Thinking about leaving the law, but not sure where to begin?

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Above The Law


For so long, we were normal. Ever since we could remember, we got good grades. We did well at our extracurricular activities. We had energy, independence, ambition, goals.

We happily did what we were told. We pleased most everyone. We were liked. We moved through life at a nice clip. We had a plan.

And now as practicing attorneys … well … this isn’t always the case. Just like that, we’re kind of now the odd ones out.

We’re not ourselves. Our confidence as an attorney, and as a person, is lacking. Our direction seems off. Our sense of hope is not strong. We may even feel desperate. We’re down.


We’re going a little crazy.

We feel our schedule is no longer our own – we know too well that pit in our stomach when the partner hands us that assignment on a late Friday afternoon.

We feel we’re not good at some essential aspect of our job – we feel that we’re weak negotiators or we really hate to litigate or we’re horrible at managing a trial calendar or we just can’t build up a client base or we just can’t cite case law like we feel we should, and yet our job requires us to do this, day in and day out.

We don’t feel comfortable around clients – we may be introverted or just quiet or we feel anxious advising them because, really, we don’t feel we know what we’re talking about.

We feel tremendous pressure to keep up with the law – but we just can’t handle keeping up with the changes in the law or our research skills aren’t the best or we just don’t care enough to be up to date on every aspect of the law … but then we feel nervous that we might be missing something, and our brief won’t be that watertight and our work product won’t be that good and then we could be looked down upon or reprimanded or fired or worse yet sued for malpractice.

We view our life now in 6 minute increments – we are resigned to the fact that billable hours is how we measure our self worth and progress through a year, even though we know there are so many other ways to measure success.

And on and on and on. So much misalignment with our jobs as attorneys. We are confused and wonder how we got here.

And we’re scared. We are scared to admit that we have failed in some way. We’re scared to say that we have let people down. We’re scared to say that we wasted time and money in our lives. We’re scared to say that we may just not be all that great. We’re scared to think that we should just be grateful we have this job, even though we’re so unhappy. We’re scared to think that we’re going crazy.


But wait. Wait a minute.

Maybe now is the time for us to go a bit crazy. Just a bit. Hear me out.

Maybe now is the time for us to just set our gauge off a bit. We’ve been on a straight path for so long, and maybe our bodies and mind and spirit are calling for us to adjust course slightly.

Not to be crazy to jump with no net. Not to be discourteous. Not to disconnect from our loved ones. Not to retreat from society. Not to be harmful to ourselves. Not to be irresponsible.

But to be crazy to think just of ourselves for once. To let our skills and strengths and enjoyments (and not stature or prestige or money or title or because-we-should) to inform what our professional steps should like. To listen to our inside voice. To read more into coincidences.

To be crazy to put ourself out there. To have nothing to lose. To not worry about being embarrassed. To not worry about making a (small) mistake. To not worry about taking a (small) risk.

To be crazy to iterate on something. To be open to producing. To begin to create. To begin to help people.

To be crazy to make money off selling something we love. To be thought of as an expert in a certain area. To be interviewed. To be read about. To be followed. To be admired.

To be crazy to be courageous. To be motivated.

Crazy to love. Crazy to do good. Crazy to stand up for something. Crazy to care about yourself. Crazy to care about others but not care necessarily what others think. Crazy to do something you’ve always wanted to do but haven’t.

“Some people never go crazy,” Charles Bukowski said. “What truly horrible lives they must lead.”

The crazy ones are the ones who help the world, for themselves and for others.

Let’s be crazy. And let’s do it together.


How I coach my clients to leave the law

by Casey on August 11, 2014


When I speak with a prospective coaching client, I make it a point to discuss in detail how we actually (step by step) leave the law behind.

This is because we often think leaving the law cannot be that easy. We think we can’t do this. We think we can’t excel. We think it won’t actually happen. We think leaving the law must be difficult.

The good news is that it’s not. Leaving the law is not difficult. It just takes a lot of hard work. And it must be done properly. It must be done patiently. It must be planned.

But leaving the law is easy to comprehend. Because there is a structure to it.

Five main steps. All taken gradually. Baby steps. Small, non-sexy, but nonetheless formative baby steps.

The baby step is how we build courage (I can do this). It is how we build motivation (I can do this again and again). And it is how we experiment and try things and successfully fail (Ugh, I actually can’t do this part, but I can easily pick my self back up and try again).

Let’s dive in.

1. We start with money. Yes, it may seem strange. When we think of leaving the law, we likely first want to talk about what new job we want, what role we should take, and where we should go into life, what title would fit us best.

But to leave the law, that isn’t where we start. Its starts with money.

We have so much student debt. We have personal and professional bills to pay. We have people to support.

We are worried about money. We have anxiety about money.

But many of admittedly don’t spend the time to deep dive into our money situation and really understand it and reduce the anxiety and find ways to be creative and empowered.

So that’s our first baby step. That’s where we focus initially. We focus on our money situation, we see what flexibility, if at all, we have, we let this situation help inform what we can and cannot do: Do we leave our job now? Do we stay put so we can continue to pay our bills and save up? Can we forecast the next 12 months to see what alternatives there are to staying in our job? Is there a light at the end of the tunnel? If not, what can I do to create some light?

