Saturday, December 27, 2008

It's Hard Being a Douchebag


Earlier this month, attending my very last law firm holiday party, I almost had a heart attack. Well, maybe that’s a bit over-dramatic. Let’s just say that for about 5 minutes I saw my life flash before my eyes.

I was having a conversation with my mentor and some other colleagues when a partner who had flown in from an office out West joined the conversation. The topic, as it has been for the past several months, was the extensive layoffs in the legal industry. Here’s a non-verbatim summary:

Partner: “Yeah, the shit is definitely hitting the fan. Who knows how many people will actually make partner this cycle.”

Lawyer 1: “Who knows how many of us will still be here next year,” he said half-joking.

Partner: “That’s absolutely right; we probably won’t need any of you come next year,” he said with some seriousness.

[Everyone laughs nervously]

Partner: “The way I see it, many lawyers are going to have to burn their law degrees for heat this winter. Like that guy from Harvard.”

[Everyone laughs more nervously. I start to hyperventilate silently]

Mentor: “Oh yeah, I heard about that. But, hey, Jack actually went to Harvard. Maybe he can get the fire going,” he says with a wink [he does, after all, know I am leaving in a couple of months].

Jack: “No way. I would NEVER be that much of a douchebag,” I say with a laugh.

[Everyone laughs]

I wait three or four minutes before excusing myself to get the biggest shot of whisky I can find.

Tuesday, December 23, 2008

Thoughts of Christmas

As Christmas comes upon us this week I can’t help but think about one particular Christmas that changed my life.

I had been living far from home for some time, trying my best to feel AND be lost to my family. Maybe there was a lot of anger inside me. Or maybe I just felt numb and preferred to ignore the fact that I actually had a family. Regardless, I was oblivious to their calls, mocked their emails and threw away their letters. “I’m living my own life,” I would say to myself. “I can take care of myself.”

And then something happened that tore my heart out. Suddenly, I was by myself, far from home and inconsolable. There were days during that period when my tears never stopped and my thoughts turned to dark places I never knew existed inside a person. I was ashamed. I was confused. I was alone.

Somewhere in the mist of all that darkness I realized that I could not make it alone. So I decided to come home for Christmas.

As I opened the door that Christmas eve I was greeted by the smell of a roast in the oven, a large Christmas tree in the living room and the warmth of my mother’s arms. “Don’t worry Jack,” she said to me. “You are now home. Everything is going to be ok.”

I’m not ashamed to say that I am crying as I write these words.


Happy Holidays everyone.

Wednesday, December 17, 2008

Budgeting (Part II)


Now that I’ve had a couple of months to track my spending I’m finally getting a sense of how much I will really need to finance my post-Plan life. This is definitely an improvement from my first preliminary budget. The process has been quite straightforward:

  1. Figure out what activities make me truly happy (as subjective and ephemeral as the term “happy” can be), and
  2. Draft a conservative, long-term budget that incorporates these activities

You guys can view the working draft here. A couple of thoughts:

*Anything highlighted in yellow represents fixed costs

*The Housing line-item is my pride and joy. I don’t think I want to ever pay more than $800 a month for housing ever again.

*While I already consider an annual budget of approximately $32,000 a real accomplishment for someone who somehow managed to live off a gross annual income of >$300,000 (or $190K post-taxes), there is still a ton of places where I can economize further.

*The Personal Spending, Clothing and Gear line-items are ripe for additional cuts, depending on where I am and what I am doing. You can imagine how these expenses will change and shift depending on whether I am backpacking in Vietnam, bicycling in Patagonia or teaching English in Bolivia.

*On the other hand, I have yet to include a bike expense category. Need to really think about how to incorporate my bike riding expenses into this budget. Would definitely appreciate people like Jill, Nancy, Chris or anyone else with some knowledge to weigh in on this, particularly as to how long-term bike travel adds to the budget.

Any other thoughts, comments, and suggestions very much welcome.

