Privilege and Hard Questions

8 min readJan 20, 2021


Yesterday, over dinner, one of my colleagues, VS, revealed that she grew up in a single-parent household. She was the youngest of 3 siblings and is the last amongst them to get married. She lives with her mom now and said that her mom will continue to live with her even after she gets married. VS told us stoically that she and her fiance will never enjoy an “二人世界” in their life, and that this temporary assignment to Shanghai is her last taste of freedom. (Her fiance was supposed to accompany her to Shanghai, but Covid hit)

VS is, by company standards, very talented. She works in the prestigious consulting department and was promoted to a managerial role ahead of her peers. The company entirely sponsored her 6-month assignment in Shanghai. Her sharing last night made me feel embarrassed because it made me realise how privileged I was. And that when I say I’m independent, or when people tell me they admire my free-spiritedness, that I am bold to live in a foreign country so young and do a LDR, I realised so many things enabled me along the way. Shackles are not just about money and the socio-economic class you are born into (even though it could be correlated to other means), but I always like to carry it as a chip on my shoulder, because I’m surrounded by people who always seem to have more. More so-called “class”, more money.

In MBA essays, people tend to bring in their low Socio-Economic Status/ background as an illustration of their personal story. Your SES is valid because it shapes your worldview, but at the same time it’s a card to differentiate us from the rest of them, people who had access to resources and parents where attending a school like Wharton was the most 理所当然 natural thing in the world. For us it was grit, determination and a hell-lot of resourcefulness.

I see that people in the US like to use the label “first-gen”. It has become a badge of honour, to show that you have overcome the odds. Yesterday I showed my boyfriend how this guy who eventually became an intern at NASA put his experience at McDonalds busting tables onto his LinkedIn profile. (Where in the past one might be more discreet about the hustling) There’s nothing wrong with that — and all congratulations to you, sir — but it’s a signal that it has become an acceptable personal brand to tout the first-gen-ness and the hardships you have to overcome.

People got a lot to say, but don’t know shit ‘bout where I was made/ Or how many floors that I had to scrub just to make it past where I am from

Work — Iggy Azelea

To some extent, the first-gen card is overplayed. As a video compilation of PAP candidates running for the 2020 elections showed, many of the candidates liked to stress their “humble backgrounds” — as the state media wrote in a headline “PAP new faces come from humble beginnings, took unconventional routes to success”. The idea is that people who don’t come from privilege are people best positioned to serve you because they have overcame the odds. They are one of/with the people, and not elites sitting in their ivory towers who graduated from ACS/ Raffles/ Hwa Chong and went straight into an Ivy League or Oxbridge, sometimes under a government scholarship as they are groomed to. So vote for them!

I digress. I was reflecting on the sources of privilege that I unknowingly had — that I sometimes refuse to admit to myself, because I’m not as self-made as I make myself out to be. For example, the fact that I could drop everything in Singapore and move to Shanghai…

… is because I’m not a single-child, as a example, as my friend Vivian pointed out to me once. She said that as a single child she had to consider her parents more before making decisions like these. It made me wonder if I take things for granted, like the fact that I have a younger sister who is still in Singapore, or that my parents are still relatively healthy (none in debilitating conditions). And that my parents live near their kin, who could take care of each other as they grow old. So I don’t have to entertain the thought of my parents moving in or the Nursing Home — at least not yet.

And the fact remains that I grew up in a loving, stable household. The money I earned in my part-time jobs were completely my savings. My parents paid off my tuition fees upfront so I didn’t have to worry about anything other than my studies during school. Then most of my loan was waived off after I started work. It wasn’t like other colleagues I had, or friends of friends, who not only had to pay off their student loans in full, but had to pay off their parents’ gambling debts. I always felt ashamed hearing my colleague talk about how he always had to think twice about engaging in a social activity, because of the costs incurred. And how in spite of a relatively high income (75th percentile I reckon), he would prudently eat 菜饭 for lunch.

My dear friend Fairul pointed this out to me nearly 4.5 years ago, when I emailed him a bratty rant about my lofty ambitions working in consulting, did not mince his words:

Cut the crap about being a self-made man. Nobody’s a self-made man, not entirely anyway. Come back and declare yourself a self made man when you can attribute all your success to you alone and that you’ve actually struggled to get where you are now. Did you work to pay your school fees? How about those tuition classes you had prior to uni? Ever had your parents asking you for money to pay the utility bills? The difficulties we had to face to get to where we are today probably pales in comparison to people living in poverty/financial difficulties. We’ve somehow or another enjoyed the privileges that our parents allowed us to have and I believe we’re probably low grade “Second Generation Inheritors”.

