Posts Tagged ‘Sullivan & Cromwell’

24DB-PEARSON-master675The People’s Therapist just got profiled in The Financial Times (with a couple other therapists.)

To read the full article, click here.  (Yes, I know, it’s behind a pay wall…but go ahead and subscribe, it’s worth it to read The Financial Times!)  The headline of the piece is “Care from lawyers turned therapists”  and the sub-headline is “Behind a polished exterior can be anxiety, say those who listen to the angst of legal professionals.”

Many thanks to the lovely Emma Jacobs, and Annabel Cook, in London, and the estimable Pascal Perich, in New York City, who took that smashing photo of me with my senior colleague, Simon Dachshund.

Alas, I’ve had to take down my delightful screenshot of the article…the charming Barbara Volkar of the FT’s syndication sales department emailed me, and apparently it violates copyright to reproduce it.  Posting a legally sanctioned reproduction of the article would cost literally thousands of dollars.  And that’s why this post appears a bit truncated.

Sigh…damned lawyers.

Oh poop – here’s a teeny tiny screenshot, just so you can see what it looks like.  It’s hardly even legible.  Let ’em sue me!  They’ll have to tear this moment of glory (a profile in the FT!) from my cold, dead online fingers.

Screen Shot 2016-02-05 at 7.09.52 AM

…and here’s what it looked like in print (again, really teeny, to fend off the copyright police…)




Please check out The People’s Therapist’s legendary best-seller about the sad state of the legal profession: Way Worse Than Being a Dentist: The Lawyer’s Quest for Meaning



And now there’s a new Sequel: Still Way Worse Than Being a Dentist: (The Sequel)


My first book is an unusual (and useful) introduction to the concepts underlying psychotherapy:Life is a Brief Opportunity for Joy





I’ve also written a comic novel about a psychotherapist who falls

in love with a blue alien from outer space. I guarantee pure reading pleasure: Bad Therapist: A Romance


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enhanced-buzz-13963-1374365048-27This one really happened – and it happened to yours truly (as opposed to the usual disguised anecdote loosely based on a factually altered tale from one or more carefully anonymized clients.)

One night, (or morning, or sometime between night and morning, since we were working an all-nighter) shortly after my arrival at Sullivan & Cromwell, a fairly senior partner at the firm took a moment to lean back in his desk chair and impart the following to little junior associate moi:

“You hang on by your fingertips, kid.” He raised his hands and bent his fingers, as if to demonstrate. “Till it starts to seem normal. Just dangle there and wonder how long you can last – or what happens if you let go.”

Apparently that was all he had to relate on the topic, as he snapped back to focus on reviewing a purchase agreement. I recall wondering if he, after (presumably) a zillion sleepless nights just like this one, felt as bleary-eyed, sweaty and slightly sick to his stomach as I did. I’ll never know the answer to that question. Maybe partners don’t need sleep – maybe that’s their secret.

I also recall wondering if this guy was exaggerating with that whole “dangling by your fingers” routine to impress me – or if he was a little bonkers. In retrospect I think he simply meant it.

Working in biglaw is a straight-forward exercise: You’re paid a lot of money to sit at a desk and work long hours. Someone provides the work, and you do it. That typically means arriving at around 10 am, working on something complicated, with a short break (maybe) for lunch, and then (maybe) for dinner, until about 10 or 11 pm, every day. You also sometimes work all night and sometimes weekends and sometimes all night on weekends.

To review: You arrive in the morning, you sit at a desk, you work until late night. Then you do it again the next day.

An additional factor is that the work is hard. Not rocket science hard, but not stuffing cotton into little bottles either. Initially, there’s a lot of “running changes,” “creating a chart,” “putting it into a table,” “checking cites,” and that sort of thing. Even that stuff can freak you out when nothing you give them is ever what they want and they keep handing you more. “Firm culture” can take getting used to, as well. A junior associate client of mine closed her office door one night, as was her habit, so she could break down and have a good cry, only to realize (through the paper thin walls) that someone else was also weeping, in the office next door. There’s nothing like feeling part of a team.


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King-Kandy-1306451680I recently attended a conference at a law school – a pretty good law school – and they invited me to appear on a panel and paid for my transportation and even offered a hotel (if I needed one, which it turns out I didn’t, but still…nice.)

I am a psychotherapist, which means, under ordinary circumstances, I never go anywhere, let alone on anything resembling a “business trip.” Instead, I sit in my office and listen to someone else talk. Whether that someone else is sitting on a chair in front of me, or in a chair in Australia via Skype on my computer screen, there I sit, listening, in my office, in the morning and in the afternoon, and in the evening, too. If I didn’t work out at the gym four times per week, I’d probably go all soft and pudgy and endomorphic and begin to assume (like many of my peers, who shall go nameless) the contours of the chair I sit in. Which is to say I’d look like a pear. It turns out there are two kinds of therapists – those who make the effort to step outside their offices and get some exercise, and those who look like pears.

