The Preppie Connection

Like every story, there's going to be a better one. 

Like every experience, there's going to be a better one. 

Like every nice person you meet, there'll be a nicer one. 

It goes for anything. Mainly because we're young and mainly because there's a subtantial amount of life left to live.

But one thing that I have learned, and most of it came right from a small town high school experience is that no matter who you encounter, no matter what traits they have or how much they can do for you or how much money they have, there's always going to be someone who has more. 

And the people with more, they don't always come from the fancy families and the big estates. They don't need that. They have their own sense a life outside the bubble of suburban white picket fence private school childhoods.

I got this idea to write this because earlier I watched The Preppie Connection on Netflix which was a movie about a kid at a boarding school who stood out because he wasn't from a millionaire family and ended up selling cocaine bla bla bla - good movie highly suggest. 

But the whole underlying point of the movie was that the main character ended up at this prestigious boarding school in Connecticut because he was on some scholarship, and he was nothing like the rest of the kids.

Watching it brought back a ton of nostalgic moments in my memory of Massachusetts growing up - knowing kids from families with food stamps to knowing kids with families with so many millions of dollars that the amount of cars they had couldn't be counted on either of their hands. 

And the whole "middle class kid at preppy school on scholarship stand out because he's not rich" thing super hit home. Not because I was a middle class kid who went to a boarding school and had no notable famous family members on the alumni list, but because my home town was set up a super similar way and I saw this whole money-power dissidence thing from a very clear perspective. 

There's this prep school in my town and a bunch of rich kids end up going there and they all cherished their 'brotherhood' and wore khacki pants and boat shoes and collared shirts and played lacrosse and it seemed like every one of them had two rich parents and two great looking siblings and two mercedes benz cars and two ivy league schools lined up to go to after we graduated. 

I had a lot of friends who were that case. And, well, I had a lot of friends who were the opposite, and most of them just wished in envy that they were that way.

And I'd be lying if I sat there and said wow I wish I grew up with a ginormous house on a private estate and a boat and a bunch of family friends with Fortune 500 companies, but the dice rolled differently when the simulation game was picking my character. 

But the point is, when you're growing up and you go to school with a diverse group of people, there's always going to be that rich kid that everyone wants to be friends with. There's going to be tons of them, actually. The more money people have, the more they have to offer. That's how I always saw it when I was younger. Like the kids with the Fortune 500 families always had the craziest brand new cars that cost like $80,000 that they'd drive to school, and they had these ginormous houses on the water that everyone would party at and the parents would just pretend it wasn't happening, and they had big boats and cool girlfriends from other private schools and it just seemed like this perfect preppy lifestyle that I watched from afar but was so indulged in from up close. 

Maybe that made sense to some of you, because I'm sure most people reading this have experienced this preppy lifestlye from some stand point. 

But no matter how rich the coolest rich kid is, one day when you get out of the small town and go to the big city and the real world, there's going to be some one ten times as rich, ten times as cool, or ten times as humble. 

The big moral of it all, which I can't express enough, is that when you do get to the point when you leave high school and go off to college or move to LA or NY and you get out of your small town, no one cares how rich your parents are. Like yeah, maybe it'll help you to get a job or something down the road, but those kids get thrown into the pool of every other kid who made it to that point in life, and they become just another number, not a kid who can show off their car driving to school every day. 

So as cool as it might seem to care about wealth and social class and money and families in high school, just know that not everyone comes from that. 

The coolest kids I knew in high school were the ones who came from lower income families. Maybe that's because them and I got along because we were the outliers to the rich kids and the Fortune 5 Families. Scratch that, it's definitely why we all got along. But we still lived the same way everyone else did, like we belonged there. 

I don't think I'll ever forget the night that we were all at this kids house, his parents were on the cover of Forbes one time, they had a crazy house on the ocean with a light house and stuff. I was really good friends with a bunch of prep kids growing up, even though I didn't wear the khacki pants and boat shoes to school. I was an outlier, of course because no, I didn't go to their prestegious brotherhood school and I didn't get to invite preppy girls to their exclusive formal dances. It was like I was a part of their private club, but I never got my face on the wall. That type of deal. Me and a bunch of kids were in this kids room and there were tons of people over and one of the kids was describing his class mate, and he's like "Yeah that kid's cool and all but he's an only child and he only has one parent isn't that super fucking weird. Like - imagine that. How'd he even end up talking to us?"

To be fair I don't think I'll ever forget that. I don't know who the kid they were talking about is. I probably will never know. I think the ending question "How'd he even end up talking to us?" rang in my head like ten times after that. 

Here I am, this outsider to their rich kid club sitting in this fifty million dollar mansion with all these kids I wished I had grown up like; an only child with, yup, one parent. 

