What Suffering a Broken Foot Taught Me About Leaving the Law (Part I)

I broke my foot recently. Freak jogging accident. On crutches for four weeks, and then a walking boot for another four. But no surgery needed, and I’m healing well.

And while I can see my injured foot each time I look down, my recuperation has made me think of other injuries we suffer from, but cannot see that easily … many of which firmly get in the way of our path to leaving the law.

There’s a big revelation in the short video I shot this week, and it’s one that you absolutely need to consider and face as you explore leaving the law.

To your success,


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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.

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[LLB Readers Write In] On Finding My Inner Duchess: How I Went From Attorney to Fashion Entrepreneur

I love hearing stories from the Leave Law Behind community, of unhappy attorneys first realizing they want to do something different to those amongst us who take that first step and actually leave and do something else.

Here is the story of Christina Arenas, a Leave Law Behind community member just like you, who recently took the courageous step to leave her full time attorney job and pursue her dream as an e-commerce entrepreneur.

Her online store Duchess of Dupont curates an eclectic mix of lingerie, swim, and leisure wear. And she’s providing discounts for LLB readers! – email Christina directly at

In the below post, Christina takes us through her journey of leaving the law, how she identified her entrepreneurial vision, how she managed her finances to make this shift, and the 3 main lessons of becoming your own boss that she wants to share with you.

I think you’ll find her experience and bravery in facing the unknown and following her dream insightful, actionable and inspirational. I surely did.

Take it away Christina …

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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.

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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.

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If you’re not happy as an attorney, then you’re likely this

We attorneys have been trained to be right.

Whether it’s in a contract negotiation, a trial, an interaction with a law firm partner or advising a client, we are trained to be right.

Doesn’t mean we always come out on top, but we sure do try.

Because being right is synonymous in our eyes with being strong and in control and admired and winning and valued and making it and success.

And that need to be right all of the time continues as we explore leaving the law.

But needing to be “right” as we leave the law can also be one of our biggest blockers to leaving. Because instead of being right about a fact or a point of law or a policy, we instead perpetuate being right about why we can’t or shouldn’t or won’t leave the law.

  • I know for near-certainty that I’m not worthy of a non-law job.
  • I’m sure I could never do the work of leaving the law.
  • I’m 99.9% positive I will never make in a non-law job the money I make now as an attorney.

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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.

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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,

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How to have one of the most insightful, inspiring and life-changing talks of your life

Hello ~Contact.FirstName~,

At Leave Law Behind, we are real people who are committed to helping you leave the law and transform your life for the better.

One way we do this is by offering you free consultation calls with us to talk through your fears of leaving the law, identify best next steps and discuss how we can help you.

These calls are life changing. As one fellow Leave Law Behind community member exclaimed at the end of our call, “Casey, it has been a very long time since I have had this much hope for my life!”

We want you to have the same hope

But I know some of you aren’t signing up for our calls, because you think you can’t find the time, or you feel you can’t find a safe, confidential, quiet place to talk.

You don’t want to call from your law firm desk, or you can’t sneak away from the office, or you feel someone at work might hear you talking about leaving the law.

I spoke with a Leave Law Behind community member this week while she sat in her car in a parking lot safe enough away from her law firm’s building.

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