But I digress. And regress. Which is okay in psychotherapy – free association and all – but I was talking about this conference at the pretty good law school.

The conference’s first discussion panel – which I wasn’t invited to be on, for reasons which will become obvious – was titled “An In-Depth Look at Firm Life.” (Well, actually, this was a conference for Asian Pacific American law students, so it was titled “Peering Through the Glass Ceiling: An In-Depth Look at Firm Life for Minorities” but being Asian Pacific American seemed a minor consideration compared to dealing with biglaw, even at a conference for Asian Pacific American law students.)

I wasn’t on that panel – I was on the one about Mental Health and lawyers (once again, Asian Pacific American mental health and lawyers, but whatever – I’m married to a Chinese-American and I love my Asian Pacific American fans and their mental health and their lawyers.)

What struck me, at least in retrospect, about the classy panel – the one I wasn’t on – was who was on it. Just for reference, my panel – the one about going nuts – was staffed with a research psychologist, two psychiatrists, a psychotherapist (me) and a guy who runs a recovery/support center for lawyers. Two or three of us were lawyers, but mostly incidentally. There was also a third, afternoon panel at the conference about Asian Pacific Americans being a “model minority.” That afternoon panel was populated with academics (no lawyers at all, so far as I could tell) and so things predictably took a highfalutin, theoretical turn – more like college than law school.

Only the panel purportedly concerning the actual reality of law firm life was stocked with 100% lawyers. Clearly, there was to be no fooling around with non-lawyer riffraff for them. The breakdown among the lawyers on this panel was interesting, too (for reasons I’ll disclose shortly.) First, all five of them were lawyers at biglaw firms, with the exception of one former biglaw lawyer who is now a corporate counsel at a humongous, famous, fancy-pants software company. Two panelists were partners at humongous, fancy-pants biglaw firms. There was also a senior associate at another biglaw firm, but she’d clerked for two federal judges and looked like she meant business; she was clearly not planning to be a mere senior associate for much longer – at least, if she had any say in the matter. And there was a lone junior associate, who looked slightly terrified, but she was at a top biglaw firm. Slightly terrified or not, she looked like she was dead set on going places, too.

So? Nothing wrong with that panel, right? Here were a bunch of success stories – Asian Pacific American lawyers in top jobs, reaping the success that comes with hard work. And they said all the stuff you’d expect them to say – advice on getting ahead and racing to the top, stuff like seeking out mentors, checking in to make sure you’re delivering what they want and…well, a lot of stuff about working hard and achieving success like they did. That’s hard to argue with.

But here’s the issue with that panel. The thing that stuck in my craw. The problem (if there was one) – which only dawned me in retrospect: They were only telling us the good news.


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munchkins3-lgReaders of my blog express surprise when they discover that all my clients aren’t lawyers – indeed, a small but sizable percentage of my clientele consists of ordinary civilians, non-combatants, plain folk who have nothing whatsoever to do with law. But the people surprised by this situation are mostly biglaw lawyers – and what really surprises them is not that I work with non-lawyers, but that I work with non-lawyers employed in biglaw – secretaries, law librarians, human resources folks, paralegals and so on. In other words, what surprises them is that I work with those people, those other people.

You know…the Little People.

Before you pile, on accusing me of snobbery, let me point out that I’m the one who’s treating these card-carrying members of the hoi polloi, and often for sliding fees. Let’s also admit that a rigid social hierarchy exists at law firms – in fact, a very rigid social hierarchy, something akin to the caste system under the Raj.

At Shearman & Sterling, where I summered one year, and at Sullivan & Cromwell, where I worked after blowing off Shearman & Sterling because it wasn’t (sniff sniff) quite up to snuff (yes, that’s a social hierarchy, too), I distinctly remember encountering what were referred to as “attorney dining rooms.” These were private dining rooms – partners and associates only. The very existence of these exclusive (as in, everyone except lawyers was excluded) dining chambers sent something of a…uh…message. The lawyers at the firm didn’t require separate water fountains, but message-wise, the effect was along the same lines.

Granted, back in the days when I worked in biglaw, partners arrived at the office in horse-drawn broughams and sported top hats and tails. I fondly remember Old Caesar, the darkie who toiled cheerfully in the S&C stables, and Irish Polly, the scullery drab – and who could forget wee Pip, the cripple foundling lad who maintained the fire in my office, always stoking it high with coal on a cold winter’s morning to earn his ha’penny and an affectionate pat on his cinder-begrimed cap as he hobbled off on his homemade crutches. Those were merry times.

But I shouldn’t permit misty nostalgia for another era to distract from my serious message: No kidding, there really were dining rooms reserved for the lawyers (and for all I know, there still are) and the message around them was clear: No Little People allowed.


