Leaving the Law Step One: Recognizing and Overcoming Risk Aversion

Tips for Lawyers Who Want to Leave Their Job But Are Struggling to Conquer Their Fear of the Unknown


Are You Risk Averse?

A while back, I wrote about a “disease” many professionals and most law firm lawyers I know develop over time: the “Sunday Scaries.”  Today, I’m talking about another “disease” that is quite common in the profession: extreme risk aversion.

In my last post (which you can find here) I wrote about how anyone can and should take a page from Sandra Bullock’s character (Debbie Ocean) in the movie “Ocean’s 8” to become less risk averse and take more chances in life.  Today, I’m going to delve a little deeper into this concept, specifically as it relates to Biglaw attorneys and those lawyers stuck in a career rut who can’t seem to figure out why they can’t just move on already.

First off: two questions for you.  1. Are you a lawyer?  2. Do you think you are more risk-averse than the average person?  If you answered yes to the first question, I can almost guarantee that you answered yes to the second one.  If you’re a Biglaw lawyer, then I’d bet the farm that you said yes to the second question, because really, is there any group in the world more risk averse than Biglaw lawyers?


Why Are Lawyers So Risk Averse?  It Starts Even Before Your First Day of Law School

Let’s take a few steps back.  How risk averse you are is part nature (maybe you were simply born to be a bit more fearful of taking chances) and part nurture (the environment you grew up in and the one you live in now).

For many lawyers, the aversion to taking risks started even before law school.  How many lawyers do you know who went to law school because college was coming to an end and they had no idea what they wanted to do?  I’m raising my hand really high over here.

For many, going to law school is a way to postpone that career decision for another three years.  At the time, you think that you are just putting off the decision for later, but really you are making a HUGE decision!  Of course you can get out of the profession whenever you want, but by going to law school you are making a giant commitment.  The financial sunk costs alone of law school almost guarantee that most people who graduate from law school end up in some sort of legal career for at least a few years.

So you choose your profession, all because you were too scared to take a risk and try something “different.”  Instead of taking the chance at a non-traditional job, trying out a few industries, dabbling in one thing and then the next, many people go to law school because it is simply the easy, safe choice.

Everyone knows the old phrase “you can do anything with a law degree” (wait, can you? I’m not sure of that yet, but I do know there are skills you learn in the law that you can transfer to almost any other industry, like the ones I wrote about here) so getting a law degree is a no-brainer for many.


Law School: Where the Serious Risk Aversion Training Begins

You enter law school, already having stopped taking risks.  And when you get to law school, that is when the real, full-time risk aversion training begins!  Law school trains you to “issue spot,” which basically means: look for problems everywhere.  Law school exams usually consist of just one giant “fact pattern” that students read and are told to identify all of the issues (problems) they can find before the time is up.

In law school, you don’t really learn to solve these issues, you just learn to identify them.  Which means you are training your brain to look for problems everywhere – the more you find in a fact pattern, the more legal issues you can raise in your exam essay, and the better grade you’ll get.

What’s unfortunate about this is that you are training your brain to find problems (many times even when they don’t exist), but you are never training your brain to find the solutions to them.  So your worldview becomes one of problem here, problem there, problem everywhere – with no resolutions in sight.


Biglaw: Where Full-On Risk Aversion Sets In

If law school trains you to issue spot, what Biglaw does is beat that into your head every day.  A Biglaw associate’s day consists of issue spotting and then, hopefully (if you’re good at your job), coming up with solutions for your client.  That’s the main difference between law school and the real world – in law school, your job is to identify the issues, but if this was all you did in the real world, your clients would be out the door and into the offices of a more business-savvy lawyer before you know it.


What Is So Wrong With Being Risk Averse, Anyway?

So you’ve become risk averse.  You don’t take chances.  You over-prepare for everything.  You see problems everywhere because you can’t just turn off that switch.  When I worked in Biglaw, there were rumors that someone I worked with had a sort of “apocalypse bunker” in his Manhattan apartment.  Since it was Manhattan, it wasn’t really a bunker, but supposedly he had a spare room where he kept canned food and some sort of weapons for self-defense in case the apocalypse were to ever descend on NYC.

While this is the extreme, and this dude was weird (I don’t think he built this bunker just because he went to law school – there were other issues going on), it is certainly an example of how risk aversion can trickle into all aspects of your life.  Always looking out for the worst, always on high alert thinking that the apocalypse is just around the corner.


What Does All of This Have to Do With Career Change?

What does any of this have to do with career change?  For those lawyers who are stuck in their Biglaw or other jobs, a main roadblock to getting out is the fact that they are so risk averse.  They see problems everywhere and can’t imagine how they’ll possibly survive if they take the leap and leave, so they stay.

“The Devil you know is better than the Devil you don’t,” is a phrase people around the firm would often cite as a reason why they would never leave their current firm for another one.  They figured it was better to stay somewhere miserable but predictable than to try something new.  If some lawyers are so risk averse they wouldn’t leave one firm for another, imagine what it feels like to leave the profession entirely?  Most lawyers can’t even imagine this, so they stick around.  For just one more year.  Ok, maybe two.  Until that “just one more year” turns into a whole career.