To address your so called flaw: Sometimes I feel you look upwards too much Celeste. At times, take a break and look at the people below. And it will ground you. When you chase the stars, don’t forget the ground (and what lies beneath it). Your same class friends may be coming from a different angle: They know the abundance that YOU have in comparison to themselves or others they know in their lives. Or they’re in your shoes: contrasting the barrenness of their experience to you while you contrasting your barrenness others up in the social ladder — doubly barren. So maybe they’re right: Stop being a brat. I still think you can approach striving for more… But with gratitude for what you already have.

Another point on being brought up in a loving household… I have a friend in Shanghai a couple years older than me, called S. She’s what I imagine to be a Taiwanese socialite, the queen of cool, went to a private boarding school in the States when she was young, and lived all over the world including Bangkok, before we met in Shanghai. She always embodied the effortless and at-ease upper class for me. She didn’t blink when I told her I was going to Harvard Business School. She isn’t impressed with consultants. She said her life was surrounded with so many of such people that it’s natural for her to hear about these achievements. (I then told her it was an evidence of class, because I was the first among my friends to broach this barrier, having never attended an elite school in Singapore, and that at least 3 people told me I would be their first and only Harvard friend. But back to the original point) At one particular hotpot dinner, S opened up to me more. Apparently her family, which looked perfect and successful from the outside, was dysfunctional in the inside. It was heavily 重男轻女, where her brother would receive 2–3x the angbao money that she did, and even stole her money when she was young. Now he’s a consultant who takes other people’s money :) Their family lived separately when she was quite young, her father in Taiwan and the rest of them in the US.

When I heard her story, I realised how safe and warm an environment my parents had provided for me. And even though my family has never travelled together beyond Asia, and my parents used to get upset when a dinner bill exceeded $100 for the 4 of us, it was warm and functional.

So to wrap up all these random recollections, I realised that I have been blessed in so many ways in my background, and I should always remember the upbringing I enjoyed with gratitude, and never lose sight of it when I enter a business school where it’s classicisms and wealth and ambitions and success on steroids. And to reflect on my identity which has shaped my decision making on how easy it is for me to hop around between places. My oldest aunt, my 大姨, is fuming that I’m relocating to the States this year, amidst a pandemic. How could I be so selfish? Didn’t I care about how I would make them worry? This actually makes me recollect similar patterns in the past, like when I insisted on traveling to Paris alone in 2016 summer after the Nice terrorist attacks. I wrote a death note to my mother in case I died and gave Fairul the password to my Dropbox. I thought I was being very enlightened about death like Jean Paul-Sartre and Norman Mailer, when actually I was just being selfish. As selfish as the Covidiots of 2020/1.

My reply to Fairul’s email back then was horrific. In fact, when I read my Tumblr posts of the 2015–2017 years I am horrified by this brash arrogance of a 21–22 year old girl, caught up in too many enneagram personality tests and amateur successes. I’m glad that I’ve grown up from that girl, many years older and hopefully many years wiser. But I think that pensive girl who put up so many barriers still lurks in me. And she might rear her ugly head when she enters the HBS bubble, goes for her gym classes, pays for $7 coffees and rents an apartment in the city center. But that’s why I need diverse people and friends to keep me honest.

You are a different personhood from me: your attitudes towards the world, your amazing empathy, your goals in life and the environment you were nurtured in university. When I first stepped into business school I was probably very much like you and my parents: I didn’t know nor cared what Deloitte is. You however have to understand that I belong to this business subculture where jaws drop when I mention I’m doing consulting in Deloitte, the sort of newfound respect I earn in people’s gaze. This is the reality of the “world” I now belong to and am a functioning member of. Likewise, understand that while I can see where you’re coming from, I find it difficult and non-instinctive to adopt your frame of reference.

Another thing about frame of reference: compared to my frame of reference, I’m for sure a self-made man. Compared to your frame of reference, I’m a filthy capitalist born with a silver spoon in her mouth. I would invite you to plunge into my world so you can see where I’m coming from rather than vicariously through me, but the system is such that the barriers to entry only get higher.

Whereas lovely Fairul, woke Fairul, in Dec 2020, sent me an email with an excerpt from an academic paper about poverty:

Why does this make me feel so sad?

Thinking about my privilege, thinking about my inaction. As we chase our desires and expectations, those in poverty suppress their own abilities to self-actualise because of the circumstances that they’re found in.

Is there any use in thinking and feeling sad when nothing is done? Some might just say — that’s how the world works. Exploitation is a necessary evil for the luxuries we enjoy today. Is there a responsibility for us to care for them? Oh privilege, how I enjoy you with a heavy guilt :(