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I had the pleasure of sitting down for an interview last week with Spencer Mazyck, of Bloomberg Law, at their studio in Midtown.  I’m happy to report Spencer is the nicest guy in the world and this was the most fun I’ve ever had.

The discussion was far-ranging.  I’m used to talking about the state of the legal profession, but Spencer asked me about my life, my loves – and just about everything else.

Here’s the interview:

Please check out The People’s Therapist’s legendary best-seller about the sad state of the legal profession: Way Worse Than Being a Dentist: The Lawyer’s Quest for Meaning

My first book is an unusual (and useful) introduction to the concepts underlying psychotherapy: Life is a Brief Opportunity for Joy

My new book is a comic novel about a psychotherapist who falls in love with a blue alien from outer space. I guarantee pure reading pleasure: Bad Therapist: A Romance

(In addition to Amazon.com, my books are also available on bn.com and the Apple iBookstore.)

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daffyIf you’re a lawyer appearing at my doorstep, and you work in biglaw, there’s a good chance you’re seeking a way out. You don’t know what you want to do next, but the status quo is insupportable. That’s the standard set-up.

If you’re a lawyer appearing at my doorstep and you work in biglaw, we’ll likely talk about the challenges ahead. Trapped in the bathysphere of biglaw, it’s hard to see out let alone get out. You’ve heard rumors about human beings who enjoy their jobs. In your experience, big firm attorneys loathe their chosen profession the way other people breathe air.

If you’re a lawyer appearing at my doorstep, and you work in biglaw, we’ll probably talk about a sideways shuffle I call the “crab-walk.” You can’t transfer from a big law firm directly to a tolerable work environment in one leap – the chasm between biglaw and anywhere anyone would want to be is too great. Crab-walking is the next best thing, based on the indisputable principle that a tiny step in the direction of somewhere else amounts to an improvement. Take a reduced schedule at your current firm (if such a thing exists in theory or practice.)  Give a “kinder, gentler” mid-law shop a shake. Go in-house at a bank. Dial for dollars as a headhunter. Switch to consulting and live in a hotel in Indianapolis all week writing reports recommending the firing of middle managers. Get a sales and support position at WestLaw teaching summers to concoct search terms. Small crab-walk-y steps remove you one centimeter at a time from where you are right now. That, by definition, is good.

If you’re a lawyer appearing at my doorstep and you work in biglaw, you probably want out, and have since your first taste of the Kool-Aid. You need to hear you’re not crazy or alone, and that there are others who long for a job without constant anxiety attacks, where Sunday nights aren’t a horror show, where a partner won’t tell you without a trace of irony to “go ahead and take the weekend off,” where it isn’t considered an easy night to get home at 11 pm.

These generalities hold true for about 96% of the lawyers appearing at my doorstep who work in biglaw. They do not, however, apply to everyone.

I don’t want to exaggerate the phenomenon, but there are folks who actually “fit in” in biglaw. They actually like it there. These are the “odd ducks,” and from time to time some of them also appear at my door.


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Someone posted the following astonishing comment in response to one of my columns a few months back:

“I’ve never worked in a biglaw firm, but what happens if an associate just says no, I am busy this weekend, or no, I am on vacation that week, so I won’t be able to do that project. Do you immediately get fired? If that’s true, then you must not really have much to offer to the firm in the first place. In a situation where the associate had some real value to offer to the firm, I do not see why the firm would fire someone for that. Am I hopelessly naive?”

Go ahead – laugh. Get it out of your system. You know perfectly well your guffaws wear thin, right about when that twinge of poignancy creeps in. You, too, once mulled the notion of rising above the fray – going all Bartleby the Scrivener and muttering “I’d prefer not to” when asked – oops, I mean told – to work and work and work and work and work.

This “pure fool” of a comment-writer has raised a troubling issue (and that, by the way, was a combined Parsifal and Magic Mountain reference…this will be one of those classy columns larded with literary allusions.) Cower behind your carapace of cynicism, but sooner or later you’ll admit you weren’t always like this. You weren’t always a broken, cynical wreck who jumps at the slightest command. You used to be Bartleby The Scrivener, too. You imagined you were valued as a unique, complex individual. You imagined you held some sway over your own existence – some “preferences.”

I know it’s no fun trying to remember the stuff you read in college, but please attempt to keep up. Even if you weren’t an undergraduate English major, you might recall that the narrator of “Bartleby the Scrivener” was called “The Lawyer.” That’s right: “The Lawyer.” The whole thing takes place in a law firm! And remember what a scrivener did? It was the worst job in the firm – probably one of the worst jobs of all time. You sat at a desk copying legal documents – handwriting them – for hours. Reminiscent of doc review, or due diligence, or “running changes” – scrivening was mindless and, if you kept at it for too long, guaranteed to drive you bat-shit. You – and everyone else – would obviously “prefer not to.”

