I’ve always been awestruck by tax lawyers. They are the dudes.
As a transactional attorney, you can’t make a move without a tax guy. M&A is based on IRS consequences. It’s the tax guy who hands you a chart with boxes and arrows, holding companies and off-shore limited partnerships buying and selling and re-selling and issuing and repurchasing and spinning off. Everything starts there.
Tax lawyers do stuff no one else would attempt. They swagger out the door at 5 pm.
“Don’t start with me. I’m in tax.”
Way back when, I took an advanced tax course in law school – to see if I could roll with the gangstas. I even took it the wrong semester, so instead of JD students, it was LLM’s snickering at my desperation. I received my lowest grade ever. I also discovered tax law is like higher mathematics: there is no big picture. Tax is not intuitive or guided by over-arching principle; it’s a mess of staggering, intimidating complication.
What I’ve come to realize lately, as a therapist working with tax lawyers, is that these seemingly unapproachable superstars are human. And being “the expert” can exact a toll.
One guy – a senior tax lawyer from a big city firm – walked into my office last week. He had the usual frustrations. In an ordinary economy he’d be making partner soon, but business was terrible, so even the partners at his firm were being laid off. He was expecting a pink slip.
There was a deeper issue, too: He didn’t like being a tax lawyer.
I gave him a speech about my admiration for his kind.
He appreciated the fawning worship, but his expression remained grim.
“What you describe is actually what I hate about it.”
It turns out being “the expert” can be isolating – and scary. From where he’s sitting, there’s incredible pressure to know everything and solve every problem.
He clued me in to his experiences, and in the process brought me down to Earth. Tax lawyers aren’t a race of super-beings from Planet Krypton. Tax is incredibly complicated for them, too. The job is about helping rich people avoid the IRS, which translates into “gaming” each tax law to create loopholes that the government closes up in the next version the following year.
There isn’t just a “tax code,” either. There’s an endless labyrinth of fine print: contradictory court decisions, administrative regulations, IRS guidances, state and local and international consequences for every move you make…it goes on and on and on, twisting and turning like something from the imagination of Borges or Kafka.
The mind reels. At least my mind reels. I always believed that – by some miracle – if you were a tax lawyer, your mind didn’t reel.
My client was a senior tax guy at a top firm. His mind was beginning to reel.
“They want to hear you say it’s possible – whatever deal they dream up. So you’re under massive pressure to find a way to do it. And it’s all riding on you. If you screw up… I try not to think about it.”
I thought about it. The entire deal blows up – probably in the papers. Millions of dollars lost by your client, who might try to sue you. Criminal penalties. Malpractice. Disbarment. All that bad stuff.
It’s like writing an opinion letter. No lawyer wants to write an opinion letter. Why? The same reason no one wants to step into the sights of a high-powered rifle.
“I can’t do this anymore,” this guy said. “I feel like I’m wracking my brain, dealing with incredible complexity, holding on by my fingertips – all to save billionaires from paying their due.”
It isn’t only tax lawyers who end up “the expert.” We had a bunch of experts at Sullivan & Cromwell. I remember an environmental guy whose only job was to review deals for pollution issues. There was an ERISA guy, too, who only reviewed stuff for ERISA issues (whatever they are). And there was a strange tall guy with a mustache who always smiled and whistled to himself. He was the ’40 Act guy. I once sat through a CLE presentation he gave, and remember thinking it wasn’t that I didn’t understand the details – I couldn’t figure out what the ’40 Act was.
Sometimes the role of expert seems like a hot potato – everyone wants to pass it off to someone else. I remember doing a deal with AIG – some complicated nightmare with a dozen side agreements and sub-corporations selling and repurchasing their own holding corps. At the umpteenth drafting session, a banker scribbled down a formula on a napkin – no kidding, it was a mathematical formula, and he said “stick this in there.” They’d been arguing for days about some clause in the back of the contract and this is what he told us to stick in there. I looked at it. There was what I recognized as a numerator, and a denominator, and a bunch of letters.
The partner glanced at it and told the of counsel to stick it in there. She handed it to me, and told me to stick it in there. I stuck it in there, but I didn’t know what it was.
