Drunk advice from your school’s headmaster

I’ve visited ten private schools that charge more than $40K per year. And they have a lot of impressive similarities like the interior design (kid-friendly Barneys with a splash of Ikea) and the students (friendly confidence with ballet-lesson poise). So I started interviewing the headmasters  (rich-kid word for principal).

I thought I might learn about new trends in education since most limits on my own ideas for education seem purely financial. I ended up really liking the people I met, but I learned very little. Until one (who has now been properly disguised to be one of ten) took me out for lunch and Apricot Sours and started spewing advice she wants to give to private-school parents.

1. Don’t treat me like household help. I am not your employee. My job isn’t to be at your beck and call like a nanny, or to validate your opinion like a designer.  Please do not bring

My take: This is not to say that the headmaster would not like these parents as friends. But parents do not want to be friends with the headmaster because they are not in the same social circle. The headmaster, on the other hand, took this job because it’s fun to hang out with rich people. What else is the benefit to helping rich kids preserve their spot in the elite?

2. Perks from parents are a necessity. There’s a huge economic gap between the parents and the headmaster. Even the headmasters in NYC who make seven figures don’t earn enough money to put their kids through their school. There are no bonuses, IPOs or bitcoin windfalls in the life of a headmaster, so parents should find other ways to compensate the headmaster.

My take: If you have the money, show it at gift-giving times. But also, enterprising parents treat headmasters like politicians and offer non-financial compensation. And that photo up top? Gold-plated Lego purses. Which should be on someone’s list of top-ten gifts for the millionaire headmaster.

3. Don’t get attached to teachers. Get attached to the school. Its impossible to deliver innovative, trendsetting education with sub-par teachers. Trust the headmaster to know who to fire. Just because staff has been there since your kid was in first grade doesn’t mean your kid cares. And don’t defend a staff member from getting the ax until you know what it’s like to manage them. Every time I fired someone I have to deal with a long line of parents complaining. Which means that if I’m actually firing someone, they really suck. So just let it go.

My take: If you want to be part of an institution where people with a lot of experience never get fired, then go to public school.

4. Don’t give me your list of colleges. Tell me where you are an alumni, that’s fine. Tell me where there’s a building named after you. That will help us map out which seniors are applying where.

You pay exorbitant tuition so your kid can go to an elite college. This does not mean you can pick the elite college. We have a class of 60 kids, and most could hold their own at Harvard; Jared Kushner graduated from Harvard, it only takes money.

Therefore our school will tell you which college is the best fit for your kid, and the school will tell the college which kid to take, and we will look at what’s best as a whole: for all the seniors and for the on-going reputation of our school. We will not say this to you directly. But you hurt your kid’s prospects when you bother me and my staff incessantly by pretending you don’t know how this system works.

My take: To say top private schools collude with top private colleges would not be right. But there is some word that has a colluding nuance, which may or may not exist in the English language, that would be appropriate.

5. Go ahead and sue me. I get that threat at least once a semester.  Few people follow through, and those who do always lose. Keep in mind that the school is prepared for your threats, and if it does come down to court filings, you as a parent paying tuition will fund the defense against you as a parent acting like an entitled jerk.

My take: If you want to control your kid’s education, you can’t do it with money. Private school means giving up control of your child’s future to someone else. No amount of money will change that once you put your kid in school.


21 replies
  1. Mel
    Mel says:

    Under #1. the first paragraph ends without an actual ending. I think you forgot to type the rest of your thought :)

  2. christy
    christy says:

    I think that the short version of this: Elites will be elite.

    The headmasters may not have the liquidity of the students’ parents, but they definitely have the attitude.

    • Penelope Trunk
      Penelope Trunk says:

      I’m going to write something that may or may not be insane. I can’t actually remember what I was going to say. I’ve been taking notes for this post for a long time…

      So I am trying really hard to make posting easier for me so I can post more regularly on this blog. I miss having the community that comes with regular posting. And, in the spirit of that, I’m going to not try to figure out what I was going to say. I’m going to just move on to the next post.


  3. Bostonian
    Bostonian says:

    I’m guessing this article was inspired by multiple visits to local private school with the purpose of investigating enrollment of your older son. If, as you have stated in previous posts, you are paying for 3-4 hours of tutoring daily, then you are already shelling out more than the cost of private school for an education that is by no means certain to lead to college placement. I further surmise that the sour-grapey nature of the article indicates that either none of them would accept your kid or you balked at losing your control over his education to the school.

    There are some things in this post I disagree with, and some things that crossed the line from hyperbole into just plain fiction. In the camp of fiction: that school directors who make a million dollars can’t afford to send their kids to their own schools. Nonsense, easily disproven nonsense. Even headmasters who make half that can afford it. Headmasters at smaller schools making 250K might need some help.

