America loves a good story of someone “making it” — starting off in a position of disadvantage, and working their way into the higher echelons of society. The American Dream. This country is built on the notion that anyone can make it, because privilege (especially economic and social privilege) is attainable; it isn’t just something you’re born with or into.
Privilege looks like many different things from the outside — wealth, social connections, race, color of skin, education, or natural beauty. But from the inside, what does privilege feel like? What are the subjective markers of privilege, and do they always line up with the objective markers of privilege that we can all identify?
A tale of two privileges: objective markers, and subjective experiences.
I think over the course of my life thus far, I’ve loosely lived out some iteration of this American Dream. I came from relatively few objective markers of privilege, and over time, I attained numerous.
I was an immigrant kid, learning a new language in a new land, with no extended family or roots. Over time, we navigated my way into a top private high school, then Harvard University. I went to a top law school, a top clerkship, then a top New York law firm. My peers in my wide social network are at the top of their respective fields. By any objective standard, I have “made it”; I am privileged, mostly by the measure of the advanced degrees I can list behind my name.
What does privilege feel like to me? It feels like confidence — the measured kind that doesn’t feel like you’re going out over your skis. It feels like security — the kind that grounds you and gives you a solid foundation that is indestructible.
But here’s the thing: I had all these feelings back when I was a scrappy Korean girl growing up in Canada. I had the privilege of being raised by parents who provided emotional and financial security to me, even if they themselves didn’t feel it. I had the privilege of having my parents pour confidence into me as if they were pouring concrete into my existential foundation that is now indestructible.
My subjective experience of privilege was borne from the advantage of having parents who loved and supported me. And my hunch is that the objective markers of privilege I have earned through hard work, and attained through sheer luck or leveraging my existing advantages, have helped solidify the confidence and security I now enjoy. And this begs the question: did I really need those objective markers of success and privilege? This is the ultimate question that is now haunting me as I navigate parenting.
Passing on privilege.
It is fact that my undergraduate experience at Harvard was the most formative four years of my life. In late August after high school graduation, I flew to Boston by myself and arrived on campus solo. With me was a watermelon-green hard-case Samsonite and a tall black immigrant bag (if you don’t know what that is, it’s like a standing body bag that is used by immigrants moving their lives very far distances). The immigrant bag was teetering on four tiny wheels that gave up immediately between the crushing weight of its contents and the uneven cobblestones of Harvard Square.
I must have looked so out of place. I remember many kind strangers offering to help me — all of whom I kindly rejected, until this very large man made the executive decision that I didn’t really know what I was doing and just picked up my luggage and told me to direct him.
It was the perfect beginning of four years that cracked opened the world to me.
Everyone told me that what you get at Harvard isn’t really the education — it’s about the people you meet. And I was lucky enough to meet some incredible people who are now my chosen family — friends that are more embedded into my life and well-being today than they were in college. And despite the stereotypes, many of my friends from Harvard didn’t come from wealth or connections — their stories were similar to mine.
So fast forward 15+ years, many of us are now parents. And we are now grappling with this question of how to raise our kids who have now been born into privilege… I think about my classmates at Harvard whose parent had also graduated from Harvard or another Ivy League school and I remember the differentiated air of privilege they breathed. And now, I have to confront this strange fact that regardless of where they are headed for college, my own children are cut from that cloth.
Should I feel good about it? Proud? In truth, what I actually feel is… discomfort.
When my parents were raising me, their deepest anxiety about my future was existential. My deepest anxiety about my kids’ future is that they will grow up to be entitled, and unable to care for themselves as a result. The American Dream, once realized, doesn’t have a built-in second chapter for the next generation.
And if I’m being honest, I know that that chapter isn’t for me to write.
Privilege Gen 2.
I find myself telling my kids a lot of my childhood stories to emphasize how privileged and lucky they are. A lot of stories that start with When I was growing up… and end with you’re so lucky to have this. It’s usually triggered by something very specific like when they grab a fresh sheet of white paper and use it up in one sitting. When I was growing up, fresh white paper was treated like precious metal; my parents made me use every square inch, both sides, with careful planning. Just because my 3yo takes white printer paper for granted doesn’t mean they will turn into an entitled monster as an adult. But because of my own personal narrative, I can’t help but wonder if their relative privilege is robbing them of something really important.
Privilege takes away friction — it doesn’t make things automatically possible, but it makes everything less hard. There’s less struggle, less figuring out. And so I keep asking myself, how will they build character and resilience, when their baseline is so easy?
These queries linger at the back of my mind in moments small and large. On that fuzzy yardstick of privilege, my kids are starting far ahead of where I started, and I will continue to have conflicting feelings of relief and pride, but also anxiety and guilt.
Perhaps that is precisely the price of privilege.
Such captivating questions, Sy, and so tied up in our feelings, values, and lived experiences. Interesting thinking about navigating all of this with a partner, too. I wonder what percent of our family decisions or habits are made explicitly/intentionally (e.g., we are going to take this approach to celebrating children's birthdays, eating out at restaurants, talking about our various privileges) versus organically.
Beautifully written Sy! There are parts of your story that resonate with me. Thank you for this thought post!