What could you have been like if you were told “yes” more growing up?

[Quick note: Our Leave Law Behind Free Consult calls will be ending on July 15th. After that date, we will need to charge for our time. Sorry about that, but the demand on our time requires this. If you’re serious about leaving the law, sign up now for a Free Consult with me.]

Yesterday I saw a recorded talk from the businessman, speaker and author Simon T. Bailey.

He said that by the time a child is 17 years of age, he or she is likely to have heard the word “no” over 150,000 times.

And he or she is likely to have heard the word “yes” only 5,000 times.

We grow up hearing the word “no” 30 times more than we do the word “yes”.

30 times more.

He pointed out that the result of hearing all of these “no’s” creates a neurological pathways in the brain that shut us down from attempting what we are being told is forbidden.

The more you hear what you can’t do, what you can’t become, what you shouldn’t do, the more you don’t ever consider doing it.

Continue Reading

Do you feel that you can’t trust the process?

Many of us hesitate to leave the law because we feel we do not have an ironclad guarantee it’ll work. So we remain stuck as an unhappy attorney in a law job that makes us feel miserable.

In other words, we trust in the process that we can leave the law once we see that it’s certain we can leave the law.

But that isn’t how life works.

We know that. Guarantees only becomes obvious in hindsight. As Steve Jobs said, “You can’t connect the dots looking forward; you can only connect them looking backwards. So you have to trust that the dots will somehow connect in your future.”

I know, I know … I know what you’re thinking.

Trust?” you say, “Casey, I’m a lawyer. And I know Steve Jobs was a great business person, and sure, I admire him, and I put weight in his words … but still, I don’t dabble in trust or faith. I’m about evidence and what can be proven and what can be made certain and what can be guaranteed, or at least come real close to it.

Continue Reading

This email may make you angry

“A mind that is stretched by a new experience can never go back to its old dimensions.”

—Oliver Wendell Holmes, Jr., Associate Justice of the Supreme Court of the United States, 1902-1932


And that’s exactly what scares us about leaving the law.

See, we unhappy attorneys are miserable practicing law.

We lack hope that we can ever really enjoy our lives.

We are frustrated that we are not making enough money.

We wonder what we can ever be “good” at.

We feel alone and that no one in our lives or at the office understands what’s going on in our heads.

We feel guilty that we aren’t enjoying our profession, which we’ve spent so much money and time and effort to attain.

We all nod our heads at this.

But even with all of this misery … we still stall in taking even that small babystep to change our lives and explore leaving the law because in doing so we know we will evolve ourselves. We know we will transform ourselves. We know we will change.

Continue Reading

There’s no right way to do the wrong thing

There’s no right way to do the wrong thing. I heard this quote recently and it stuck with me.

It stuck with me because I am designing my life to do the right thing.

So too are the people working their way through leaving the law.

And, no, not the perfect thing, not the best thing, not the better-than-you-do-it-ha-ha thing.

The right thing. The right thing. The right thing.

The right thing for me. The right thing for them. The right thing for you.

The go-through-my-fear-and-do-it-anyway thing.

The I-went-to-law-school-without-really-critically-thinking-about-it-and-that’s-okay thing.

The connect-with-my-soul-and-not-my-ego thing.

The that-which-feels-good-with-me thing.

The don’t-check-the-box-to-be-successful thing.

The what-am-I-really-chasing-this-for thing.

The what-am-I-waiting-for thing.

The this-feels-right-I-want-to-explore-this-further thing.

The help-someone-else thing.

The I-don’t-care-any-longer-about-getting-a-ROI-on-my-law-school-and-career thing.

The surrender-and-accept-where-I-am thing.

The this-current-be-a-lawyer-at-all-costs-belief-system-I-subscribe-to-doesn’t-work-for-me thing.

The I-want-to-model-the-right-life-for-my-kids thing.

The I-am-really-powerful thing.

The I-am-not-alone-and-can-ask-for-help thing.

The I-have-this-one-ilfe-and-what-meaning-do-I-subscribe-to-it thing

The I-am-not-afraid thing.

The I-am-here-to-grow thing.

The I-am-stronger-and-grittier-and-more-persistent-than-I-can-ever-imagine thing

The I-realize-now-playing-it-safe-as-an-attorney-actually-doesn’t-really-make-me-any-more-safe thing.

The I-don’t-fear-death thing.

The I-can’t-disappoint-anyone thing.

Continue Reading

From Billable Hours to Bars: How I Left Restructuring Law to Help Skateboarders Find Nutrition

One of the most important choices you make as you leave law behind – before identifying which career outside of the law to pursue or how you format your resume – is about how comfortable you feel with evolving yourself from being “just an attorney” to being your “ideal self” … is about how you overcome your fears … and is about how you just keep moving forward even in the face of doubt. 