Sunday, December 14, 2008

On Marriage

[The photo above was actually taken at City Hall here in DC]

Honestly, I just don’t get it. One moment you are sitting in a dive bar with your guy friends drinking beer after beer, mourning yet another Redskins loss and arguing over whether sex with a blonde is actually better than sex with a brunette (welcome to my last couple of Sunday afternoons). And all of a sudden you are married with two kids, living somewhere “quiet and safe,” and hoping the market recovers because you really need that college fund to start compounding. What. The. Fuck.?

Having never had the pleasure, I really, REALLY would like to know what makes a person decide to get married in the first place?


Could it have something to do with that 14th century construct called ROMANTIC LOVE? You know…“I am so in love with you that marriage is the only thing that can fully express the depths of my commitment to you,” or the venerable “Baby, I love you so much that I need to be married to you!”

But wait a sec! The last time I checked a person can, in fact, love someone strongly, fully, and deeply without being married. Why does a couple need a piece of paper to prove to them that their romance will continue unabated, that their commitment to each other will long endure? I think the most disturbing question of all is this: is it possible that some people get married because they are afraid that if they don’t get married their love could run its course and flicker out as many loves tend to do? Are we so afraid of being alone that we seek to trap those we love with a signed piece of paper and a rehearsal dinner?


Love and marriage definitely gets more complicated when kids are involved. There is no question about it: kids are better off when they are raised by two parents. But where does it say that both parents have to be married to raise a child? The way I see it, if married parents really can’t get along they will just get divorced. Similarly, if unmarried parents can’t get along they will just end their relationship. What’s the difference? And, isn’t it far more traumatic to go through a divorce than to end a relationship?


Maybe this whole post is essentially moot given the gay marriage issue. Depending on the state, marriage may, indeed, be the only way that some couples can protect their assets, maintain legal custody of their kids, and have a rightful say in how their loved ones are cared for.

On the other hand, marriage may, indeed, be the only solution for many couples, but only because of the current lack of safeguards afforded by contract and family law. NOT because marriage is some kind of panacea.


For many people, having children, indeed, the very act of sexual intimacy requires that you be married in the first place.

Well, you got me there. I guess if you’re really into someone and your heart tells you that you can’t even get to second base without stepping inside the church/synagogue/mosque of your choice then who am I to criticize. Actually, I admire a person that can place so much of themselves in the hands of faith. Personally, I would need to get further than second base before popping the question. A LOT further.


Oh, who am I kidding? I can sit here and criticize marriage till the cows come home but the real reason I’m not big on marriage is because I’m just plain terrified of it. You spend years putting up walls around yourself, hoping to protect every inch of your heart from every kind woman with a nice pair of legs and a penchant for being brilliant. Then, one day, one sneaks behind some crevice you never quite got around to fortifying and she manages to scale the walls. Suddenly you are that dude with the two kids, a house in the suburbs and the college fund. And then you start asking a bunch of painful questions like “Where did all the beer go?” “When was the last time I watched the Redskins with my friends?,” and, the most crucial, “Is sex better with blonds or brunettes? I just don’t quite remember…”

I don’t ever want to ask myself these questions. Besides, I already know the answer to the last one.

Friday, December 12, 2008

Jack is now on Facebook

That's right! I've finally decided to embrace my inner 18 year old and have set up a Facebook account. This is still a work in progress but you can now add me as a friend using "Voluntary Simplicity Jack". Expect new videos, pics, and related voluntary simplicity craziness. Plus, definitely relish the thought of chatting with some of my favorite readers, wherever they might be.

On an unrelated note, I wanted to give a shoutout to G., the Chinatown DC-NY bus driver who found one of my envelopes. This dude is pretty hardcore; he actually noticed me leaving an envelope in one of his bus seats somewhere near Baltimore, somehow tracked me down using my ticket info (don't ask, it was totally shady) and called to thank me last week. After 2 or 3 denials I came clean and we chatted for like half an hour. Very sweet guy. Looks like he gave half of the cash I found to one of his daughters.

Wednesday, December 10, 2008

House on the Market!


