Ed. note: This post is by Will Meyerhofer, a former Sullivan & Cromwell attorney turned psychotherapist. He holds degrees from Harvard, NYU Law, and The Hunter College School of Social Work, and he blogs at The People’s Therapist. His new book, Life is a Brief Opportunity for Joy, is available on Amazon.

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 tax LLMs 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 overarching 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….

Continue reading at The People’s Therapist…


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