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Small Firms, Big Lawyers: How I Became a Small-Firm Lawyer

Ed. note: This is the first installment of Small Firms, Big Lawyers, one of Above the Law’s new columns for small-firm lawyers.

I’ve been working in small law firms my whole career — nearly 17 years. I’d like to tell you that I chose this path for carefully considered and noble reasons, but I can’t. In truth, I ended up on the small-firm path for one simple reason:

A blonde.

Let me explain.

Now it’s not what you think. I didn’t turn my back on a BigLaw career to pursue a flaxen-haired beauty. That would almost be romantic, and this is a serious law blog. Ish. No, the story is a bit more prosaic.

I entered Boston College Law School in the fall of 1991. At the time, I had a serious girlfriend (the aforementioned blonde) who was not going to law school. And that became a problem. You see, like most 1Ls, I got caught up in everything that was new about law school: new friends, new challenges, new vocabulary (I mean really: how many jokes should there be with “res ipsa loquitur” in the punchline?). I didn’t realize it at the time, but I paid too much attention to my new law-school world, and not enough attention to my girlfriend.

So she left me….

Problem is, she chose to do it in early May of my first year — a week before my first-year finals. Not a fun time. I basically sleepwalked through exam week. I was majorly bummed. (I mean, we’d been living together, and she took the cat and the TV remote with her. I really loved that remote.)

I could tell you that I got my ass kicked in exams, but real life is more subtle than that. Where I might have gotten an A- in Property, I got a B. A likely B+ in Torts slipped a half-grade. Not a total failure, but enough to change my life. Although I wouldn’t realize it until September.

When second-year on-campus interviewing started up in the fall, the damage from that week in May became clear. My first-year grades had put me in the top 40 percent of my class — barely. Fine, but not good enough for the big Boston law firms I thought I wanted to go to. I got a few “lottery” interviews, and even a couple of callbacks. But if you were outside the top third in my class, there were no big-firm summer-associate offers coming your way. My postbreakup exam-week tailspin dropped me below the magic threshold.

Over my second and third years, I managed to pull my grades up, finishing in the top quarter mainly by loading up on survey courses and classes taught by Republicans. (Yes, seriously.) But it didn’t matter. I got an unpaid internship second-year summer in the Attorney General’s Office. A few desultory BigLaw interviews at the beginning of third year (“Sorry, we’re really looking for someone with summer-associate experience”). Next thing I know, I’ve graduated into a lousy law-firm economy (May 1994) without a job. Nice. Not thinking particularly kind thoughts about my ex-girlfriend. (Yes, I know: my fault.)

I ended up getting an interview with a four-lawyer employment-law boutique. I finessed my lack of employment-law coursework and feigned an undying interest in the field. I basically got the job because a teacher who knew the managing partner made a nice phone call on my behalf.

And so I landed in the world of small law firms, and I’ve been there ever since.

But the funny thing is, it’s exactly where I belonged. Even though I spent most of law school thinking that I had to go to a big law firm, the truth is that I wouldn’t have lasted about six seconds in one. I know this now: many of my friends and classmates work in BigLaw, and my wife (whom I never would have had the good fortune to start dating if the blonde hadn’t dumped me when she did) is a partner at an Am Law 100 firm here in Boston. Basically, it would have been a footrace to see if they fired me before I quit.

It’s not about intelligence or work ethic. It’s about personality type. White shoes just don’t fit me.

I wish I had known more (read: anything) about small firms while I was in law school. If I had, I might have realized that I belonged there. Instead of ending up in small firms by happenstance and a departing girlfriend, I might have gone purposefully. Not accidentally.

I’ve stayed in small firms because it fits my style of lawyering. After four years at that first boutique, I started my own firm, Shepherd Law Group. Over the years, it’s had as many as six lawyers and as few as one (that would be me). And we’ve enjoyed being different from big law firms: for example, we stopped tracking and billing hours in 2006. Wouldn’t have been able to do that in a big firm.

In this column going forward, I’m going to talk about all the things that make small firms great, as well as some of the things that can make them suck. Maybe together we can help reduce the suckage. But most importantly, I want to help people identify themselves as small-firm lawyers, and go to small firms on purpose.

Welcome to the world of small law firms.

Jay Shepherd has run Boston employment-law boutique Shepherd Law Group for the past 13 years. Jay also founded Prefix, LLC, which helps lawyers and clients value and price legal services. He writes the ABA Blawg 100 honoree The Client Revolution, which focuses on reinventing the business of law, and Gruntled Employees, a workplace blog. Follow Jay on Twitter at @jayshep, or email him at

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