colby/Villanova/Rochester/UMich, at least if you’re in the same league as my high school.

So: you taught French and Spanish for three years out of your MA program, did a second MA at Klingenstein, were dean of students for three years (while also teaching AP French and a section of Spanish III) and now, at the age of 34, with a drop-dead gorgeous wife and kid #2 on the way, you are head at a decent if not spectacular boarding school somewhere on the East Coast; let’s call it Boardton Academy. You are gunning for Deerfield within a decade. How do you get there?

Boardton’s alums are well-to-do, and there may be one or two true tycoons who will show up to Homecoming for the 30th reunion, but it is very unlikely that they will just whip out their checkbook and cut a $50M check to make the school Better, in some vague fashion, just so that you can leave for greener pastures. After all, Boardton is doing just fine under your leadership, the new Algebra II teacher is just like Mr. Brown when I had him. I will of course be happy to make my usual gift to the Annual Fund (this is, as we all know, $75,000, a sum which I will adjust for inflation every three years and which nobody involved will ever say out loud).

And even if they did do this, then what? You can hardly call up St. Paul’s and say “we’d like a list of your top Boston Brahmin scions and freshmen taking real analysis so that we can poach them.” Every male-line member of the first crowd has been going to St. Paul’s since it was founded, and the only four schools that could possibly compete with St. Paul’s for the second group already tried (and under no circumstances do you ever poach students once they’ve started freshman year; if they transfer it is because they initiated it—generally no later than the start of sophomore year and never later than junior year).

If you are shooting to be head at Deerfield in a decade, you will have a limited impact on the school you are at now. You may be better at raising funds, especially if you are a Boardton alum¹⁹, but increasing its selectivity is a long-term project, and while you can hire hotshot new teachers as positions open, it would be career suicide to non-renew more than one or two mid-career faculty members for no better reason than that you’d like to pick their replacements (encouraging late-career faculty to speed up their retirement plans is a bit different, but even that must done prudently). If you do a good job as head, Boardton on the day you leave will still be in most fundamental respects the same Boardton that hired you ten years ago, and there isn’t much you can do about that.

But there’s one thing you can do in that time frame, and that’s to leave your mark on Boardton’s physical campus.

This does two things. One, it is immediately and unmistakably obvious. Alums and parents will remember what the campus looked like before you arrived, and the minute they drive up to pick their kids up for Spring Break they will see a new Boardton. They will see your Boardton, the Boardton you have envisioned and are now building among the children of men.

Secondly, it’s a fundraising vehicle. Remember that science building from the ‘60s? Over the summer it will be demolished and science classes will be in the nearly-finished Parker Science Building, which Ben Parker—you played lacrosse with him, didn’t you?—very generously helped make possible. No more incidents with mice and picric acid in the chem lab. Spick, span…we are also starting to think about replacing the boys’ dorms; I know they were just fine when you were there but at this point they’re 70 years old and, between you and me, the maintenance bills are starting to pile up. Oh, the timeframe for replacing the dorms? Ah, that’s not set in stone quite yet but if you’d like to know more about it, just call the office and we’ll get coffee set up…

I do not, I should add, know (or even have much reason to suspect) that the incident with the tantamount-to-McMansions four-bedrooms was conceived for this particular reason. But I do know that it is the sort of thing that heads trying to climb the ladder do²⁰, and that—whether or not six four-bedroom houses is what the faculty need—they certainly look more impressive than adding a few cheap duplexes. So we’ll need to go on another capital campaign next year, so what? The school will still exist. It’s existed for 130 years and there’s no reason to think that that’s going to change.

I will not lie, cheat or steal…

Many schools used to have honor codes—a few still do—along the lines of something like this: I will not lie, cheat or steal, or tolerate those who do. Break it and risk expulsion.

But in practice we are educating teenagers. Who hasn’t lied about the reason they needed an essay extension?

So you have a conundrum. This is how you want the kids to behave, in large part because it’s how you need them to behave when they're adults. But—they're teenagers so you can hold them to this standard, but not in the same way you can when they're 40. You can't even really hold freshmen to quite the same standards as seniors.

Add, to this, the fact that many of these kids are quite rich and their families may in some cases be quite powerful. I've run into last names you might recognize, and a few other kids whose parents ran institutions you probably would. This means their lives are...precociously complex.

So what this looks like in practice is strategic obliviousness: I'm going to pretend that you have a very good reason why you didn't finish your essay or were so busy you forgot to give Katie her iPod back. In exchange you're going to go fix it so I don't have to pretend again.

