If you’ve considered quitting work forever, my story may interest you
I did it, so I can tell you about it
I looked round and was like, “well, red or black, what am I going to do?” I didn’t know. One would be the right answer – I just had to pick that.
In July 2020, I called one of the named partners at my boutique law firm in DC and asked if he had a few minutes to talk. It was a conversation I had been rehearsing for a while, but for all my practice, I found myself in a state of sheer fight-or-flight. With stakes this high, I wondered, was I really about to go all in?
Employment at this partner’s firm had been a dream job for a hungry young attorney. I had spent something like half of my time there working on cases before the Supreme Court, for clients that included the President. Late nights working on filings were often followed by mornings reading about my work in the New York Times. I was still very junior, but I was collecting credentials that would set me up for a shot at the choicest and most competitive gigs that law had to offer. And I was working with amazing lawyers: measurably at the top of their field, yes, but also genuinely good people, no kind of Grisham nightmare.
Now I was on the phone with maybe the kindest of them, pacing the rooftop of my expensive apartment complex through the velvety Virginian humidity. I stalled with small talk—not the best tactic for dealing with a man who could charge eye-watering sums for every six minutes of his time. I said a quick prayer1 and, duly fortified, I pushed in my chips and got to the point: I was calling to quit.
To my relief, he could not have been nicer about it. He told me I was welcome back any time. And he even surprised me by offering a flexible part-time arrangement, a luxury virtually unheard of in the legal world. I thanked him very sincerely.
But I wasn’t planning on coming back. Not to that job. Not to the law. Not, in fact, to employment at all.
This fall makes five years since, from my resume’s perspective, I died suddenly and unexpectedly of mysterious causes. It must have been hard for her. Up to that point, she and I had enjoyed an ardent romance. We had grown up with each other, fallen in love, and built a life together. I invested my time and energy into her, and every major decision I made was at least partially, and sometimes exclusively, based on the bullet points I could add to her growing record of my professional experiences.
In return for my nurturing, that little page rewarded me handsomely. I grew up comfortable and middle class, but with that document in my hand I was permitted into a new social echelon, one full of people who were almost always rich, often powerful, and occasionally even famous. That resume was easily the most valuable thing I had to my name; a real-life golden ticket.
You don’t get a resume like that by accident. You get it with hard work, shrewd strategy, and a healthy dose of good fortune. The key is to leverage each of your successes into shinier opportunities. For me, a strong performance in college led to acceptance at an elite law school. Then I got a position on the law review and secured offers from strong firms. That opened the door to one coveted clerkship, then another, and then the aforementioned job at the Supreme Court litigation firm in DC. Each was a key to a door to a room holding a key to a door to a bigger room containing a bigger key. And thus the rich get richer, and the prestigious get prestigier.
Someone wiser than me might tell you that this perpetual hustle for gold stars is ultimately meaningless. But whether or not that is true, I can at least tell you this: it’s pretty fun. It’s almost like a sport. You can really get swept up in playing for wins. And for plenty of people, it’s enough just to put the ball in the hoop, whether the points mean anything or not.
But it wasn’t just fun. It also made a lot of sense. It made sense on paper—my resume purred like the engine of a muscle car by the end. It made sense to other people—friends, mentors, and prospective employers all extended their approval by default. And it made sense to me. When I thought about how I was spending my life, I knew that I, um….
Deep down, I felt assured that, uh….
Well, anyway, it was supposed to make sense. The truth is, I could never really tell whether it did or not. First of all, for all my accumulated prestige, I wasn’t very happy. As great as my senior partners were, high-profile work meant a high-pressure environment—and it left me feeling constantly anxious. And despite the social consensus that what I was doing was a Big Deal, it rarely felt like I was personally making much of a difference. After all, there were plenty of super-talented attorneys out there eager for my spot on the roster. If I left it all behind, I knew nobody would miss a beat.
Now, I think it’s pretty normal to have—let’s call it “mixed feelings”—about one’s job. And as far as I can tell, no one loves to complain more about their career than lawyers. But I think it’s usually just a lot of sound and fury. Most people stick around, because for all the downsides, there are enormous offsetting benefits.2 So you take the good with the bad and just keep truckin’. I very well might have kept doing that myself.
But what finally got me on the phone with my boss on that beautiful summer day was that I had had another big opportunity come up. A position where I thought that I could make a huge impact. Where I might even be irreplaceable. The only thing was, there would be no keys to any doors where I was going. No bullet points to add under “Professional Experience.” And I would be working for someone far junior to me. Only two months old, to be precise.
So it was that in July 2020, I decided to gamble everything on a persistent impression that there was something better I could be doing with my life. I pawned my beloved resume—along with its considerable expected lifetime value—and I put it all on red and spun the wheel.