And yet, somehow or other, our narrator – “The Lawyer” (i.e., a partner at the firm) – is astonished when Bartleby, after being asked politely to scriven something, even more politely states in return: “I’d prefer not to.” The Lawyer explains his astonishment at Bartleby’s resistance by pointing out how he, as a partner – even in 1853! – possesses a “natural expectancy of instant compliance.”

You know all about that, right? The “natural expectancy of instant compliance”? Sure you do.


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When I launched The People’s Therapist, my intent was to get stuff off my chest – process a smidgen of psychic trauma. I’d write a column or two, exorcise the odd demon, piss off Sullivan & Cromwell and call it a day.

It never occurred to me I’d be deluged with lawyers as clients.

It never, ever occurred to me I’d be deluged with partners as clients.

It never so much as crossed my mind they’d be so unhappy.

It turns out being a partner can be…not all that. For many of my clients, the job boils down to evil middle management.

Permit me to explain.

Biglaw associates resemble the low-level evil henchman in James Bond movies – those omnipresent guys in jumpsuits who all look the same and do what they’re told. They drive around evil headquarters in little golf carts, manipulate dials in the control room, shoot at James Bond (always missing) – then get shot themselves. Presumably – like biglaw associates – they’re mostly in it for the money, rather than a genuine penchant for evil.

I felt like an impostor at S&C – only pretending to be a genuine low-level evil henchman. I was more like James Bond after he bonks the real low-level evil henchman on the head, then reemerges strolling through evil headquarters sporting that guy’s jumpsuit.

I was an impostor – trying to look like I drank the Kool-Aid, going through the motions. I wasn’t even a clandestine agent, battling evil, like 007. The plan to blow up the moon wasn’t my problem. I just wanted a way out of that crummy job – one not involving a fatal dunk in the evil piranha tank. Somewhere in that evil-lair-secreted-in-a-hollowed-out-volcano there had to be a door marked exit.

Most of the partners I work with are looking for the same thing. The difference is, as a partner, you’re not an impostor pretending to be a low-level evil henchman – you’re an impostor pretending to be evil middle management.

“Preposterous!” you sputter, outraged. “Partners never condescend to be middle anything! They crouch, smugly, at the pinnacle of the evil pyramid! With one wiggle of their evil little finger…they manipulate human life!”

It can look that way from the bottom rung, whence a partner appears as far removed from a low-level evil henchman as a junior associate from a positive bank balance.

From the vantage of the pyramid’s sub-sub-basement, all partners appear interchangeable – the unifying feature being their utter dissimilarity from anyone like you. A partner’s one of them – evil incarnate, possessing his own evil headquarters – his own creepy evil white cat (for stroking purposes) – and his own weird evil European accent (with which to mutter, “Come now, Mr. Bond…”) A partner doesn’t have to drink the Kool-Aid – an iv bag of the stuff dangles by his bedside.

If only that were true. After getting all up-close and personal with a bevy of partners, I’ve caught wind of a terrifying reality: All partners are not the same. Most are nothing more than evil middle managers.


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A visit to my office has evolved into something akin to the road to Lourdes. Pilgrims arrive red-eyed and defeated, faces etched with misery, searching for a way out of a trap.

The standard story is some variant of the following: You are either out of work or loathe your work. You have $180k in loans. You have either no income or an impermanent income paid to you in exchange for any joy life might offer. You see no hope.

Let me spell out the critical element here: You are one hundred and eighty thousand dollars in debt.

Just to fully drive the point home: that’s bankruptcy-proof debt.

You’ve yelled at your parents, but it’s not really their fault. You’ve wept and wailed and gotten drunk and stoned and consumed a script of Xanax. You’ve tried sleeping and pretending you don’t have to wake up.

Then comes the pilgrimage. Perhaps I can heal with a laying on of hands.

Okay, here’s the feedback I’ll receive for what I’ve written so far:

You’re exaggerating. You’re bringing me down. Law isn’t so bad. I love law.

Yeah, well good for you. I’m not exaggerating.

It’s their own damn fault. No one made them go to law school.

Yes. They. Did. Stop kidding yourself – the entire system is engineered to lead smart, conscientious kids exactly where it leads them. And get off it already with the no sympathy/blame the victim routine.

How bad are things? How many times can I pose that (at this point rhetorical) question?

Young lawyers look me in the eye and ask, how am I supposed to carry on with my life? What they mean is – how is one supposed to live a life worth living – a life that satisfies one as a human being – trapped in the hell of law and law school loans?

Sometime, I ask them what they would be doing with their lives, if they didn’t have loans. Here are some of their answers:

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Atul Gawande is a medical superstar – a surgeon at Harvard who’s also a New Yorker magazine writer, and the author of several books. His latest push is for doctors to use checklists to prevent common mistakes during surgery. A scary percentage of the time, it turns out, things grow overwhelmingly complicated in an operating room and a nurse or an anesthesiologist, or a resident (or whoever) gets distracted and forgets to do something basic – like confirm there’s extra blood in the fridge, or plug that little hose into the machine that keeps you breathing.

