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This week, I am very excited to have former BigLaw attorney now author Amy Impellizzeri come by Leave Law Behind to answer a few questions that seem to always come up for many of us looking to leave the law.

And Amy is perfectly positioned to help us out. Amy practiced for thirteen years as a corporate litigator at Skadden Arps in New York City. She left the law, became a start-up executive and now is a full time author.

Her most recent book is a non-fiction piece, Lawyer Interrupted, published through the American Bar Association. I was honored to be interviewed by Amy for the book, along with others in the space like Liz Brown and Marc Luber.  It’s an extremely informative, well written and entertaining description of what it takes to leave the law (buy the book).


So, without further ado, let’s ask Amy some of our pressing questions!

How can an unhappy attorney “give up” all they worked on to become an attorney (law school, climbing up the law firm ladder, etc)?

This identity issue that you are describing is tied with financial uncertainty as the NUMBER ONE hurdle for attorneys thinking about transitioning from the law. And the truth is that successfully transitioning lawyers do not report that they have given up anything, or that they miss practicing law when moving on to another career.

You will still be an attorney in the next leg of your professional journey. Three years of study, a degree, and bar membership(s) do not need to vanish into thin air when you stop practicing law. And in fact, these assets will be the very tools that will distinguish you from other candidates as you transition. Every single transitioning attorney that I interviewed for Lawyer Interrupted reported that his/her law degree was the differentiator in helping them succeed in their next career.

Unhappy attorneys need to embrace the versatility of their law degree in making their next move rather than accepting the falsehood that the pinnacle and brass ring of every lawyer’s career has to be partnership at a law firm.

One way to look at the issue is this: you can graduate from the practice of law just as you graduated from law school. No one ever asked whether you were going to stay in law school forever … why would you assume you have to stay in the practice of law forever to honor all that you have worked for up until now?


What about money? Lawyers are often very worried that they won’t be able to make a sufficient living if they leave the law. This uncertainty is often the greatest objection most lawyers have to leaving the law. How can lawyers, who want to leave the law, attain a comfort level that they can also succeed financially?

So, the real question is NOT the one lawyers ask themselves when they contemplate leaving. The real question is NOT: “How can I replace my law firm salary with an alternative career salary?”

The real question is: HOW MUCH MONEY DO I NEED?

Transitioning attorneys need to take a hard look at their finances for areas of potential belt tightening. I spoke with attorneys who moved geographic areas to cut costs, who downsized homes, cars, caregiving expenses, and other costs. And nearly EVERY transitioning attorney (including me!) reported that one large category on the spreadsheet falls away when transitioning – that category I call “self-soothing.” These are the expenses that nearly every attorney admits to incurring while practicing law: Expensive meals, clothes, vacations, and things that are often unnecessary (—and indeed often go unappreciated) —but are accumulated in an attempt to comfort dissatisfied lawyers who feel entitled to spend the money they are working such long hours to earn.

Interestingly, of all the transitioning attorneys I interviewed for Lawyer Interrupted, the most financially successful attorneys (in the shortest amount of time) were those who “did it on the side.” That is, transitioning attorneys who pursued side ventures at night or on weekends after long days/weeks of practicing law. Attorneys who planned and experimented without the burden of completely abandoning their law firm salaries until financially viable had the quickest financial success, (and also reported not having to “jump” at every opportunity – good or bad – just to make money).

One of my favorite transitioning stories (in addition to yours, Casey!) comes from Nathan Sawaya – now internationally acclaimed Lego brick artist – who reports working on his art at night for years alongside his corporate litigation career. He would post pictures of his art on his art blog and started doing more and more commissioned pieces. One night, he reports that his “website crashed.” Literally. From so many hits on the art blog. And that was the moment Nathan knew that his full transition from the law would be financially viable. I use the “website crash” as a metaphor in Lawyer Interrupted for the moment when financial viability occurs for every would-be transitioning attorney. It might take months or years. Patience and hard work are important factors. And the reason the metaphor of a “crashing website” works so well is that it is not passive. You have to build your website, maintain it, create content for it.

And then you will be ready when it does, in fact, crash.


And almost every lawyer feels they have a book inside of them. And you actually wrote a book? How did you do that?! :) Take us through what drove you to write a book, and how you actually did it.

So I did not leave the law to write a book. (And I wouldn’t recommend any lawyer do that, actually, unless she/he is independently wealthy!) Most writers I know spend many years writing alongside other careers – doing it on the side if you will. I myself wrote for years alongside my position on the executive team of a start-up company before I transitioned to full-time writer last year.

