On Teaching Rich Kids
My first job out of college was with a tutoring company. It’s astounding the difference a few years can make in a young person. Here I was, 22, hardly an adult myself, and in some ways not so different from the people I was teaching. However, at the same time, we were living completely different lives. As much as we could relate to one another on so many levels, for the hour or two I spent with them each day, I was responsible for these people. But I was also often their friend. You want these kids to like you but the danger is that they will get too comfortable and nothing will get done. If nothing gets done, the parents get angry. If nothing gets done, the kids stop coming. If the kids stop coming, you lose your job.
More dangerous still is the possibility that the kids will get so comfortable around you that they’ll tell you things you don’t want to know. Of course you want them to trust you because you can be someone who understands things that their parents and teachers cannot. You were them not so long ago. But it is a fine line. Soon the information starts flowing a little too freely, and you may find yourself in an uncomfortable situation. It was just my second or third month with the company and I was teaching Algebra to a girl I’d been seeing for a few weeks.
“I stole condoms from Safeway yesterday.”
I knew then that I was in over my head.
That same week another student of mine, probably 16 at the time, popped up on my Tinder as a potential match. Of course my settings were not set to include teenage boys, but apparently sometimes teenagers lie. I deleted my account immediately, praying he hadn’t seen me. It was never mentioned but I really never felt comfortable around the kid after that. Fortunately he was shipped off to military school not long after.
The company I worked for was based in Marin County, California. The average gross household income in Marin County is $159,000. Our students were white, rich and entitled, and their parents were worse. For some parents, tutoring was just a convenient place to send the kids after school. At $100 an hour, it was a small price to pay to ensure that they were staying away from any juvenile shenanigans. For others, Harvard had been the goal since their child turned 3. But regardless of why kids started coming, it became a sort of cool after school hangout spot for a lot of students.
This is why 10 pm condom water balloon fights became a part of life that I found myself dealing with. Yes, I taught the Pythagorean Theorem and discussed the narrative motifs that appear in Lord of the Flies. But I also drove a thirteen year old to his first date at the Fro-Yo parlor down the street, and froze a spoon for a kid who came in with an atrocious hickey covering her neck. I had chewed up hamburger spit into my face when I made a kid laugh too hard. I went to the 8th grade science fair to see projects I had helped design. I sat with parents at ballet recitals, school plays and choir concerts. I dog sat their extravagant homes when their families were away on tropical vacations. At the end of each school year, I jumped around from mansion to mansion attending high school graduation parties. I grew to love these kids.
The job had its other perks, as well. As impossible as these crazy helicopter moms were, they were also extremely generous once you were on their good side. My Christmas gifts included $50 gift cards, massages at the local spa, expensive bottles of wine. One mom in particular really took a liking to me. She asked me out for drinks one night and after an evening of expensive wine and delicious tapas she asked my pants size.
“I’m cleaning out my closet and have bags full of clothes. We’re going away this weekend, I’ll leave a key under the front mat and you make sure you go by and try on anything you like. Everything else is just going to the Goodwill.”
And that was how I got my first pair of designer jeans.
By the time I was manager, I’d even convinced the owners to get me a membership to the bougie fitness club where everyone who was anyone in Marin was a member. I told them it would be good for networking, which, it turned out, was entirely true. I’d go to spin class with the rich, hot moms and afterward we’d talk about their kids’ progress and goals while getting ready next to one another in the plush locker rooms with their fuzzy complimentary bathrobes and private vanities.
But in order for the parents to like you, the kids have to be succeeding, and, as it turns out, kids don’t always feel like doing their homework. So it was often up to the tutor to find incentives, and because these were kids who already had everything, sometimes one had to get creative. One semester I had a particularly stubborn group of Geometry students so I came up with a reward system. Every time the group finished an assignment we would watch one episode of R. Kelly’s Trapped in the Closet video series. I’ll be the first to admit that in retrospect that may not have been the best choice, but at the time my plan was successful. The plot twists and cliffhangers just kept coming for 33 episodes and for weeks those kids came in dying to get through their homework and find out who was knocking at the hotel door.
