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I haven't had a job for a few months, and I've been using some of that time to work with Sasha Chapin on my writing. I thought it'd be nice to reflect on that in this piece.
What did I hope to get out of writing?
I was hoping that someone would explain my life to me. I was hoping that I would feel more understood.
All of these things just happen. Sometimes you feel sad, or lonely. Sometimes you expect to feel happy but you feel nothing. Sometimes you are happy for no reason.
You get on airplanes, you sit in classes. You type some words into a computer and they make twenty million dollars for someone else, somewhat less than that for yourself. Your parents get sick. You meet a girl and together you have a baby.
There are a hundred different stories you could tell to weave these things together. Most of them would be absurd, or leave you unsatisfied. Maybe one of them would make it all make sense.
When I started working with Sasha I asked him to explain some process to me that I could mechanically repeat to generate good writing. This isn’t as silly as it sounds. I have some mechanical processes for having difficult conversations with people, for writing good software, for finding great companies to work at, even for making friends. Why not for writing?
The process I had in mind was something like: idea dump on paper. Write an outline, then flesh it out. Edit to remove the extra stuff. A mechanical process doesn’t mean that it’s easy. But it means that if you have the will, you can just turn the crank and at the end you’ll be done.
Did I get that?
No, I never learned to do any of that. My life makes no more sense than it did when I started, probably it makes less. I did write some pretty sentences.
What did I learn instead?
Try to lean into the things that make you a little uncomfortable. The frisson comes through into your writing and makes it come alive. Write at the edge between what you know and what you don’t.
You have to write things that are true for you. It’s already hard to write things that are true, so it’s nearly impossible to write things that aren’t.
Editing is for amplifying, making a piece more of itself.
If something feels really boring to write, it’s probably kinda boring to read too. But you have to be able to distinguish resistance (natural) or discomfort (good) from being bored (probably bad).
Wasn’t there something else you wanted to get from your writing time?
When I was in high school, a girl a year ahead of me wrote this book called How Opal Mehta Got Kissed, Got Wild, and Got a Life. Here’s the Wikipedia summary: “Opal Mehta centers on an academically oriented Indian-American girl who, after being told by a Harvard College admissions officer that she is not well-rounded, doggedly works to become a typical American teen: ultrasocial, shopping- and boy-driven, and carelessly hip.”
She was a first-time author and reportedly received a $500,000 advance for this book. We were all flabbergasted. How was that even possible? Were all of the chick-lit authors pulling in this kind of money?
It was a real light-bulb moment for me when our English teacher explained it to us. Chick lit is one thing, but the author had actually gone on to go to Harvard. The surface message of the text was that there’s more to life than academic success and that it’s important to have fun and be well-rounded. But the barely-veiled subtext was a how-to guide for legions of immigrant families hungry to get their kids into the Ivies. That was worth half a million dollars to the publisher, easily.
So that was the brief: write about my own immigrant success story: magnet high school, Stanford, Google, hypergrowth startup, cloak it all in some self-deprecation, and ride the trend to a nice little payday.
So what happened?
It turned out that I couldn’t really write about most of this. I wasn’t sure which parts of my life people would care to emulate. The writing felt boring or inauthentic.
I guess the core of it is that I couldn’t figure out how to write about the “success sequence” in an interesting way. I don’t know whether it was nature or nurture but I was already very smart by the time I had any conscious awareness of it, and it feels like being smart was the main thing that really mattered in my life. Be smart, take a few smart risks, figure out which one is the gravy train and ride it for as long as you can.
There are a few tricks for getting out of your own way, if you’re the kind of smart person who doesn’t ever feel like doing anything productive. Make a plan and execute it. Work on it for five minutes even if you don't feel like it. But is that really what you’re interested in reading about? I was boring myself as I tried to write about it.
It turns out that the things that felt alive and interesting to me were the moments in between. Figuring out how to talk to girls, or how to know what you really want, or what you’re supposed to do with yourself at a party at two am when you don’t know anyone or why you're even there. What it feels like to have a baby daughter.
I do want to write about the headline parts of my life at some point, I just don't know how yet. I still need to learn how to talk about my successes without sounding like I'm bragging, and about my philosophy without sounding like a fortune cookie. If you find some writing that does this well, please send it my way.
I'm probably going to get a job again.
There was a little more to the Opal Mehta story, by the way. Shortly after it came out, pretty conclusive evidence came out that large parts of it had been plagiarized from another author's books. The publisher recalled and destroyed all of the Opal books and clawed back the advances. That's probably what most people remember about that story, if they remember it at all.
There's something really poignant and also disturbing about this sequence to me. An author writes a semi-autobiographical novel, ostensibly about how getting ahead isn't the only thing in life, but the book is wildly successful because people want to hear her thoughts how to get ahead, but it then turns out that huge swathes of those thoughts were actually someone else's! Even though she had in fact lived through that life, and presumably had access to the thoughts behind it.
What does that mean?
I think it means that writing is just kind of hard. It's hard to create a narrative and some kind of meaning out of the bare facts of your life. It's hard to remember how it really felt to live through something, and hard to put those feelings into words. And it's a lot easier to do something else instead, just paste in the parts of someone else's story that you find along the way.
Probably it's inevitable that you'll do some of that. I’ve heard it said that there are only seven different stories in the world and everything else is just remixing. But you have to try, at least, to change some of the words as you go, to make them yours.
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