We first come to terms with our finances. This builds clarity, honesty, responsibility and motivation. And it informs what we can actually, realistically, sincerely do as we move towards our dreams.

2. We then begin to focus on our identity and connection with the law. Some of us are so ready to leave the law and can’t wait for the day when we can call ourselves something other than “an attorney”.

But many others of us still can’t imagine calling ourselves something other than a lawyer. Our identity is so closely intertwined with being an attorney.

We can’t imagine being at a barbeque or a cocktail party or with family member and not being able to say that we are an attorney. Many of us feel we need to continue as an attorney because we have put so much time and effort and money into being an attorney. We have those lingering student loans from being a law student, and we all know those don’t go away in the event we leave the law.

So many of us feel we should keep being one … regardless of whether continuing to be one means we will still be an unhappy one.

So as we plan to leave the law, we take the time to thoroughly assess and come to terms with our need to identify with being a lawyer. And we discuss ways and incentives and alternatives that would enable us to break away and call ourselves something else.

3. Then, we delve into our Unique Genius. This is a huge portion of leaving the law. Many of us at this stage want to jump right into jobs. We want to focus on which roles would be best for us. We want to discuss how our new career path should frame out.

But here, at this important stage, we do not focus on any of this – jobs, career path, profession, titles. Not any of this. At this stage, we focus on ourselves. Us. Just us.

For so long in our lives, we haven’t thought of ourselves. We’ve thought of everyone and everything else as we’ve done things throughout our lives.

I know it’s not natural, but now let’s think of ourselves.

Be selfish and focus on what our skills, strengths and enjoyments are. We poll 5 to 15 of our friends, family and colleagues. We ask them to compliment us and we ask them for what advice do they come to us and then we ask them what do we really, really enjoy.

This takes courage to do. Some may snicker at us or not understand why we are doing this.

But others will understand. Others will be helpful. Others will give us great feedback.

We will distill what they say, parse it out, segment it into themes, and become comfortable with what we are good at. We become comfortable with ourselves and our Unique Genius. Some of these Unique Genius Traits will be predictable; others may come as a surprise.

Exploring our Unique Genius is a lifetime pursuit, so doing it now is the first step in a lovely and motivating dance to really learn who we are, what we are good at and what we really, truly enjoy doing.

And then, only then, only once we are gaining some solid footing to identify our Unique Genius, do we begin to see what jobs align with our skills and strengths. Doing work that requires what we are good at is a good formula for success, happiness and confidence.

As Maya Angelou said “You can only become truly accomplished at something you love. Don’t make money your goal. Instead pursue the things you love doing and then do them so well that people can’t take their eyes off of you.” 

So let’s brainstorm about jobs that we think align with our newly uncovered skills and strengths. List real ones (HR Manager, Compliance Director, Analyst) and make some up for fun (Chief Issue Spotter, Executive Consigliore, and Chief Cat Herder).

For once, let’s not think of jobs for reasons of security or salary or stature or because-we-should … but rather let’s think of jobs that may be the best for ourselves.

4. Then we prepare for the inevitable loss of confidence. Yes, we will get amped up and psyched up and totally excited about our future as we refine our Unique Genius and begin to see hope for ourselves.

And then something will happen. Someone will say something. Someone will inject doubt into our plan. Someone will call us crazy. Someone will call us entitled. Someone will say a bad attorney joke.

Or a fellow unhappy attorney will say it’s impossible to leave. Or our family won’t understand. People we respect will criticize us. People we want to please won’t be happy. World events will be ominous. The economy will take a lurch.

We will look at our children and wonder how we will provide for them. We will look at our spouse and wonder whether he or she approves.

We will feel we can’t take a risk. We will feel we will run out of money. We will feel that we can’t do it. We will feel that we have no right to do it. We will feel that we are not special. We will feel we do not have the energy or drive or ambition to be who we really, really want to be.

And we will be afraid. Really, really, truly, sincerely, to-the-bones afraid. And all we will want is this fear to go away, just to go far, far, far away.

But then, after struggling with the anxiety, things will settle down. We will realize that we are still standing. We will realize that we still have hope. We will realize that unlike other times, now we are not beaten down. We will realize that now, unlike other times, our will to make our dreams a reality remains strong. We realize that things are different now.

We will also realize, however, that we cannot eradicate our fears. We can’t banish them to a far, far, far away place.

But we can mitigate them. We can reduce them. We can proceed notwithstanding. In short, we have proven to ourselves we can show up and handle the pressure.

In short, we have realized that our fears our just that … ours. They are part of our identity, they are part of our drive, they are part of our strengths. Our fears can become part of our narrative, and part of our success.

Understanding and embracing our fears is an essential step in understanding who we are and why we want to leave law behind. As they say, our fears are obstacles to signify how bad we want something.

