Sunday, March 8, 2009



One cold Friday afternoon several weeks ago I walked out of my office for the last time. I spent most of the morning tossing memos, binders and assorted law firm crap into a giant trashcan. In the afternoon, I met with Human Resources to talk about my final paycheck. At some point, I returned some library books and walked my firm-issued laptop over to the IT department. In between, I said my goodbyes to those partners, associates and staff members that have earned my respect over the past several years.

In the end, it was as simple as putting some picture frames and assorted personal effects into a backpack and handing my Kastle key to the security guard at the front desk. And that was it. I was free.


Those of you who have followed this blog since its inception know well that I had originally planned to work through the end of this year. The advantages were obvious: the longer I worked, the more I could save and the more options I would have following my departure. And then, a chance meeting made me realize that living my life NOW is more important than any Plan. So I decided to leave early.

And yet, I can’t help but wonder whether working through the end of the year was ever going to be realistic. Those of you still in the trenches know full well how uncertain the legal market is at the moment, particularly on the corporate/M&A side. I am almost certain that if I was still following the original Plan I would be increasingly preoccupied with my billable hours, checking the internet for layoff rumors and otherwise making the kind of contingency plans that led me to leave my law firm early in the first place.

And maybe this is why I feel lucky to have left law firm life when I did. In the end, I was able to leave on my own terms and at my own pace.


I am still surprised by the number of emails I get from other lawyers who are contemplating life beyond law firms. When I first started the blog, the vast majority of emails came from lawyers who, like me, were struggling to deal with the long hours and the intense pressure this particular branch of the legal profession demands. I am now receiving more and more emails from lawyers who have been laid off and from law school students who are frantically trying to find a job.

Regardless of the author, the common theme in all these emails is always the same: how does a person find happiness in a profession that is seemingly antithetical to one’s core beliefs and innermost goals and demands so much of your personal time in exchange for what our culture has conceptualized as the upper-middle class American dream? More importantly, is it all worth it?


If there is one thing I know, my dear reader, is that I don’t have all the answers. I’m still feeling my way through this wonderful journey and have no real sense of how it will all turn out.

But I do feel that I have gained some valuable insight. And I am willing to share it with you, if you let me.

My journey began in a place where meeting and exceeding billable requirements was paramount. Where drafting perfect work-product was expected every day. Where success was measured by your paycheck and your law school pedigree. And you know what? I am now at a point in my life where I can say the following unequivocally:

*Fuck billable hours.

*Screw the bonus.

*Fancy cars, houses, furniture, vacations, credit cards, etc…have the potential to imprison your mind, your ego, and, worst of all, your spirit.

*The so-called upper-middle class lifestyle absolutely sucks and can go fuck itself.

If you want to find freedom as well, here’s my advice:

  1. Figure out your own personal definition of freedom.
  2. Come up with a rational, flexible way to attain it.
  3. Start changing your life from day one.
  4. Don’t let anyone or anything stand in your way.

Don’t look back. Don’t wait. Don’t second guess. Take the plunge and do it now. Before it’s too late.


Anonymous said...


How are you doing on your budget? I don't recall you posting about this in quite some time.

Thanks for sharing your journey. As a business school grad I relate to your experience, albeit on a much lower-sloped basis.


Jennoit said...

Exciting times, Jack! I didn't know how close you were to being finished at work. I look forward to hearing about what life brings you over the coming weeks and months!

Anonymous said...

I was near tears for ya there, Jack. And I only cry once every three years or so. And usually at the hands of a nice sunrise or my kids' attempts at cartwheels.
I'm just really excited for u. Thanks for sharing with us.

Anonymous said...

I am so excited to hear you made good on your promise. My BF is an attorney in NY and he works so much that our relationship is struggling. I am going to send him your link. I wish he would see that there is life beyond law.
I hope we get to follow your life away from law?

Jack said...


Probably reposting an updated budget later this month. And thanks for the kudos.


Sweet! Always nice to hear from you.


Thanks for the note. I just hope you can keep following this thing wherever it leads.

Maitreya said...

Isn't it great to taste Freedom?
Letting go of all that stress and responsibility and expectations.
Saying goodbye can be tough sometimes, but when you can look ahead and know you can start really LIVING, it makes it all OK.
Good for you.
Great post. I'm doing it NOW too.

