What I wish I had known

This post is a very personal one, and a long one at that. It’s been in the making for a while, but I’ve been putting off actually finishing and publishing it, partly because it’s painful to write this stuff out and partly because I’m afraid of alienating people who might not like what I have to say.

But dealing with pain and facing your fears–isn’t that part of growing up? Part of what it means to be human?

This is my story. If I don’t tell it, no one will, and I can’t let it wither away inside my head.


The main reason I’m publishing this post now is that yesterday I read a post by Tracy Chou on why every tech worker needs a humanities education. I already wholeheartedly agree with that premise, so I was inclined to like the article before I even opened the page, but once I got to the first paragraph, which mentions my favourite author, I was hooked:

In 2005, the late writer David Foster Wallace delivered a now-famous commencement address. It starts with the story of the fish in water, who spend their lives not even knowing what water is. They are naively unaware of the ocean that permits their existence, and the currents that carry them.

She goes on to talk about how she wishes she had known about the value of a liberal arts education when she was younger, which was like a balm for my soul, since I feel exactly the same way:

Ruefully–and with some embarrassment at my younger self’s condescending attitude toward the humanities–I now wish that I had strived for a proper liberal arts education. That I’d learned how to think critically about the world we live in and how to engage with it. That I’d absorbed lessons about how to identify and interrogate privilege, power structures, structural inequality, and injustice. That I’d had opportunities to debate my peers and develop informed opinions on philosophy and morality. And even more than all of that, I wish I’d even realized that these were worthwhile thoughts to fill my mind with — that all of my engineering work would be contextualized by such subjects.

I’m publishing this post now because I want to share what I wish I had known. Before I found myself on a seemingly inescapable trajectory toward the tech industry. Before I accepted a full-time offer at Google. Before I reneged on that offer to rush into a startup instead.

I can’t go back in time, but maybe it doesn’t have to be that linear. Maybe my writing this will make someone else examine and then change their trajectory. Maybe my writing this will absolve me of the unexamined life I’ve lived for the last few years. Maybe then it won’t have been for naught.


Here’s what this post is not.

This post is not about salary negotiation, or how to ace a tech interview, or what programming languages you should learn. Those topics have been covered extensively, and I have nothing constructive to add on those fronts.

Neither is it about how the tech industry is toxic, or filled with mediocre and malicious people in seemingly unassailable positions of power, or plagued with racism and sexism and other forms of institutional oppression. All of those things are true to some extent, but that’s all been covered in various other posts and news articles recently, and I don’t really have any stories that are worse than what’s already out there.

What I wish I had known before entering the tech industry isn’t specific to the tech industry. The problem isn’t tech. The problem is something more systemic, larger than even the tech industry, but (I think) you need to understand it if you want to both be part of the tech industry and live an examined life.

This post is about water, and what I think it means to know what it is.


What I wish I had known is very tied up with my particular journey into tech. So here’s my journey.

All my life, I’ve felt like I needed something to work towards. Like I needed something bigger than myself to give myself away to. A tragic case of heroism without a cause, basically. I needed a cause worth fighting for.

I considered becoming a doctor, a lawyer, a UN peacekeeper. There was even a brief period when I had this dream of joining U.S. law enforcement. I had it all planned out: I would marry an American, then get my green card, then naturalize, then join the FBI or the CIA or something and then finally I’d have a cause worth devoting my life to.

I know, I know. It sounds so silly now. But I was young and the world didn’t seem to have that many causes anymore and I was searching for something that would be worth the effort I wanted to put in. I was looking for something to believe in.

I don’t remember when I stopped looking for that something. I must have grown out of that: that youthful idealism, that desire for something to strive for, the naive hope that things really were black and white. I do know that when I was applying to college, I felt like I was scrambling, lost, adrift in a vast ocean of possibilities. I had no clue what I wanted to do, and so I latched on to something that I felt I should do.

College brought with it a whole host of things I didn’t expect. Initially a physics and CS major, I soon found myself fully immersed in programming, with a rapidly declining interest in physics. I was spending almost all my spare time building software and very little time doing any metacognition about what that signified. Eventually, I realised that I was firmly on a path to becoming a full-time software engineer, without ever really choosing that path, or being aware of what I was doing.

