Friday, June 20, 2008


There is nothing inherently wrong with my job as a lawyer. In fact, for several years, I really felt that it was interesting and intellectually challenging. On the other hand, coming into work was a wonderful way to play adult and pretend that I knew all the answers that really mattered. Putting on expensive suits, traveling all over the world, representing important clients, knowing the location of expensive restaurants, etc…were all just a way for me to tie additional knots in an ever-expanding invisible chain of hopeless materialism. For a while there, I was just too busy having a glass of expensive pinot to notice that I was losing my life.

And then I started getting…well…bored. The mind-numbing effects of sitting in front of a computer for 12, 13, 14 hours a day 6, sometimes 7 days a week making very rich people even more rich definitely caught up with me. Even worse were the times that I actually was able to go away on vacation. After spending a couple of weeks a year doing what I truly love most (hiking, mountain biking and climbing, getting lost in the middle of foreign cities with only my perceived decency and sense of adventure to guide me) ONLY TO get back to staring at that fucking computer again was infuriating.

So here I am. Making hundreds of thousands of dollars a year in a job that infuriates me and gets me no closer to fulfilling my potential.

Simplicity Meets the Enemy
The way I see it, I need to take advantage of my current salary until I can do the following:

1. Dispose of my townhouse.

2. Get rid of my existing consumer debt.

3. Arrange to sell/give away most of my possessions.

4. Have enough saved so that I can earn a certain amount a year in interest.

The plan at this point is to continue working until December 31, 2009 before giving notice. It’s quite possible that this date may change as things progress. I may meet my goals more quickly. Or I may just be so exasperated with work that leaving early will be my only option. We shall see.


Anonymous said...

Move into a van. It'll go fast. And you can always pick up little jobs. Seriously, I'm sure I make way less money than you, and I just work like two months a year (and that's with saving half my earnings for retirement, too).

donna said...

good luck with your quest to change your life, i'm sure it will be worth it

Anonymous said...

Definitely thinking about it. But first, I have to figure out what to do with the house I own now. Probably going to short sell it sometime soon...

Anonymous said...

Selling a house right now isn't as easy as it was a few short months ago. I wish you well with that.

You are, however, on the right path! I'm on the tail end of the path myself. I work online and have trimmed my client list down to the people I really ENJOY serving. Beginning in three weeks, I'll be working only three days a week in front of the computer, one away from the computer and the rest will be spent following MY goals.

My dream is to write, while living in a tiny cabin in the woods. I may try a mobile lifestyle for a couple years later.

So far, I've purchased the plot of woods, have nearly finished building the cabin (only finish work remains) and I've whittled down my debt to the point I'll be debt free by the end of this year.

Every step I take to get rid of more possessions and claim more of my life makes me happier.

There's a sheer joy to having only those things that you 1.) love, 2.) find beautiful and 3.) have utility in your life.

I wish you ALL the best!

Jack said...


Always inspiring to see how personal journeys evolve into something concrete. I admire where you have taken yourself and where you will be going in short order. Definitely keep in touch. I would appreciate any bit of wisdom/encouragement you may have up your sleeve.


Anonymous said...

Jack, have you thought about taking a sabbatical? This might be an option to consider as the first stage of your life change.

A career as impressive and established as yours sounds to be is not to be taken lightly. I would hesitate to toss it to the wind.

One option could be to change the direction in which you are using your skills. Perhaps being a servant to the wealthy is not satisfying (maybe at times demeaning?). Perhaps a direction could be found where your skills would be used to improve the lives of people or the communities they live in. A sabbatical could help by giving you time to research and make those decisions.

I believe yours could be a high stress career which would have it's effects on a person. And as such, a healing time would inevitably eventually be needed.

Whichever way you go, I am wishing only the best for you.

Jennifer @ Conversion Diary said...

Can I just take a moment to make a prediction so that I can go back and link to this comment and show everyone how smart I was?:

Your blog is going to be huge.

Your journey is so fascinating and the way you lay it out (in true lawyer fashion) is so clear and easy to follow. I'm so excited to have found it.

Also, again, your story is strikingly similar to my husband's (I can relate to a lot of it as well, but it's VERY similar to what my husband did a few years ago). He was on the fast track to big bucks in law (Yale undergrad, Columbia law), was in the M&A group at one of the big Manhattan firms, doing really well...and walked away from it all.

He got a lot of pressure from his colleagues not to walk away, mainly in the form of subtle comments about how much money he was giving up, but he's never looked back. Even when money has been tight and we hear about his friends from those days renovating their mansions in the Hamptons while we try to figure out how to buy groceries without going over budget, there hasn't been a single day that he's looked back and thought, "Gee, I wish I could go back to working 90 hour weeks to help big corporations get richer!"

All that is to say: you'll never regret what you're doing here. Kudos to you for having the courage to do something big.

Jack said...


One of the things I struggled with for some time was the possibility that I was just burnt out and that what I needed was just 6 months away from everything so that I could continue on with my career.

What I think I've come to terms with is that I am just not the same person anymore. I have yet to make the leap to not caring about status, $, material wealth...but what I have been able to accomplish is to know that there are other nicer, happier, richer ways to live a life. I have learned that the mold can be broken and that I am the sculptor.


