In-House Counsel

Decisions, Decisions: Why You Should Never Make Them While On Vacation

You're probably a piss-poor lawyer when you're on vacation, so leave your cell and laptop at home.

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I’m not going to sit here and pretend that my Biglaw experience resulted in life lessons of Good Will Hunting proportions. At no point did I climb on my desk and shout “O Captain, My Captain,” as a particularly inspiring partner was unceremoniously booted from the firm. Most of the advice I received from my overlords was either technical in nature or barely coherent, half-assed dribble after a few too many drinks at a firm function.

That being said, there were a couple of gems that have stayed with me along the way.

One of my favorites, which remains as applicable in Biglaw as it does in the in-house jungle, is to never make important work-related decisions while on vacation. Zero exceptions. No carve outs for long weekends attending weddings where you don’t know a soul or week-long visits to the in-laws that test the limits of your sanity. No using the “I just have to answer this work email” excuse to get out of beach volleyball or yoga at dawn.

This particular pearl of wisdom came from a partner who, as far as I know, had never actually taken vacation. Or smiled. Ever. Very much like the Grinch looking down on Whoville as it prepared for the holiday season, this partner stared down at me over his desk as I squirmed and wiggled in my chair explaining that I would be gone two weeks for my honeymoon, but available by cell and email.

The partner, let’s call him David, just scoffed and asked if he could offer me a piece of advice. Expecting some sort of joke about the wedding night, I sat there waiting in mute horror. In those days, my poker face wasn’t nearly as good as it is now.

But I needn’t have worried, because David told me to leave my cell and laptop at home. When I stared at him with a new kind of horror on my face, he suggested if I felt so bad about it, to take the cell with me and chuck it in the ocean the first moment I got. Go ahead, he told me. You know the firm pays for one freebie a year. If you’re worried about what people will think, toss it in the drink.

I began sputtering about my deals and my responsibilities and the confusion that my absence would create when it would really just be more efficient for me to answer calls and emails, but he waved me off with a dismissive flick of his hand.

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He said something along the lines of, “Don’t be a goddamn idiot. I don’t give a damn about your honeymoon or your whining, sniveling associate work-life balance. You’re a piss-poor lawyer when you’re on vacation. Everybody is. Step back and think about the crap you buy on vacation. The coconut purse and shell necklaces, t-shirts featuring your vacation destination that no local would be caught dead in, keepsakes made from real beach sand, only the thing says it was made in China. And don’t get my started on what people eat on vacation. Honestly, who the hell would ever go out to a restaurant at lunch and think, I’ll just order myself some fried abalone?”’

Like I said, my poker face hadn’t been hardened yet by 10 miles of bad in-house counsel road yet, so I can only imagine the expression on my face as he continued.

“My point is, you’re not using your noggin. You’re on vacation, you should be like any other mouth-breathing idiot out there, drinking Windex-colored booze. That’s the precise reason that you don’t make legal decisions.”

David went on to recount a particularly salacious tale of a former, rival partner who, while on a ski trip in Aspen with wife number three, drank his weight in hot toddies and advised a client to accept a major concession in a merger document as part of an inadvisable long-term acquisitive strategy. Only, in addition to giving the client that completely disastrous advice (as was later remarked upon as out of character by anyone who had ever met this guy), he copied the target’s business lead on his email to the client. And the target’s general counsel. A general counsel who did not appreciate being referred to as “Satan in heels.” Needless to say, this partner was never heard from again.

David’s story, while extreme and recounted with more gleeful malice than was probably necessary, was instructive. I’m a different person on vacation. It may take me a few hours to acclimate, but I gradually lose my cynicism and my edge. The “life is short, don’t sweat the small stuff (like why is the salmon 10 bucks more than the most expensive place at home)” mentality sets in. And, if you’ll remember my vacation ATL column back in May (shameless, shameless plug here), you shouldn’t be taking time away from your vacation anyway. Otherwise the business wins.

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But you’re going to do it anyway, aren’t you?

Admit it, you’re going to check email only in the morning and night. Fine, do it (if you must let the business win), but be cognizant of the fact that you are likely moving through emails at a swifter clip than you would at the office (because that s’more is not going to cook itself). Slow down and think it through.

For example, my business partners love to take what I will charitably call “creative license” when recounting an issue or deal point to me over email. When you go on vacation, that darling character quirk of theirs doesn’t disappear. Your business people aren’t going to be more straightforward because you’re on vacation (one might even argue the opposite), so if it didn’t smell right when you read about it at the office, don’t let the sea salt or fresh mountain air fool you. It still stinks.

And of course, things seem so much more remote on vacation, don’t they? Maybe the sky overhead is cerulean blue and dotted with the fluffiest white clouds you’ve ever seen. Maybe the ocean sparkles like diamonds at dawn. Maybe the full moon is high above the mountains in a star-filled night. So, what are the odds that the new customer will actually trip the warranty threshold anyway? Or go after your company for inconsequential damages? Or manage to co-develop IP your company would actually want to own? The answer is, I have no freaking idea, you’re the legal expert, but I’m willing to wager those worries and concerns seem less realistic when you’ve just spent the most amazing day sipping drinks with tiny umbrellas in them and wearing flip flops.

So do yourself a favor, pick off the low-hanging fruit if you must, but save the big decisions for when you’re back in the office, sporting a slight sunburn and pants that don’t seem to button properly. Because unlike the gorgeous weather, bad decisions can have a habit of following you home.

Kay Thrace (not her real name) is a harried in-house counsel at a well-known company that everyone loves to hate. When not scuffing dirt on the sacrosanct line between business and the law, Kay enjoys pub trivia domination and eradicating incorrect usage of the Oxford comma. You can contact her by email at [email protected] or follow her on Twitter @KayThrace.

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