The most convincing, forceful, undeniable reason that compelled me to leave the law

 December 21, 2013

By  Casey Berman

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A recent story:

I was in my friend’s law office last week, and we were discussing a side project that I’m working on. We were interviewing and brainstorming with another person who may help us with this project, a person that my lawyer friend introduced me to. As we discussed things, in his beautiful law office conference room high above the city, I could tell how my friend was enjoying himself. I wasn’t sure if he was really interested in what the other person was saying, or if he was interested in what I had to say, or in the subject matter. I wasn’t sure. But he was excited, engaged, interested. And he was very talkative and collaborative and engrossed.

At a break in the conversation, when we were summing up the talk and discussing next steps, he leaned back in his chair and put his hands behind his head and smiled a bit and said “This is real good. Real good. I like this kind of stuff. There is no deposition to manage, no judges to persuade, no briefs to trudge through. This is so creative. We’re doing something, we’re making something, we’re planning something. It’s so proactive. What I do every day as a lawyer is SO reactive.â€

Another story, from 9 years ago:

I was VP Operations and In House Counsel from 2001 to 2004 for a company called Workshare. We developed the redlining tool that many transactional lawyers use, DeltaView (now Workshare Compare). It was a great product, used by almost all law firms and consulting firms, and I really enjoyed my job. It was a start-up that we grew into a fully functioning robust company. It’s still around. I have great memories and learned a ton.

But I left in July 2004. Pretty much just leapt and hoped the net would appear. And the main reason why I left my job – a job my friends called me crazy for leaving, a job that was perceived as being so much better than a normal firm job, a job that for many was a stepping stone to greater and greater in-house jobs in Silicon Valley – was because my role was so reactive. And I didn’t like that.

I was the one who negotiated the final (often mundane) details of the licensing agreement (“Let’s do a 30 day termination clause, instead of 45, okay?â€). I was the one in the office late on March 31, June 30, September 30 and New Year’s Eve finalizing deals so our sales guys could get these commissions in before the quarter’s close (“Casey, we’re gonna close tonight, right?â€). I was the one telling the VP of Biz Dev that his (sincerely) great marketing idea might violate our partner agreement (“Sorry, man, I just don’t think we can do it.â€). I was the one scrambling to put out fires (“What do you mean we don’t have our tagline trademarked?â€). I was the one who dealt with ongoing issues with our landlord (“We need to renew our lease.â€).

And while these scenarios seem par for the course for an in-house counsel, and may be even attractive to many of you who aspire to be an in-house, I gradually grew uninterested in the role. My day to day task mostly required me to react to certain things and find a solution. Sure, we did long term planning, and there was some preemptive risk management – I did “look ahead†some times. But a lot of the job was about responding to an external circumstance. There wasn’t much creating, brainstorming, thinking outside of the box or collaborating.

And back in 2004 was when I realized that an in-house counsel role, for all of its perceived goodness, just wasn’t for me. It was right for others, but not for me, and I needed to get comfortable with that. I needed to realize that I wasn’t crazy or going insane, and just because everyone else thought being an in-house lawyer was great and ideal and perfect, it was okay if I didn’t share that sentiment.

For me, I wanted to be more proactive. I wanted to create the deal. I wanted to do more public speaking. I wanted to ring the bell. I wanted to write more and publish it publically. I wanted to make something and service something. I wanted to shake hands and schmooze and brainstorm and whiteboard. I wanted to create something … and then hand it off to the attorneys to work out the details. I wanted to lead.

I didn’t know what Unique Genius was then, and I wasn’t really sure which actual job would let me do all of these new things I suddenly knew I wanted to do, but nonetheless I left my job in 2004 with a rough plan, not much savings, a wedding coming up in a few months and wide eyes and a whole lot of burgeoning excitement and almost debilitating anxiety. I was fully invested in exploring my strengths and skills.

And while I was pretty clueless about a lot, I knew I still needed to pay the bills. So I had taken a few baby steps and in the previous six months had lined up a consulting gig and convinced my company to let me do freelance legal work until they found a new in-house counsel. I was off and (crawling … stumbling) running.

And now, almost ten years later, after a lot of mix ups and mistakes and successes and creations and sleepless nights and blog posts and accolades and public speeches and near misses and far misses, when I hear another attorney tell me how he wishes he could be more proactive, I can only smile and think back to when I thought the same thing … and then (instinctually, clumsily, cluelessly, passionately) acted on it.

The best way to be proactive, I’ve learned, is to be proactive. Act. Take a step. Get on. Show up.

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  1. This post completely sums up everything that I’ve been feeling for, well, years now. Thank you so much for making me feel like I’m not the only “crazy” on out there!