Anonymous said...

You may already know of this book, but in case you don't, I highly recommend it. Your Money or Your Life was written for people in debt because they fell for the notion that buying stuff equals happiness. Even if you aren't in huge debt, however, it is well worth reading.

I actually just reviewed the book on my blog at

Jerry Critter said...

Wow! Congratulations Jack. You are now on your way.

I like your advice. It makes a lot of sense.

I was somewhat skeptical when you began this journey. You have exceeded my wildest expectations and I think you are really on a path to happiness and peace.


Elizabeth G said...

Jack, I am not a lawyer, nor did I play one on TV. I am however a former business professional that took the same step you did.

I look forward to reading more.

Jack said...


Let me know what he thinks. And yes, there are still plenty of things to focus on going forward. I'll probably be blogging for a good while longer.


Absolutely. And well put.


Yeah, I actually bought that book a couple of years ago when I was thinking seriously about this issue. Very practical, though I have to say not as life-changing as it apparently has been for other people.

Anonymous said...

Hi Jack and congratulations, you did it. It takes guts. :)

I look forward to the things to come from you.

-jd said...

Congrats Jack, I'm happy for you. Let us know if you ever come our way.


FIFI said...

Hi Jack,

I've been following your departure from all things pointless from the start but have remained silent until now.

First of all, congratulations!

Secondly, keep up the good. Your blog is inspiring and keeping me on track as I follow the same road (three days ago I quit my stress-filled, well paid, boring job. This morning I awoke at 5.20am and headed down to my local yoga shala to practise ... what a difference a day, or three makes)

Finally, congratulation and keep it up! So often we're a miserly species, mean on praise and compliments, hence the repeat.

All the best,


Anonymous said...

Hi Jack;
As a business owner it only took me 45 years to do what you are doing now.Good advice to the youngesters "Do it now"

Jack said...


As always, thanks for the encouragement.


Thanks for the comment

@Move to Portugal,

I just can't wait until you make your own move:)

Jack said...


thanks for the offer. And congrats by the way; I don't think I offered it when I first heard.

@Losing 5 Stone,

Thanks for those kind words. Always nice to hear from long-time readers for the first time.

@Did it my way,

Nice to meet a kindred spirit

dtb said...

Marvelous. I can't wait to read subsequent posts.

kate said...


I'm so happy for you, following your heart and making your own choices!

I'm making some choices now too. I think it's likely when my license renewal comes due in June, I will choose to retire, after 18.5 years. I've been working very part time, by choice, as a solo practitioner. The other option is to renew it, but do even less, or nothing.

I had tears of joy in my eyes over the weekend (and again now) when I realized I could rent out my city house and live in my tiny country cabin, and make enough from the rental income. I think I'll do that for a few years.

Just want to say I enjoyed practicing law most of the time, and working for myself later was a great choice too. I didn't hate being a lawyer, I just feel like I've finished.

In New York, I can continue working pro bono if I want to.

I wish you all the best!


Kristina said...

I'm so excited for you Jack. We closed our eyes and jumped about 7 years ago and we haven't looked back since. Don't get me wrong -- there have been tough times but my God! We are happy! Take care!

weston said...

Godspeed Jack.

Following up on your response to Debbi, was there a particular book, article or website that finally inspired you to actually go on this journey?

I find it fascinating the different paths people take in first searching for voluntary simplicity. Some come from religion, some from environmentalism, some stumble on the book Your Money or Life, or stop channel surfing when Affluenza runs on PBS. Was there something in particular outside your own life experience that inspired you to leap?

Jack said...


I'm curious myself.


Wow, I'm definitely envious! Good luck with what's coming next. That cabin set up sounds pretty sweet.


Good to hear from you. Let's hope it's a great experience going forward as well.

Frithstool said...

Congrats. I enjoyed following the process, and look forward to more. I was in your place but took a different path out, and I'm pretty happy about it. BTW, I guess you still can't "out" yourself, huh? The person I thought you might be is still on the firm's website, so not you.

Elizabeth Halt said...

exciting news - CONGRATS! :)

Jack said...


I don't think there was any particular thing that led me down this path. It was more intuitive and it took me a couple of minutes of googling to figure out what to call what I was craving (voluntary simplicity/simple living).


Thanks. NO worries. Coming "out" sooner rather than later.