It’s done! The townhouse is now officially on the market. I can’t tell you how relieved I am. This has been a long time coming. There is still a ton of stuff to do (dealing with open houses, cleaning, paperwork, etc…) but the fact is that I am one step closer to embracing freedom. On my own terms. You can’t beat that!

Ok, back to work. Term Sheets, SPAs and APAs are easier to read when you actually see the end in sight. Only a couple of more months to go...

Wednesday, December 3, 2008

Cage Free Family in DC


As some of you might know, the Cage Free Family stayed in my place this past Thanksgiving weekend. If you recall, these are the guys who were profiled in the New York Times article earlier this year as they gave away most of their stuff and ventured out on the open road in an RV. Having Aimee, Jeff, Quinn, and Nichola over was a wonderful distraction from all the planning, packing, and assorted downsizing going on at the moment. Besides giving me an excuse to experience DC as a tourist again, their stay had a pretty big impact on me personally.


Having sworn off meaningful relationships not too long ago, it was absolutely refreshing to see the love and compassion Aimee and Jeff have for each other. These guys aren’t just married; they are partners in a wonderful adventure that has no end in sight. When one is overwhelmed with life stuff, the other steps in seamlessly. When one is enjoying life stuff it’s probably because the other was there to make it happen.

Maybe love is alive and well all over the place and I’m just not privy to it. Maybe all those meaningless sexual escapades of the past few years have truly jaded me. Or maybe all my crazy family stuff has left me damaged beyond repair. Regardless of the reasons, I hope that one day I can be as strong, as caring and as vulnerable with another human being.


Hanging out with the kids was the highlight of my weekend. Making paper airplanes, shooting down invisible monsters, and entering a blackberry case tossing contest (I lost, by the way) certainly puts the idea of having kids of your own into perspective. For a brief moment, it felt like the most natural thing to do.

Sunday, November 30, 2008

Back from Sabbatical


Greetings my dear reader.

Wow, was that awesome! Two weeks away did wonders for my psyche. Nothing like an impromptu sabbatical from blogging to provide some added perspective. And it was perspective that I needed. For a while there, I felt like one of the things I had been relying on to help me through this process of simplification (blogging) had actually become an impediment to simplification. At some point, there were just too many comments, too many emails, too much COMPLEXITY. I have a feeling some of my fellow bloggers understand this all too well. Taking some time off was good in that it helped me find my focus again.


I want to thank the dozens and dozens (hundreds at this point?) of people who submitted a comment and/or emailed me with their own versions of the Plot. For those of you who received an envelope feel free to comment publicly, though I would ask that you do so anonymously. I will, of course, keep your email acknowledgements in confidence. Finally, I wanted to thank R. from a certain veterans group for helping me distribute some of the envelopes. I don’t think I could have finished without you.


I also wanted to apologize for not replying to any emails the past couple of weeks. I really needed total radio silence during this self-imposed sabbatical. I promise to get back to everyone as soon as possible.


Over the next week or so I hope to add a couple of links to sidebar on the voluntary simplicity movement. I have a feeling that some people stumble on this blog without any real sense of what I am doing, why I am doing it, or what Voluntary Simplicity really entails.


I’ve come around to the idea of adding comment moderation to all of my posts. As you may recall, I had originally rejected that approach a couple of months ago in favor of a more Millsean marketplace-of-ideas approach. The benefit of this new approach is not to stifle ideas but merely to make my job a little easier. Constantly reviewing the blog for troll comments and meaningless fluff is super annoying and time-consuming. Now that I have comment moderation turned on, I can review all comments at once and streamline the whole process. The underlying policy remains the same: anyone with a legitimate, cogent perspective may comment. Anything that is outright offensive will be rejected.

Monday, November 17, 2008



How about it, my dear reader? Do you feel like starting a little revolution? I’ve got nothing better to do and I figured it might be fun. :)


So, what are we rebelling against, you ask? Materialism. Consumerism. Apathy. Injustice. The feeling that all the problems we face are impossible to solve. And, above all, our irrational reluctance to love our fellow man.


