Ask Me Anything: Lawyer Career Transition
How do I overcome the fear of leaving big or the law?
Elena Deutsch, founder of WILL – Women Interested in Leaving (big) Law, and Casey Berman, founder of Leave Law Behind, are doing something new and exciting with Above the Law. They are writing a regular AMA column, where you’ll be able to ask the career coaches who specialize in helping lawyers, ANYTHING to help you clarify and take action towards a new role or alternative career.
Today, we address the question: How do I overcome the fear of leaving big or the law?
Below are our responses. At the end of the conversation, we invite you to pick ONE thing to put into action. Are you willing to do that?
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Elena: Welcome back to Ask Me Anything: Lawyer Career Transition. Today Casey and I are talking about the fear of making a wrong next move. Casey, often I hear from lawyers who want to leave big or the law, but are scared of making a wrong move. They say…”I’m scared of making a mistake. Should I stay with the devil I know?”
Casey: Thanks for bringing it up, Elena. This is fear of failure, rejection, and so on. There’s a few ways to look at it. I think the first thing is to understand where this comes from…and we can probably guess that you don’t want to “be a loser”. There’s perfection. It’s about winning. Fear of failure is something pervasive for people in general and when it comes to lawyers, there’s a level of perfectionism that we have in getting it right, the A-plus, 100%, no typos in the brief. There’s a level of perfection that’s demanded in the job.
Second, I want to pose a new definition for perfection, which is that “something is perfect if it is as it is intended to be”. For example, if you have an idea about going on a vacation or a birthday or a surprise for your loved one, and it all gels, even if it was raining that day, or even if the flight was long, but then you look around at the palm trees and say, “God, this is perfect.” It’s not because there were no mistakes or issues, but rather it just all turned out as to how you generally had it in mind. I like that idea of perfection better.
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Third, when we talk about fear of failure, I would ask, “Why is it bad? Why do we fear it?”
Perfection comes from how we’ve been programmed. There is a Leave Law Behind member who was a privacy and security expert in the law. He was up for a privacy and compliance role at a management consulting firm…totally his sweet spot. It was different from the law, more creative, and he applied and didn’t get the job. Talk about falling down to earth with disappointment. But this rejection actually guided him to a new firm where he left the law, and now he’s doing even more than compliance. Sometimes rejection is the universe nudging you in a different direction. The folks that didn’t hire him, gave him a ton of color as to why they chose the person they did who had 10 more years of experience.
They also validated for him that he was exploring the right “non-law” career space. “Yes, you’re not crazy to leave the law.” They validated his idea and gave him great interview tips. Then they gave them other ideas and people that talk to him.
Elena: That’s great.
Casey: Out of his rejection he got feedback, validation, and new contacts that steered him in the right direction. Literally, 30 days later, he landed his alternative job. That’s how I would read the cause as well as the benefits that can come out of this horrible thing we call rejection.
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Elena: Casey, that story exemplifies that he was taking massive imperfect action, or a perfect action, given your definition of “it’s just meant as it’s meant to be”. Let’s remember: Lawyers are trained and paid to think. When you want to make a change and leave the law, your practice or firm, you have to do something that you are not trained to do, which is take action outside of the well-defined guardrails.
Casey: Right.
Elena: You can’t think your way out to the next thing! You actually have to take action to become clear and informed as to ideal new options. Like your client did, he went on the interview, he took a huge courageous step to say, “Thank you so much. Can you please give me feedback on how come I didn’t get the role?” That gave him rocket fuel to land his next thing within 30 days. Kudos to him!
That reminds me of this quote I love, “Fear kills more dreams than failure ever will.”
Casey: Yeah, that’s beautiful.
Elena: Many lawyers stop themselves before they start. You’re stopping yourself in your head when you think, “Oh, I can’t. I wouldn’t like that because…” or, “I don’t know how to do that.”
This is the paradox, you’ve got to take action to get more information. Clarity comes from information and action. It doesn’t come from thought alone.
Whether it’s taking a course like Leave Law Behind or WILL, or calling that person from law school who made a great career change and you’re curious how they did it…you have to take action that goes beyond your comfort zone.
Casey: Yes – sometimes you have to take huge, massive action! Whether writing that email or reaching out to someone, it is about acting, which is a beautiful compliment and counterpoint to the inner work.