Of course, I knew the general rule that you’re not allowed to put math into a contract, you have to put it into plain English. So that’s what I tried to do: “the Pre-determined Selling Price shall be determined by a formula in which the numerator shall be the amount of the Settlement Price and the denominator shall be one added to the amount of the Sales Price multiplied by the First Pre-Settlement Price minus the Third Sub-Corporation Preliminary Offering Variable…”
You get the idea. I had no idea what I was doing. I tried, a few times, inserting numbers, just to see what would happen. The first time I got something like one hundred billion dollars. I knew I’d done something wrong. The second time I got something like 0.000125782 dollars.
I should add that it was late at night and I’d been wearing the same wool suit for 17 hours.
I gave up and handed it nonchalantly to the of-counsel. No biggie. I’d “taken a stab at it.” She might yell at me, but she’d know what to do. If she had to, she’d fix it herself.
But she didn’t.
I watched her disappear into the partner’s office, then return. Her face was set. She approached my desk and plopped the offending passage down in front of me.
“Just double-check this and make sure it’s right. Thanks.”
I knew right away what had happened. The partner had no idea what the damn thing was either, so they passed it back to me. I’d bragged once about my brother, the nuclear physicist, so maybe they thought I could do math. And this little nightmare was in the last page of a side agreement. It was indecipherable. It wasn’t that important. It would probably never matter. I wasn’t about to create a fuss, so I pretended to “look it over” and left it in whatever shape it was when they gave it back to me.
I still have no idea what it was or how it worked, but it is buried somewhere deep in an agreement on the books of AIG Corporation. I think we can all agree that AIG is a stable, trusted cornerstone of the American economy, and there’s zero chance it will ever experience financial distress. So relax. We’re fine.
That’s the essence of being “the expert.” As a lawyer, you’re “counsel.” You’re supposed to know everything. You’re also supposed to be risk-averse and spot every possible problem before it happens, and be able to predict the future. And you’re supposed to “know the law” – as though anyone could ever really “know the law.” And you’re supposed to make it happen – whatever it is – for your client. Some of those goals are impossible – or at least mutually exclusive. So you start to fake it. And that’s what happened to that tax lawyer I was working with. He was feeling more and more like a fake, and he wanted to run away and hide.
I’ve seen it before. One of my clients was a partner at a medium-size firm in a medium-size city who told me about his “garbage can deals” – the ones where you throw it all into a contract and get the thing closed then hope no one ever opens it back up. Every lawyer who’s ever done a few deals knows he has a garbage can deal in there, but he’d probably never admit it. After all – he’s the expert. He must know what he’s doing.
At some level, it’s a big fake-out. Posing as the guy who knows everything can make you rich. Or land you in jail. Or keep you up at night.
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This piece is part of a series of columns presented by The People’s Therapist in cooperation with AboveTheLaw.com. My thanks to ATL for their help with the creation of this series.
If you enjoy these columns, please check out The People’s Therapist’s new book, Way Worse Than Being A Dentist: The Lawyer’s Quest for Meaning
I also heartily recommend my first book, an introduction to the concepts behind psychotherapy, Life is a Brief Opportunity for Joy
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The People's Therapist 
At this stage in my life, I’m thinking that getting a Ph.D. in nuclear physics may have been better idea than being a lawyer. Althought I could be quite wrong.
At least that would have played to my strength, scientific intituion, as opposed to my weakness, leagal writing.
You have the same problem in tax as you do in patent drafting. Basically, you have to convert a physical or electricial or biological device into words. That is a major pain.
Thanks for the shout-out to patent drafting!
After 5 years of patent drafting, I still can’t believe that most lawyers get to use more than 10 lines of boilerplate in a 40 page legal document.
The hard part of patent drafting for me is actually having to predict where both the law and the technology will go in 3 years when the application will be in prosecution and in 10 years when the patent will be in litigation.
As someone who used to work at the PTO, I understand your pain. I remember reading cases and being able to tell when the attorney had no idea what the invention was. “This attorney probably has a B.S. in biology, but got stuck trying to describe the novelty and non-obviousness of a diesel engine.”
