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

Enter your email address to sign up for my FREE newsletter, full of motivations, inspirations, steps-to-take and ideas.


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.





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 to say “no” too often for my liking (I often had to shoot down exciting business ideas that may have run counter to our existing agreements) and I saw a limit on my ability to make real money (I did not receive any sort of sales commission or success fee on deals closed).

Since I left the law, I am proud to say that I have made a lot of professional and personal progress. First, I have done the work to really understand who I am. All of my writing about our Unique Genius comes directly from my own exploration of my strengths and skills and enjoyments. While our Unique Genius is always evolving and refining, right now at this stage in my professional life, I am very confident in what I am good at, at how I can help, where I bring value and what I enjoy.

I’ve also learned how to effectively apply and transfer my various skills as an attorney (issue spotting, persuasive writing, analytical argumentation, public speaking) to my non-legal jobs and responsibilities.

And I have networked a lot, enabling me to uncover new and cool work opportunities, and build a web of like-minded professional contacts that I can help and who will also help me. I have researched what jobs, career paths, lifestyles, and income streams are out there, and I have a very good idea of what I like in a career and a job … and what I don’t.

I have also encouraged my entrepreneurism. Through all of my one-step-back and two-steps-forward, I have taken risks, helped build companies, jumped into the unknown, started ventures with no guarantee or precedent (like this blog), and taken responsibility for opportunities that require hard work, execution, accountability and creativity.

I have left the law. I have done a lot since. I am in a good spot professionally. And I am happy with my career trajectory.

Yet there is still something that I have struggled with, that has always nagged me, that I am only now just coming to terms with.

Overcoming the fear of success

Only now am I really ready to be successful professionally.

Only now am I ready to really, really be extraordinary.

Only now am I no longer afraid of being successful.

Which begs the question: What does it mean to be afraid of being successful?

I began law school in 1996 for a lot of reasons: To stay in school longer, to avoid having to find a job right out of college, to get an advanced degree, to (one day) make some money and have job security and … really, because I was a Jewish kid that didn’t like blood so I didn’t consider going to medical school.

All not the most critically thought out reasons, of course.

And sure, I didn’t want to be a failure in life, and I went to law school because I wanted to do well. I wanted to create a nice life for myself. I wanted to make money and be respected and to help in some way.

But never did I really think of going to law school to be really successful. To be really unique. To be absolutely extraordinary.

Never did I ever say something like “I am going to law school because this is going to help me become a success, a really big success, a huge success, and live an extraordinary life”.

I never said that. And I’d venture that many of us have never said that.

Definitions may differ, but for me professional success includes being able to help – let’s say I can make investments or create business opportunities that I feel the world needs. For me, success includes being financially independent – let’s say having $10 million. For me, success includes being well known – let’s say widely recognized within my personal and professional circles. For me, success includes being influential – let’s say I can run for office or single handedly drive initiatives or gather support for positive change in my community.

Throughout all of the “risks” I have taken in leaving the law, and all of the entrepreneurial attempts I’ve made, and all of the initiatives I’ve created, and all of the work I’ve done on myself, I still have had a mindset of settling. I still have had a mindset that I wouldn’t be that phenomenal. That I wouldn’t be so unique. That I wouldn’t be extraordinary. That I wouldn’t be hugely, wildly, outrageously successful.

I knew what great success looked like for me, but I didn’t believe I could attain it. I didn’t believe it was possible for me. I didn’t believe I deserved it. I didn’t believe my friends and family would accept me as a huge success. I didn’t believe it was right for me.

How I now know I’m becoming a huge success

But now I’m ready for it. As hard as this is for me to write publically, for fear of being viewed as arrogant or crazy, lately, I have realized that great things are in store for Casey Berman. Big things. More money. Authentic accolades. Greater influence. Increased time. Laser focus. Genuine contacts.

And as we leave law, as hard as it can be, I feel we need to also begin to realize that being successful – hugely, wildly, immensely, intensely successful – is in store for us. We are not just going to leave the law for a better job and life. We’re going to be a huge success at it.

And here are some ways to do this:

1. Define it: First off, let’s define what success means for us.

List the tangible (I will have $10 million) and the intangible (I will be courageous) and the enjoyable (I will be a published novelist) and the ostensibly crazy (I will be something other than a lawyer). Keep writing and brainstorming.

List it all, and as we explore our Unique Genius, identify which definitions of success begin to align with our skills and strengths.

List it all, and let’s not hold back for fear of seeming arrogant or conceited or haughty or egotistical or materialistic or money-loving or narcissistic or overconfident.

List it all, have huge expectations, and let’s begin to feel really, really good about what success means for each of us.

2. Realize that being successful is the new normal for us. I recently realized that my being a huge success was going to become the standard for me, and not the exception.

Let’s begin to think that being a huge success is not just for other people, it’s for us unhappy attorneys too.