And for a time, the destination was motivation enough. I would read about tech salaries, management styles, perks. I followed working software engineers on Twitter and thought of them as role models, people whose lives I wanted. The novelty of the industry and this path I found myself on was exciting enough that joining this world seemed like an end in itself. In short, I bought into the collective hallucination that is Silicon Valley.

The summer after my third year, I interned at Google in San Francisco and managed to secure a return offer. When I returned to school for my last year, people would ask me if I knew what I would do after graduation.

Yeah, I would say. I’m working at Google in San Francisco.

The response was almost inevitably something like: Congrats! That’s amazing! Are you excited?

To which I would usually say, Thanks! Yeah, I’m excited!

Or, if I was willing to be a bit more honest: I guess … I mean, I just did an internship there, and it wasn’t that exciting. It probably won’t be that different when I’m there full-time.

Or, in those rare moments of radical vulnerability: I’m not, no. I’m really not excited. Should I be? Is this really all I have to look forward to? Sitting at a desk, writing code for a huge corporation I don’t really care about? Is this what I’ve been working so hard for? Is this it?

No one else knew, either.

When I look back at the way I used to think during this period, I inevitably come up with the same few words, none of which are particularly flattering: unconsidered. Narcisisstic. Trapped. On bad days, I would fall into this pit of self-pitying despair about my future, thinking that it all just seems kind of hollow. On good days, I would convince myself that I was so privileged to even have this opportunity, that I was so lucky, that I should appreciate what I have, that other people would kill to be in my position.

But you can’t live your own life by chasing other people’s dreams.

In the face of this uncertainty, I turned inward in a bad way. I focused on concrete, quantifiable things, like how many vacation days I would have, how many tech conferences I could attend, how much I would earn after taxes. I estimated my expenses to figure out how much money I would be able to save every year. I found an apartment building I wanted to move in to and planned out what unnecessarily expensive furniture I would fill it with. I started shopping for dresses I would never wear, handbags I didn’t need, shoes that have no purpose other than to show how much money I was making.

All of this while avoiding the obvious question, the elephant in the room: for what? To what end? Or is this already the end? Is this everything I’ve been working for? Is it supposed to feel this empty?

Sometimes I wish I could go back in time and smack myself, make myself wake up.

Then along came the opportunity to start a tech company with people I knew in Montreal. My own involvement was supposed to be temporary, in light of the fact that I had already accepted a job offer at Google, but I kept pushing back my start date until I eventually told my recruiter that I could no longer commit to a date. This despite the fact that the startup was barely off the ground and our prospects for success were, objectively, not great. Google would always be there, I reasoned. At least, that’s what I told others. On some level, subconsciously, I think I was trying to escape a future that I knew I wasn’t ready for, a future I associated with cubicles and OKRs and the nagging feeling of some stifling, mortal dread.

And so I threw out my lifeline and plunged headfirst into the startup.

Of course, that wasn’t the answer either. We didn’t have a clue what we were doing. We were kids, playing at being entrepreneurs, flirting with risk and challenge in our coddled little microcosm, dipping our toes in the ocean and thinking that made us brave. But it was fun and challenging and new and for a while that was enough. I found a cause that I could dive into, could sink to, could devote myself to. Something that made me feel alive.

But it didn’t last. Eventually, a voice in my head started asking: Why am I doing this? I’m working this hard for what, exactly? To make the marketing technology industry slightly more efficient? Is this a problem that I’m passionate about? Honestly, is this a problem that anyone is passionate about?

I was starting to understand that my foray into tech startups had nothing to do with the product and everything to do with ego. I wanted to build a challenging system so I could know what it was like to have built such a system. I wanted the new experiences. I wanted the badge of honour. I wanted to prove myself.

It wasn’t about the product I was building. The product could have been anything, for all I cared.

Here’s the thing about startups. The escape that they represent is very possible, but there’s an enormous asterisk. Startups can be a solution to meaninglessness, futility, absurdity, alienation, the stereotypical soul-crushing drudgery of the modern office job. But. Only if you are building something you absolutely 100% care about.

