Leaving Litigation: How Do You Know When You’re Ready to Leave?

Open DoorIn her last post, Elaine talked about how she networked her way into her new job. Today, she discusses a critical question for anyone considering a career move: How do you know when it’s time to leave?

How Do You Know When It’s Time to Go?

People often ask when I knew I was ready to leave. I know that it’s easier to say than to do; there are many reasons we find it difficult to leave the firm — substantial school debts, supporting a family, the fear of “falling behind,” not having a job during a recession or not being as marketable as a lawyer if you didn’t have something lined up already, the belief that you had already invested so much in a legal education and therefore couldn’t possibly throw it down the drain, the desire to maintain a high-income lifestyle, etc. etc.

Rarely is anybody ever 100% emotionally ready to leave. And rarely do you ever know if you made the right choice until you’ve had the benefit of hindsight.

Unfortunately, not all of us have a DeLorean with a flux capacitor that can make the decision easier for us.

It took me a few years to realize that I didn’t have the personality to be a good litigator or trial lawyer. Even if I put in the long hours and made sacrifices, my best would simply be average or sub-average.

I don’t think my path is right for everyone; it was just right for me.

I also recognize that I had a number of lucky circumstances that aren’t always available to everyone. For example:

  • I don’t have law school debt.
  • I don’t have children or other family members to support.
  • I could afford to be out of work for a period of time.
  • I live in the Bay Area, a hot bed of start-up activity.
  • I have a family member who happened to work in the venture capital/start-up industry.
  • That family member happened to sit next to one of the investors in my current company at some random business luncheon.
  • I went to two fancypants schools that helped get my résumé noticed.
  • I was able to get a taste of working at a start-up through my friend.
  • I never worked for the partner or boss from hell who would have forced me to leave the “reference” section of a job application awkwardly blank.
  • And I can barely tell the difference between Chanel and Jansport and therefore don’t spend that much on shopping — a blessing to my bank account.

I don’t mean to say things will always end well if you leave a miserable job.

I just think that you shouldn’t give up trying . . . especially if the choice is between staying in a situation that you are certain brings you unhappiness versus taking a (calculated) risk with uncertainty.

— – —

Word. I couldn’t agree more!

Read On:

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  1. Becca Bloomquist says

    What a touching, inspiring, and well-written article!!! Not to mention hilarious! Elaine, thank you so much for sharing your fascinating and educational story with so much heart, empathy, and practical advice. If the start-up gig ever gets boring, you should become a writer! 🙂 Alison, thanks for featuring this extremely helpful and interesting guest blogger!

  2. Bozo the Clown says

    I worked in BigLaw for 5 and a half months. I knew my time had come that I must leave BigLaw, when I left the restroom, with a large shitstain on the back of my neatly pressed, gray pin-striped suit pants.

    BigLaw was not for me.

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