It happens. People forget things. Best to err on the safe side, and use a checklist.

The idea comes from aircraft pilots. It turns out they use checklists for absolutely everything – a pilot literally can’t step into a plane without a checklist. Pre-take-off, take-off, pre-landing, landing, and every possible contingency that might happen in-between is assigned a checklist. That’s because when you’re a pilot and you forget something, well…it can be a problem. Kind of like a surgeon.

Or a lawyer.

This isn’t exactly a new idea. The first thing I received at Sullivan & Cromwell when I arrived there was a checklist – and my first task was to start ticking off items. That’s how you handle a corporate deal closing – otherwise you’d never keep track of all the officer’s certificates and securities certificates and side agreements and various other bits of paper required for that six hundred million dollar acquisition of the rubber plant in Brazil (or whatever.) If you’re the junior associate and you forget something that needs to be on a closing table, well… it can be a problem.

But there’s another surprising finding in Gawande’s new book, “The Checklist Manifesto.” One required item on pilots’ checklists simply instructs them to stop and introduce themselves. During that process, they explain their responsibilities to one another, including any pertinent details regarding that specific flight. It sounds like this:


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I was chased down the sidewalk by a breathless woman.

“You’re the guy who made me vegetarian!” she announced between gasps.

I didn’t know what she was talking about.

It turned out she’d worked as a paralegal, years before, at Sullivan & Cromwell.  I didn’t feel guilty about not remembering her.  We only toiled together once – a grueling all-nighter preparing for an M&A closing.

We ordered take-out burgers that night, and I opted for a veggie burger.  She asked why I wasn’t eating meat.  At first I played it down – mumbled something like “don’t feel like it.”  Carnivores can grow testy if you fail to consume meat in their presence – they take it as a personal affront.  I’ve learned to tread lightly.

But she persisted, with genuine curiosity, so I told her the truth:

“You don’t have to go there – no one’s asking you too,” I said.  “But if you do go there, you’ll stop eating meat.”

That was it.

Ever since that night, she told me on the sidewalk, she’d been vegetarian.

All it took was going there – well, having someone tell you there was a “there ” to go to, then making the trip.

No, I’m not going to spell out where “there” is – you know perfectly well and I’m not here to preach.  I’m here to talk about consciousness-raising, not vegetarianism.  Specifically, consciousness-raising around alcohol.

You know, alcohol – those lambent elixirs stored in gleaming bottles; the all-American can of beer that pops open to seal friendship and inaugurate cherished memories; the cork shooting from a pricey bottle of champagne to harken in merriment and delight.

Yeah.  Ethanol.  Ethyl alcohol.  Let’s tackle the popular mythology surrounding this stuff. We can start with what I call the Maya Angelou rule.


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I received an offer recently that I couldn’t refuse – an invitation from “legal search consultants.”


They were having a convention and asked if I wanted to drop by, and, you know, say hi.

Vague images flitted through my mind – guys in suits dancing in a conga line wearing hats with silly horns.

I don’t often get invited to shindigs. I’m a therapist. Mostly, I visit my office, my dog and whoever’s sitting in the other chair. Or I sit at my desk and write columns. Ask me to a party? Hell yeah, I’m down. I’m all over it like a tall dog in a cheap suit. You looking to turn it out? Count me in.

I never say no to headhunters, conga lines and hats with silly horns.

So I went. And it was fun.

Here’s the newsflash about headhunters – they’re good peeps.

At very least, they’re more fun than lawyers. In fact, many of them were lawyers, but had to get out because they were too fun.

They can also teach you stuff you need to know – not just pointers on beer pong and naked Twister.

Behold three key lessons acquired whilst getting down with my bad self in the company of legal search consultant party animals…


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It’s mid-September. I’m talking with a client , a 3L at a top-tier school.

“Here’s how it works,” she explains. “There’s the have’s and the have-nots. Either you have a job offer, or you don’t. If you don’t, it sucks. You feel like an illegal alien.”

Unfortunately, she’s a have-not. Yes, she’s working to correct that situation – trawling small firms in her hometown, attempting to milk connections. But “have-not” might as well be printed on her forehead. Around her peers, she says, it’s the body language that betrays have-not status. As a have-not, you don’t talk much, keep your eyes down, and behave generally like the undocumented guy lugging tubs of dirty dishes back to the kitchen. The aroma of failure – let’s say it, loser-hood – clings to the fabric of your clothes.

Some thoughtful charity – maybe it was Oxfam – threw a fund raiser dinner some years back, with the worthy goal of educating socialites about world hunger. The guests were divided the way the world is divided. Behind velvet-ropes, at a small central table, a handful of diners savored a gourmet meal. Across the ropes, a larger group picked at bowls of plain rice. Further out, beyond non-velvet barriers, a sizable fringe of outsiders observed the others and listened to their own empty stomachs rumble.

