American Dreamin’

What is the American Dream, Really?

Yesterday, Rob asked me whether or not I believe in the American Dream. I said, “Yes,” and began to expound on how much exciting innovation there is taking place and how that is representative of a healthy, vibrant economy with endless opportunities for all. Look at all of the happiness and wealth tech is creating. That surely is indicative of American Dreams coming true, no?

I cited the obvious college dropouts turned billionaires and Joe “Oprah for Men” Rogan, but, after a challenge from Notorious, it became pretty clear to me that I was conflating my personal experience–that of a highly educated man who’s had plenty of opportunities–with what the majority of Millennials might experience. It didn’t take long for me to realize my arrogance. My fortunate upbringing (thanks Mom and Dad) is an exception, not the rule. Maybe my idea of the American Dream was warped by the privileged opportunities my parents provided me with. I’ve been in my own bubble.

College Costs How Much?

America’s economy now requires over 80% of its job applicants to have a bachelor’s degree(Georgetown study). Compare that to 1970, and you’ll find the exact opposite. Back then, NY Times reported 8 out of 10 jobs were available to anyone who graduated from high school. Now, you basically HAVE to get a four-year degree to have any chance of just getting a job. When I realized that less than half of the now largest Millennial demographic in America does not have a college degree, I was shocked.

The cost of education, housing, and mere survival has gone up significantly in America. In comparison to our Baby Boomer parents, Huffpost found it will take us 4,153 more hours of minimum wage work to pay off the average cost of public university than our parents. In other words, college tuition has gone up 3000% percent(Yahoo Finance). As someone whose parents paid my tuition, I was, again, shocked to discover this. I can’t even imagine being in debt and having to pay off 3000% more to compete with 80% of the workforce. It’s a very difficult battleground.

Haunted House Market

Housing has become unaffordable for the most privileged Millennials. This past weekend, for example, I was with some friends in San Francisco. We were talking about buying homes. We were a group of five Ivy Leaguers, all with steady, white-collar jobs. Every single one of us, without any hesitation, fully accepted the fact that unless we started the next billion-dollar company, none of us has a chance of owning a home in the Bay Area. Keep in mind, we are the privileged. If we privileged elites don’t see a path to homeownership, how on earth can someone still paying off their student loans afford it?

To give you a specific example, one of my best friends from college and his other half both went to Ivy League schools. He went to Dartmouth, she to Harvard. They’re 28 years old, and they’re married (which, by the way, already puts them in rarified air. I’ll have more to say about this in a later post). They got elite jobs and are very smart about saving. They also come from wonderful, supportive, financially stable families. In other words, this is about as much of a Millennial power couple as you’ll be able to find. They are the creme de la creme.

Despite all of that, they have been struggling to purchase a “starter” home in LA. To date, they have lost out on every single offer. We just caught up yesterday and he said every one of their bids loses to an all-cash offer $300,000 above the asking price. Mind you, these are just starter homes and my friends, as I have said, are as elite as it gets. Imagine what it’s like to be making minimum wage.

The aggregate data shows that Millennials are hurting due to all of this. Apartment List reported only 43% of us own homes. When compared to Boomers at 77%, it definitely made me realize Millennials are behind. 

One thing is for certain, I definitely am no longer naively assuming that my situation is equivalent to that of the average American Millennial. 

What’s worse, I don’t see a path forward. If my elite friends and I can’t even afford homes, how will the rest of Americans be able to?

Trust Me, I’m Lying

The American Dream is kind of like social media. On the surface, everything is great, but once you spend a little bit of time there, you begin to see how much of it is bullshit. There is no shortage of so-called “influencers” who post about how they jump out of bed every morning at 5 am, land directly on their Pelotons where they incinerate calories while simultaneously practicing perfect mindfulness to finish up a 3-day water fast. They do all of this, of course, while day trading from their bungalow in Anguilla.

I must admit it. At 24, I totally fell for it all. I totally thought the way to “live” was to get rich quickly, travel and show it all off on social media. The reality is so much of the dream life influencers promote is, more often than not, a mirage.


This is kind of how I think about the American Dream now. On the surface, you can look at the elite tech, finance and media billionaires and think that is how everyone lives. When you dive in yourself, however, the reality is very different. The rags to riches stories are becoming less and less attainable for Millennials. At first, I thought the opposite. I was very wrong. Just like how incorrect I initially was with social media.

Reality Check

To answer Rob’s question, I’ve seriously adjusted my understanding of the American Dream. I do still think America is a place of incredible opportunity, likey still the best in the world. But, I’m becoming increasingly aware of the shrinking pool of Americans to whom that opportunity is available. I hope to research why adult life has become so much more expensive in the United States, the effect it is having on my generation and the Gen-Z coming up behind me, and what we can do to turn the tide. We have work to do.

Stay tuned and thanks for reading!


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Pedro Robinson

I grew up on the Stanford campus, where my Dad worked and still does. I went to Dartmouth College where I majored in Classical Studies, walked onto the football team for 2 years. After Dartmouth, I went to Palantir Technologies, where I did operations and strategy work for 3.5 years. From there, I went to ITAM startup where I did business development for a year. Wanting to get back into writing, I started free lance writing for some tech startups, at which point I met Rob. Since then, I have been helping him out with his content production and creation.

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