This is a guest post from a long-time reader. It stems from an email exchange we had about her kids going to a top private school for high school. I learned so much from her that I edited the emails—with her permission—into a post.

I am a single mom—very single with two sperm-donor kids—and I didn’t know anything about the world of private schools until my older son ended up in one. Except: I was hugely mistrustful of the elite environment.

[This well-known school] always seemed especially traditional and super preppy. And when my son was accepted as a boarding student on a full scholarship I kept saying to people, “I worry my kid is going to lose his soul.” But once he was there I came around 180 degrees pretty fast, and I have sent my younger son there as well.

Now I see the school as a partner, which I really need! The school leadership is great. And my kids are supported and fulfilled in ways I could never do alone.

Some benefits are obvious: facilities, school trips, great curriculum. But other benefits were more surprising to me.

Interpersonal opportunities. My kids are making connections with a slew of adults who are fantastic role models, and my kids’ friends come mostly from the pool of scholarship kids who have a high level of drive, intellectual ability, or some other standout quality that got them into the school from unlikely places.

Positive peer pressure. My younger son is maybe less intense about intellectual life, but he takes himself much more seriously as a learner in that environment than he did during the brief time I tried to homeschool him. They’re both taking accelerated/honors classes, and those are the kids they hang out with.

Structure. It’s overwhelming to just survive financially and logistically as a single mom so my life is very seat of the pants. At boarding school the kids get structure that I can’t provide. All the kids live within the same structure and that’s just the way it is for everybody. Any discipline is soft and impersonal—not me freaking out! It’s nice to not constantly be worrying about whether I’m doing a good job organizing and supporting everybody’s life (too much? too little?) or fighting those tiresome battles.

The bubble is not so bad. You hear the word “bubble” a lot about private schools and selective colleges—but our house and our life is its own sort of bubble. Being away at boarding school means my kids get to have a lot of independence from me (which I think is good because a single-parent household can start to seem kind of claustrophobic), but it’s a really contained environment, so I don’t worry about them the way I would if they were just roaming.

Consistency with my homeschooling values. I’ve always felt that, ideally, my job as a parent is to present opportunities and then get out of the way, and a good boarding school is a pretty great opportunity. Along the same lines, I don’t believe that parents should “instill” values so much as model them and then stand back and let their kid figure out what they value.

Exposure to new interests and ideas. Both my kids have always had a strong aptitude and interest in STEM subjects, but now both of them have ended up also becoming enamored with language as a result of the school’s requirement that they master something besides English. My younger son wants to learn Chinese because he has made so many friends from China at school; my other son developed an interest in Italian, Spanish, and Greek and fell in love with the classics in the course of taking three years of Latin.

I do feel like I need to add that I am still extremely ambivalent about the private school world, and I’m always queasy about the malignancy attached to a lot of that money. I just read in the comments to another blog that I love (Nonprofit AF): “I have two major American thinkers duking it out in my head. The first is the famous Audre Lorde quote, ‘The master’s tools will never dismantle the master’s house.’ The second is Thurgood Marshall’s life, in which his mastery of US law enabled him to overturn public school segregation.”

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13 replies
  1. Mary Kay McGowan
    Mary Kay McGowan says:

    I love this email/blog. I think she has her eyes wide open and obviously is an amazing mom to have managed to homeschool her boys and have them achieve this high academic success to be awarded scholarships to this outstanding school. What a life changing four years this will be for those boys. I’m a person who attended a very good private college prep school and I was from a bit of an entitled background but that was mostly fostered in my home not at school. I think the grounding of these boys early life will likely anchor them to a work ethic and humility they’ve earned in the best way possible through life lessons. It would have seemed tragic to me had her own leeriness and prejudices of the elite world of prep schools stopped her from exploring and pursuing this path. The private school I attended was also very nurturing with good role models and leaders who made lifelong impressions on me. I’m so happy to hear her humility in letting go of her own prejudice which like all prejudice, is a generalization of all based on the experience with a few.