These are difficult topics to address and something most of us only talk about in private or in our own minds … so it’s a great topic for us as we go through the Leave Law Behind Program!

That’s why I asked recent Leave Law Behind graduate Jonathan Lozano (who left BigLaw and just started his own nutrition company) to share his experience in evolving from being just a restructuring attorney to becoming an entrepreneur, to embracing the unknown and to celebrating risk. His piece below is very insightful, inspirational and actionable, I encourage you to spend some time reading it.

And Johnny has just launched his new nutritional bar company,

Continue Reading

How knowing what you don’t like can help you

A core tenet at Leave Law Behind is exploring and then identifying and then continually refining your Unique Genius – those skills, strengths and enjoyments that you are so good at, that come so naturally to you that you don’t even think of them as special – and then finding “non-law”, alternative jobs and roles and careers and problems that call for your Unique Genius.

In other words, you identify your Unique Genius in order to see how you can best help and add value to the world and which jobs and roles are the best medium and channel to do this.

One of the reasons we are so unhappy as attorneys is because there isn’t a fit between what we do well … and what the job description of an attorney calls for.

But if you’re having trouble identifying what you’re good at, or what you enjoy, sometime it’s easier and a good first step to focus on what you don’t like … and what you don’t do well.

To be able to confidently and sincerely say “don’t like this” or “just kinda like it” 

Continue Reading

What his mother said when he told her he wanted to leave law school

I spoke last month at an event at my alma mater, University of California, Hastings College of the Law here in San Francisco. The event focused on highlighting for students across the Bay Area what alternative careers can you do with a JD.


After the talk, I answered questions from many students. A 1L, who is an undergrad math major, loves to code in his free time and, deep down, wants to become a software engineer, told me his dream job is to work at Twitter or AirBnB right down the block.

But he ended up going to law school because it felt then that law school was the right and responsible thing to do for this life. He said a JD is like a “pseudo MBA” and with his student loans, he can (for the time being) afford to live in San Francisco.

He followed up with me via email and described how anxious and confused he felt remaining in law school. In theory, he liked the idea of getting a JD, but he didn’t really feel the degree was aligned with what he wanted to do in life.

Continue Reading

“Permission to float”

I met with a client last week. We celebrated … she recently left the law!

So great!

But now she was struggling with the (apparent) uncertainty of her new life.

While she loved being away from the grind and the anxiety and the long hours of a lawyer, and she was excited about the new, “non-law” work she was doing now … she still felt she was missing something.

She said she felt like she was “floating aimlessly”.

I told her she now has permission “to float”.

And that floating was actually a good thing, and not to be feared.

I shot a short video to tell you more about what I mean: https://leavelawbehind.com/leave-the-law-permission-to-float.

Continue Reading

Five Skills Lawyers Like You Have That Non-Law Companies Need

What do you want to do? …Better to have a short life that is full of what you like doing than a long life spent in a miserable way …If you do really like what you’re doing, it doesn’t matter what it is … you could eventually become a master of it. It’s the only way to become a master of something, to be really with it. And then you’ll be able to get a good fee for whatever it is. So don’t worry too much.

—Alan Watts, British philosopher, writer, speaker, and popularizer of Eastern philosophy for Western audiences


This article was published in the September issue of the ABA Law Practice Today. And like that audience, if you’re reading this here, there is a very good chance you do not like practicing law.

You are likely bored by it. Or don’t like the adversarial nature. Or want a more collaborative profession. Or want to make more money in ways other than the billable hour.

You likely don’t consider yourself a good attorney. Maybe you even feel like a “fraud.” And you just want to identify a career that will call on your strengths and empower you to be more confident,

Continue Reading

How he got his non-law dream job through a cold email

I spoke with a client last week who recently left the law. A former estate planning attorney who just recently transitioned to lead the direction and management of planned giving for a local university.

In his new role he helps provide the strategic direction and long & short range planning to support the development of major gifts and alumni relations related to cultivating and soliciting donors.

Sounds pretty cool, huh? 🙂

It’s close to his dream job. “Planned giving” is an area he identified early on in our process that was in alignment with his skills and strengths, his Unique Genius, and also something he cared a lot about.

He did explore and interview in a number of other areas. His Unique Genius seemed to align with Strategy jobs and Project Management jobs. He got interviews through his network at a Fortune 500 company and a small startup.

But he just didn’t see a fit with these paths.

A (sincere, authentic, aligned) cold email

So I asked him how, then, did he get an introduction to the university which ultimately just hired him.

I could feel him smile over the phone.

Continue Reading