We can also view this sort of scenario through the lens of cultural evolution, as a practice whose true value is somewhat covert and not necessarily clear to its practitioners. Face-saving white lies are a fine art—a fine art whose practice is abundant in white-collar America. There are a few people whose integrity is so unquestionable that they’ll never have to tell them, but that’s not most of us, and the problem of staffing the ruling class only with people like that is never going to be solved. Your job is therefore to make sure that your charges don’t lie about things that are truly beyond the pale, and otherwise have the grace and awareness to deploy white lies infrequently and carefully, as a tool in their box of social skills.

And, let's face it: it's a school that borders on a kibbutz. Your neighbors are also your coworkers and bosses. Why do I see John at Megan's place so often when her husband Frank is on study hall duty? Why does Tom always have so many beer cans whenever I see him at the dumpster? People are complex; at a normal 9-5 you simply wouldn't see this stuff. And boarding schools at their best have a high tolerance for eccentricity, because the good ones attract sharp, eccentric students who do well there.

The perils of eccentricity

But we can imagine where this goes.

$School has always been known for a friendly relationship between teachers and students; teachers are often called by their first names and have been since the '70s. In the '80s it was well-known that students and teachers would sometimes smoke weed in the woods.

So one May evening in, oh, 2017 or so, it comes out that a teacher about to retire in a year or so had kissed a senior. News breaks out on a Thursday. By Monday, he is gone, with two weeks left in the school year.

There is a catch:

The kiss happened in 1978.

Are you saying it was appropriate? No, of course I’m not saying that.

But should he have been fired nearly forty years later? That’s a thornier question²¹. Non-renewal of contract certainly seems justified, if mainly for reasons of optics. But—and this is really what it boils down to—if you think this was the worst thing that happened in 1978 at a hippie-ish school in rural New England then I’ve got a memecoin to sell you.

Boarding schools are strange institutions where strange people—teachers and students—often really, really thrive. I was one of them. Strategic obliviousness has costs but it didn't come out of nowhere.

These institutions are loved for a reason.

1. The mildly derogatory term is ‘fac brat’. Like military brats, boarding-school fac brats come from a strange little world unto itself that is very difficult to describe to people who have never experienced it. This blog post attempts, however inadequately, to do just that.

2. I went to UOklahoma—they offered me quite the scholarship—and kept getting strange looks from my classmates when I informed them my dad was a boarding-school teacher. After about three months I mentioned this to my mother, who grew up on the West Coast, and was informed that in most of the country a “boarding school” is decidedly not an institution for people with Roman numerals at the ends of their names.

3. Or it was founded as a girls’ school, probably a bit later, and in that case is a bit less likely to have gone co-ed.

4. Children of resident faculty in attendance—there are usually a couple—are neither fish nor fowl, as they live on campus but walk to class from their parents’ house every morning. More on this later.

5. Nor were all the boys [at Groton] rich. “Pierpont Morgan was President of the Board of Trustees,” Ellery Sedgwick wrote, “and there were a number of boys whose mothers’ names appeared regularly in the social column of the New York Herald, but I am mistaken if term bills were not of major concern to at least half the parents.” — Michael Knox Beran, WASPs: The Splendors and Miseries of an American Aristocracy, pg. 75.

6. FY2022 included extra donations above baseline of about $10M, so I am using FY2021 for comparison.

7. Andover does have more endowment than campus—about $1.1B securities vs. $540M of campus—but its expenses are $150M a year and it only gets about $77M a year in tuition fees, so the main difference is that it could run for seven or eight years rather than only one year if it had to draw on the endowment alone. Of course, if this were to happen it could ring up the alums and get the mother of all bailouts, but the point stands.

8. If only because your father knows you much better than any of your classmates and can tell exactly when you have turned in an essay that was written at the last minute in between checking in on your game of Dwarf Fortress. I still have, in my possession, a term paper on the murder of Sergei Kirov that I wrote in three hours in the library during finals week the spring trimester of my senior year for my father’s Russian history class—skipping other classes to do so despite an extension. I got a B+/A- and the comment “good info, but irritatingly lacking in style”, but it was going to be a C until my mother pointed out that every third-term senior in the history of time has half-assed their final assignments and that if I were any other student I would be graded accordingly. For the curious, I did indeed address him as ‘Dad’ in class rather than ‘Mr. Jonathan’.

The truly awkward Heated Fac Brat Moment™ comes when you need your father, who is department chair, to move you mid-year out of your history class into another colleague’s section because you have a cripplingly bad crush on the faculty member teaching it. (Like any good WASP, I asked my mother to arrange this by proxy to avoid directly shattering my tweed-and-bowtie-wearing father’s feigned illusion that I was the only fifteen-year-old boy in history to be devoid of any sort of romantic or sexual desire whatsoever.)