  2. Emily ENTP
    Emily ENTP says:

    I have so many different thoughts about this – I was homeschooled for all of school, EXCEPT my junior year of high school which I spent at an all girls boarding school. It radically changed me, in arguably mostly positive ways. I am also 100% glad that I returned back to homeschool to graduate, and believe that also impacted me in a lot of great ways. There were challenges every, life is challenging. I’m so happy Penelope included this perspective.

    I wonder, Penelope, what do you think about the boarding school system? Do you think that boarding schools are an option only for single parent households? Are dual parent households who send their kids to boarding school just Meredith Blakes, who want to get the children out for nefarious reasons?

    • Penelope Trunk
      Penelope Trunk says:

      I published this guest post because I think I’d die sending my kids away to boarding school, but I do think that maybe I don’t have enough money to justify keeping them home. Because increasingly I see how limited I am in what I can give my kids compared to what those kids get in boarding school.

      The boarding school this post is about is one among the very very top in the US:

      These schools are not like other schools. The opportunities, the teachers, the daily life, it’s completely different. For example, you don’t need to take standardized tests at these schools. The coursework is so difficult and the students are so competitive that SATs are irrelevant.

      And you don’t do extracurriculars that you’re not good at. Because there’s no reason to. There are so many opportunities that if you are not great at one thing you can try another.

      You end up having different standards for yourself. I’m not sure how to give that to kids without sending them to these places. And the kids in boarding school miss out on home life, for sure. But you have to weigh the benefits of both. And I wanted to float the idea by you all — that top boarding schools have merit.

      I could never send my kids away. But I wonder if it was selfish.


      • Shelley
        Shelley says:

        Penelope, I thought you did send your youngest away for a time when you were overwhelmed and couldn’t offer the support he needed. I believe you mentioned it in a blog post, but I don’t recall any follow up, including saying he was back home. Am I misremembering?

        • Penelope Trunk
          Penelope Trunk says:

          Me sending him away to Lauren’s house lasted a week. He couldn’t handle being alone. And I was happy to go get him. We ended up in Boston with Lauren. During that time he got a scholarship to boarding school but he wouldn’t have started until the following fall. So, we all just ended up moving to Boston. Just writing this makes me feel sick inside. It was such a terrible time. I don’t know how he even lasted a week. He was so sad. We were all so sad.


  3. Kimberly Rotter
    Kimberly Rotter says:

    This just doesn’t compute for me. I was a late starter as a parent, age 41. At that point my career was secure enough that I could drop to part-time, work from home and focus on being a parent. I cannot for the life of me imagine giving up that role to someone else after just 12 or 13 years. I enjoy parenting, and that’s one of the big reasons I homeschool. To send a child away is unfathomable to me. I’m not saying it’s a damaging experience. I’m just saying that the time is going to come so fast when these children will have lives of their own. Why rush it?

    On the flip side, I’m very glad this woman’s experience was a positive one. And I also acknowledge that it help is needed more when you’re a single parent and when you have multiple children. Put those two circumstances together and it’s perfectly understandable why she would look at the boarding school option. Please don’t take this as a criticism of her parenting choices. It’s just hard for me to get my brain around it.

  4. Sarah M
    Sarah M says:

    I always wanted to go to a boarding school (specifically, an all-girls one) and I would have been that older kid. I ended up going to a private Catholic high school, and did well, along with working 15-20 hours a week from mid-highschool on. I also was raised by a single mom.
    If they have the drive and it works financially, then what’s the matter? A huge scholarship is a gift, the cherry on top is the kids want to be there. I’m happy for this family.

