The Brutal Truth About Growing Up In The Top 1%

This is not an easy topic to talk about, but I’ll do my best.

I grew up in the top 1%:

  1. Our house formerly belonged to Dick Portillo, the founder of Dick Portillo’s Hot Dogs (a famous food chain here in Chicago that recently sold for close to $1 billion)
  2. The first car I ever drove as a 16 year old was a BMW x5 — and the same goes for my younger sister and two younger brothers.
  3. The first time I traveled out of the country was when I was ~8 years old, and I went to Jamaica with my family on vacation. Every vacation I have ever been on with my family, we have stayed in a very nice hotel. The most extravagant was when I was 16 years old, and we went to Hawaii for Spring Break. We stayed in the Presidential Suite on the top floor, with a full bay-window view of the ocean, a living room, dining room, and big screen t.v’s in every bedroom.
  4. Our neighbors have two bright red Ferraris. Our other neighbors have a Rolls Royce. Our other neighbors have a Bentley. A house two blocks from us has a helicopter pad on the roof. Etc.
  5. The high school I attended is (supposedly) one of the top public schools in the country, with a 98% graduation rate.

I think you get the point.

Here are the advantages of growing up in that sort of environment:

  1. You have access to the best everything. The best schools, the best summer camps, the best teachers, the best equipment, the best sports teams, the best technology, the best clothes, the best opportunities, etc.
  2. You never have to say no. Most kids can’t go to the college of their choice because their parents can’t afford it. They can’t go to the summer camp they want because their parents can’t afford it. They can’t play a musical instrument because it’s too expensive. In the 1% environment, this is never the case. If you want to do something, and you have access to do it, you can.
  3. You are surrounded by extremely valuable influences. That’s the truth. In the 1%, your dad’s friend that you see every other weekend is, to a lot of other people, an untouchable CEO. You have direct access to powerful, influential people in a way that 99% of the world could only dream of having.
  4. Your childhood friends will most likely go on to become those same valuable influences. “It’s all about who you know.” 10–20–30 years down the line, it’s a whole lot easier to reach out to an 8th grade classmate of yours, who is now the CEO of this or the President of that.
  5. You learn, from a very young age, how to act successful. That bravado you see the movers and shakers and business moguls in the world have? Imagine that in 7th graders, except it’s filled with false confidence, arrogance, and is often seen as “being spoiled.” But the seed has been planted, and tends to eventually grow into the business bravado everyone celebrates later in life.

There are more advantages, but those are the big buckets.

Here’s the thing nobody really talks about — the flip-side to each of the above points.

Growing up in the 1%…

  1. Because you have access to the best everything, there are no excuses. If you fail, it’s YOUR fault. Not the teacher, not your parents, not your peers, not the environment, nobody except you. And as an 8 year old, or a 12 year old, or a 17 year old, that’s a lot of responsibility on your shoulders — and you have no out. You have access to the best of the best, and if you fail, in any way, then you are simply a sub-par individual.
  2. Since money is no object and you have access to any opportunity you want, you aren’t allowed to say no. You have to say yes. You have to take every opportunity. You have to work harder. You have to be smarter. And unfortunately, since money is no object to a lot of parents, they use that as leverage to continue pushing you to say yes — until you are a 12 year old in so many activities that you are up at sunrise and going to sleep at midnight.
  3. As you are surrounded by extremely valuable influences, a couple things happen: For one, you realize (again, at a young age) that you really don’t have to work very hard. You have no incentive to work, actually, because your dad’s friend can get you an internship or a full-time job, no problem. You get bored. You don’t learn work ethic. And you just coast — because you know in the end it doesn’t matter.
  4. Your childhood friends, who will most likely go on to become “successful,” probably won’t (or tend not to) grow out of those same coasting qualities. Worse, they follow in similar footsteps, grabbing high-paying jobs and then spending their time on their dad’s boat, drinking excessively, and carrying on the tradition of throwing money at their kids, hoping those money-based opportunities will make up for the fact that Dad is always traveling for work and Mom is at the country club sipping martinis.
  5. You learn how to become an imposter of confidence, instead of actually being ok with who you are deep down.

The saddest truth about growing up in the 1% is that the outside tends to be a very poor reflection of the inside.

Eating disorders in teenage girls are common. Drug use, prescription especially, is heavily abused. Everyone is prescribed Adderall. A lot of the fathers drink a lot. A lot of them cheat. A lot of the mothers drink a lot. A lot of them cheat. And the kids grow up believing, or worse, wanting to embody those same traits.

I grew up feeling extremely insecure in that environment.

I thought everyone was smarter than me.

I felt like I would never be good enough.

I hated myself.

I was constantly depressed.

Nothing I did could measure up to my father or mother’s success.

I was constantly compared to other kids, who were getting accepted to Harvard or Stanford or Yale or MIT.

The star athletes were closet pill poppers.

The popular girls looked like miniature versions of their mothers, and did a lot of unhealthy things to maintain that image.

Kids overdosed.

Kids committed suicide.

And meanwhile, the town just went on pretending, pretending, pretending that everything was fine.

My experience was extremely unique in that, although I grew up and was molded by that environment, my parents also made me work for things I wanted. I was given every opportunity in the world to succeed, but I was not given $5 for lunch because that was considered “excessive spending” to my particularly frugal father. I always had new clothes to wear, a king size bed to sleep in, a new computer for school—but if I wanted to go to the movies with some friends then I had to mow the lawn to earn that for myself.