9. By contrast the difference between the working/middle-middle class and the UMC is primarily cultural and not financial. A good read, though one that in my opinion gets unfoundedly conspiratorial in the second half, is Michael O. Church’s "ladder" model of the American class system. Boarding-school teachers are high G3 to low G2 (and second-generation G-ladder at that; the culture has to be natural), while their students’ parents are usually G2/G1 or E3. Heads are a strange hybrid of low E3 and solid G2: they’re paid very well and hobnob with important people, but they are one scandal away from cancelling the yearly trip to Aruba and going back to teaching history. E2s are around, but there aren’t generally enough of them to constitute a student body.

10. In practice this did not get rid of Campus B on the balance sheet: it only reduced the associated expenses. Even abandoned buildings must be heated to at least 45 degrees Fahrenheit or so in the winter to keep the pipes from exploding, and in New England this does not come cheap; you also have to pay a security guard or two to drive around and make sure nobody is doing anything worse than walking their dogs on it.

They did eventually find a buyer for the campus (thankfully—it is absolutely gorgeous, in my opinion moreso than Campus A), selling it for $1 plus a pile of deferred maintenance and back taxes, but only many years of turning down a number of very conservative Protestant denominations that it would have been extremely bad optics for that particular school to sell the campus to.

11. To be fair, that path was never common, but it certainly didn’t used to be unheard of.

12. The eagle-eyed reader will notice that although the program is via Columbia’s ed school, it is an MA, not an MEd. They also have a full-time one-year MA; my dad never had the slightest shred of interest in climbing the ladder, so I don’t know if you persuade your school to let you take a sabbatical year, or if you save up the cash to do it in between jobs in hopes of using it to polish your CV.

13. You might also want to go back to teaching at some point because, well, being head is exhausting. There’s always at least one lawsuit ongoing, you are constantly entertaining, and you’re never able to take off the “head” mask and just be you for the summer. But, as is usual in political arenas, the people who make it past a certain threshold usually have too much drive to simply call it a day, and the salary cut is going to bite.

14. Heads, of course, used to be virtually always men, even at girls’ schools, until well into the 1990s, but things are now more balanced. It does remain the case, and probably always will, that the fastest and surest way to climb the ladder from teacher to dean to head of school via the Klingenstein Center is to be a young, good-looking, charismatic guy, usually with a humanities background—not so much from sexism as from possessing a disproportionately male type of charm.

15. The yearly audit is usually done by a local accounting firm, not one of the Big Four. Traditionally it would be quite normal for the head of that firm to be on the board, but that’s less common these days to avoid the appearance of conflicts of interest (though it’s probably not unheard of even now). There is still a very good chance that the accounting firm is owned by an alum of the school, however.

16. “That’s the [British] public-school system all over. They may kick you out, but they’ll never let you down.”—Evelyn Waugh, Decline and Fall (1928), chapter 3.

17. Mistakes are even more common, of course, when people—who are only human—would have some reason not to be more careful. This is probably part of why heads get paid such colossal salaries: it is the same logic as Lee Kuan Yew decreeing astronomical compensation packages for Singaporean civil servants. Teachers’ salaries are mediocre, of course, but they don’t have a school credit card (if they want to order special supplies they send a note to the supply-office manager). The more opportunity you have to spend school funds on yourself, the smaller your motive to do so needs to be.

18. This is not as fatal as it sounds. My high school had a very good reputation and only had AP classes for calc and the foreign languages, though this was explained by the perhaps inevitable statement that all the classes offered, including the upper-division English elective Where the Commas Go, were honors classes. (It should be said, though, that its classes were reasonably rigorous—and as long as college admissions committees know that, it gets a pass.)

19. Of course, if you’re an alum, you’re somewhat less likely to view your headship as a stepping stone to greater things…but it doesn’t confer immunity.

20. There are some other moves you can make as a head to try and burnish your résumé that are in something of the same category which, again, often look more impulsive than decisive. One school my dad taught at had historically had seven-day boarding but had then gone back to five-day boarding; upon arrival, one new head decided he wanted to bring back seven-day boarding. This was eventually implemented, it seems, but the implementation was delayed by the fact that it was not well-thought-out at all initially. The dorm parents already hate it when there’s a sudden snowstorm on a Wednesday and they have to entertain the kids all day with school closed; now that’s going to be every weekend and you have to have an entire program of things for them to do, you have to restructure the dining hall…

You may perhaps be wondering if new heads often find themselves completing their predecessor’s pet projects. The answer, of course, is that this happens constantly.

21. And thornier still: they got married shortly after she graduated, with an announcement in the New York Times (!).

Should someone have been fired? Oh absolutely: everybody who was in an admin position at that place in 1978, along with the New York Times society editor, pretty much every rock star and movie director at the time, and so on and so forth. And, fine, the teacher, sure, but let us be clear about what actually happened here: you fired him four decades afterwards to try and fire the year 1978 by proxy, but you cannot fire the year 1978.