Otherwise, the things that seem unfulfilling and troubling about a 9-to-5 aren’t resolved, they’re just temporarily suppressed by the fact that you’re in a more uncertain environment with lots of other things requiring your attention. You don’t resolve the existential perils of an uninspiring corporate job by going to a different company, or even by starting your own company. You can only truly resolve them by the extremely difficult and painful task of figuring out who you are and what the hell you want to do with your life. In short, you have to live an examined life.

I suspect no VC is going to tell you this when you ask them if you should quit your job to do a startup. And for a good reason: it’s not easy. It’s not something you do once and then tick off your checklist. It’s a neverending process. It’s this horrific, Kafkaesque struggle to create a self, which of course produces a self whose humanity is inseparable from that horrific struggle.

You also can’t do it solely by turning inwards. You have to understand the world as well. You have to understand the water.


What do you think is the water you swim through?

For me, part of the answer to this question is something that I’m only just starting to understand: capitalism. That all-encompassing world-order that feels so eternal, so intrinsic to society, that it’s hard to even conceptualise it. You can see it so many different ways. Maybe it’s this wonderful engine behind a breathtaking amount of innovation. Maybe it’s the creator of perverse incentives that lead to some really mindboggling inefficiencies. Maybe it’s cause of humanitarian and environmental tragedies that could have so easily been avoided. Maybe it’s a dynamic system that’s constantly being reinvented to keep up with the times. Maybe it’s a fragile tangle of internal contradictions that, through its very functioning, will inherently bring about its own downfall.

Maybe it’s all of these things, a wild, messy, ticking time-bomb that most people never think about because it’s seen as too fundamental to question.

But how do you see it? How do you know what theories to trust? How do you differentiate between what you believe by virtue of the world in which you grew up and what is–to use a David Foster Wallace expression–the capital-T truth? How can you truly understand anything in this absurd era of late capitalism where everything is mediated and thus suspect?

I’ll tell you how: by thinking for yourself. By exposing yourself to different, even contradictory, ideas and having faith in your ability to synthesise the truth. As someone who is currently trying to make up for a lack of a liberal arts education, I recommend that if you still have the chance to do so, you should seriously consider taking liberal arts classes. Take philosophy, English, economics, sociology, political science, whatever looks interesting. Supplement that by reading the writings of giants and treating them as shortcuts for your own epiphanies. My personal recommendations, in no particular order, would be: Marx, Rorty, Camus, Sartre, Hegel, Žižek, Barthes, Kierkegaard, Benjamin, Harvey, Jameson, Kafka, Rousseau. Even Ayn Rand, if you have some large grains of salt at hand. And, of course, David Foster Wallace. Read whatever you can get your hands on and make up your own mind. Don’t let learning be a substitute for thinking; you will still need to evaluate whatever you read on its own merits. Treat everything you learn as a potential but not authoritative tool for better understanding the world you live in. (I’m actually working on a post, targeted at programmers, on how to understand capitalism better; if you read it, you’ll have to walk a fine line between putting your authorial trust in me and taking my advice in the previous sentence. I think you should definitely put your trust in me, but of course, that’s me talking.)

And look. Once you have a better understanding of the world-system, once you really know what it means for you to get a job and get a mortgage and raise a family, once you see how you fit in within the larger system of capitalism, you start to see your options. You’ll see that you don’t necessarily have to stay on the path that you’re on now. That you have the tools to really examine, to really interrogate the path you’re on and ask yourself why you think it’s the right one. That you can, if you so choose, make your own path.

Which is both liberating and terrifying at the same time: on the one hand, you’re free of your chains; on the other hand, where the hell are you going to go now?


I feel like a lot of my friends in the corporate world are afflicted with different strains of the same existential malaise. Most of the time, they’re not really happy. They don’t really feel fulfilled. Their job is challenging but it feels kind of empty, somehow. They look at their boss and they think, Wow, I really don’t want that life. Something seems missing, but they’re not sure what.

