What Bilbo Baggins can teach us about leaving the law

I am a big fan of the J.R.R. Tolkien books.

I just re-read the classic “The Hobbit”, and it inspired me to shoot a short video about what the hero of the story, Bilbo Baggins, did time and time again … and how what he did is something we all need to do as we leave the law. Watch the video here. I hope you enjoy it.






Are you ready to leave the law? Are you really serious that now is the time for you to explore your dream career?

If so, you have found your tribe.

At Leave Law Behind, we have developed the proven process to find your dream career. Click here to find out how it can work for you.


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How not saying these two words can accelerate your dream career out of the law

I recently emailed with a fellow member of the Leave Law Behind Online Coaching Program who is at the exciting stage of identifying and then interviewing for careers out of the law.

She’s building momentum – some of these job descriptions are shaping up to be a fit with her Unique Genius … with her skills and strengths.

But as we reviewed many of these specific jobs, her fears and self-sabotage of the actual change required to leave the legal profession would still arise.

This manifested specifically through her saying “I don’t …“, as in:

  • I don’t think I want to do [“NON-LAW” JOB X] ”, or
  • “I don’t know much about [THIS ASPECT OF “NON-LAW” JOB X], so I guess I won’t pursue it” … and on and on.

Fear of change

Saying “I don’t” is a manifestation of our fear of change. It’s a way we think we protect ourselves from the unknown … but we are really just sabotaging our growth and development.

So she and I worked together on some new ways to re-phrase … or reposition … or rethink …

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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 christina@duchessofdupont.com.

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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