If you are on board, then I think the operative question becomes: what can we offer to this revolution? More to the point, what do we possess that might prove useful to changing our world? Some people bring their own particular strengths to bear when it comes to overthrowing the old order. Lenin had an overpowering intellect and a ruthless purpose of mind. Margaret Thatcher had experience, intelligence and a charm all her own. Clinton was the consummate technocrat. As for myself, at this point in my life, I just don’t have a fully-defined world view and/or the real-life experience that could prove useful in a revolution. Give me some time and maybe I will get there. For now, all I can contribute is this:


I always wanted to be in the Sopranos:

I am leaving my law firm. Maybe I should consider a career at Chip ‘n Dales:


Sorry, I just couldn’t help myself:

Ok, now that we got that out of the way, let’s start plotting our revolution!


The plot is actually fairly straightforward: give away a sizable amount of money I don’t really need to random people. Here are the basics:

*Stuff blank envelopes with bills of random denominations.

*Include a note with the following narrative:

“To the person who finds this envelope,

I am a person who has enough. Take this money and use it as you wish. In return, I hope you can search within yourself and realize that all that matters in life is love. So, call your family. Help a friend. Lend a stranger a hand. In the end, all we have is each other.”

*Drop off the envelopes at random and not so random locations throughout the East Coast.

*Separately, send anonymous donations to (1) a variety of organizations and non-profits I support; as well as (2) certain bloggers chosen at random.

* Hope that in some small measure, these hundreds of random, anonymous, convention-upending acts of social rebellion spark something meaningful and essential in the collective unconscious of our world.

Unrealistic? Probably. Idealistic? Absolutely.


Why don’t YOU get in on the fun? I challenge you, my dear reader, to take the time this very day to express your love and kindness to (1) someone you care about, as well as (2) a total stranger. There are sooo many things you can choose from:

*Hug your kids and tell them you love them

*Call your grandparents

*Help a friend move

*Sign up to volunteer

*Donate to a local charity

The list is endless. If you take up this challenge do let me know what awesome, SIMPLE, things you decided to do.

Spread the word. Remember: a journey of a thousand miles starts with one step.


After the whole diploma burning thing, I came to the conclusion that it is a good idea to provide added context when it comes to some of my posts. I am still amazed how normal, rational people can have such intense, knee-jerk reactions to anything that appears out of the ordinary (have you seen some of the comments left on YouTube? Woa…). This time, I figured I would anticipate some of the questions/comments people might have. Here you go:

Come on, Jack, you must be insane!

Maybe a little. :)

If one of the prerequisites for insanity is the inability to reason then I think I’m in the clear. This didn’t happen out of the blue. I thought long and hard about how to do this the right way. I searched within myself to figure out what I want out of life, the kind of life I want to live and the kind of world I want to leave our children. I made a detailed budget that was realistic and incorporated contingencies, changing needs, and everything else that I felt I would need to live a simple, yet meaningful life for ME. After I finalized the budget I realized there was some money left over. This posed a quandary. Extra money meant that I had the following options: (1) leave the money in the bank to collect interest; (2) upgrade my lifestyle; or (3) give the money away. Leaving the money in the bank is certainly an attractive option, but I fail to see the point of keeping money stashed away for no reason. As for upgrading my lifestyle, that makes absolutely no sense to me. The budget I came up with, by definition, represents an opportunity to live the life I want to live without the need for anything but a steady, meaningful, super-low-paying job.

What’s crazier? Giving away money you don’t need OR voluntarily upgrading your lifestyle so that you are forced to spend MORE money, in order to have MORE stuff that would actually mean MORE headaches for myself and my family and putting MORE strain on our natural resources? I’ll let you, my dear reader, be the judge.

If people will find the money randomly, how can you be sure that people who need the money will actually get it?

I am, in fact, leaving some envelopes at certain targeted locations (missions, churches, shelters, etc…). Beyond that, I want to make something very clear: the focus of the Giveaway is NOT about giving people charity. My hope is that hundreds of small but meaningful surprises can lead to hundreds or even thousands of selfless, loving acts of kindness. The person who has nothing and finds an envelope with $50 dollars will, indeed, be ecstatic. The person who actually has something and finds an envelope with $20 dollars may be moved to give away $100 to several people who have nothing.