Elena I think that willingness to not be an expert is part of it, right?
Casey: It is.
Elena: A WILL member recently made partner at the same time she had a baby. After her mat leave, she went back and hated it and being a partner. She then got recruited by a vendor.. They created a job for her. Now she’s super happy and out of the firm! In all honesty, she’s scared because she’s never done this before AND finding it exhilarating!
Casey: Yeah.
Elena: We talked about this thing that exists in most companies outside of law firms, which is an acclimation period. They don’t expect her to perform at her highest level the first 3-6 months in the role. She’s expected to learn.
Casey: Yes!
Elena: It’s about trusting that you are smart enough and capable enough to learn something new.
Casey: I’ll add on to this by saying that, when you leave the law you’re not diving in the deep end. You’re not just blindly doing something. As you go through these steps that we’ve laid out, you talk to people, you research the job, you do your own due diligence. You meet them, they meet you. So when you do finally accept that offer and go into that alternative career, it’s been two, three, nine months, not nine years. You’ve talked with a bunch of people. You’ve gotten feedback. You’ve done a number of informational interviews. It gets to that point where you say to yourself, “This feels right.” So that fear that you had dissipates as you build momentum and confidence through the process.
Elena: Also, can we discuss that your next role might not be the perfect role? It might not be your dream job. That’s okay too, because you are going to learn so much about what you DO and DON’T want! You’re going to learn what feels right and what doesn’t. One WILL member, left her big law job for a hybrid legal/business side role at a startup. About nine months in, the startup began to wind down. It wasn’t going to become the next unicorn. She was excited to look for her next role because she knew so much more. She was focused and clear that she didn’t want any more legal, and wanted to be on the people management and organizational culture side of a business.
Casey: Right.
Elena: She’s on a path to be a chief people officer. It was a great stepping stone.
Casey:. Having a bridge, whether it’s non-law job number one, can then lead you to a non-law job number two. That first job can be a breather. You continue making money, do what you need to do, and learn new things.
Elena: Exactly.
Casey: It’s like getting into the club, you’re behind the velvet rope! You start meeting people, networking, connecting, and seeing what other opportunities arise. The fear you have to get over, is that you know and have to control everything. If you’re embracing the unknown, great, fantastic and lucrative opportunities can come your way. They will.
Elena: All right. Any take away tips from today’s topic: fear of failure?
Casey: Yes, let’s summarize what we talked about into a few key take-aways. Pick ONE to put into practice today:
- Adopt a new definition of perfectionism or reframe it. Try this out: “Something is perfect if it is as it is intended to be.”
- Look at rejection and failure not as a black mark or social shame, but rather as redirection, guidance and an opportunity to learn more.
- Take action, because we learn through action, not just by thinking. Pick one action to take today and do it.
- Choose to believe that the more action you take (informational and job interviewing) the better you get at it.
- See that any new role will help you learn more about what you like, don’t like, make new connections and open new vistas to future opportunities.
To send Casey and Elena your questions, submit them here: AskCaseyAndElena@gmail.com
Listen in as Casey and Elena discuss how to leave (big) law and more on the Love or Leave the Law Podcast.
Learn more about Leave Law Behind here.
Learn more about WILL – Women Interested in Leaving (big) Law here.
Elena F. Deutsch, MPH is the CEO of WILL – Women Interested in Leaving (big) Law. She helps attorneys who feel stuck and unhappy, clarify what else they can do, experience relief and act on their dreams. Since founding WILL in 2017, it has been her joy to help women (and a few men) transform their careers and lives. Her work has been featured in Above the Law, Bloomberg Big Law Business, The American Lawyer and more. You can find her on LinkedIn or at www.womeninterestedinleavinglaw.com.
Casey Berman (University of California, Hastings College of the Law ’99), is the founder of Leave Law Behind, a career coaching program that helps unhappy attorneys leave their legal practice for their dream, “alternative” career. Casey focused primarily on software licensing for five years before leaving the law behind in 2004. Since then, his career has helped him develop a wide range of skills, as Management Consultant, VP Operations, Chief Communications Officer and Investment Banker. Casey just wrote an in-depth article to help you land your dream “alternative” career out of the law, click here to read more.