Anita said...

Hi Jack,

Congrats on leaving your job!! That must feel SO good. I have been following your blog for a few months now, because I feel like I am in a similar situation as you right now. In a highly paid consulting job that I have done well at, have an MBA, am 31 years old, live in NYC, enjoying the single life and yet....I'm still missing something. I am totally miserable going into work everyday.

Recently I decided to take the plunge and apply for an international development position in India that is short-term. If I get it, I will likely take it (much to the chagrin of my parents) and figure out my plan later. I feel somewhat confident (though not sure why) that something I actually like will pan out from this short term gig.

Do you know what your plan is now that you quit? You mentioned in an earlier entry that you would like to travel and eventually find a law job at a non-profit. Is that still the plan?

Best of luck!

Kady said...


How very very awesome. You've done what so many say they will do but never get up the courage to.

I'm not happy at biglaw, but not because I don't enjoy the work. Surprisingly, the work is great. But I just can't stomache the fact that I'm complicit in the great raping of America (and Americans). And no, I'm not being dramatic.

I feel sort of like a spy. I've only been a lawyer for 2 years, but I already abhor the advantages I'm able to give to my clients, who really need no additional advantages.

I'll be out by year end (assuming I don't get laid off sooner) for family logistic reasons, and then I'm going to spend the rest of my life making life hell for the financial industry.

Like they say, a crisis is a terrible thing to waste.

Jennifer @ Conversion Diary said...

Congratulations! The adventure begins.

Also, I had to tell you:

A few weeks ago I started reading Thomas Mertons's spiritual classic, Seven Storey Mountain, and I kept thinking, "This guy really reminds me of someone." It kept bugging me but I couldn't think of who it was. Then yesterday it finally clicked: he reminds me of you.

He was a young man with an elite education (excellent English boarding schools, Cambridge, Columbia, etc.) who always had a wry distaste for it all and ended up going on the ultimate "adventure in voluntary simplicity" by becoming a Trappist monk. (His book was a huge bestseller but he never saw a dime of it because of his vow of poverty.) Anyway, his thoughts on the decadent, uppity society that surrounded him are hilarious in a really dry way, and remind me of your observations. Anyway, you might enjoy reading it now that you have some free time.

I'm excited for you! Keep us posted!

Jack said...


Good luck getting that gig. Keep me updated. India is one of those places I would love to go if I get the chance. And yes, that is still the plan. But I want to have some time to explore my options and figure out next steps. Let's see where that goes.


Interesting. Do you have any specific ideas as to how you will be in a position to make life hell for the financial industry?


What's funny is that someone else mentioned that a month or two ago via email. I guess I should read it but regardless, I am flattered. :)

bill h said...

Congrats. I'll give you more thoughts later. It's prompting to think alot about being a lawyer, what I love about it, what I don't.

I'm really excited to see where you are a year from now.

Here's my commentary on local public radio this a.m. Writing these pieces is a part of me keeping fresh and creative in areas of life outside of law.

I mention a friends' death in that commentary. We went to law school together. He left the practice to be a teacher, which he loved. He died young, and it was cool that he got to do what he loved for his final years. You never know. Life is short.

Anonymous said...

I am so happy for you!
Can't wait to see what else is in store for you.

T Marie

Jill Homer said...

Exactly. Embrace the unknown and never look back! Awesome! Good luck.

Anny said...

Good for you! I'm recently unemployed too and loving it!

Homeless said...

Congratulations, Jack.

Hopefully, you wont regret it. We haven't so far. There is a lot to see and do. And, you can't possibly see or do it over a long weekend or during your two week vacation.

We don't pretend that we wont have to work again, but I don't think that it will ever be work that chains us to our desks again. That kind of job sucks all of the life out of you.

I am also curious about your budget. I hope that you are able to enjoy financial freedom. I couldn't imagine this lifestyle with the burden of debt over my head.

Best of luck to you.


Jack said...


I won't lie. That was a very moving commentary. Made me think of unfinished business and reconciliation in my own family.

@T Marie,



Thanks. I know you are one of those people that have.

Jack said...




Need to know more about your situation. Do you have a blog? I will check it out. And yes, there is a measure of financial freedom, but I long to do interesting work going forward. Thanks for the comment.

Unknown said...

Amen to your advice.

Carpe Diem. Hehe.