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Lawyers on the Beach

The Careerist

July 20, 2016


Truth or urban legend that lawyers are often too work-crazed to tear themselves away for vacation during the heat of the summer? Despite their neurotic, overworked stereotype, most lawyers I know do take a chunk of time off for summer vacation. But I guess there's something so incongruous about lawyers at leisure (picture a lawyer at the beach—pants rolled up, feet in the water—struggling to read messages on his mobile device under the blazing sun) that we are intrigued by the mere idea of lawyers having fun.

So what's the real deal about lawyers in the summertime—particularly those privileged ones in Big Law? Are they capable of unwinding and having a modicum of fun? Do they blow big bucks on lavish, exotic vacations? Or are they secretly huddled in their offices or homes (albeit in shorts and sandals) doing work?

Let's start with the top of the lawyer-glitterati chain: David Boies and Ted Olson, the dynamic duo who successfully argued for the defeat of California's Proposition 8, the anti-gay marriage ordinance, before the Supreme Court last year. So how do two of the most successful (and presumably rich) lawyers in the land pass the summer?

Boies and Olson belong to the work hard, play hard summer school. No lounging around the pool sipping Cosmos, reading trashy novels, for them. In June, they biked for two weeks (50 miles a day!) through Normandy and Brittany, along with their respective wives (Mary and Lady), plus five other couples, according to Olson. Apparently, the team that argues together vacations together. "We do this every year," says Olson, adding that they've also traveled to Provence, Croatia, Ireland, the Dolomites and Umbria. 

Some lawyers, though, need to go somewhere more remote than Europe to get away from their normal high pressured jobs. Kannon Shanmugam, Williams & Connelly partner and Supreme Court litigator (he's argued 18 cases before the high court so far), says he and his family are going to Australia. "I hope to find a part of the Outback where there is no Internet service or cellphone coverage," he says. Yvette Ostolaza, managing partner of Sidley & Austin's Dallas office, essentially takes the same approach. To get away from it all and to celebrate her 25th wedding anniversary, Ostolaza and her family are going on safari in Kenya. To prep for the trip, Ostolaza says, "we're watching 'Out of Africa'."

On the other side of the spectrum are lawyers who wouldn't be relaxed CnbikoxXYAEhDA3unless they stayed in constant touch with the office. Their idea of a summer holiday is to work through it, but in more bucolic, hedonistic surroundings. That describes Gibson Dunn & Crutcher partner Randy Mastro (right). For him, work and play are just two sides of one big, beautiful beach ball.

Though he spends ample time at his weekend house in Southampton, Mastro professes, "I don't have any summer vacation plans. And I'm never off duty." He adds proudly, "I don't sleep much. I'm high energy, low maintenance." That said, it's doubtful that Mastro isn't enjoying some of the perks of the Hamptons. As co-chair of the Hamptons Film Festival, Mastro is probably hobnobbing with his co-chair Alec Baldwin and God knows what other members of the rich and famous.

Of course, there are plenty of lawyers who will work through August—and not by choice. And that's because what ultimately decides any lawyer's schedule is the client. So if the client insists that everyone be locked away in a steamy conference room, that's where you'll be.

Even Boies will be grinding away in August, preparing for the fraud trial of former AIG chief Hank Greenberg in September. (Boies does have another bike trip in Switzerland coming up before the trial, sans Olson. Boies also owns a huge sailboat that he bought from Larry Ellison where he might do some work.) Likewise, Olson seems uncertain whether he can take August off. He says he'll take the rest of his summer "one day at a time"—meaning, it seems, he's on call.

Other businesses might slow down in August, but Big Law is a different animal. Indeed, law firms seem to be fully functional throughout the dog days of summer. "Why wouldn't we be?" asks Paul Weiss litigation partner Roberta Kaplan, who successfully defeated the Defense of Marriage Act before the Supreme Court. (Kaplan took a fly fishing vacation at Big Sky with her wife and son earlier in the summer.)

"In my little world of financing M&A deals there is not likely to be any break this summer," says a partner at Latham & Watkins. That sentiment was echoed also by lawyers at Wachtell Lipton Rosen & Katz and Skadden, Arps, Slate, Meagher & Flom. In fact, several lawyers seemed a bit confused, if not miffed, that I would even suggest something as silly as a slow down in August.

And what about lawyers unshackled to Big Law? Well, that's not a guarantee of a carefree season either. Marcia Clark (yes, that Marcia) says she's swamped with brief writing (she does court-appointed appellate defense work) and under deadline to finish a draft of her next crime novel. "August might as well be the dead of winter for me," says Clark.

So who's really enjoying a long, uninterrupted summer respite? The Europeans, of course. Even the Brits, facing a rocky post-Brexit world, will let nothing come between them and their sacred August holiday. "The flow of work slows down dramatically, almost to a trickle," says a London-based American partner. "That is why I have been forced to join the exodus, as both clients and lawyers are away." English lawyers, he explains, expect their privileges, no matter what: "Because so many lawyers at the elite English law firms, including the battalions of insipid and spoiled trainees, are private school graduates from the upper middle class, they tend to view a three to four week summer holiday as an entitlement rather than a respite." 

"The work ethic in the U.K. has never been comparable to what prevails at New York law firms," sniffs this American lawyer, who laments that he's often the last guy at the office and the only one on weekends.
Ah, we should all be forced to adopt such indolent ways.


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The Careerist takes an inside look at how lawyers shape their careers and manage their lives. The blog aims to dissect developments in the profession, provide useful information and advice, and give lawyers a platform to voice their views. The goal is to provide a fresh, provocative take on the state of lawyering.

About Vivia Chen

Vivia Chen

Vivia Chen, The Careerist's chief blogger, has been covering the business and culture of law firms for a decade. A former corporate lawyer, Chen is fascinated by those who thrive (as well as those who don't) in the legal profession. Her take: Success in the law (and life) doesn't always travel a linear path. If you have topics you'd like to discuss or information to share, contact her: VChen@alm.com

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