Most liberating three words a lawyer can say: “I don’t understand.” I’m laughing about the math formula story because, while I never had an equation in any of my documents, I’ve had exactly that experience — including handing the whateveritis up and down the chain. Then I learned to say “I don’t understand” and that prompted the person above me to have to admit that they didn’t understand and then the partner had to admit that s/he didn’t understand and we finally were all on the same page. Phew. Best three words in the world.
Part of the problem is posturing — biglawyers always have to put up an image of competence to justify their high incomes & billing rates, job security, etc. This translate into never, ever admitting you don’t know something/made a mistake/are wrong/human/mortal/etc.
What could go wrong?
Better to be a law prof where inevitable mistakes have zero consequences. As a professor, you can spend your adult life yelling at 20-somethings about what was in the cargo hold of the In re Peerless and no one will know or give a turd if you’re correct or not. It won’t even be on the exam.
This is one of the major problems with being a lawyer (doctors and accountants probably suffer the same fate to varying degrees). In other fields, you can succeed while being right the majority of the time – you don’t have to be right *all* the time. Heck, the best baseball players get on base only about 40% of the time (and you can survive with a 30% on-base rate if you play a premium position like shortstop – yes, I’m a baseball fan).
One thing I like about my job as a research lawyer for a public interest organization is that I can be exacting without always having to be perfect. Some of the best work I’ve done has involved helping clients in “gray areas” where the law isn’t entirely clear, and I haven’t had to come up with mathematically precise answers. Usually I get to focus somewhat on “bigger picture” issues, without having to dwell endlessly on every last microscopic detail in a case.
As a tax (and corporate) lawyer, I can confirm to you that what I liked about it once now makes me want to pound my head into the desk. The never ending busyworkproducing mess of loopholes and bad legislation AAAAAGH. And that doesn’t even touch on state and local.
The stories I could tell about tax lawyers. I’m pretty “normal.” I can pass for Normal in society, but so many coworkers cannot (Rainman Syndrome!). Sometimes I worry that they might be smarter, but then I look at where they are on the Aspergers/Autism/Savant spectrum and remind myself that just being “pretty smart” and “normal” is better than “frighteningly brilliant and deeply weird.”
Next life I’m going to be a large animal vet, or screenwriter, or something else not-this.
This is very accurate and why I’m experiencing some depression right now (truly). I dread going to my job as a junior tax associate at a big firm because I’m petrified that today is the day that they are going to come into my office and realize that I am a big fraud. Subchapter K? What? Subchapter M? As junior associates in my firm, we’re encouraged not to specialize yet, so I sit by the phone in fear that someone is going to call me and ask me to do a deal or a placement agreement or a bankruptcy or any number of other huge transactions about which I have no knowledge. It’s awful, it’s just awful. I used to like being a tax lawyer in that it was a more precise discipline — there was the Code, and you were supposed to interpret it. But, as you point out, what it means in reality is that you are called in at the last minute by some corporate associate who wants to save the deal. I’m going to make “I don’t understand” as my motto for awhile and see if that makes things better. Thanks, as usual, for the perfect post at the perfect time.
I was a securities associate in a big firm and when I was hired, I didn’t even know what a 10-k was (why securities? because they needed warm, billable bodies in securities, that’s why). Believe me, I feel your pain. I called it Miller’s Daughter syndrome because every time I got an assignment, I’d come back to my desk and feel like the miller’s daughter in Rumpelstiltskin surrounded by straw with no clue how to make it into gold. If you’re still junior, this is the time to say “I don’t understand” and “I don’t know what that is.” Will they be frustrated? Sure. (Try to ask an associate and not the head of the tax department. They’ll still be frustrated but less so.) Will they wonder if you’re a bit dumb? Probably. But everyone thinks that junior associates are dumb and worthless. Better to ask and then turn around a good product than not ask and screw up. Because the asking doesn’t go on your review and no one is going to have a sit-down in your office because you asked a question. But any mistake on an assignment will follow you forever and ever and ever. And even if you squeak by your first few years, you’ll then have to keep up the facade because asking a ton of questions when you’re new is one thing. If you’re still doing that as a third or fourth year, uh-oh.