But what can they do? They’ve been working there for a while now, and there’s a promotion coming around the corner, and then they’ll make more money, and maybe once they’ve saved up enough money to pay off any debts and take care of their family and keep a nice cushion they can–what? Quit? Well, maybe not immediately, but once they’ve figured out what they would rather be doing. And in the meantime the chains get tighter and tighter.

True self-actualization is difficult to prioritise in a world that values you according to how much capital you can accumulate.


I’m not writing this to try and tell you that you’re living your life incorrectly and that I know how you should be living instead. I don’t, and only you can make that call.

I just want you to remember one thing: that this is your life, right now. As you sit in front of your computer, as the world spins on its axis, as Unix time gets increasingly closer to calamity. What do you do day in, day out, is it. You are ineluctably using up the finite number of days in that fleeting flicker that will be your life.

I’m not trying to invoke despair here. I’m saying this for the sake of liberation. Because if this is it, then you have to make sure that this is what you want. Ask yourself if you’re working toward something that’s worthy of your time. Ask yourself if perhaps there’s an alternative path that’s more optimal in the ways that matter to you. Ask yourself if you’re sure, really sure, that all the hard work you’ve put in so far and will continue to put in is, in the end, worth it.

These are some of the toughest questions you can ask of yourself. And it pains me that I can’t answer them for you. I wish I could. I wish that I was writing this post with a list of rules to follow and the sure knowledge that I was right. I wish that I had been blessed with wisdom from on high, with the details of a miraculous 12-step program and the promise of ALiberated Self Or Your Money Back. I suspect that deep down, we’re all desperate to give ourselves over to something bigger than us: a cause, a job, a team, a family. Something. Anything. A lit path to guide us as we stumble through life, bewildered, disoriented, lost.

But I can’t give you that. No one can. You have to make your own path. You won’t have any guiding lights, and it will be terrifying, and you will never really know if you’re going the right way, but that’s the way you build a self. It’s the only to build a self. It’s the Sisyphean task that we’ve all been assigned. Our endless and impossible journey toward home is in fact our home.

All I can do is tell you about my own path in the hopes that you’ll find some inspiration, some nugget of wisdom, something.


So here’s what I’m doing now. In September, I’ll be starting a master’s degree in inequality at the London School of Economics and Political Science. I’m still not sure if I’ll find what I’m looking for there–and, believe me, the irony of forking over a significant portion of my life’s savings in order to study inequality is not lost on me–but I feel like it’s a step in the right direction. If you want to know why someone who used to think her exclusive interest in STEM subjects was a badge of honour would ever voluntarily enter a sociology department, take a look at my personal statement. It feels very dated now–I wrote it four months ago, which is really a lifetime ago given how much I’ve changed lately–but one paragraph in particular still holds true:

It is clear to me that the technology industry will change the world. It is uncertain whether it will change it for the better. The exact nature of the relationship between the technology industry and inequality is not a problem that can be addressed without truly understanding inequality: its historical and political context, its intersectional nature, its mechanisms of reproduction within the greater structure of capitalism. There is a startling dearth of attention being paid to these issues within the technology industry right now, and my ultimate goal, after obtaining my degree, is to change that, either from within the technology industry or without.

Or, more succinctly, as per Tracy Chou’s post:

It worries me that so many of the builders of technology today are people like me; people haven’t spent anywhere near enough time thinking about these larger questions of what it is that we are building, and what the implications are for the world.

I believe that technology has the potential for radical, unprecedented change, and that those of my generation who are working in tech are uniquely positioned to direct this change. It’s not going to be easy–it’s going to require a lot of people to wake up and decide, seemingly irrationally, that they want to eschew the rules of the socieconomic system that pervades their lives. That they want to make the effort to understand the world they live in and find something worth fighting for in the process. That they want to go against the currents that carry them.

It’s going to take a leap of faith, I’ll give you that. I can’t argue for it rationally. I don’t have a reasoned argument to convince you that it’s worth doing. But at the same time, is it any less of a leap of faith than devoting yourself to something you don’t really care about? Than spending your life within the confines of the existing system because that’s what you’re told you should do? Is that not the most absurd thing of all?

I don’t know. You tell me.