5. And then we get out there. All of this work has been preparation for one thing. To get out there.

Okay, let’s recap, let’s think about us, let’s imagine us in our mind, view what we have to achieve as we leave the law behind …

… we get a handle on our finances, we need our job now to help pay the bills, but we see a way out of the lawyer job we currently have and we see the light at the end of the tunnel and we have hope that we can one day leave …

… and we work to free ourselves from the need to always call ourselves a lawyer and now are we giddy and nervous to find out what else we can be and what else we can call ourselves …

… and then we do very difficult, time consuming, courageous, introspective, honest, scary work in delineating our Unique Genius, and really defining what we are good at and what we enjoy and for one of the few times in our lives, we think just of ourselves, and while we don’t feel comfortable being selfish and we still want to please others but we know it’s right …

… and then we crash and anxiety kicks in but know that we now have the momentum and the confidence and there is no turning back, we have seen that our dreams are attainable so even though we cannot see what is really ahead of us we derive comfort from the quote which says something like life is like driving a car at night with the headlights on – you can only see as far as your lights, but you know you’ll make it all the way home that …

… and so we move forward, to this step, step 5, and we take all we have prepared and we find people who have jobs or are in the industries we think our Unique Genius aligns with and we go meet them. We connect with them via our network. We find them through friends. We meet them for coffee. We meet them at their office. We call them. We Skype them.

And we aim to do two things: (i) research what they do to see if we like it, and if we do like what they do, we (ii) get leads of other people in the industry we can talk to.

We research their jobs and their lifestyles and what they do to make sure it’s not drudgery and should be crossed off of our list but rather that it could be in alignment with our skills and strengths. And if so, we ask for introductions to others in the space.

And we meet with them, we keep meeting with them, and hone our networking skills, and hone our narrative, and we cross some jobs off or list, and add others, and become more and more confident, and become more and more sure, and gain courage, and motivation and most of all, and we take our time (3 months, 6 months, 9 months, 12 months, 18 months whatever it takes) to create opportunities, and find opportunities out there so in alignment with us, that once we find them, we will be so confident in who we are, what we are good at, and what we enjoy, that there will be little doubt this job is for us.

And it doesn’t mean that we need to keep this job forever, or that this next job is the perfect fit for us.

But it will mean that this is the next baby step, the right step to take, for us to leave the law behind and start the career that is for us. To start the career and life that will mean success.

This is how we begin to leave the law behind. This is how the world wants us to succeed. This is how we show up and take the necessary steps to enable this success to unfold.


4 things you must do before applying to the cool job at the end of this post

July 29, 2014

Today, I want to introduce you to a job. It is a legal job as an attorney for a cool startup called Hire an Esquire. The description and hiring manager Jules Miller’s contact info is at the end of this post. For some of us, this could be the legal job we’ve always wanted that [...]

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5 simple ways for us unhappy attorneys to start becoming an extraordinary, huge success

July 9, 2014

Leaving the law It was in 2004 that I really left the law. That is when I left my in-house job at Workshare. The job was too reactive – and not proactive enough – for me (I was tasked with creating the legal framework to support initiatives created by Sales or Business Development), I had [...]

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3 ways to help us find the time to leave the law

June 24, 2014

While leaving the law takes a lot (of courage, effort, desire, confidence, momentum, hard work, flexibility, mindfulness) most of all, it takes time. A bunch of it. And for many of us, time is hard to find. We have trials to manage. We have court hearings to attend. We have agreements to draft. We have [...]

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Why we will not fail at what we really want to do

June 9, 2014

An amazing thing happens at a certain point with my coaching clients. As we explore our Unique Genius, we begin to get comfortable and more confident with our true skills, and strengths, and with what we really enjoy as a person. Through our Unique Genius exercises, we of course identify many of the traits we’d [...]

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We are scared, but here is why we shouldn’t try too hard to get over our fears

June 1, 2014

Many of the conversations I’ve had in the past few weeks with readers and clients have included some discussion about fear. Our fears can get in the way of just about anything and everything. They can get in the way of our dreams and goals and big plans. They can also get in the way [...]

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The real reason we lawyers are unhappy (and how we can turn it around for the better)

May 22, 2014

We are unhappy as lawyers now. We’re just not clicking in life as much as we’d like to. We’re in a funk. We are not as optimistic as we want to be. We’re wondering where all of our potential went. I have had and still have a lot of moments like this. Self doubt, anxiety, [...]

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I was interviewed by and all I got were some further thoughts I’d like to share with you

May 14, 2014

As some of you may know, I was interviewed for yesterday’s feature on titled “You Can Do Anything With a Law Degree: That’s what everyone says. Turns out everyone’s wrong.” (read it here) The article explores the misconceptions around the perceived broad usability of a law degree. Writer Jim Saksa (former-lawyer-turned-freelance-writer) encourages readers to [...]

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Only when I was really honest with myself did I realize why I had to leave the law

May 8, 2014

The main reason why I left the law is because I wasn’t really that good at it. I’m not looking for pity or using this as an excuse. I’m just being honest with myself. The skills that were required in my practice of the law as in-house counsel – attention to minute detail, detailed contract [...]

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