Jack said...


Thanks for the comment, and the encouragement! I've been perusing your site all day, so have some idea about the process you and your husband took to get to where you are now. Does he have his own blog? Would actually love to know more about his own process and how he finalized the transition away from the law firm. It’s soo weird, because I can pretty much guarantee that I know/deal with his former colleagues on a semi-regular basis.

Take care,

Anonymous said...

Ahhh, I see, good, you are further into the process and have thought that through already. Good!
I am finding you to be a very intriguing person.

Jennifer @ Conversion Diary said...

Does he have his own blog? Would actually love to know more about his own process and how he finalized the transition away from the law firm. It’s soo weird, because I can pretty much guarantee that I know/deal with his former colleagues on a semi-regular basis.

I know, I keep thinking that, esp. since you mentioned in your latest post that you went to an Ivy League law school -- I bet we know a lot of people in common. :)

My husband doesn't have a blog but I'm sure he'd be happy to offer any advice. He actually went to business school after he left law (yes, our student loan debt boggles the mind -- with our lifestyle simplification it's now close to our house payment!), and in the meantime worked for one of the big consulting firms. So, actually, the real leap came when he left the corporate world altogether a couple years ago.

We were actually talking about this last night (I was telling him about your blog), and he said that it was tough to leave the big firm world and he got a lot of pressure not to...but he went to business school because he still thought that there was something else "out there," i.e. that if he just got on a better career track it would bring him the fulfillment he was looking for. It was after business school and success in the world of high tech startups he realized: a job is never going to do it, never going to bring him lasting fulfillment (quite a revolutionary message after going to one of the top b-schools). It was a couple years after that that we got married, sold the jag, left the downtown loft and set out on a whole new course.

...And now I have just taken up your combox with the story of my husband's life. Sorry for the rambling. :)

Jack said...


Wow, that's sort of a double-whammy= law school and b school. I sure bet those payments are pretty high.

Would be interesting to get his perspective, although I'm so early in this process that I may wait a bit to reach out to like-minded people in similar situations for advice. But I definitely appreciate it. Tell him it made me very glad to hear that I am not alone...


Jae Jagger said...

What happened, Jack? Something happened here. We didn't get the full story.

My last boyfriend hated money, and I tried explaining to him more than once, although he argued with me, that money is nothing more than a vehicle, and how we relate to it reflects how we feel about ourselves and how we feel about other people.

Read Philip Slater's "Pursuit of Loneliness"?

You have a great opportunity.

Jack said...


Not sure what happened, really. Nothing wrong with money. It’s how I am currently making it that’s making me unhappy. Will have to check out the book. Can’t say that I have heard of it.

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MW said...

Hi! I just discovered your blog.

For the last few years, I've been feeling that my career's shelf life is coming up.

I've been cutting back my hours so that I can spend time building the life I would like using the money I'm still able to make.

I'm still resenting work but want to put another couple of pieces in place before cutting out completely. My timeline is a blt longer than yours -- 5 yrs.

It has been difficult doing all this without family support but not having it and constantly being challenged in irrational ways has made me (and you and others who go against the family grain) strong.

Kim Richard Smith said...

A truly successful life is one in which the difference between work and play cannot be distinguished. Once you've figured that out, you'll know that there's no time like the present to quit your job--seriously.

Shewee2001 said...

Hi Jack.... I just now got a chance to check out your blog, very interesting. I shared the site with my fiancee and he said, so cool! I met you in ElDorado Kansas at the ( Bella Casa)Italian resturaunt you stopped and had lunch. I was the waitress you gave blog info to.) By the way , THANKS SO MUCH! We enjoy the blog, keep up the great adventure you are making. Be safe and God BLESS. Looking forward to updates. :-)
Lots of tornadoes been around the area lately. and go to weather pictures will show you somepics..

Jack said...


It's great you got on the site and that you enjoy it. Glad to hear from you.

A said...

Strange. I made just the plan this week. My deadline being March 31, 2010 (my last day at work, when I will be done saving enough and done paying off my debts!). March 10, 2010 will be when I put in my notice. And I happen to chance upon your blog. :) And yeah. Same here. Lawyer. Big Firm. Countless hours of my life spent in front of my comp and wondering where is my life going. Finally realising this is not just my quarter life crisis!

All the best!

Julie Groenewald said...

Hi there,

I also just found your blog and have read on it some stuff here and there. WOW how it fascinates me. I totally admire your type of lifestyle and SOH wish I could do the same thing. Me and hubby are newly found fruitarians and I surely wish with my whole heart we could just give up this mad house city and rat race in making a living, barely just surviving.
What a beautiful blessing you have. Now you can focus on the true things that really matter in life.
How I long for a life similar to this type of simplicity.

Have a blast and thanx for sharing with us.


Anonymous said...

I seriously feel like telling to you to quit your fucking whining.

A lot of people are way worse off.

Alternately, I am in a similar middle-class existential crisis, so I get where you are coming from, so that would be a bit hypocritical of me to tell you to quit fucking whining.

Of course, there are a lot of people worse of than I am, too....

...maybe we should both quit our fucking whining?

Nice to meet you.