Boutique Law Firms, Small Law Firms

From Biglaw to Boutique: Recalculating

Tom Wallerstein

I recently met with Keith, a long-time friend who worked for years in Biglaw before leaving the practice of law entirely. We were reminiscing, and he reminded me of an incident I had forgotten about:

He had worked on an appeal in which the amount at stake exceeded $10 million. He spent dozens of hours conducting legal research and probably another 100 or so writing the brief.

He finished his draft months before the brief was due. So when he turned in the brief to his supervisor, it was not immediately reviewed. Every week or so, Keith would send a reminder, but the weeks turned into months.

Keith planned to file the brief with a Court of Appeals on the East Coast via Federal Express. E-filing was not yet available and, in any event, onerous binding of the exhibits and other requirements made that impossible.

What happened next?

Just days before the deadline, the partner in charge finally turned his attention to the brief, and demanded that it be completely re-written. The brief that had sat unread for months had turned into an all-too-familiar fire drill. Keith fretted that implementing the changes would mean missing the filing deadline. He also tried to explain some of the arguments, but the partner wasn’t interested in exploring those nuances. After several rounds of re-writing, the brief gained sign-off and was copied and ready for filing with little over an hour to spare.

It was only then that Keith learned that the deadline for shipping to the East Coast was two hours earlier than he had been told. He had missed the last pickup.

I remember Keith’s panicked call about his “$10 million mistake.” I tried to explain that filing the brief one day late did not necessarily mean that the appeal would be lost, but Keith was inconsolable. He was certain he would be blamed and fired.

I told Keith about a similar situation I had faced, and that there was one FedEx office that could still get his brief to the East Coast for filing the next day. The office was located just behind SFO, about 30 miles away, and we figured that if he hurried he should be able to make it there just before it closed at 9:00 p.m.

Keith was terrible with directions and would often get lost on simple trips. He didn’t know precisely where the office was, the actual address was unusual, and the directions on MapQuest didn’t look right. This was back in the day before smart phones, but Garmins were getting popular, and Keith carried one in his car out of necessity.

I wished him Godspeed as he hung up the phone and raced to the airport with his $10 million parcel.

Keith told me later that as he pulled out of his firm’s lot, he heard a loud “bump!” followed by (his words) “thump-thump-thump-thump-thump.” Before he could pull over to see if he had hit something, the sound went away and he allowed himself to forget about it.

Keith got to the airport at about 8:20 p.m., but the Fedex office was nowhere to be found. He knew it was located somewhere in an isolated industrial park, but it was late, and everything was closed and looked deserted. The fog was heavy, giving the night a surreal effect.

Even his Garmin betrayed him that night. Keith followed her every direction, but suddenly, inexplicably, she intoned the dreaded words, “recalculating.” She instructed him to drive back the way he had come, which he did. He muttered to his Garmin that he was feeling lost; lacking in some direction. But again, without him even making a turn or passing any road, his Garmin repeated that she was “recalculating.”

Near tears, he stopped his car and flung his Garmin out of his window in frustration. He expected to hear a crash, or at least some satisfying “thud,” but instead he heard, far away through the fog, the taunting, mocking voice: “Recalculating . . . Recalculating . . . Recalculating.” He told me that he half-expected Rod Serling to appear from the mist to offer his sardonic lecture.

Desperate, he raced against time with his career on the line. As he continued down the road behind the airport, he noticed his engine light had come on and smoke was pouring out from behind his car. Before he could react, he heard and felt his tire explode, and pulled the car over while driving on his rim.

Sure enough, Keith’s tire was not only punctured, but had melted away to virtually nothing. Next to the rim were the remnants of the tire, a two-by-four, and a dead goose. He didn’t have time to consider the implications; he grabbed his box with the brief and continued his quest on foot. As if on cue, it started to rain.

A few minutes later he came across a human body lying in the middle of the deserted dirt road. He rubbed his eyes in disbelief and gently nudged the body with his foot, receiving a mumble in response. When he bent down, the stench of alcohol hit him, and some mumbled conversation confirmed that the stranger was not injured, but had simply chosen, as Keith put it, “to rest his bones.” Keith half cajoled and half dragged the guy to the side of the road, stuffed 10 dollars into his pocket, and threw a Hail Mary, asking, “I don’t suppose you know where the FedEx office is around here?” The stranger gestured with an unsteady hand, and, lo and behold, there it was, the promised land!

Moments later Keith stood in the FedEx office; panting, dripping and exhausted. The brief got safely handed off and filed on time. A $10 million tragedy was narrowly averted, and a career was saved.

* * *

Fast forward two years. It was a Sunday night at 8:00 p.m. Keith’s wife had just gone into labor, and he was driving her to the hospital. His cell phone rang and he remembered that the next day was the oral argument on the appeal and that the partner was on the East Coast, preparing. He answered the phone.

“Hey, Keith, what are you doing?”

“Well,” Keith gushed, “actually, my wife just went into labor! I’m in the car driving her to the hospital right now!”
“Wow man, that’s great. Congratulations. I’m really happy for you, and I’mma let you finish, but . . . I gotta ask, what the hell were you thinking with this brief?! The argument in Section Two makes no sense at all. I understand how you’re reconciling the cases, but it seems to me . . . .” Keith couldn’t hear the rest over his wife’s anguished cries.

Suddenly, a bad signal caused the call to disconnect. Or, perhaps, Keith just hung up.

There was no fog on the road that night. Keith knew exactly where he was going, and he had no trouble finding his way. Adrenaline rushed through him as he thought of the impending birth and all it entailed. Despite the call, he felt strangely calm. There are things you can replace, and others you cannot. The time had come to weigh those things. For the first time in years, his path was clear.

I can only imagine how his mind must have flashed back to his harrowing trip to the airport and his “$10 million” parcel. Next to the birth of his child, that drama surely seemed trivial. Keith told me that as he drove, all the sounds drowned out except for his memory of a persistent voice, reminding him of what he knew he should be doing: “Recalculating. . . . Recalculating.”

At that moment, my friend did just that. He resolved to make a change and figure out the next phase of his career, which turned out to be running a five-star restaurant. Keith told me that he will never forget his fateful trip to the airport, his Garmin, the homeless guy, and even the dead goose, all of whom helped point the way.

Tom Wallerstein lives in San Francisco and is a partner with Colt Wallerstein LLP, a Silicon Valley litigation boutique. The firm’s practice focuses on high tech trade secret, employment, and general complex-commercial litigation. He can be reached at

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