He first had to forgive himself

I’m always on the lookout for stories from the Leave Law Behind community, of people first realizing they want to do something different to those people who take that first step and actually leave and do something else.

Here is the story of Joseph Castelli, a Leave Law Behind reader, who recently left his BigLaw job doing M&A. He asked me if he could share how he just left the law.

Here it is. I think you’ll find it insightful, actionable and inspirational. I did.

Forgiving myself

The decision to leave my six-figure law firm job didn’t come quickly. But as I looked down into my desk drawer, I realized I had to do it. Lined up neatly were orange prescription bottles of Adderall, Xanax, Effexor, and various headache medicines. I had the Adderall to wake up in the morning, the Xanax to relax at night, and the Effexor as a backup if I had to stay all night at the office.

I knew the statistics. Lawyers suffer from depression, anxiety, and substance abuse at higher rates than most professions. I could see it around me; everyone looked miserable, exhausted, or insane. Now it had happened to me.

I began to get bitter. I kept a folder of resignation emails I’d written. I daydreamed every day about walking out and not returning.

But there was one thing I had to do first: forgive myself.

Pain

At the firm, I’m not sure which was worse: the anxiety or the depression. The anxiety floated all around me. I was in a perpetual state of vigilance, constantly on guard of making a mistake. I checked my work email first thing in the morning and last thing at night. Even leaving the office was dangerous because any second a work email ruining the night could come. I jumped when my phone vibrated.

Physically, my heart rate and blood pressure soared. My shoulders bunched up around my ears, my face and jaw tense. It was exhausting just keeping up the front of being okay, of acting interested.

The depression left me listless. I was bored, and I felt boring. It’s a strange feeling to be anxious yet bored at the same time. During the week, I struggled to roll out of bed. On the weekend, I swung between drinking excessively and doing nothing, worried about leaving my apartment because work might surface.

A law firm is a perfect place to make depression worse. I had an absolute lack of control over my schedule. There was little time to exercise, and I ate terribly and gained weight. During the winter, I sometimes wouldn’t get sunlight for days. I’ve been on a lot of antidepressants, and I’ve been diagnosed with depression for over a dozen years. But the law firm amplified everything.

In retrospect, I think the depression was partly an expression of my disappointment. I had worked so hard to get here, and it wasn’t what I wanted. There was also guilt – so many people would want this job, so why didn’t I? And of course the shame of leaving. I couldn’t allow myself to think these things, so I became depressed instead. I devoured self-help fluff articles, not realizing I was so frustrated and desperate because I couldn’t face how I felt.

How had I put myself in this position? I was a liberal arts major as an undergrad, which meant I didn’t have a career path when I graduated. I taught English abroad for a few years after college. It didn’t feel sustainable. For me, law school was the path to a stable, lucrative, and prestigious career. I remember receiving my law school scholarship email on a beach in India. I was ecstatic.

Doing for myself

But now, I had to accept that this path was not for me. In a way, this was a bigger challenge than everything that had come before: the LSAT, law school, the bar exam. I hadn’t learned to be friendly to myself, to allow myself to quit.

I had a wealth of intellectual arguments for quitting: If I didn’t leave now, it was going to be too late. I didn’t want to be in golden handcuffs for the rest of my life. I didn’t want to endure the broken relationships I saw in the lives of senior associates and partners. It would be risky to leave, but considering what I was going through, it would be actually riskier to stay.

But before I could accept that reasoning, I had to practice acceptance of my unhappiness and take responsibility for it. This was unfamiliar. For years, I had been shuttled from one achievement to the next. But I would be fully responsible for the decision to leave. I realized I had no idea what success even meant.

I vacillated between remorse for making a terrible decision and trying to convince myself that it didn’t matter how much money I made if I were so miserable. Who knows what the correct decision is? Narratives are necessarily created by looking backward. And it’s really a moot point: what I do now doesn’t change the past. Move forward.

I saved up an emergency fund. Every time I was tempted to buy something non-essential, I told myself that saving thirty dollars meant gaining another day traveling. The fear tried to convince me I didn’t have enough money. It was absolutely important to have a financial cushion when I left – and I didn’t have a family to support – but I had to be careful not to use money as a pretense to stay.

I reversed my thinking on money. Instead of making money just to spend it, I looked at what I actually needed in my life and worked backward. Money is a means, not an end. Though I make a fraction of the money I did before, I actually feel richer now. My life is richer in experiences, time, and family. As I write this, I’m looking at tea plantations in South Asia, where I’ll take a hike this morning. After that, I’m going to read a novel I started but never finished at the law firm. I can eat a holiday meal with my parents without checking my email. These things cost less than my canceled Amazon Prime subscription.

Joseph Castelli worked in the mergers and acquisitions department of White & Case’s New York office and received his law degree from NYU School of Law. Before that, he taught English in South Korea for three years, hiked and meditated in the Himalayas, and competed in powerlifting competitions. He now writes at Esquire No More.

I’m on a mission to help attorneys get to themselves better so they can leave the law to become happier, and here’s what I’m doing to help:

Sign up for the free podcast I just launched “Love or Leave the Law” with fellow Leave Law Behind reader, former attorney and published author, Adam Ouellette

Check out the online course I designed specifically to help you begin to leave the law right now at your own pace.

Or schedule a (no charge) time to speak with me to see if my one-to-one coaching is a fit for you.

Share this page

2 thoughts on “He first had to forgive himself

  1. Thank you for your post. I just got accepted into law school but at the cost of not being there for my husband and kids. After some research I have decided not to pursue law school. It was a struggle to make that decision since it was my dream but I feel like reading your post and others have saved me from years of disappointment and dissatisfaction by deciding not to pursuing law. Thanks again and God bless

  2. Casey,

    Your course lacks to be absolutely terrific. My name is Melvin Simensky. I practiced entertainment/intellectual property law for over 35 years. I left the law because I couldn’t stand having to bill over 2200 hours/year. I taught at NYU Law School for 17 years and loved it. While there with colleagues we published 5 legal texts. I would like to teach a coaching course, preferably for college, and of course with your permission, if such is required, to base my course on some of the issues in your course. And if you feel that we should license your materials, we would do such. Please tell me your thoughts on the aforesaid.

Leave a Reply

Your email address will not be published. Required fields are marked *

You may use these HTML tags and attributes: <a href="" title=""> <abbr title=""> <acronym title=""> <b> <blockquote cite=""> <cite> <code> <del datetime=""> <em> <i> <q cite=""> <s> <strike> <strong>