  5. Homeschooling Mom of Three
    Homeschooling Mom of Three says:

    We just sent my son to boarding school after six years of homeschooling. I never thought I could send my kids away but my incredibly hands-on sister blazed the trail before me and I just thought “I’m not special. If she can let go, so can I.” As she says “Once they’re in high school, they are barely home anyway.” The whole thing was my idea from there. Because our homeschooling community is so small, he was hungry for friends. He could have found that at a local private school but we live in an affluent area and stories I hear from friends with kids in the schools here is more than I could handle. I know I’m not equipped to navigate all the drama so we explored boarding school. He got into one of the top ten in the US and is doing great. I missed him terribly the first few months but always felt he’s in the best place. I LOVE that everyone has the same set of rules to live by so not a lot of funny business. You mess up and you’re out. He’s found an incredible group of boys that we are so impressed with. Everyone comes from a vastly different background, they all share some interests but are each incredibly dynamic. The only thing I’m not convinced of is that these top boarding schools offer kids more than they could get from homeschooling at a private school. What’s special about the boarding school is the deep community they develop. My son’s school is big on all classes mingling and because of that, my son spends his free time mostly with freshman and sophomores, but also with juniors and seniors. It’s this community that we sought after lonely years isolated at home. I was worried my son wouldn’t be challenged in high school because he was operating at such a high level on his own, but I was wrong there too. He operates at a crazy level when he studies what he wants. When in school, and forced to study other subjects, he is challenged. That was a relief to realize as we want him to enjoy all aspects of school and get his butt kicked a little too. We recently returned from our first parent’s weekend and I loved meeting all the parents and shedding tears with them. We all had our hearts broken when we let our kids leave home their freshman year of high school. But we also are all believers that our kids are in the best environment for this age.

  6. Mimi
    Mimi says:

    I honestly think for me it’s not the right choice , because giving my kids away just like that , they will be missing on a lot of things in my opinion ; family , home life , friends and experiencing altogether life .
    As for curriculum , the world of knowledge is infinite and one cannot stop learning or will not stop learning, Once a young adult wrap their heads on a profession or a skills they will like to further till adult life, the education will get narrowed to that subject even tough after mastering the skills ,they will still have opportunity to learn other thing.
    For me a boarding school can not replace a parent , no matter how well prepared these teachers are or how far they are on their doctorate level , it is still a job for them and they will obviously go back after teaching to their love family away from campus.
    I am a doctor , with my busy life I still find the time to be a mom , a teacher and also delegate to my chosen team of teachers certain emphasis on a curriculum .
    But I guess they have different path on a parental education , if that’s what ‘s her choice then it fits her family and surroundings .
    Kudos to her , she knows her child better than everybody .

  7. Sunny
    Sunny says:

    My daughter dreams of going to boarding school, especially one with horses. She is 14, and we are caretakers of a CT house where the owner went to boarding school in Switzerland, and very talented musically. Our girl is adopted, has challenges with learning and social skills as she is high functioning autistic with epilepsy. A scholarship seems unlikely. Though I would love for her to have opportunity to expand with more teachers and develop her tribe.

  8. Stephanie Kanitz
    Stephanie Kanitz says:

    She said she homeschooled her children briefly. Whether it worked out homeschooling or not is beside the point. I’m sure there are private schools without boarding that could have just as well educated and made her children reach their goals. What can she give to her children? Her time, your children grow up way too fast to waste each precious day with them away. Her children undoubtedly will turn out to be responsible adults, hold jobs etc, but will they feel a strong connection to family with their mother? I have to say after experiencing this personally, unequivocally NO. I appreciate they sacrifice my mother made for me, but I don’t have a strong bond with her, mainly because we didn’t have that day to day parent/ child interaction. Weekends/ holidays can’t make up for that.

  9. J.E.
    J.E. says:

    I think it makes a difference, as well, if the kids are older and wanting to go to boarding school versus automatically being sent away when they’re little like was often done in certain British social classes. If it’s their decision and financially feasible, try it out. It doesn’t have to be permanent and they can always leave if it’s not working out.

  10. Derek McDoogle
    Derek McDoogle says:

    I found it interesting when you said that your job as a parent is to present opportunities to your kids and then getting out of the way. My wife and I are thinking about what school district to choose from for our son. After reading your article, it helped me realize how good can be taking our son to a private school.


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