Leaving Litigation: What Comes Next?

NetworksIf you’ve read the prior posts in this series (about Elaine’s motivations for leaving BigLaw litigation, her pre-planning, and what happened when she gave notice), you’re probably on the edge of your seat wondering what came next?!?

What did she end up doing, and how did she get the job? Well, your patient waiting has paid off. Here’s the story, in great detail.

What did I do after I left?

I did a whole lot of nothing in August. I gave myself one month to travel and to not worry about money and to marvel at what life was like without seeing the perpetually blinking red light on my blackberry.

Then I started at the DA’s office.

I had an amazing experience for the next three months — despite never having previously appeared in court on a substantive matter, I spoke in court almost every day, argued motions, interviewed witnesses, and did three trials.

Some funnier and more embarrassing moments included a judge reminding me not to point an (unloaded) gun at the jury during a gun possession trial, as Juror No. 4, an elderly lady, looked really freaked out.

Yes, it was amazing . . . but I’ve never been so anxious, stressed, or sleepless in my life. I wasn’t a natural on my feet, I didn’t like performing before the jury, and I hated the combativeness of the proceedings. In short, I wasn’t a good trial lawyer. Nor did I care to be one.

It was good to know what I didn’t want to do. Problem — I had no idea what I wanted to do.

Coincidentally, a friend of mine was a few months into his start-up — he and a friend were developing an application for doctors’ mobile devices. He asked if I wanted to help on random legal projects, since his start-up involved a substantial amount of regulation but he and his co-founder were quite a long time away from being able to hire any sort of regular in-house counsel.

Since I obviously had nothing else to do except watch paint dry, I started helping him out.

Thanks to the power of Google, I cobbled together some agreements and policies and researched trademark and copyright law. It was pretty random and haphazard, but I found that I liked it.

And it seemed like a better fit for my personality:

  • I liked being in a more advisory role where I wasn’t fighting with somebody all the time.
  • I liked the collaborative, energetic, and innovative atmosphere.
  • I didn’t think contracts were boring; they were very rational and made good business sense.
  • I liked the general problem solving that came with the role.
  • I was satisfied being part of a team that was building something, even if I wasn’t solving world hunger or curing cancer.

In the meantime, I watched as my bank account continued its downward trajectory. I needed a job. And now I had a better sense of what I was looking for. I decided to look into start-up law, which probably meant “starting over” again.

How did I get an offer for my current position as in-house counsel at a start-up?

I had two main strategies:

  • The first strategy was more conventional — I went to legal recruiters and talked about finding a law firm that had good start-up law practices. In Silicon Valley, that was Fenwick, Gunderson, Cooley, and Wilson Sonsini. Of course, now that I had been free of the shackles of the blackberry for several months now, I was reluctant to put them back on again. However, I needed the training — and there was no way any company or start-up would hire me with my complete dearth of start-up law experience. I spoke to friends who either knew about these firms or worked there. (Perhaps the most useful was to talk to somebody who had just left the firm; that person knew the skeletons in the closet and had little incentive to paint a rosy picture, assuming you kept your discussions confidential.)
  • My second strategy was to talk to anybody I could who seemed like a good resource in the field of start-ups, venture capital, and law. I never realized the value of networking until now — where you talk to somebody in the area of your interest, ask that person for another person to talk to, and then grapevine from there. I talked to a lot of people.

Again, I got lucky.

I happened to have a family member who worked in venture capital. At a business luncheon in December, he happened to sit next to a general partner of a venture capital firm, who used to be a Biglaw partner. When I heard about the general partner, I didn’t think too much of it at the time. But by the time February rolled around, I was getting antsy for a paying job. I emailed the general partner.

Because he had been successful in both the law firm world and now the venture capital world, I thought he would be a great resource for me to better understand what start-up law was like, what in-house counsel did, and where/how I could get the best training.

