Sunday, October 19, 2008




I’ve gotten quite a few emails/comments on this question. The short answer is that (1) it was inevitable; and (2) something happened this week that made chucking the Plan the most natural thing to do.

On Inevitability

I think Jennifer said it best:

“I thought this might be coming. :) Based on my experience, once you mentally check out of a job you cannot check back it. You're done, even if you don't know it yet.”

The truth is that while I have been practicing law for the past few months I’ve already pretty much checked out of the profession. It’s hard to be an effective lawyer when your eyes start glazing over while reading contracts. It’s hard to build good client relations when all you want to do during conference calls is to throw the phone against the wall. It’s hard to draft good work product when you no longer care whether that one case is cited correctly.

Seriously, how can I continue coming into an office wearing $1,500 suits when my mind is in Alaska, or in a van somewhere out west, or on a freight train in North Carolina, or on a sail boat in the middle of the ocean. In the end, I came to the conclusion that leaving earlier than next year was inevitable after I asked myself this question: How can I continue to live in a prison voluntarily when I’ve found the key to freedom?

On Living

If leaving my job earlier than next year was inevitable, the only question on the table was when, precisely, I would leave. That answer came to me on Wednesday. An old friend came to town that night and we met for a couple of drinks. After catching up a bit I told him about my new commitment to voluntary simplicity and about leaving my job, selling the townhouse, even this blog. He seemed genuinely happy for me, which was strange coming from him. The last time I saw him he had been drinking Patron between two very expensive-looking women in the VIP section of some exclusive club in NYC.

Jack: “Dude, seriously, you look different.”

Friend: “Really, how so?”

Jack: “Well, I don’t know. Just different. Maybe more…serene…happier?”

Friend: “Well I am happier. I’m leaving for Botswana on Friday. Doing a safari and then heading to South Africa.”

Jack: “What! No fucking way! YOU are doing a safari?” I laugh out loud.

Friend: “Jack, I’m dying.”

Long silence.

Jack: “I’m so sorry”

Friend: “Don’t be sorry. We are all dying Jack. It’s just that some of us are dying a little faster. The key is to not live your life as if you are already dead.”

At that moment I decided to quit my job.


I approached my mentor the next day to let him know I was thinking of leaving. He was very supportive. There are still some details to figure out but by February or so I will no longer have any connection with big law firm life.

I am now one step closer to freedom. I feel lighter. I am serene. I am ready to live my life.

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