Just because we may have made a mistake in going to law school and didn’t think critically about it, doesn’t mean we can’t reignite our career and create a life that is awesome.

Just because we have a lot of student debt we have to still pay off doesn’t mean we can’t be extraordinarily rich down the road.

Just because we work in a depressing law firm now doesn’t mean we can’t be working in an awesome, dynamic company in the future.

Just because we feel that our legal skills are only for use as an attorney doesn’t mean we can’t find other roles and jobs and paths in which our legal training could be highly valued.

Just because the skills we are really good at and enjoy (public speaking, advocating, collaborating, creative writing) we may use in short supply now doesn’t mean we can’t soon be utilizing them as we grow our career down the road.

Sure it takes work and dedication and luck. But it begins with us. No one else out there is going to try and convince us that our career is extraordinary. We need to take our definition of success and believe we can do it.

3. Admit that we can handle the pressure. Being hugely successful is not without its challenges and hard work. There is a lot of pressure: The hard work to earn that money. The need to perform. The criticism from others. The accountability.

There is real pressure in being really great. That’s why many of us might be afraid of it; whether we realize this or not, we may feel that we do not want the added stress and exposure and responsibilities that come with being a success.

And many of us in fact want to leave the law because of all of the pressure and stress we face as attorneys is just too much. We handle the stress of always needing to be right. We handle the stress of always needing our research to be up-to-date. We handle the stress of fiduciary duties. We handle the stress of filing deadlines.

The difference here is that when we are open to being a huge success and we have worked hard to find that opportunity and that job that is in alignment with our Unique Genius, the pressure and stress is something we can meet head on. We are confident in our abilities and strengths. We enjoy what we do. And so this pressure and stress is a different type of pressure and stress than what we face as unhappy attorneys.

This pressure and stress is proof we are doing the right thing, because this pressure and stress is the form of the challenges we need to and should be facing. This pressure and stress is essential for us to grow. This pressure and stress is evidence that we’re leading our life in a meaningful way.

We can handle this pressure and stress, because when we believe we will be a success and we do something we are good at and we enjoy, this pressure and stress is no longer a cause for anxiety and knots in our stomach, but rather it is an opportunity to shine in the face of a surmountable challenge.

4.  Being a huge success means that we can finally really help. While we went to law school for many reasons, helping (the world, the underprivileged, the shareholders, our clients) was one reason that likely aligned with many of us.

And we sometimes find that now, ironically, being a practicing lawyer means we can’t really help as we intended.

We may not like the clients we represent. Or the partners of the firm we work for are only after making money for themselves. Or we are too busy managing the trial calendar we can’t really meaningfully interact with clients. Or we really want to help one set of clients (foster children) but can’t make enough money doing so and now need to represent people we can’t stand (soon-to-be-divorcees).

Being wildly successful means that we are in a position now to really help others. We can give money and time and our backing to those causes that are close to our heart. We can now mentor. We can now give advice. We can now lobby. We can now influence. We can now make investments. We can now lead. We can now sponsor. We can now inspire. We can now lend our name.

Being hugely successful means we can really give meaningfully to our world.

5.  It is who we are. This post was not easy for me to write. Who do I think I am to say to everyone that “Great things are in store for Casey Berman”?!

I worried what will people think of me. Will people think I’m arrogant? What will my friends and family think? Will readers think this is still impossible for attorneys?

But I have realized that being a huge success is the person we are all going to be. We are not frauds. We are not selling out. We are not bad if we are more successful than our friends or family. We are not horrible if we make a lot of money. We are not narcissistic if we thrive with attention. We are not becoming someone we are not. We are not being someone a lawyer isn’t meant to be.

In fact, when we begin to be ready to be a success, a huge, unadulterated, extraordinary success, we actually are beginning to become who we truly are. We are beginning to live our life with meaning and satisfaction and confidence and skill. We are beginning to live our life with strength and courage and optimism and ambition.

We are beginning to live our life again as we intended.

So …

We did not likely go to law school consciously thinking we would be a huge success. So as we leave the law, let’s make sure we do.


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 [...]

Read the full article →

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 [...]

Read the full article →

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 [...]

Read the full article →

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, [...]

Read the full article →

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 [...]

Read the full article →

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 [...]

Read the full article →

Some people critiqued what I did and here’s how I found a way to deal with it

April 21, 2014

I wrote a guest post for Above the Law’s Career Center last week. I thought it was pretty good, and some readers did too. They thought the article was helpful, answered some top of mind questions for them and laid out what transferable skills lawyers possess in a clear and accessible way. But some others [...]

Read the full article →

Seven skills attorneys have that the rest of the world would die for

April 5, 2014

Some of us lawyers want to leave the law: We are unhappy and dissatisfied with our work situation. We suffer long hours. We find our day-to-day lawyer tasks mostly uninteresting. We are demotivated because we are not included in the partner track discussions. We feel we receive little-to-no mentoring. We are weighed down by high [...]

Read the full article →