It was just like law school – at least at the good law schools. At the second and third tier joints, it seems like everyone’s a have-not. If the personal experience of poverty derives from comparing oneself to one’s peers, then maybe everyone feels less impoverished at the lower-tier schools, where no one gets a job, everyone’s in massive, crippling debt – and the whole class occupies the same boat.


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I tell the truth in these columns – at least, to the degree I find convenient or advisable. There is such a thing as a surfeit of veracity. My clients are lawyers, so god help me if I record something a little too candid with regard to their doings. Just talking about myself raises issues.

I haven’t worked at Sullivan & Cromwell since 1999. A statute of limitations must cover misdeeds perpetrated in that dim, dusky epoch. But I’m not betting the farm on it.

I will, therefore, tread with caution as I recount events that occurred in the life of a close friend who practiced at Sullivan & Cromwell during that time, someone whose tenure at this august institution coincided precisely with my own. A dear, personal friend.

It is possible this person occasionally misrepresented his billable hours.

I know. You’re sickened. Awash with a visceral revulsion.

Could I be saying what you think I’m saying!? Not that. It’s unthinkable.

I shall not shy away from the painful truth. I’ll say it: my close personal friend cheated on his hours. At least I think he did. I only think, because he was so sloppy in keeping track of his hours it wasn’t clear what they actually were.


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To judge by the accoutrements of “the profession,” lawyers, as a group, maintain an inflated self-image. They think they’re all that. It’s easy to get sucked into this mind-set – especially fresh out of law school. Perhaps, when you’re not “thinking like a lawyer,” you’ve spent a few minutes admiring the little “Esq.” printed after your name on an envelope from school or a law firm – or some company in Parsippany trying to sell you a genuine mahogany and brass pen holder featuring a statue of “blind justice” for only $59.99 with free shipping.

Back when I passed the bar, I was offered the option by New York State to purchase a printed document – “suitable for hanging” – to memorialize the event. I figured what the heck and blew the twenty-five bucks. The “parchment” arrived in a cardboard tube, and it was huge – like a royal proclamation. I felt ridiculous, rolled it back up and stuck it in a closet, where it remains.

It’s hard to imagine accountants (who often make more than lawyers), or bankers (who always make more than lawyers) laying on the pretension to quite the degree lawyers take for granted.

My father was a physician, and in his early days, he fell for the professional ostentation thing, too. After he graduated from medical school, he ordered “MD” plates for his car. Sure enough, the next time he took the rusty old Mercury Marquis in for a repair, the mechanics charged him double. That was enough – he sent back the plates.

At least doctors are highly regarded in our society. My father was a psychiatrist, not a brain surgeon, but there was grudging respect for the fact of his MD. If you were in a car accident or had a heart attack on a plane, theoretically my dad could save your life. That meant something.

With lawyers, self-esteem outpaces public acclaim. That’s because, for the most part, non-lawyers view lawyers as worthless parasites – or at least, as existing on the more worthless, parasitical end of the esteem spectrum.

I’ll never forget the time I asked a Wall Street-er what he actually thought about lawyers.

I’d received the nudge from Sullivan & Cromwell, which meant I had six months to find another job. A head-hunter somehow or other set me up with an interview to be a bond trader at JP Morgan.

I considered the whole idea misguided – I was a lawyer from one of the top firms in the world, and far above working as a trader. I thought of bond traders as slick goombahs with Staten Island accents shouting into a phone all day. I was an attorney, with a degree from Hahvard. I showed up at Morgan as a courtesy to the headhunter. I radiated disdain.


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Some big law firms are like the mob. They do ugly things, but prefer to avoid “ugliness.” The partners, like the capos of major crime families, have delicate constitutions.

Ugliness could result from ill-considered communication. For that reason, a capo – or a partner – isn’t going to tell you what he really thinks. That would be indelicate. It could lead to misunderstandings.

You, in turn, shouldn’t tell a partner what you really think. That could lead to sleeping with the fishes.

My client recently received a lesson in partner communication.

The firm was dead slow, and she was dedicating her time to a big pro bono case. An email suddenly arrived announcing a new policy: you now needed special permission to bill over 250 pro bono hours annually. In two months, she’d billed 220, and the case was coming to trial.

She called the pro bono partner.

“You’re close to the limit,” he noted.

Last week, there was no limit, she explained. This is an important case, coming to trial.

“You’ve nearly exceeded the cap on hours,” he helpfully re-noted.

She inhaled deeply, and re-explained the situation.

He ingeniously pointed out that the 250 hours cap was the firm’s new policy…

…at which point she snapped, and did the unthinkable: she said what she really thought.

