LIVING the DREAM

For the most part, associates have no real effect on the outcome of a deal or a case—or anything of real consequence, for that matter. The one place we can really shine—or really fail—is proofreading. When I was at Skadden, I remember hearing that a well-regarded senior associate was passed over for partner three years in a row because he distributed a merger agreement with a “significant typo” in it. Not sure if it’s true, but sure seems possible. And that’s the thing about big firms, one little screw up, and you’re dead. On the other hand, if you actually find a typo or two, and your boss (who in this episode is played by the talented Michael B. Silver) is in a good mood, you’re suddenly a hero.

One associate I worked with years ago loved to brag that he was the firm’s best typo-hunter and would challenge me to typo-bets. Needless to say he won every single time. PS—He’s a partner now.

This episode is simply a riff on the ridiculous ways young lawyers earn their reputation and become “superstars.” The tiniest things get blown out of proportion. Finding a stupid typo—something that has no real significance—can turn a regular associate into a legend. The worst part is, as an associate, you actually sort of believe it. You actually feel like a rock star for finding a goddamn typo. Which is fine, I guess, as long as you don’t have a date that night with a cute “civilian” who doesn’t quite understand the whole typo/street-cred thing.

Again, when you’re billing 2400 hours a year and proofing documents with a zeal typically reserved for curing fatal diseases, it’s tough to relate to regular people—and it’s even tougher for them to relate to you. At least that was my experience. And now it’s Nick’s too.

Interesting tidbit: Nick’s (John T. Woods) cute blind date is played by Jen Lyon, a semi-finalist on Survivor: Palau.

Years ago, when I was a first-year associate at Skadden, I was at a bar, drinking, hanging out with a bunch of super-intense associates, when a cute girl smiled at me. I smiled back. Moments later, I was talking and flirting with her. She was young, cute and drunk. It was perfect—until I responded to some inane question with the following question “Do you mean that in the connotative or denotative sense?” The sexual energy vanished instantaneously. Her smile turned to confusion, then contempt. Did you really just say that? Are you that big of a loser? Moments later, she was gone. Just like that.

I’m not George Clooney, but I’m not a total dork either. So why did I say something so stupid to a beautiful, buzzed woman?  Because I was a first-year associate at a big firm. Because I was inundated with annoying smart-people banter and witticisms.  Because I was surrounded by insecure Law Review geeks who were constantly trying to sound smarter than everyone else. Without knowing it, I’d lost all context for what normal people find funny–or even acceptable. I’d been trapped in a bunker with over-achieving M&A geeks for months at a time. What’s funny at 2 a.m. in the middle of a hostile tender offer ain’t necessarily so interesting at Bungalow 8 on a Saturday night.

So this episode is a simple homage to my junior-lawyer-pseudo-intellectual-self-consciously-arrogant lameness–and a cautionary tale to all young, single lawyers on the prowl. Never, ever use the words “connotative” or “denotative” when talking to drunk, sexy women.

First off, I have nothing against Loyola. It’s a great school. All 3,000 of them, which is I why I picked it. It’s not meant to be any one school in particular. It’s sort of a proxy for a good school that’s not Harvard. So please, those of you from the various Loyolas out there, don’t be offended. To me, it’s much funnier to have some partner asshole thumb his nose at a good school than some random, no-name school.

The real-life inspiration for this episode was a truly horrible interview I had years ago at some swanky Washington, D.C. firm—the kind that likes to brag that they only hire from Harvard even though they don’t. So here I am, a nervous second year with decent grades at American University Law School sitting across from some douche bag in a bow tie, when he glances at my resume and says, “American, huh?  What’s the matter, didn’t want to go to Harvard?”

And just like that, I was toast for the rest of the interview. I wanted to put a pencil through his goddamn throat. Instead, I just sat there like an insecure fool rambling about American’s highly ranked international law program. He just nodded, wallowing in my pathetic second-tier shame. Then, with a sadistic, Brahman grin, said, “Are you saying you got into Harvard and chose American instead?” Yeah, that’s what I’m saying, dick! I’m the one guy in the history of the fucking world who chose AU over Harvard. Yale too. Got into all of them. Stanford, Chicago, Columbia. I just really wanted to live in DC and go to American. Because of their terrific international law program and proximity to the Portuguese Embassy.

Anyway, you get the idea. Not a great interview. This cat was clearly the most annoying man I’d ever met. So, I figured it made sense for our lead character, Nick Conley (John T. Woods), to interview with him too.  I thought the actor (Ed Kerr) who played the asshole partner was terrific. Far more intense and intimidating than the effeminate loser I interviewed with years ago.

The whole idea of the episode is to have Nick suffer the worst interview of his life, then somehow, magically, get an offer and say yes – even though, deep down, he knows the place is a little crazy. Or evil. But he says yes. Because that’s what you’re supposed to do. Chase the prestige. Work at the best firm possible.

The mentally unstable, cross-dressing drunk—the thick dude Nick’s dancing with at the bar—is clearly meant to be the Ghost of Christmas Future.  The last shot of Nick says it all. I just made a deal with the devil. And I’m terrified. The exact same feeling I had years ago, when I called the hiring coordinator at Skadden Arps and said, “I accept.”

Check Out LTD’s Press Coverage:

• WSJ Law Blog
• Tilzy.TV