    1. Hi Anna

      Thanks so much for the comment, I appreciate it. Yeah, it can be a lonely place sometimes, and you can feel like you’re the only one going through it. But we’re all in it together.


  2. As in so many prior posts, you conflate leaving the law with leaving a law firm. You wanted to:

    be more proactive. create the deal. do more public speaking. ring the bell. write more and publish it publicly. make something and service something. shake hands and schmooze and brainstorm and whiteboard. create something. lead.

    I’m a lawyer who does these things every day. And my path to all that has been through Legal roles.

    Your post dismisses–as its premise–the very best way for a lawyer to move from a reactive to a proactive career: by being a proactive lawyer! True, many lawyers don’t do the fun stuff. But surprise dear readers, many do! That’s why this silly caricature below hurts–not helps–people who want to DO, MAKE, and PLAN things:

    “This is real good. Real good. I like this kind of stuff. There is no deposition to manage, no judges to persuade, no briefs to trudge through. This is so creative. We’re doing something, we’re making something, we’re planning something. It’s so proactive. What I do every day as a lawyer is SO reactive.”

    You’re advancing a false notion of some narrow kind of lawyering, suggesting people should “leave the law.” But the fastest path for existing lawyers to the fun stuff is by being the kind of LAWYER they want to be.


    1. Hi Michael

      Thank you very much for the comment. I think you make a great point – many lawyers feel or think they should leave the law … when they really shouldn’t. They could be (or already are) great lawyers, and should likely explore how to grow and optimize their Unique Genius within the law. They actually are in the right profession, but something else (the firm, the grind, the practice area, etc.) is not working for them. When things get down, it’s easy to play the blame game, and sometimes law is blamed unnecessarily.

      But your point that the fastest way to the fun stuff (which I’ll also take the liberty to interpret as also being more confident in one’s role, enjoying what one does, being good at what one does, gaining self worth, etc.) is not always by being the lawyer one wants to be. That’s because many of us have realized that we do not want to be lawyers any longer. It was a mistake for us to go to law school in the first place. Our skill set is not in alignment with the role’s requirements. We are not confident in what it takes to be a lawyer. We are not capable in, nor do we enjoy, managing the anxiety and responsibilities and duties that being a lawyer requires. And our working environment in reality does not allow us to find or create paths to lead a career in law that we would like. And the legal jobs that we might enjoy are few and far between, or we feel intimidated even applying to them. In short, for us, the law isn’t fun, it won’t ever be, and we need to change.

      It’s unfortunately not a silly caricature: it’s a reality for many now, and something I personally have worked very hard to put in my past.

      I think is a great point you bring up, and many people who contact me say they are so tired practicing the law, but I think that there needs to be more critical analysis of whether leaving the law is the right thing to do, or just an easy excuse and really just a distraction. I see a future blog post … ☺

      Thanks again

  3. Thanks for the thoughtful response Casey.

    You summarized my critique well as “the blame game.” I just want to be sure that lawyers who are unhappy don’t assume that the entire Legal profession looks like their current job, since that faulty assumption rules out a bunch of alternatives. Shouldn’t we ask, “what alternative jobs (Legal or Other) have features that take advantage of my Unique Genius”?

    I do understand that many lawyers can and should leave the Law.

    I also understand that sometimes reaching escape velocity takes such an explosive rocket that it can’t be done without causing some serious destruction to what was. But for those with the stomach for a little more nuance, the path to the fun stuff might not require a different profession, just a different job.

    Thank you Casey for guiding so many of us to everything we can be!


  4. Every day I fantasize about that moment when I can sit back, put my hands behind my head, and count every element of my current law practice that no longer plagues me. And I’ve done that for the better part of the three years I’ve been practicing.

    As with most, however, the thought of making that first leap terrifies me — overwhelms me — to the point where my eyes gloss over as I skim job listings and become nauseated. It’s not as though I’m making a substantial salary working in a small, one-office, < 30-attorney general litigation (read: insurance defense with a dash of collections and workers' comp) firm. But the money I make is consistently deposited every other Thursday evening, and, at 30 years old, I've grown to like being able to pay the bills without nail-biting over my budget.

    Nonetheless, I recognized "long ago" that my Unique Genius wanted no part of this adversarial, pedantic existence, replete with manufactured urgency, angry letters, "effective billing," and lifeless writing. I look at the partners at my firm (and elsewhere) and realize that I have no desire to be in their shoes someday. And, to date, I have been exposed to no area of legal practice that appeals to me.

    Fortunately, I have begun to take baby steps, and have been gradually increasing the balance of my savings account just in case my time as an attorney ends before my time as something else begins. Still, though, I struggle to find my calling, and I fear being in this same position on January 7, 2015.

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