“I didn’t know there was a new policy. No one communicates at this place. And what is the point of this crap? Look at my hours – it’s not like I have anything else to do!”

There was a lengthy pause.

“I’m sorry to hear that,” said the partner.

He hung up – and she began to harbor second thoughts.

I’m sorry to hear that.

Behold, a singularly dreaded phrase. It is not good news, at a law firm, when you hear “I’m sorry to hear that.”

Generally speaking, when you hear “I’m sorry to hear that,” at a law firm, it means “you will soon be fired.”

There is something worse you could hear – worse than “I’m sorry to hear that.”


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I raced downstairs to break the news: I’m leaving. I got a new, non-legal job at a major online book-seller.

The reception at the firm gym wasn’t what I expected. My favorite trainer looked pensive, mumbled “good for you, man,” then gave me a half-hearted fist bump. The other two trainers, both women, exchanged looks. One grimaced, and quipped to the other, “see, I told you – the nice ones always leave.” She caught my glance, and turned serious. “Hey, it’s good news. We’ll miss you, that’s all.”

The nice ones always leave.

My client ran into this phenomenon recently. She’s a first year, assigned to a major case with two senior associates. The partner’s missing in action, so she and the two seniors are running the show.

The good news is the seniors are great guys – and, as a result, she’s been one of the few not-unhappy lawyers I’ve seen all year.

“They’re just plain nice,” she told me. “The hours suck, the work itself is kind of boring, but nothing’s that bad if you’re working with people you like. Sometimes, we even have fun.”

One guy was super thoughtful, and bent over backwards to take time to explain things and create a sense of teamwork. The other was a bit of a kook, with a goofy sense of humor and a light-hearted way of defusing crises.

Then, Monday last week, the firm distributed bonuses. On Tuesday the first senior associate gave his notice. On Wednesday the other said he’s leaving, too.

Neither of the seniors said why they were taking off. Maybe it was the demanding, ungrateful client – maybe the partner, who never acknowledged their hard work. Maybe they were just burnt out in general.

As a result of their departure, an office that used to be fun has turned grim. It’s like watching a friendly college dorm turn overnight into der Führerbunker. The partner is melting down. He pulled in another senior associate, an anal-retentive who doesn’t know what he’s doing. People are hiding in their offices. The atmosphere among the paralegals is funereal. Even the contract attorneys look more depressed than usual, if that’s possible.

“It’s a shit storm,” my client said. “And from my perspective, a lose-lose proposition. The partner’s overwhelmed, the new senior is clueless and I don’t know whether to try to help – and get yelled at – or lay low and hide – and get yelled at.”

There’s no winning, and it’s no fun.


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Two guys from my high school. One year apart.

Hipster…and Lawyer.

Hipster plays in jazz band with Lawyer. They have the same academic advisor, and fall into a casual friendship.

Hipster has trouble in school. He plays drums and guitar, but struggles to maintain the grades. It’s nothing to do with behavior – everyone likes him. The academic advisor does his best, but after failing a few courses, Hipster’s expelled. He ends up bouncing from school to school, and manages to graduate, then heads to a halfway-decent state university known for partying. He spends most of his year there jamming with his buddies and soon drops out. They start a rock band, smoke dope, wear tie-dye, collect Grateful Dead tapes and call each other “dude.”

Lawyer thinks it’s a shame Hipster got kicked out of school. His own grades are A’s. He wins academic prizes, a scholarship to study in England, and advanced placement at Harvard, where he graduates magna cum laude. He heads to a first-tier law school, and places near the top of his class. An offer arrives from a white shoe firm.

Stop the tape.

We know what happens next:

Hipster grows a beer belly, loses the tie-dye and winds up working in a call center. He moves into his old bedroom at home and turns morose. His parents mumble excuses about dyslexia.

Lawyer makes partner and earns a million six. He purchases a loft in SoHo, a little country place upstate and a vintage Porsche. His parents seek opportunities to smugly mention his doings to their friends, who hate them for it.

Here’s what actually happens:


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My tenure at Sullivan & Cromwell ended – along with my legal career – in a smoking crater. Picture scorched earth. Nuclear armageddon. The fat lady sang.

That said, I actually got off to a pretty good start. At least for the first couple weeks.

I was assigned to a rather jolly partner, fresh back from running an office in Asia. He didn’t seem a bad sort, and I was feeling on top of the world, commencing my career after a month’s vacation. Off I scrambled to the library to write a memo on a detail of securities law. The topic was complex, but I kept my cool, summarized what I found – with a touch of wit – and called it a day.

Things went swimmingly. The partner loved the memo. He deemed it clever and refreshing and pretty close to accurate. Apparently, I’d managed to lighten the mood at a key moment in a tough deal. I decided I loved him.

The next week we did the deal closing. As a first year, I arranged for execution of the documents (a trickier proposition in those antediluvian days of fax machines and actual, non-cell, phones.)