Since the Fall of 2020, I have been a full-time parent. My daughter, Charlotte, is now four years old, and I have a two-year-old son named Thomas. They just started banging on the door as I write this. You’ll get your snack, just give me a minute!!
If you’re bracing for a trite conclusion where I tell you—loudly enough for myself to hear it—that everything came up red, you can relax: that isn’t where I’m headed. It’s so much more complicated than that. It’s like you’re betting on thousands of roulette wheels with hundreds of colors. And they’re all spinning and stopping at random, dizzying and chaotic. And you rarely lose or win big—you just endlessly tally up little credits and debits, on a ledger that no one will let you see. And when you try to cash your chips, you’re given currencies you’ve never seen before, in denominations you don’t understand. And what, exactly, would you even spend it on?
It was like that before I quit my job, and it’s like that now. The only difference is that these days, my money is on a different color. Which, in fairness, changes a lot. But it’s all still pretty unclear. And at some point all you can do is just live your life and hope for the best. You try to exercise. You call your friends. You hold your kids’ hands when you cross the street. And maybe you start a Substack—because you might figure something out if you lay your thoughts out in a nice little row.
I suspect I’m not alone in feeling like I’m on a colossal roulette wheel hurtling through the universe. Maybe you have felt that too. And maybe you’ve even considered quitting your job, or your career, or your purpose—or even your identity—and putting your chips on a brand-new color.
I appreciate that for most people, going through with that may be anything from inadvisable to impossible. Certainly we can’t (and shouldn’t) all be like Ashley Revell. In 2004, Revell sold everything he owned for one all-in bet at the roulette table. (He won.) A crew filmed the stunt, and when I watch that clip, my stomach churns—even though I know it happened 20 years ago and that he came out ahead. I mean, can you imagine actually doing that? I’m convinced he’s completely insane—which is a little ironic, considering he bet much less than the going salary for a first-year associate3 the year I graduated from law school. Pots and kettles, as they say.
But while I wouldn’t exactly call him a role model, I’m definitely curious to know more about him. How does a guy like that think? Why did he do it? And how did he feel about it before and after? I guess what I’m saying is, if he had a blog, I’d read it.
Now, I’m no Ashley Revell—nobody’s going to be making a reality show about me anytime soon. But I think there are things worth considering in my little version of his big gamble. Or at the very least, I have some ideas and experiences that I’d like to lay out in a little row and try to make sense of.
And if you happen to find any of this interesting or useful, I’d love to send you what I write through this neat little platform.4 And equally, I’d love to hear your stories and engage with your thoughts. I’d really like to make a personal connection here with anyone interested in so connecting. So please say hi and chime in with comments!
In the next few installments, I plan to delve a little deeper on how I got here, where exactly “here” is, and what the weather is like there. But for now, my sincere thanks for reading. We may be on an enormous roulette wheel revolving around the sun, but it’s nice to know we’re here together.
“Help me not be such a chicken, amen.”
One of these benefits rhymes with “baking tons of bunny.”
Not every associate, of course. Just the ones whose resumes are fancy enough to get them into the tier of firms that the legal community unironically refers to as “BigLaw.” I’m not making that up.
If you want to follow along, just hit that little subscribe button above and future essays will be routed to your email inbox. I follow a few writers here and I’ve really enjoyed the experience; it makes a palate-cleansing contrast to all the short-form social media that is trying to slowly liquify all of our brain cells.
I went from being a top achieving student in college directly into motherhood, having held no job more prestigious than waiting tables at a Pizza Hut. I speak three languages fluently and my IQ is estimated to be quite high, though the actual number is meaningless to me. I remember my college advisor’s crestfallen face as I told her that I had no plans to go to graduate school and her stunned « but you are too smart to just stay home and have babies! » I was too polite to ask whether only marginally intelligent people should raise children? Ultimately, I knew very early on that I did not have the temperament to climb any kind of corporate ladder, though I had the brains for it. I lacked the ability to be cutthroat, to argue a position which was morally compromising to me, or to drop a crying baby off at a daycare center knowing that all he wanted was to be with me. I was home for 20 years, taking part time employment that interested me, quitting when it became a burden. When the kids were grown, I taught in public schools for 7 years, and then quit again when I became a grandmother so that I could be available for my grandkids at any time during the year. I once again found part-time work that feeds my soul, but does very little for my bank account… I will never grace the cover of Vogue, Ms Magazine, Glamour, or Good Housekeeping, my name will never be remembered by anyone beyond my immediate family, and that is more than OK with me.
I think it takes a great deal of courage to swim against the current that places more importance on money, prestige, and power than on sacrifice, love, and peace.
I needed this deeply. I am an anaesthetist in the UK, it’s been my adult’s life work to get to where I am but the itch to slow down, take a U-turn and focus on my family is getting stronger and stronger. I’m excited to follow along!