That same year I had another student, a goofy 10th grade athlete who came in most nights around 8:00, stinky and sweaty, after Lacrosse practice let out. He had recently been to see The Interview in theaters. It was the satirical 2014 James Franco and Seth Rogan film about Kim Jong-un, which was banned in many theaters out of fear that it may lead to nuclear warfare. The kid was obsessed! For weeks he spoke in an offensive and mildly racist Korean accent, and would refer to me only as “Supreme Leader.”
“Jonathon, finish that paragraph. You’re almost done and I want to get out of here.”
“Yes, Supreme Leader!”
“Don’t call me that.”
“Yes, Supreme Leader!”
“That better be done by the time I get back from the restroom!”
“Supreme Leader have no butthole!!”
“Don’t be ridiculous, of course I have a butthole!”
“Yes, Supreme Leader!”
The problem was, I didn’t really care because I thought it was just as funny as he did. Everything the kid said was funny. He constantly thought he was sick or dying of some obscure disease or another. He came in complaining about a new ailment every other day, whether it be that his skin felt itchy or his heart was beating too quickly. I would constantly look over to check his progress, only to find him scrolling through WebMD, looking totally freaked out. One day as he was listing his myriad new symptoms, I said, “Jonathon. You’re a hypochondriac.”
With dead seriousness, he looked at me and responded, “I don’t know what that is, but I’m sure I have it.”
Sometimes the things I look back on and laugh at didn’t actually seem so funny at the time. Tutoring sex ed. It’s hilarious in retrospect, but was often very uncomfortable in the moment. And believe me, I’m no prude. I’m as comfortable talking about sex as anyone, but even I feel that there are words more suitable to an indoor voice when said in certain public places.
I once had a particularly loud eighth grade student obsessing over an upcoming female reproductive system quiz yell out in frustration “I keep mixing up the cervix and the cliTORous!!!”
I fought the urge to tell her what a common problem it seemed to be.
While we saw a lot of kids for a lot of subjects, the real money maker for the company was standardized test preparation. Because when Yale has been the goal for your child from the time of conception, there is NOTHING. IN. THE. WORLD. MORE. IMPORTANT. THAN. STANDARDIZED. TESTS.
Most people are familiar with the concept of the SATs, but I would bet that you may never have heard of the SSATs. If not, consider yourself very lucky. The SSAT is a soul crushing exam given to fragile middle school children that determines which elite private high schools they are smart enough to get into. And for half the year, preparing children for this test was my life’s purpose.
I was in charge of the SSAT program because I was good with the 12 and 13 year olds. They’re tricky because you can’t give them shit like you do juniors and seniors, but they don’t want to be treated like children, either. But more importantly than being good with the kids, I was good with the parents. The only way to appease an SSAT mom is to forego all dignity and do absolutely whatever she wants, regardless of other students’ needs or even your own personal life. If the student does poorly and mom blames you, you accept the blame. If mom decides the student is dyslexic and needs extra testing time, you write that reference letter. If mom says the student needs an extra three hour lesson on Saturday because their daily sessions just aren’t enough, you don’t have plans on Saturday. And when the child arrives on Saturday, broken and exhausted from spending every waking hour preparing for this test, you wait until the mom’s Escalade disappears and you give them candy and show them music videos. Because you know that THERE. ARE. THINGS. MORE. IMPORTANT. THAN. STANDARDIZED. TESTS.
In the end, the kids get into the schools, the parents appreciate how much care you’ve shown for their child, and sometimes they give you the clothes they’ve outgrown. But even better than hand-me-downs and expensive Christmas presents are the friendships that I’ve maintained with a lot of the kind and bright students I spent years teaching and mentoring, who are now out doing things in the real world themselves. It’s astounding the difference a few years can make in a young person.