But that said, I do tell everyone (lawyers and non-lawyers) who approach me at book events saying, “I really want to write a book” to: write the book they have been wanting to write.

It was a hugely rewarding endeavor to have my first novel, Lemongrass Hope, published in 2014, and a few months later, to have the American Bar Association publish my first non-fiction book, Lawyer Interrupted. And I know no other way to write a book than to write. Every day. No matter what.

Of course (or maybe this is not obvious – as it wasn’t completely obvious to me at first), the writing is not enough. If you really want to have your book published, it will take collaboration. With other writers, critique groups, and most importantly: a high quality editor. When my first novel manuscript was “finished,” I was introduced to – and ultimately worked with – a New York Times best-selling author who also works with authors on developmental editing. Those months that I spent working on Lemongrass Hope with my editor helped to convert my manuscript into one that was actually commercially viable.


If you had a group do lawyers in front of you, all wanting to leave the law, what is the best advice you can give them … in 20 words or less …

Do not leave at your angriest, most frustrated moment of burn out.

Take a deep breath.




Amy is a reformed corporate litigator, former start-up executive, and award-winning author. Amy’s first novel, Lemongrass Hope (Wyatt-MacKenzie 2014), was a 2014 INDIEFAB Book of the Year Bronze Winner (Romance) and a National Indie Excellence Awards Finalist. A favorite with bloggers and book clubs, Lemongrass Hope was named the #1 reviewed book in 2014 by blogger, The Literary Connoisseur.

Amy is also the author of the non-fiction book, Lawyer Interrupted (ABA Publishing 2015), and numerous essays and articles that have appeared in online and print journals including: The Huffington Post, ABA Law Practice Today, The Glass Hammer, Divine Caroline, Skirt! Magazine, and more.

Amy is a Tall Poppy Writer and a volunteer for the Women’s Fiction Writers Association. She lives in Pennsylvania with her husband, three kids, and one energetic weimaraner, where she is currently hard at work on her next novel, Secrets of Worry Dolls.

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A break

by Casey on August 17, 2015


On Sunday mornings, I play basketball with a group of 10 to 20 guys at the neighborhood park. They say the tradition goes back over 30 years. And the rules haven’t changed much in that time: 4 on 4 half court, first team to hit 24 points wins, must win by two baskets, no three pointers, side of the backboard is in play, last game goes to 32.

We usually play four to five games over the course of two hours. The pace is fast, the guys are competitive but nice, and sun usually breaks through the morning clouds soon after we begin.

This past week, I played pretty well. I made some real good turn around jumpers, got two steals, I was active on the boards and had a nice pass after a pick and roll.

But of course being the perfectionist-obsessive-compulsive that I am, as I walked home after our last game, all I could focus on was what I didn’t do well: the missed (easy) 12 footer, the layup I clanged off the rim because I thought it would otherwise be blocked, the fumbled pass I made that resulted in a turn over, the overcompensating on defense that let my man get free and score an uncontested layup. And all of those other missed shots.


Seeing other attributes of success

As I sulked the flew blocks back to my house, one of the players caught up with me and said good game.

I said thank you very much, but I had to admit that I felt I missed too many shots.

He is an older gentleman. Having coached and mentored his kids, it really shouldn’t have come as a surprise to me when he stopped walking, turned to me and told me that I bring more to the game than just making shots. He said I bring energy and leadership and motivation. He said I had the energy of Jim Havlicek of the Celtics in the 1960’s, who was so quick throughout the game, that by the time the third quarter came around, his opponent was often burned out, but he had the stamina to keep playing hard.

He also said that I made more shots than I was giving myself credit. He said I was ignoring the three really good, hard-to-defend turn around jumper shots I made.

And what he was essentially saying was Casey, you’re not focusing on the whole picture. You’re just focusing on what you (think you) did wrong.

Give yourself a break.


We aren’t a lost cause

And the same advice can apply to us unhappy attorneys looking to leave the law.

We get so down on ourselves for the stuff we (feel we) have done wrong in our professional lives, that we feel we are off course, that we do not pay attention at all to the broader picture, of the things we have accomplished.

So with that in mind, here are three ways for us to appreciate all that we have done and begin to realize that we are exactly where we need to be:

1. Realize that we know what we don’t want

Our unhappiness is just a sign that we are doing something not in alignment with what we are good at. It is just a sign that what we are doing is not connected with our Unique Genius.

But finding out what we do not want to do (be a lawyer) is not something to be depressed about. It’s actually something that we should celebrate. Knowing what we don’t want to do only gives us permission to now find out what we do want to do.