I give my parents a lot of credit for instilling those habits.

The day I graduated college, I was off my parents payroll.

They had made that clear for a long time, and I did my best to prepare for it — but it is impossible to prepare for that kind of drastic change.

I went from spending my senior year of college living in a penthouse apartment downtown Chicago, to a studio apartment on the north side of the city with no air conditioning, a $15 desk from Good Will, and an inflatable mattress. When I asked my dad if he could help me get a real desk and a real bed, he said, “When I was your age…” and that was the end of that.

I slept on an air mattress for 3 years.

My parents, although extremely wealthy and successful, wanted me to learn how to work for the things I wanted out of life.

Truthfully, I learned how to do that at a very young age. I tell the story often, but I’ll mention it here again: I learned the difference between doing something for external success and money vs doing it because you love to do it by playing World of Warcraft. Imagine growing up in the neighborhood I’ve described and saying, “I want to play professional video games” to my peers, parents, teachers, and authority figures. I got laughed at — by everyone. But I loved what I was doing and I believed I had a future in it, so I worked my ass off to become one of the highest ranked 3v3 World of Warcraft players in North America, and one of the most-read gaming bloggers on the Internet in 2007.

I think where I grew up is why I have chosen the pursuits I have in life. I could have leveraged my dad’s relationships and gotten a silver platter to just about anywhere — but I didn’t want that.

I wanted to earn it for myself.

I think that’s just part of who I am. So I deliberately chose interests where he had absolutely zero influence, forcing me to figure it out on my own and earn my own success. A harder road, but for me a more fulfilling one.

Now, a little over 4 years out of college, and I can confidently say that the life I have built for myself, I built on my own. Yes, I am eternally grateful for what positive things I was exposed to growing up in a privileged environment. Yes, I realize my parents’ influence on who I am as a person is not to be taken for granted. Yes, I realize I have been given a lot more than other people in life—but it has always been on me to do something positive with it.

That’s a big part of why I write, actually. I think the most valuable thing I could possibly do is share what I’ve learned with other people, so that they too can be exposed to the same lessons and learn as I did.

But, I also want to acknowledge that getting to where I am now was not easy. It’s still not easy. It’s actually very difficult saying no to the silver platter.

It’s hard telling your parents and your parents’ friends that you don’t want to do the same kind of work they do, and that you want to go your own way. It’s tough when you choose a pursuit nobody understands or respects, and to continue pursuing it even in the face of people you love telling you it’s a waste of time. It’s not easy to spend 21 years of your life having all the nicest things in the world, and then all of a sudden you wake up on an air mattress in an apartment the size of a closet boiling at 105 degrees. And it’s even tougher knowing that if I turned around and said, “Dad, I want to become a doctor like you,” he would stop at nothing to give me everything to make that happen. But when I said, “Dad, I want to be a writer,” he said, “All the best.”

But you know what?

I’m thankful for that.


EDIT#1: This Medium post has since gone viral, and the comments I’ve seen have, for the most part, been a colorful collage of insults.

Thank you for proving exactly what I believe is a topic worth talking about.

You see, when you grow up in a wealthy environment, you aren’t allowed to speak up about how you ever feel insecure—because you have money.

You aren’t allowed to say that you’re going through the same human fears the rest of the world goes through—because you have money.

You aren’t supposed to ever complain or talk about what it is you don’t have—because you already have so much.

But the truth is, we’re all human. And growing up in wealth made me realize, at a very young age, that money doesn’t change any of those human capacities we share. We all struggle with adolescence. We all struggle to be heard, to follow our dreams and feel understood. And while certain classes don’t struggle with them on a monetary level, what we do share in common are the emotions that come with this journey.

I’m surprised how many people read this and commented things like, “Yeah, life sure sounds tough for you—you trust fund baby.”

I have no trust fund. When I finished college, I didn’t take a dollar from either one of my parents. All of the opportunities I have found for myself since, I did by building myself here, on the Internet, writing. All of the people I work with, I met on my own—not through family relationships. And I did it this way because, growing up, I felt so much guilt for having started with more, for having been put in a position that I know others will never get to experience, that I wanted, as best I could, to try to do it my own way.

To anyone reading this post and saying that I am just another “trust fund baby” who doesn’t have an ounce of understanding of how the world works, I’d like to clarify:

When you’re a kid, born into privilege, for a long time you don’t understand what you have. Meanwhile, from the outside, everyone feels like they know you perfectly. That’s a dangerous duality, and the comments surrounding this post are a great example.

The point I wanted to express, however, is that money doesn’t make any of those human emotions go away. Growing up in a big house doesn’t really make the feelings you go through during adolescence any more or less intense. Being able to go on nice vacations doesn’t mean you, as a boy, girl, man, woman, don’t feel things like sadness, frustration, uncertainty, anger, or depression. And, dare I say, there are times when those luxurious privileges actually make those feelings even more intense, because they are harmonized with the overwhelming feeling of guilt for feeling such things surrounded by marble countertops and sports cars.

The brutal truth about growing up in the 1% is that living in the 1% doesn’t mean life is perfect.

And I think a big reason there is so much hate surrounding this topic (especially when written by someone who grew up in that sort of environment) is because that means pulling back the curtain on, quite essentially, The American Dream.

A big house and all the money in the world doesn’t fix everything.


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