What You Can Do

If you are one of those lawyers looking to leave, but are too scared to make the jump, there are so many things you can do to shift your mindset and make the change happen.  Here are a few to get you started.

1. Imagine the worst case scenario and then think about the steps that it would take to actually get there.

The “worst case” is going to be different for everyone.  Usually what comes to mind is that you’ll end up homeless on the streets, so let’s work with that scenario.  Becoming homeless is quite the leap from a Biglaw lawyer’s reality.  Could that really happen?

Think about all the things that would have to happen for you to really end up homeless on the streets.  Your entire support network would have to abandon you.  You wouldn’t be able to find a job anywhere (and I mean anywhere – not in fast food, retail, babysitting; nothing).  You’d blow through your savings.  Nobody would lend you a hand.  Etc., etc.

After you’ve listed that all out, reflect again on your “worst case” scenario.  It probably isn’t as bad as what you imagined.  Maybe your worst case is really that you’d have to get a retail job to pay your rent.  Or move in with your sister or your in-laws.  You’d have to give up your expensive dinners out or your vacations while you figure things out.

Not exactly as terrible as your gut instinct’s “worst case” scenario was, now is it?  Hopefully thinking this through will help you to become a little risk averse when thinking about your career change – it might be a little risky, but you’re not really risking everything.

2. Take a few mini risks.

Your dream might be to walk into your boss’ office right now, tell him you’re quitting, and walk out the door without ever turning back.  But that’s not most people’s stories.  We might daydream about this moment, but the reality is that a lot more time goes into getting up the courage to take the risk to quit.

If you can’t even fathom being the person who goes into her boss’ office one day to resign (whether it’s dramatic or not), you should start practicing what it feels like to do things that give you that same adrenaline rush.

Start with something small.  Maybe you micro-manage all aspects of your life in order to cut the risk out of everything you do.  If you choose where you’re going to go to dinner, what party you’ll attend or what movie you’re going to watch every time, there is a low risk you’re going to be disappointed or uncomfortable.  Why not let someone else make the plans once in a while?  Sure, there’s a risk you’ll end up doing something you don’t love to do, but the stakes are low and you’ll start to feel what it’s like to give up some control.

Do this little by little and pretty soon you’ll be able to picture yourself turning in those resignation papers, maybe even leaving Biglaw with nothing else lined up.  You might feel scared, but you’ll be used to that feeling and will recognize it as excitement rather than fear.  Being a little risky sometimes is fun and the reward can be sweet.

3. Cut back on expenses.

For many people who want to switch jobs or careers, money (or rather, lack of) is their biggest fear.  How will you possibly survive if you don’t work in Biglaw?  Hopefully you haven’t trapped yourself into golden handcuffs yet (if you want to learn more about this, read my post on Golden Handcuffs here).  Even if you aren’t wasting money, there are still things you can do to prepare for a job change and a decrease in (or temporary suspension of) your income.

Think of all the areas in your life that you spend on and experiment with where you can cut back.  To give you some ideas, here are a couple of things I cut back on when I decided I was going to leave my corporate job, but still didn’t know when (it wouldn’t actually happen for another year or so):

  • I stopped buying new work clothes. This helped me both to both financially prepare (since that was a big cost of mine) and mentally prepare (since I was constantly reminded, when I put on the same work clothes over and over or stopped myself from buying new ones that I wasn’t planning on staying in a business casual environment for much longer) to leave.
  • I used the free gym at work and stopped spending money on expensive fitness classes. Our gym at work had everything you’d need to work out, but I told myself for so long that it was “weird” to work out with my colleagues, so I never used it. Once I decided that these people were not going to be my colleagues for that much longer, it was easier to suck it up and work out with them.  I should have worked out there much sooner than I did and really I was silly for not doing so, but that’s a post for another day.

4. Get inspiration from others who’ve already done it.

You might feel like a rebel, but you’re hardly the first one contemplating leaving a traditional career.  I felt (and still do, sometimes) like I was doing something totally crazy when I left my Biglaw job, but once I started looking around I realized I was definitely not alone in taking the jump.

There are so many resources out there to turn to for inspiration!  I’m going to do a round-up post soon on all of my favorite law-related (and leaving-the-law-related) books, but in the meantime check out Life After Law: Finding Work You Love with the J.D. You Have by Liz Brown, Leap: Leaving a Job with No Plan B to Find the Career and Life You Really Want by Tess Vigeland or When to Jump: If the Job You Have Isn’t the Life You Want by Mike Lewis, all of which you can find on Amazon (affiliate links).

Oh, and you can always talk to me, too!  Feel free to send me an email (hi@theunbillablelife.com) if you have any specific questions or just want to chat more about what it was like to leave Biglaw and what it feels like to be one year removed from it all.


Remember: You Can Always Go Back

Lastly, I have a special note for those contemplating leaving Biglaw – remember you can always go back.  Really, you can.  And when you do decide to leave, people are going to tell you just that and you’ll wonder if you will be back in a few months, lost after not figuring out what else you wanted to do with your time.  It’s comforting to know that Biglaw will always be there, but of all those people who went before you, all of those associates who “ripped the Band-Aid off” and left Biglaw – did any of those people ever really come back?  Probably not.

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