He was incredibly generous with his time and, at the end of the meeting, suggested that I contact the general counsel of a start-up his firm had invested in. He knew that the start-up was looking for a lawyer, and even though I had little (read: no) experience, perhaps I could still learn something.

I contacted the general counsel for an informational interview. When we spoke, we seemed to hit it off on the phone, and he asked if I wanted to apply and go in for an interview.

There were a number of other secondary strategies:

  • I signed up for a bunch of legal job websites so I would get emails whenever a position opened up. These websites ranged from government positions to NGOs to in-house positions.
  • I called up my old law school’s career development office and got login information to access the alumni database and career database.
  • I visited the Stanford Law career development center and — after obtaining a letter of reciprocity from Yale — was able to access the Stanford Law database. I spent an afternoon at Stanford reading a bunch of books on Vault rankings and careers in legal and non-legal sectors.
  • I searched for MCLEs that might have speakers I’d be interested in meeting.
  • I briefly flirted with the idea of applying to another clerkship.

I ended up applying to the start-up and one law firm that was reputed to have a great start-up law practice and to treat its associates well.

With the law firm, I stated in my cover letter that I was seeking a first-year position. At this point, money was far less important than the training, and I was afraid that I would never get good cases if I were billed at a higher amount but had less experience than others in my class — and I knew start-ups were extremely money conscious.

As for my application to the start-up, I emphasized in my cover letter what I did at my friend’s start-up and how I wasn’t completely blind to what these companies needed and how they operated.

I decided to apply in waves; if these two top choices didn’t work out, I would apply to my secondary and tertiary choices.

I just wanted to be careful about not getting too scared, sending out a billion resumes, and then jumping at the first offer given to me.

Most recruiters had already told me that it was unlikely I’d be able to get a good firm position, given that I had been out of work for so long. The best and most experienced recruiter said that I had a decent chance — and that it would primarily boil down to whether I could sell my story on why I pulled the switcheroo from litigation to corporate.

My main theme was that, while I liked the substance of litigation, the practice of it was not a good fit for my personality — which I learned at the firm and at the DA’s office.

It wasn’t until I helped my friend out at his start-up that I realized I greatly preferred start-up law.

In the beginning of March, I was lucky enough to get offers from the law firm and start-up.

What made me decide to work at the start-up?

It was a surprisingly tough choice.

  • I felt like I would get better training at the law firm because I would see more companies, more deals, and see the life cycle of a start-up — from incorporation to financing to acquisition or IPO. But emotionally, I wasn’t sure if I could go back to a law firm again, even if that law firm was supposed to be humane.
  • The start-up was incredibly attractive because it was new, was still figuring out processes, had different departments I could work with — and I would be the client instead of outside counsel. My concerns about training were alleviated by the fact that the general counsel — who would later become my boss — liked training associates.

I ultimately chose the start-up. The firm would always be there, but when else would I get the opportunity to join a start-up as the second lawyer without five years of corporate experience behind me?

I don’t regret my decision at all now. I have a great boss. I have a great team. I work with a variety of people, lawyers and non-lawyers.

I miss litigation, but I have a separate set of challenges now with contracts, contract negotiations, and solving whatever legal problems come up.

Compared to my previous experience, I have fantastically regular and predictable hours, where I can actually make and stick to my plans and have weekends off.

I don’t live in continuous fear that I messed something up; as a matter of fact, I feel that I’m decent at this and am appreciated for the work that I do.

And the mentors I was worried about disappointing remained supportive. For example, when I told the judge what I would be doing, his response started with, “Dear Square Peg…” and ended with him saying he would help me with references.

— – —
Next Up: How do you know when you’re ready to leave? And was it all worth it?

Did you miss the first parts of the story?

Image by gerard79 via stock.xchng.


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  1. I am a sixth year lit associate trying to make the transition into estate planning. Would you suggest saying in cover letters that I am interested in a first year position? What language did you use in your cover letter?