    Top boarding schools these days are in the 70K range, and they offer financial aid up to parental income of around 450K. Unless the headmasters have a lot of kids, they certainly can afford to send their kids to their own schools, especially given that they will get discounts. In fact, at most private schools, many of the teachers (who make an order of magnitude less than the headmasters) send their kids to the school, thanks to discounts and financial aid.

    In the realm of disagreement is the comment about giving up control of your kid’s future. There really are differences among private schools, and giving up control is at one end of a range. My good friend is sending his son off to Eton next month, and yeah he’s giving up control, no helicopters allowed. Some day schools, at the other end, can be very collaborative. There are private schools that want every parent on campus every week, attending meetings, talks, showings, and volunteering.

    • Penelope Trunk
      Penelope Trunk says:

      What? Sometimes I am blown away by what people think of me on this blog. As a single parent I could never manage one kid in a school setting and one kid traveling for cello. We travel a lot. So even though I think private school is just school BS for rich people, private school for my family has never been an option.

      Click the link about school salaries – there’s a story in there about how a NYC school had to give a headmaster who makes seven figures a non-repayable loan for housing so she could afford to live near in NYC.


      • Bostonian
        Bostonian says:

        I have no doubt you are telling the truth that you couldn’t manage a kid in a school setting. I am also sure that is one of the reasons you don’t do it. I’m sure that giving up management of your musician son to Juilliard was hard enough for you.

        I remain stunned that you are paying _more_ than private school tuition for your older son’s menagerie of tutors. I hope that works out great for him.

        If you took the time to read all the words in the article you linked, you’d find that the headmaster in question doesn’t live in the apartment at all.

        “The school provided a $500,000 loan in 2006 so she could purchase a $2 million Upper East Side condo.

        Public records show Hayot lives elsewhere in the neighborhood and rents out the two-bedroom apartment for $7,400 a month.

        As of June 2017, Hayot had made no payments on the loan, which was to be repaid by 2014, according to the school’s tax filing and mortgage documents, which show all the rental income was to go to the school.”

        So it’s clearly untrue that the headmaster couldn’t live in the neighborhood otherwise – in fact, she _does_ live elsewhere in the neighborhood, on her own dime. The condo loan is some kind of finance hanky-panky, not actual housing for her.

        So your assertion that headmasters couldn’t send their kids to their own schools is easily disproven nonsense based in part on a lack of reading.

        I’m glad you got drunk with a headmaster and she spilled her guts to you. That must have been fun. But it’s a particularly lousy way to get a clear view of what private schools are like.

        • Penelope Trunk
          Penelope Trunk says:

          One of the reasons I always read your comments carefully is you always read the articles more carefully than I do. So thank you for that.

          This post isn’t about what private schools are like. It’s about what headmasters are like. It’s about what they are thinking about but cannot say.

          And Juilliard: I took him out. It’s what I’m thinking about but cannot say.


          • Bostonian
            Bostonian says:

            I am sorry to hear about that. I know you were both very happy and excited at the beginning, and I’m sure things must have gone terribly sour for you to have made this move. I’m sure it must still seem, even though it was by your choice and after serious deliberation, like a tragedy of sorts. I wish you both the best as your son pursues his education without the aid of said prestigious institution. I hope you are able to talk about it someday.

            I admit I don’t know much about what my daughter’s headmaster is like, beyond brilliant, careful, knowledgeable, and inspiring. I wouldn’t try to be friends with her because I don’t think _I_ am good enough. I’m sure she’s got better friends than I could be; the best I can do is help her communicate her goals for the school.

            Hey, get Z on From The Top someday so we can all hear him, okay?

  4. Penelope Trunk
    Penelope Trunk says:

    I think today I will just have a personal conversation with you in a public setting.

    You can see him playing here:

    I think you should write guest posts here about why you send your kid to private school. Why the homeschooling arguments don’t sway you. Also, you are better at reading research than I am, so you would have such good links.


    • Bostonian
      Bostonian says:

      Hi PT. Thanks for sharing the video. Z is great for a 12 year old. My son agrees that he plays like someone much older. Do you expect he’ll be going to (college-level) conservatory later on?

      I can write some guest posts for you if you like, but they wouldn’t all be about why I have sent my daughter to private school. That answer is ultimately simple and non-problematic: because she asked, and it’s gone well. I think the difficulties my son has experienced make better conversation.

      Out of courtesy to my children, I would only do so without our names attached to the posts. I’m sure someone who is sufficiently determined could dox us, but I value privacy more than some people do and wouldn’t want future contacts googling my son’s name and finding posts expounding his travails.

      If it’s agreeable to you, I could probably send you four posts by the end of the summer. You could put them in at whatever interval is most convenient to you. I would like to see this blog rebuild its readership, and would be happy if I helped with that.