Why can’t you just give the money to family?

I’ve already made certain arrangements, particularly with respect to my mom. The budget I came up with takes this into account.

But, wait, if you are just giving cash away anonymously aren’t you missing out on 501.(c)(3)-type tax deductions?

Yeah. On the other hand, I’ve reviewed my tax situation for this year and as it turns out it will probably be a wash: I won’t owe anything AND will not be getting much of a refund. Ergo, declaring a charitable contribution won’t help me much. Besides, there is something about giving stuff away anonymously that may be lost if I had to declare it on my taxes.

Jack, you are nothing but a crazy lefty-hippie!

Far from it. I think most people would be surprised if they knew my political leanings. On the other hand, for any of you bona fide hippies out there keep in mind that I’m partial to free love and rock and roll. Specially the free love part…[Hint, Hint!].



As of today, the plot has essentially come to fruition. Only a couple of dozen more envelopes left to drop off. Expect additional pics and video later this week.

Friday, November 14, 2008


This week has been rather hectic. Who knew starting a whole new life would be so complicated? Ideas and desires need to be transformed into concrete plans; concrete plans need to be broken down into manageable tasks; and even those tasks need to be incorporated into an ever-expanding set of to-do lists. But hey, for the first time in my life this whole process is leading me somewhere meaningful. That’s what makes this transition so rewarding; all the planning and task-making is, in fact, reinforcing the process of simplification. In all the ways that matter, you cannot have simplicity without going through the process. And it is the process itself (with all its complexities, material purges, and inevitable emotional highs and lows) which lends simplicity meaning and definition.

Speaking of simplification, I’ve been putting together the finishing touches on something I’ve been thinking about doing for some time now. It’s definitely not for everyone but it sure makes sense to me. Stay tuned.

Monday, November 10, 2008

Dear Bank of America: F@%k Y&U


Another day, another step closer to freedom. Sometime this week, Bank of America card services will process a check with five figures on it. As of that moment, I will no longer have any remaining commercial debt to deal with. SCORE!!!!!!!!!!!

I would be pouring myself a little scotch right about now if I wasn’t still a bit hung-over from a well-deserved Sunday-NFL-watching-beer-drinking-all-day marathon…

Thursday, November 6, 2008

On Family


Boy, is this an awkward topic.

As I work to unhinge myself from a life that no longer makes sense to me I am becoming aware of all sorts of new possibilities and opportunities. On the other hand, I am also questioning a great deal of what I have been conditioned to believe constitutes happiness in the first place. In some ways, this is sort of inherent in this process of simplification. To question the need for a 3,000 square foot house, the virtue of becoming trapped in a lucrative but unfulfilling job and even the merits of living a lifestyle full of unmitigated excess is to question your own assumptions about the very nature of happiness itself. In all the ways that matter, the old paradigm is dead. In its place is an urgency to question all assumptions about what truly makes a person happy.

Which brings me to the third rail of the voluntary simplicity movement: do you need to have kids to find happiness? More to the point, is procreation a prerequisite to happiness?


When I first went to law school I felt like I was following the path of least resistance. The steps were pretty clear to me: finish law school, get a job, get married, have kids, and live happily ever after. While I don’t think I had a very clear sense of why this seemed like the right path to take, in retrospect, this seemed like the right path precisely for the same reasons buying a huge house and coveting a high-paying, stressful job seems like the right path for so many other people. Our society conditions us to accept the “normal” path from the day we are born. To deviate from “normal” by choosing to forgo our right to procreation is to embrace the unknown and accept a life outside the mainstream. More importantly, choosing not to have children challenges the choices made by those who have found their own version of happiness in the realm of the “normal.”

This is not to say that there is anything inherently wrong with the “normal” path. Every day I surf my way through people’s blogs and I get a glimpse of what it would be like to have a family of my own. I won’t lie to you, my dear reader. There have been times when pictures of a family doing stuff together have left a heavy lump in my throat. I have seen myself in those pictures, holding something small and precious, something that can live on after I am gone.