And also – as hard as this is – relax. I didn’t know what Subchapter K was once either, and now know when I’m right about a TEFRA issue and a senior partner is wrong. But it took time – be careful, do good work, ask, but have some compassion for yourself because this will take some time (and there is nothing you can do about that). The people who are juniors and know everything already are 1) freaks or 2) worked in accounting before law school.
There was a point when I had to figure out private placement offerings and the interplay of federal and state exemptions etc. and I had no idea what I was doing so I thought I was going to die of stress. I figured it out, but the stress did not help.
I majored in risk management and insurance before I went to law school, in the early 2000s. AIG was the king gold standard of corporations at the time, and it was drilled into our heads that working for AIG would be winning the career lottery. Other corporations didn’t understand insurance, but AIG was rock solid. We were also taught that Alan Greenspan was a genius who should not be questioned, just like AIG.
I remember my senior year of college I took a class on insurance premiums. It was essentially a math class, and I was totally lost for most of the semester. What I eventually took away from the class was that insurance companies base their premiums on averages of estimates. I had to take enough statistic courses in my business core requirements to know that averages weren’t always helpful, and estimates were worthless. For the life of me, I couldn’t understand how this entire ginormous industry could be based entirely on averages of estimates.
I would imagine the curriculum at my university has changed in the past five years. Here’s hoping!
In IT, there are a few areas of very technical specialisation. It’s a cliche that as you specialise, you learn more and more about less and less until you know absolutely everything about nothing. No doubt it’s similar to aspects of law as well.
I think what may be easier for IT people is that because technology changes so quickly, the specialists become outdated after a few years. The specialists then have to either retire or get a different job.
Based on this article, being a tax specialist has a longer lifecycle, but the demands are correspondingly higher. In this circumstance, maybe the IT people have it easier.
Ahhhh… the psychic inability to maintain pretense indefinitely. I have seen this phenomenon painfully played out in the lives of friends and colleagues a number of times.
In fact, “imposter” syndrome was a pop lit topic that received a lot of attention, sparked by the entry of significant numbers of women in the professions back in the 80’s. But, as experience has shown, the undermining inner voice of doubt and pretense is not limited by gender.
With the advantage of having learned from others’ struggles with this, and knowing I will get called out — once again — for being judgmental, I can’t help but notice out loud how many of us are the authors of our own critical problems. In retrospect, can we not admit that if one chooses to nurture a persona based on pretense over years of professional performance, there inevitably will be a price to such sustained heavy-lifting? Does it really make sense to lay off responsibility for the years of pretending on the expectations of us in our workplaces, and among our colleagues, clients or dependents?
One of the realities of life is that we make difficult and uninformed choices when we are very young and still immature and inexperienced, not realizing that some of these choices lead to very bad outcomes. But that does not, in my view, absolve us from taking stock along the way and causing a correction of course. That’s growing up, on the inside.
When we find ourselves living a lie, a pretense, a life that is not “real” to ourselves, no one swoops in to save us — the pretense has been way too effective. That does not absolve us from the obligation to save ourselves by starving the impostor and fronting the person behind the false persona. Yes, saving oneself by refusing to use or rely or benefit from the false persona may disrupt professional berths and even personal relationships. But, can any of us expect to extricate ourselves from this problem without any risk of consequences?
Very entertaining quip; most tax/transactional lawyers can identify and recall an event or two in their professional life and appreciate the humor. Most tax lawyers pride themselves as “out of the box” thinkers. The attribute that allows them to generate the so called “loopholes” their clients (mostly other lawyers in their firm) so desperately seek. Having been at it for some time, I had to invent my own tweak on the “out of box” thinking philosophy.
“Outside of the box lies a small box called jail; my out of the box idea is only as good as my chance to stay out of this small box”.
After reading the article I realize that this tweak is what the tax lawyer in need of therapy should practice to calm the anxiety.
As a broader comment I would say that so long as the politicians (Congress and the President) keep using tax-policy as a tool to reward or punish specific economic activity, tax lawyers’ expertise will continue to hold value.