    • This is a great question, and I’ve sent it to the author to see if she has thoughts.

      My two cents would be to try to finesse the question in your cover letters, so you imply you’re willing to take a “demotion” in seniority without saying you’d be coming in as a first year. But offhand, I can’t think of a great way of saying it! Something like, “While many of the skills I’ve developed working as a litigation associate for the last several years will be transferable, of course, I do understand I’ll need to get up to speed in a new substantive area.”

    • Here are Elaine’s thoughts on the matter (disagreeing with me!):

      I think it’s great that she is considering the transition, even though her litigation background does not obviously and naturally segue into estate planning.

      I also think it’s a good idea to say that she is interested in a first year position because:

      • It immediately addresses the concern — does she expect to be paid as a seventh year, even though she has the experience of a “0” year? That would be the worst combination because what client would want to pay a lot of money for a senior attorney with little experience?
      • At the same time, she is not really on the same level as somebody coming right out of law school. She knows what it’s like to be a professional (which is surprisingly valuable), she has established some credibility that she can work hard and won’t just nonchalantly jump ship. So in some ways, she would be the best first year ever.
      • And let’s be honest – they pay us quite handsomely. Depending on her financial situation, I’m not going to turn down the right position for me because I failed to get an extra $20K (when our starting base salary was already so high).

      As a matter of fact, during my interviews at the BigLaw firm, I think a partner actually made the comment that it was a bonus I was seeking a first year position for those reasons. He said that I knew a lot more than first year but was also willing to come in at a lower rate. I was interested in working with start-ups, and since start-ups were notoriously cost-conscious, I was more likely to be staffed on those cases given my lower billing rate.

      Anyway, I tried to keep my cover letter down to only one page, but I tried focusing on: (1) coming in as a first year; (2) briefly explaining why I wanted to transition from one type of law to another (in a way that wasn’t overly talkative and non-bullshitty); and (3) briefly mentioning some transferable skills.

      Unfortunately I’m on my work computer right now and not my personal computer, so I can’t actually dig up the specific language I used.

  2. Hello, and thank you for this series of very helpful articles. I totally relate to not having the personality to be at ease with working in adversarial situations. I am wondering how you communicated this without being seen by future employers as soft or weak? Thanks.

  3. im fighting deperession at the moment. litigation terrifies and bores me. what other area can i delve into cos at the moment no one seem to want to employ me in non law fields that ive applied to

  4. Hi,
    I am in the process of figuring out how to leave a patent litigation position for similar reasons as Elaine. i found her articles helpful in that it is reassuring someone went through similar thoughts and landed in a good place. I believe in the idea that chance favors the prepared mind, and I think Elaine’s articles resonate that as well. Everyone who knows me and with whom I have shared my thoughts has said I should consider an in-house position before I get to the point where I tell them I think an in-house position would suit me well. However, my practical legal experience is at about 3 years, but I have an advanced degree in biological science and considerable business experience having run my family’s business for five years after college. So, my question is, other than networking, which I have built up strongly and am tapping in to, do you have any thoughts about how to find life science companies that might consider a junior associate for an in-house position? I especially liked one of Elaine’s points about the general counsel being willing to train associates. I think I need to find that as well, but it doesn’t seem like something you can learn without straight up asking the general counsel – assuming they even talk to you or respond to your email/phone call.

  5. Hi there,
    not sure if you are still responding to this post, but i would like to know what type of training if any did she take to transition to working with start ups. I am in a slightly similar situation where I have not practiced for the past 6 years but would like to go back to law either as first year lawyer doing corporate law or to specialise in law related to enterprises/start ups.
    Am wondering if there is any specialised training to work with start ups.

    Thank you!

  6. Elizabeth Rodriguez says

    Just wanted to note that this story is still very much relatable 8 years later (almost to the day.) As a 4th year “litigator” I am searching for a new path that is more fulfillable and better suited to my personality. Hope Elaine is doing great after all these years…

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