Ditching the Suit: From Corporate Law to Online Startup

I remember the exact moment I realized I wasn’t happy practicing law. I was sitting in my office on a Saturday afternoon, waiting for the phone to ring. The partner I worked for had made it a habit to ask me to come to the office on weekends and wait for him to call. It was a very nice and spacious office above the 30th floor, with a view of downtown Manhattan and the Hudson River. The visitors’ chairs were nicer than any chair in my parents’ house in Brooklyn or any chair I could have afforded before or after going to law school. The large wood desk conveyed prestige and expertise. The bookcases contained very impressive leather bound books that I was yet to read. The view of the Freedom Tower construction was spectacular.

It wasn’t easy for me to make it to big law. I wasn’t born in America, my parents couldn’t afford to pay for my law school education, I didn’t go to an Ivy League undergraduate school, and English was not my primary language. I had many excuses I could have made for myself, and many that I did make. Everyone was so proud when little old me,

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Little known ways to create that awesome opportunity

It’s true that when you see that opportunity, you need to grab it

And it’s also true that good opportunities (real quality occasions to grow and prosper and develop) often present themselves only a handful of times in one’s life.

And it’s also true that these fantastic opportunities don’t just show up out of nowhere. And particularly for an attorney that is unhappy with his or her practice of law, and wants to explore moving into something else, these (mainly) non-legal opportunities that we lawyers are well suited for (the compliance manager with the promising start up, the teaching job at the university, the HR role at the Fortune 500 company, the copy-writing gig with the legal focused publication, the COO role with the marketing firm, the in-house counsel role for the tech enabled services firm, the campaign manager role for the up-and-coming politician, the policy wonk with the think tank, the VP of Biz Dev role with the global manufacturing firm, the consigliore to the C suite, the well-spoken blogger, the detailed SaaS project manager) present themselves after we have done a lot (a lot) of hard, smart, and courageous work.

This work manifests itself in many (very non-sexy,

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Who killed your intuition?

Most likely, you did. As did law school, your legal training, and the social mores of the industry.

But don’t despair, it can be revived. I have proof.

Two weeks ago I attended and spoke at the Catapult 2013 conference in San Francisco. It was held by the remarkable Alison Monahan and Lee Burgess of the Law School Toolbox and Girl’s Guide to Law School. (I encourage you to sign up at catapult2013.com for future events they put on). The conference was focused on empowering law students and young lawyers to take control of their careers and think creatively about the future … right up our alley!

One the most interesting panels consisted of practicing lawyers who actually (believe it or not) currently enjoy their job. The panel was so insightful because each shared how long it took, and how much trial and error and experiences and mistakes they had to go through, until they found or landed in the law job they currently like. Many discussed how they pursued and worked in one area of law (litigation or patent law) because they thought it would be a good fit,

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One clear reason that I knew I wanted to leave law behind

[EDITOR’S NOTE:  The following is a guest post by a current technology transactions attorney and first time guest blogger on Leave Law Behind.  Here, he tells us how and why identifying a specific reason that he wants to leave law behind has been helpful in his transition.]

In my journey to leave law behind, it has been helpful to identify and constantly remind myself of the concrete reasons why I want to leave. Of a few that I’ve been able to ascertain, one obvious example is a mismatch of my personal values with those of most in the legal profession.

I parted ways with a small boutique law firm a while back. Although I wasn’t fired, the separation was very difficult. For a period of time after I left I placed a lot of the blame on myself and even began to question my competence as a professional.

A few months later I continued to reflect on the situation, still uncomfortable with how things had ended. I recalled that while at the firm we frequently received junk mail for various CLE offerings. The other attorneys would joke about how uninteresting these offerings seemed to them while I got really excited reading the pamphlets and thinking about learning something completely new and different.

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Three simple ways to channel your Sunday night anxiety to help you quit the law

Sunday night anxiety, that dread of Monday and the upcoming workweek that infects so many workers, actually comes early for many of us lawyers. Many of us lawyers work on Sundays. We go to the office because there is so much work to do, so many in-boxes to clean up, so many hours to be billed, so many partners to impress, so much rainmaking to do. So Sunday night anxiety for us lawyers actually could be renamed Saturday night anxiety. Or Saturday morning anxiety.

One client of mine told me that the best part of her weekend was Friday late afternoon. The week was winding down, most people had already checked out for the weekend and a calm usually came over her office and the whole downtown. But she could never enjoy her Saturdays because (you guessed it) Sunday was just another work day.

While it may take a while and a lot of hard work and a re-crafting of yourself and your profession to get to a point where you don’t have to work Sundays, you can use your Sunday work days to help you leave law behind. Here’s some simple ways how:


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The Second Step in Leaving Law Behind – Cut Your Losses

This article originally appeared on Above the Law.

As we discussed in the first article of this series, through Leave Law Behind, I work with many intelligent attorneys who nonetheless are unhappy and want to leave the law behind and do something else. They want to change their life and their work and their focus with the goal to be more satisfied, more confident and happier.

I tell them the first step in leaving the law behind involves getting a handle on their money situation; to become as confident and exact as possible in understanding (i) their expenses, as well as any (ii) safety net and other sources of financial support they can call upon if needed.

The second step in leaving law behind? Before getting one’s resume ready or applying for jobs or networking, the second step often involves getting over law school. Or in other words . . . cutting your losses. Or to be more blunt: Move on. Stop living in the past. Stop thinking you need to eke out more of a return on your law school investment. Focus on the road ahead.

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How to remove the risk from leaving law behind

I'm going in

 I’m going in.

I spoke with an attorney recently, and we had a great conversation about the issues she faces with the BigLaw firm at which she works. The lack of female attorneys for mentoring. The long hours. The dwindling chances of becoming a partner. Her mild depression as a lawyer. Her unhappiness as a lawyer. The allure of working in tech or marketing (or anywhere else “hip”). The realization that there is a bigger (and more lucrative) world out there than just being a litigator.

It was a great conversation and I’m happy to say that she is encouraged by all of the potential that exist for her beyond the firm and the law.

But she isn’t leaving the law. Nope. No time soon. She’ll be at her firm for a long while. She admitted as much to me.

Why? She feels that leaving the law is too risky. She feels that the potential for some sort of (huge, unmanageable) loss to arise from her leaving the law is too great for her to attempt it. Running out of money. Inability to pay her bills.

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How a lost dog can teach you to leave law behind

We see “Lost Pet” posters all the time.  Grainy pictures usually of sweet looking dogs or cats pasted into a Word document, printed up and duct-taped to neighborhood telephone poles.  Usually there is a big headline (“LOST DOG” or “HAVE YOU SEEN ME?”), a physical description of the pet (Male, 2 years old, Rottweiler mix), a name (“Obie” but also answers to “Tater” or “Daddy’s boy”), a last location (“Last seen near Lake Merced”), maybe a reward ($50) and a plea (“Her family is very worried.  They miss and love her very much”).

And as we pass the telephone pole, even in our rush, we may look around and check to see if, by chance, a dog or cat resembling this description is lurking by anywhere.  And when of course it isn’t, we imagine a scared little animal running around the streets.  We shudder a bit, feel sorry for the cold animal as well as the eight-year old who just lost her pet, and then we walk on, move on.  Not much we can do, really.

But there is.  While we may not locate the lost pet, we can seize on a valuable babystep to leave the law behind. 

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