2. Realize that we are more than just a person with “lawyer skills”

For many of us, we think that the only skills we have are those that we use to be a lawyer.

And for many of us, we do not often have that much confidence in these skills, we may think we’re kind of a fraud as a lawyer, we may think we’re not particularly good at it either.

So in the same way that I only focused on what I messed up while playing hoops (my missed shots) and not on the other areas to which I did contribute (my made shots, leadership, quickness, spreading the floor, rebounds, hustle), we unhappy attorneys looking to leave the law do ourselves a disservice in focusing mainly on what we feel we are not good at (legal research, citations, litigating, drafting, rainmaking) and not fully realizing all the ways we can add value (client management, upselling work, issue spotting, dependability, work ethic, interpersonal skills).

Much of what we can do is in hot demand in the job world at large.

3. Realize that it is not good to bully ourselves

We can be very difficult on ourselves. We can say things that are not nice to ourselves. We can give ourselves no benefit of the doubt. We can pick at every single thing we do.

We can listen to the negative voices in our head. We can dwell on our feelings of frustration. We can feel like a fraud and a failure. We can feel jealousy for those doing well around us.

In a weird way, sometimes we feel that being real difficult on ourselves will be productive. We think it keeps us from slacking. We think it keeps us from being complacent. We think it makes us work harder.

But in reality, it only bullies us. It only makes us feel more insecure and less creative. It only hurts.


Let’s say I imagine floating up above the basketball court, not my physical body, as I’m still playing and running around, but a recording in my mind, my life’s movie, a bird’s eye view, a transcription of the game. And let’s say I were to view this recording later, a few hours after the game, I think I would like what I see. Of course the missed shots and the failed passes and the frustrations would still be there. But I would have no choice to also see it all, to see the whole court, to see what I did well, the hustle and the motivation and the stamina and the turn around jumpers and the steal and the guts and the desire. I would see this and I would smile and I would press rewind and watch again. I would like what I see, I would like what I had accomplished and I would like where I was going.



August 5, 2015

My son is five years old and this year he discovered Star Wars. And the main way he enjoys Star Wars is through playing with his Star Wars Lego toys. The Ewok Attack set. The Battle on Saleucami set. The Phantom ship. The Jedi Interceptor. He loves ‘em. And he’s actually pretty good at building […]

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The four things you need to do before applying for the job at the end of this post, or for that matter, any job

July 22, 2015

Last week, I publicly declared that I was a writer. And guess what? The world didn’t end. I wasn’t ridiculed. No one said I was arrogant or pompous or simply mistaken. In fact, I received a lot of supportive emails. I received a lot of emails from attorneys saying they felt like they were writers […]

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The one thing we cannot deny or suppress any longer

July 9, 2015

It was in the garage on a recent Saturday that I was reminded of what I want to be in life. As my wife and I tried to package items to give away or throw away, and as our kids scoured the shelves and bins for old toys they had forgotten but now wanted to […]

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How some leave the law and others do not

June 24, 2015

I was talking with an unhappy and dissatisfied attorney who so badly wants to leave the law but is having difficulty dealing with the pain and shame she regularly feels when she looks back on her time in law school and at the firm. She feels it’s been a waste of time. She feels it’s […]

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Leaving the law is first about arriving back with our self

June 2, 2015

This past Saturday night I wrote. The family was asleep. Asleep. Asleep and quiet. We have a new dog, this great, young, big bundle of energy and the dog was asleep. The house was quiet. I was quiet. Very quiet. And for the first time in what had been a busy week I was really […]

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The key to happiness (and leaving the law) is in helping others

May 23, 2015

“If you want happiness for an hour—take a nap. If you want happiness for a day—go fishing. If you want happiness for a month—get married. If you want happiness for a year—inherit a fortune. If you want happiness for a lifetime—help others.” – Chinese proverb I received an email from a reader last week. The […]

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Why our law degree won’t be considered a waste even if we leave the law

May 9, 2015

Annie Little, a blogger and writer at Attorney at Work, asked me and a number of other lawyers and bloggers to write about numerous topics on the law and alternative careers to the law. Annie had me focus on the question  “How valuable is your law degree“. For the most part, the value of a law […]

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My 21 step guide on how to leave the law and begin anew

April 23, 2015

The issue many of us run into when attempting leave the law is we have no idea where to begin. By its nature, leaving the law is kind of a formless, unstructured exercise. Sure, there is precedent of some kind in that other lawyers have left the law and we can read their stories. But even […]

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