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

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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.



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 is in line with our Unique Genius. For others, this could serve as a way to leave the firm as an interim measure to one day leaving the law altogether.

But before we email our resume to Jules at Hire Esquire, there are four things we should do first:

1. Explore our Unique Genius. First and foremost, we need to take the time to explore our strengths, skills and enjoyments … so we can then see if our skill set is even a fit for this job.

Let’s feel confident about what we are good at, and also be honest about what we don’t really excel at. We must understand where we add value, and be honest about where we add less to the conversation. We must really highlight what we enjoy doing and be honest about those things that we find boring or frustrating.

This is an essential part of the work I do with clients, and the main three questions (to ask yourself as well as friends, family, colleagues and others in your life) that are the basis of exploring the one’s Unique Genius are:

a. What compliments do people consistently provide you?

b. For what type of advice do people come to you?

c. What would you do for free?


2. See if the responsibilities of this job align with our Unique Genius. Instead of applying to a job and hoping they like us and pick us, let’s flip this dynamic on its head. Instead of us trying to fit ourselves to a job, let’s be patient and confident and let the right job align itself to us.

So, once we have a good idea of the traits, skills and strengths that make up our Unique Genius, then reconcile it to the Hire an Esquire job description below. Does working on a contract basis fit what you are looking for?  Does the fast paced life of working with a start-up align with what we are good at? Are we good at contract review? Do you think we’d enjoy working in the tech space? Do we enjoy corporate m&a? If we haven’t yet “founded and operated a business”, what have we done entrepreneurially at our firm that might be its equivalent? If our knowledge of “venture capital investments, angel investments, convertible notes” is light, what else have we focused on that could be of interest?

Let’s apply to this job because there is no reason not to. Let’s apply to this job because not doing so would be to miss a solid opportunity. Let’s apply to this job because it is in perfect (or close to perfect) alignment with our skills and strengths. Let’s apply to this job because the requirements of the job are essentially begging us to apply to it. Otherwise … let’s not apply.


3. Reposition our resume. If we see a fit between our skills and strengths, and this job description, then let’s make sure our resume reflects this.

While this is an attorney role (and not a full-on non-legal marketing or tech or account management or product management or operations job), it’s not a traditional legal job, and its description is asking for a broader skill set, so we still should consider repositioning our resume.

Really probe as to what this job is looking for. I see the words “exceptional” and “hybrid” and “innovative” sprinkled throughout the description.

I sense the themes of “consigliere” and “entrepreneurism” and “just-get-things-done” throughout the description.

Let’s spend the time to position our resume so our current skill set and experience speaks to what this job requires and really needs. We of course may want to talk about the deposition strategy we utilize, or the extensive research we have done for a case or how we have minimized litigation risks for our clients or how we have analyzed litigation exposure.

And let’s also get creative. We may also want to show how we think quickly on our feet. We may want to show how we get-things-done. We may want to show how we bring in new business (i.e. business development). We may want to show how we meet deadlines. We may also want to show how we are trusted.


4. Practice our narrative. We all have a story. We all have an arc to our life. We all are actors in our own movie.

Let’s return to our narrative. Tell your story. For Hire an Esquire as well as other non-legal companies, they want to ensure the people they hire have the required skills and experience. But they also want to hire people who are confident, relatable, authentic, trustworthy and dependable.

And we need to believe our story and who we are before anyone can believe us.

At first, maybe keep this narrative private so we can work on it and really believe it. We could say I am a closet entrepreneur stuck in a BigLaw attorney’s body and so my first step to “show up” and create a new reality for myself is to explore and apply to jobs like this one that enable me to utilize my legal skills while also possibly exposing me to other (non-legal) responsibilities that I feel very confident I could be proficient at with the right amount of training and exposure.

And while the Hire an Esquire job is for a legal position, it’s uniqueness could be a stepping stone to something outside of the law. So as we continue to explore non-legal jobs, our narrative could then continue with something like I don’t want to practice law because after three years of law school, after a number of years practicing as a lawyer, and after a thorough and patient and dedicated and fairly comprehensive exercise exploring my professional skills and strengths and identifying what I’m really good at, I feel very confident that my skill set is not in alignment with what is called for to practice law. To put it simply, being a lawyer is just not a fit for me. I feel very confident in saying this.

And then to go even further, to anticipate sitting in the chair across from that hiring manager at this future non-legal job, we could then further elaborate on our narrative, feeling so confident in all of the work we have done to get to this point, feeling so authentic in who we are and what we want, feeling so empowered in our tool kit of skills and strengths, that maybe we could go on with a narrative something like But in life, it is often times as valuable to find out what you don’t want as much as it is to find out what you do want. In that spirit, my assessment has empowered me to feel very confident that what is a fit for me is this potential opportunity at your company. Let me tell you why. While at first glance my resume may not place me as the most conventional pick for this role, I have done a solid audit of my strengths, I have comprehensively detailed a large number of skills I posses that are transferable and a real good fit for this role, I have met over coffee with a large number of professionals in this space and picked their brain, learned about their day-to-day, understood their best practices and have gained a deep understanding of what this job requires. Through all of this personal auditing and industry research, I feel very confident in not continuing to practice the law and rather pursuing this role as a next step in my career.

Good luck and let me know how it goes. Tell Jules that Casey sent you …


Lawyerpreneur – Attorney with startup experience (San Francisco)

Hire an Esquire – San Francisco, CA

Job Description: 
Hire an Esquire ( is building a small team of exceptional Associate-level attorneys to work with startups in San Francisco. Our innovative hybrid model gives you the flexibility of working as a solo practitioner, blended with the oversight and resources of an AM Law 25 firm.

You will be working directly with startups in a popular coworking space to provide legal services such as company incorporation, seed financing, contracts, and in-house counsel on demand. This will be in partnership with a top tier law firm, so you are able to tap into their document templates, Partner knowledge and mentorship, specialist attorneys and paralegals.

Work will be done on a contract basis, so you will have the opportunity to work as many or as few hours are you want.

Required Experience:

  • At least 2 years working as an associate at an AM Law 200 firm (preferably working with technology startups or on M&A / Private Equity transactional work during that time)
  • Have founded and operated a business, or have been an early employee of a venture-backed tech startup
  • Knowledge of company incorporation, start IP needs, venture capital investments, angel investments, convertible notes, term sheet negotiation, and/or start up employee benefits and compensation
  • Degree from a top 30 law school
  • Must be personable and able to interact directly with start up executives

Preferred Experience:

  • Performed legal work related to angel or venture capital financings
  • Business development

About Hire an Esquire: 
Hire an Esquire is a fast-growing venture-backed technology startup, with law firm clients across the US ranging from solo practitioners to AM Law 50 firms. We offer the first Software as a Service (SaaS) product that lets law firms and in-house legal teams find, manage, and pay contract-based attorneys online. Hire an Esquire saves clients at least 50% on both agency fees and admin time compared to traditional staffing firms, while paying attorneys a higher hourly rate.

Indeed Posting:

How to Apply:  

Email with resume and short cover letter.




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