The thing was, I was always me growing up, and a lot of people knew me for me (whatever that me was, I found a way for people to like it), and it never really came up in conversation or mattered what my life was like outside of the present me. But that kid they described, that kid who had one parent and no siblings, probably grew up the exact same way as me. 

I remember butting in and being like "what's wrong with that?" very subtlety. Not because I wanted them to be like "oh, wait, are you one of those kids too", but because I was just curious their opinion on it. 

This one kid, who was one of the cooler of the prep stars, he shrugged his shoulders a little bit. "I don't know" he said as he was re stringing his lacrosse stick head. "That's just not how most of us prep kids grew up" he finished.

The other kid who was playing PS4 (some racing game, they all loved racing games and I never knew why), had one hand on the controller and one hand in a bag of cheetos at this point. "Must be a weird life" he said as he wolfed a few cheetos down. 

The conversation died down and transitioned into "what are we doing tonight" and "what girls are we hanging out with", but I didn't put much of my two cents into the planning, I kept thinking "Must be a weird life indeed". 

To this day I wish I could have gotten the kids name - you know, the one with the lack of siblings and single parent. Maybe he was at the prep school on a scholarship. 

My mom always told me it was better off to go to the public school in my town so that we'd have enough money to pay for college without going into debt. 

Obviously that was a really shitty conversation to have to have at like - however old you are in the 8th grade, and I remember crying at one point. But sometimes you need to do what you need to do. And look, I've turned out just fine (so I hope). 

And when the time came and I branched out outside of my school, I realized that the prep kids from the surrounding towns did have much more to offer. They had cooler cars. Bigger houses. Hotter prep school girl friends. And for a while, a young version of me was very infactuated by all of it, maybe because I never had it, maybe because I always had wanted it but the simulation just didn't load me up enough points in that department. 

Who knows. 

At the end of the day I'm the exact same person I would have been if I had spent $120,000 on high school, and I'd probably be in debt quite a bit. So it's better off that I preach public school success stories.

Actually - I started OHKAY as a junior year class project. So if I never went to public school I wouldn't have gotten that assignment, wouldn't have became who I became, probably would have never traveled the world and seen my friends get famous and probably would be in a frat at some school in the middle of no where nearby corn fields. So when the sun sets, I'm glad for the life the simulation picked for me. 

But that's not the point. The point is that there's always going to be people who come from different lives. People who are the coolest kids that hide the littlest insecurities, and the weirdest kids who have the coolest stories. 

And the richest kids in high school might have the pretty girl friends with the horses at their house and the boats they cruise on in the summer time, but when college hits and the real world begins, it's like a fresh slate and no one cares how much money your parents made last year.

Hell, no one even asks what your parents do anymore. It's all about who are you - what is your portfolio like - and are you creative. 

Unless, well, you go to an Ivy league school like Harvard and try to get into a private club. 

If that's the case, me and the other kid with no siblings and just a mom, well, we'd be screwed because the "What company does your family own" conversation comes up a lot at places like Harvard. 

And I've heard it time and time again - and sometimes you can put on a front and say what you want to say to impress the next douchey guy in the khakis, but at the end of the day it really doesn't matter who your family is on the leadership boards, because it's your life you need to live. Right? 

I recently checked in on a few of my friends who sat in that room with the cheetos and the lacrosse stick. They're all in fraternities at big universities. I'm sure they love their life. I'm sure they party just as hard as we did in high school. I'm sure their friends are very similar to the ones they had in high school. And yes, of course a part of me wishes that my life was slightly different and that I got to experience that just for a split second, but then again if that was me on some random campus with school colors painted on my chest for game day, drunk as ever at 2pm with hundreds of miles of cornfields and state surrounding me, you'd be hearing me on here saying 

"I'm going to create the next Facebook so I can get rich and get the actual hell out of this place". 

Not that I'm not trying to do the whole next Facebook thing, but you get the point. 

You never really know who people are on the insides. You might know who their family is, or what first car their parents bought them, but you'll never know what goes on at the dinner table at night or if they even get to have family dinner.

Sixteen year old me would have loved a big family dinner.

But sixteen year old me was having dinner with my mom who raised me to be the person I am today.

And sixteen year old me was going to private school on monday with all my other friends who were pretty similar to me. 

But sixteen year old me realized none of that shit mattered - the money or any of that. 

Like life just throws curve balls. Fast balls. Slow balls. Every thing. It all comes at you. You just need to know how to shape your life around that to be the best it possibly can with any situation you're in. 

And never think that the single parent kid with no siblings has a "weird life"

Because I bet that kid is going to be fucking great one day. 

And damn I wish I got his name. 


p.s. wrote this listening to this song from the UP soundtrack, and watch The Preppie Connection on Netflix when you get a minute 

chris brownComment