To my amazement – remember, I’d been there all of two weeks – the jolly partner had a full-on melt-down the night before closing. I found him pacing back and forth outside the conference room, waving documents and shouting that the senior associate was “going to wreck this deal!”

I hurried over to him – again, I was new, I didn’t know any better – and tried to calm him down.

“It’s going to be okay,” I said. “The senior’s a nice guy, and he’s doing his best – we’re all doing our best. We’ll stay focused. The closing will either happen tomorrow or it won’t, but it’ll happen sooner or later, and everything will be okay.”

The partner took a deep breath, and calmed down.

I may have crawled away in disgrace two years later, but that partner at S&C appreciated what I did, and he always liked me. I still think of him fondly.

Why did he like me? Not because I was anything like a competent lawyer. I rarely did more than stand around and send faxes.

He liked me because I kept my cool. I was the calm center.

Sometimes, when the world assumes crisis status, being the calm center gets the job done. Politicians know this. Awful as it sounds, a crisis like 9/11 presents an opportunity to look good. When everyone else is freaking out, you present yourself as the calm center – even if you’re not doing anything.

Biglaw attorneys crave a calm center because they face constant crisis. In an ordinary job, if you work a late night or a weekend, it means something major is happening. Afterward, you take a break and recover. But every day is a crisis at a big law firm – and there’s no recovery. Even if you are “granted” a vacation, there’s the blackberry – and they won’t hesitate to use it.

There’s the nature of the work itself, too. Litigation lurches from crisis to crisis – it’s a zero-sum game, two combatants fighting to the death, searching for a dirty trick, trying to catch the other out on a technicality. Some of my Canadian lawyer clients tell me it’s better north of the border, where people don’t bring law suits on a whim, simply to create delay or cost, and lawyers hesitate to torture prisoners and burn villages to the ground. That might sound wussy to an American litigator, but if you’re looking for a calm center, maybe Canada’s your place.

On the other hand, it’s hard to imagine serene, tranquil M&A deals, even in Ottawa.

Towards the end of my time at S&C, when I was too frazzled to form sentences, I managed to locate two calm centers at the firm. I stumbled upon them by accident, but they did wonders towards preserving my sanity.


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In law, if you’re making big money, you’re working for the bad guys. That’s the sad truth.

I’m not talking about defending vicious criminals. I mean tougher cases – like representing the 1% of the world who own everything.

Deep in the recesses of big law, you might not realize who you’re working for. From where you’re standing, your boss is the firm. Juniors report to seniors. Seniors report to partners. Partners report to God.

In reality, up, over the partner’s head, there’s someone called “the client” – a possessor of vast wealth. Normal people don’t hire biglaw – the owners-of-everything do, and they don’t get uber-rich being nice. Things only get worse when they’re dealing with lawyers.

If and when you actually meet “the client,” you might feel like an Imperial Stormtrooper aboard the Death Star:

Lord Vader? Great to meet you, Sir. Yes, absolutely, the torture chamber is under control. Yes sir, we just checked the planetary death ray this morning. One hundred percent ready to go. My pleasure, Sir.

Then the client walks away, and you play that same argument in your head: You have one hundred and seventy grand in school loans. They’re going to blow the planet up anyway. You’re not torturing anyone personally.

Some lawyers learn to embrace the evil – to “go with it.” I knew a guy in law school who left to work for a firm that did nothing – NOTHING – but defend Big Tobacco. We ribbed him about it. In fact, we regarded him as a stinking pile of vomit. His response was to chain-smoke and brag about money. He disappeared to a hateful red state to work black voodoo, and by now he’s no doubt worth millions. Loathed by millions, too.

My first taste of evil came early at Sullivan & Cromwell. It was a deal for Goldman Sachs with an amusing codename: “Project Rolex.” At the closing I finally encountered the client – and the wry humor of i-bankers: He wore the largest gold wristwatch ever made.

I developed a fascination with Mr. Rolex. His name was all over documents I’d been staring at for weeks. The deal – a securitization of mortgages on a package of investment properties in the Mid-West – suburban strip malls and cheap hotels on interstates – was worth half a billion dollars. As I generated documents, I took guesses at his net worth. If it wasn’t a billion, it was darn close. A guy who met Bill Gates at a technology convention wrote a piece admitting all he could think about while they shook hands was “$500 per second. $500 per second. $500 per second.” Same thing with this client: I couldn’t believe how much money he had.

After weeks of late nights, the partner asked me to arrange catering for the closing. The choice was the standard Sullivan & Cromwell breakfast with rolls and bagels or the “deluxe” breakfast, with lox. For Mr. Rolex, I pulled out the stops and ordered deluxe.

He stormed into the room the next morning, sporting a cowboy hat, cowboy boots and the giant gleaming timepiece. I was awestruck.

But Mr. Rolex was not in a good mood. He turned to the partner:


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