How I Quit Biglaw Part II

(Or, Reflections on Commuting)

“We have been passing the signs for sometime now: the drug stores, the clothing stores, the patent medicine and the garages and cafes: 3 mi. 2 mi. From the crest of a hill, as we get into the wagon again, we can see the smoke low and flat, seemingly unmoving in the unwinded afternoon.” — William Faulkner, As I Lay Dying

Several years ago, I posted this piece on leaving biglaw. It was a decision I agonized over, chewing over and over in my head until it eventually became too mushy not to swallow. And while in the end, it was an extremely obvious decision to make, it was not at all easy. Life is funny like that: the obviously right things to do are often the hardest.

To my never-ending surprise, I keep getting questions about that post. Biweekly, like clockwork, a stranger will reach out and ask for guidance. They’re looking for a justification, a formula, an assurance that the great scary beyond after law is not so scary after all. Their most pressing question: how have things been since?

This post is my attempt to answer that question. Truthfully, though, it’s grown increasingly difficult to be helpful here. The biggest reason is that as time goes on, I have a harder and harder time remembering what biglaw was like in the first place. I know, from countless journal entries, that for months at a time I would feel drained, uninterested and uninteresting, a blob of a bleh. I know that it was a time when I made a lot of money and spent most of it on drinks with coworkers, during which we mainly talked about how much we hated our jobs. Times were, reportedly, not great.

I can’t say, though, that I really remember most of it. Even as I narrated my day in 6-minute increments (“9:00–9:12: Assembled deposition documents”), the increments themselves formed an indivisible foggy mass generalizable as “time wasted.”

Ah, time wasted: the worst kind of time spent. Truly, when the notion of time itself ceases to have meaning, the contents of that time also cease to make any sense. It passes so swiftly and suddenly that when one January day you awaken and realize it’s a new year, you sit stunned and aghast at all the things that you wish had happened, all the things that could have been.

Conversely, when your time is constantly being spent doing and learning new things, time begins again to take shape, to form itself into important, divisible pieces. A magical, happy side effect that you notice is that it starts to pass more slowly, as life magnanimously stretches to accommodate all the new things you’re learning and experiencing daily.

Memory is an imperfect medium through which to examine life, but we have to juxtapose past and present somehow in order to make sense of it all. So whenever someone asks me to recollect, I force myself to recall. The product is a hazy picture of a twilight-zoned-out time when tiny problems seemed apocalyptic, and time lost all sense of proportionality.

Of all the things to cut through the haze, you might not expect that the commute would be one of them, but it is. The one thing I can recall with crystal clarity and almost no effort at all about my time practicing law is the commute.

Fun times on the 10

I lived on the west side, in sunny Santa Monica, and drove east every morning to my downtown office on the I-10 — a seemingly innocuous 10-mile stretch of freeway that transforms into a hellish, interminable parking lot every day, at exactly the moment the clock strikes rush hour.

On the 10, you don’t drive so much as wait. You have a lot of time to meditate. The matters of the day are held in abeyance. Emotions like frustration are so useless that they become irrelevant. You blast your favorite song, roll down the windows, and sit. Once in a while you take your foot off the brakes to careen slowly up to the bumper of the guy in front of you.

It was on the 10 that it first occurred to me how existential a commute really is. Here I was, on a road I didn’t want to be on, driving to a place I didn’t want to end up. Did it matter, then, that I’d get there later rather than sooner? Did it matter if I got there at all?

If I had been so daring, if I had been so bold, I could have cut off the girl doing her makeup in the car next to me and exited right, turning back around to Santa Monica and cruising down the PCH. I could have exited and followed my whimsical heart to wherever it goddamn wanted to take me! But I wasn’t so daring: I stayed put, plodding onwards, on that good old path of least resistance.

Nicer than the 10: David Hockney’s take on Santa Monica and the PCH

The I-10, to me, became a metaphor for life in general. Every day I daydreamed about that exit, until the point when I realized that the daydream had become more real than the reality. I felt suffocated. I couldn’t exit, because exiting was too hard: I imagined the offramp as packed as the highway, with no real end in sight. If I ever imagined a world in which I could be free of all the things that were preventing me from achieving what I wanted, my mind would begin to clog up with traffic until it parked itself immobile, like my little red Corolla, on my mind’s I-10.

But the truth was always there, looming right above the smog line, a moment of clarity shining through a little brighter every day: I had to take the exit one of these days, or else forever go somewhere I didn’t want to go.

I gave up the law and the I-10 at the same time. I moved up to San Francisco and will never forget how magnificent that first drive across the Bay Bridge was — the pink cerebral sky, the fog crashing into the glittering skyline like waves on a beach — and how jarring it was to see all the weight loss billboards replaced by all manner of tech wizardry (here was a place where you could walk your dogs on demand and “talk IPOs over IPAs!”).

Not in Kansas anymore

Everything changed. I started working at Palantir with newly minted adults, super smart people still wiping the womb of adolescence off and blinking confidently into this big beautiful world. I (for the first time) felt old and started diligently applying sunscreen. I traded an office for an open floor plan where people took calls on yoga balls and scooters. I learned how to communicate in a post-apocalyptic (read: post-email) world of Slack and Quip and people poking you to ask you if you’re going to tai chi with the CEO at 3.

My two years at Palantir took me to places I never thought I’d go (like glamorous Canberra and (actually glamorous) London) and taught me things I never thought I’d have to ask my baby brother about (like, can you explain to me what a “stack” is and actually, can you just tell me what you do all day?). When I gave notice, my lead joked that he hoped my written reflections on Palantir wouldn’t be as acidic as my reflections on big law. They are far from that. Palantir was a great and important place to learn and grow, and I’m thankful for that experience if for no other reason than that it helped me land my current job at Ironclad. But when it was time to leave to try something scary and exciting and new, I knew I had to go; it was time to get off the road.

These days, I live in Oakland and work in SOMA, so my commute usually necessitates the twin indignities of the San Francisco BART and Muni. To say that this combination is no fun is like seriously the understatement of the century. To paint a picture: while the I-10 was metaphorically existential, I am fairly convinced that the BART is actually existential. Every morning, when the train leaves West Oakland and plummets under the great Pacific Ocean, when it starts banshee-shrieking so loudly that even your $300 Bose noise-cancelling headphones can’t block the noise, and when you accidentally make eye contact with the dead unblinking eyes of the guy across from you, it’s hard not to imagine how this may perhaps be the capital-E End of you, and how terrible dying trapped, of all places, on the BART would be!

Or maybe that’s just me.

The point is, though, that I take the BART to get to work and while I’m on it, I still like to think about where I’m going. I think back to that distant downtown office building of my past, and I think honestly and searchingly about whether the place I’m going is a place I want to be headed.


Every morning, when the BART doors release my fellow hostages and me into the bowels of Embarcadero station, I feel a flicker of relief. Not just because I’m no longer trapped on the BART, but because I’m excited to go where I’m going. I’m thinking about the day ahead and all that needs to be done but how good it will feel at the end of it, when I can say I’ve learned a new thing, done a hard thing, helped a team I love working with grow a little more in the right direction.

All of this is to say: it’s nice when the worst part of your day is the commute.