        • Bostonian
          Bostonian says:

          Hi YMKAS. It’s all a matter of verb tense. My son has attended public school, so I have a lot to say about it. In the fall, we expect my son will attend private school, and I don’t yet have a lot to say about that.

  5. Aquinas Heard
    Aquinas Heard says:

    I’m sure your top values have shifted some since I first discovered this blog many years ago but I miss you posting stuff frequently. Thank you for spreading the idea of unschooling so consistently.

  6. YesMyKidsAreSocialized
    YesMyKidsAreSocialized says:

    This was funny!

    For some reason this one made me think of the movie Wonder. The headmaster certainly had to deal with eccentric wealthy parents and I wondered to myself in that fiction what would that headmaster have confessed if he were to have too much to drink.

    Back in public school world we have a principal. We are in a wealthy district and my kids go to the elementary and middle school where the wealthiest of the area attend-preferring public over private. Somehow we found a house we could afford there. My kids attend school with NFL/NBA players kids. So it feels like a private school because of all the donations from the wealthy parents. 14 kids to a class. All the extras.

    I tell the principal that my youngest gets to move around whenever she wants in class as long as she isn’t bothering anyone. Done. I tell the principal my middle kid gets to go to gifted classes without taking tests. Done. The middle school I set up the 504 for NO homework, social skills classes, no PE, extra computer classes, allowed to use bathroom or leave classroom whenever she wants. Done.

    I don’t care what they think about me, and I make sure that I am sending appropriate gifts throughout the year. :)

    p.s. I read the article too where it clearly stated that the headmasters in fact get bonuses on top of their salaries, plus housing. Bostonian beat me bringing it up.

    • Bostonian
      Bostonian says:

      YMKAS, I cannot imagine a public school like you describe. My son had 30+ kids in a class in middle school, and a faculty dedicated to hazing out students with special needs. Locked doors and armed police.

      You’re still around Minneapolis, right?

      • YesMyKidsAreSocialized
        YesMyKidsAreSocialized says:

        Yes, we are outside the city in the burbs.

        14 students a class is the elementary school my kids attend. Middle school is about 25, and they really do an exceptional job with kids who need 504’s and IEP’s. I’m still not sure how 6th will go, but at least I know that I’ve done pretty much everything I possibly can to make middle school accommodating for her.

        I think the middle school has two “resource officers” but they are there at the parents request.

        Public schools were not like this in Southern California, so I can understand how it’s hard to imagine. The thing is, even with the nice private schools like Blake, the students attend the same exact schools as the kids who graduate from the public high school in my district. So it’s not like going there gets them anything worth the tuition, in my opinion. If it’s not a feeder school somewhere other than the U of MN I don’t see the upshot for shelling out the money.

        Your son’s school sounds like a prison. I thought it was supposed to be pretty good?

        • Bostonian
          Bostonian says:

          Hi YMKAS,

          Yes, the school my son left is somewhat prestigious. It’s world-famous all over Boston, at least. But a good school? I’m by no means certain that’s true except as a very local comparison.

          My son’s ex-school is probably the best public high school in the city of Boston, but that’s not saying much. It is by no means the best public or private high school in Boston, and probably not even the best public high school in the Boston area.

          I think a large part of the results the school brags about have more to do with casting than learning. The kids reach the outcomes you’d expect from them, given that only about 15% of the city’s kids test in, and about a third of those get thrown out or chased out before graduation. What’s not at all clear is that the outcomes they reach were affected much by the school.

          At the very top, you have around 3% go to Harvard. They have a special relationship, and that’s what they brag about. After those kids, the slide through all the other Ivies plus MIT takes up maybe one or two more percent (the Asian kids Harvard won’t take). The next ten percent go to highly selective liberal arts colleges or universities, and then the bulk of graduates go to obscure colleges, state universities, and community colleges.

          Local suburban public schools that accept all the kids in the community usually achieve better results. Meanwhile, we have private high schools in Boston that send around a third of graduates to Ivies and all of the rest to highly selective liberal arts colleges or universities.

          As a student – especially one with any sort of learning disability – the school is hellish. Apparently if you brag about being a “Marine Corps of the Mind,” it means teachers feel at liberty to act like drill sergeants.

      • YesMyKidsAreSocialized
        YesMyKidsAreSocialized says:

        And speaking of armed police in schools… the LAUSD has one of the largest police forces in the state! How did that even happen?

  7. Fatcat
    Fatcat says:

    I didn’t get much out of this post, to be honest. It’s kind of weird. But, I like community too and I started reading the comments and I followed the link to your son’s cello concert and WOW. He’s awesome! So unbelievably good. Congratulations on that, because I know a lot of why he’s that good is because he has you as his mom. I know you’ve sacrificed for him.


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