But, is having kids really for me? Believe it or not, there are a growing number of families that have chosen not to have kids in the first place. Some couples base their decision on ethical concerns (“having children only adds further stress to our natural resources…”); others don’t feel they will be good parents; still others see children as a threat to their financial and social independence (i.e., a child born today will cost a family anywhere from $130k to $260k).

All of these reasons resonate with me. The last two, in particular, brings up all sorts of conflicting emotions. I know that, at least for the foreseeable future, I would be a TERRIBLE father. I am still too selfish, too damaged, too quick to assuage my own needs at the expense of anyone, or anything else. Things are getting better every day, but this is a process that has to take its own deliberate course. I need time to heal. Right now, I just don’t have the time and/or energy for anything else.

I’m also weary of the strain having a family will have on my long-term plans. How can I travel the world when I have to be at home and do the responsible parent thing? How can I take months-long bike rides when there is a little one depending on my emotional and financial support at home? How can I embrace simplicity when the very act of becoming a parent seems anything but simple?


“Stop your whining, Jack,” I tell myself. “Just be the best person you can and everything else will fall into place. In the end, you will know the answer.” That’s pretty good advice.

Monday, November 3, 2008

Book Simplicity


I was all set to do a post about books that encourage and/or inspire simplicity until I realized that aimee over at Cage Free Family sort of beat me to it. Here is select list of some of the stuff people suggested on her blog:

*Real Food, Nina Planak

*How Far to Follow? The Martyrs of Atlas, Bernardo Olivera

*Little Women, Louisa May Alcott

*Like Water For Chocolate

*Fifth Sacred Thing, Starhawk

*The Four Agreements, Don Miguel Ruiz

*Outlander series, Diana Gabaldon

*Zen and the Art of Motorcycle Maintenance, Pirsig

*The Passion, Jeanette Winterson

*Autobiography of Red, Anne Carson

*Gilead, Marilyn Robinson

*The Contrary Farmer, Gene Logsdon

What about you, my dear reader? What books have comforted you during dark times; nourished your love for nature, family, and friends; guided you as you took that next step on your own personal journey?

I know that, at least for me, it is all about The Alchemist.

Friday, October 31, 2008

Pyro Follow Up

It’s been one of those weeks when the reality of the worst economic downturn in generations is nothing but a faint echo outside my office window. Things are actually PICKING up here at the office and I’m just trying to keep my head above water.

But hey, why worry? I have my Halloween costume ready to go and the promise of copious libations and assorted mischief is definitely in the air. :)


For now, I wanted to share the following narrative. It’s something I put together in response to some questions I got this week. I hope this adds some context to my previous post. As always, constructive comments, complaints, and annoyances are always welcome. Have a great weekend everyone.

Why did you burn your law diploma?

At some point, I realized that a great deal of my self-worth was tied to being a Harvard law grad. Burning my degree was just a way to continue this process of simplification. I still have fond memories of Harvard. My three years there were the most intellectually stimulating, most meaningful of my entire life. But, ultimately, I want to live my life on my own terms without needing a piece of paper to justify my own worth.

Was there a trigger to your move to shun excess and pursue a simpler life?

After years of working 12-hour days, giving up countless weekends and canceling vacations at the last minute, I just had enough. I eventually realized that I was slowly losing my life, one billable hour at a time. In the end, it makes no sense to trade 90 percent of your waking hours for a chance to buy expensive clothes, be seen at fancy restaurants, and indulge in all sorts of excess. More recently, a friend of mine was diagnosed with terminal cancer. There is nothing like being made aware of your own mortality to help you focus on what truly matters: family, love and friendship.

How far have you come? Are you downsizing, or is this more of an attitude shift?

I've been taking small, deliberate steps since last year to simplify all aspects of my life. Thus far, I have decluttered my house and have arranged for the sale of most of my furniture. Up next, leaving my job, selling my house and taking some time off to figure out next steps.

If you've already begun shedding material gains, is there anything you miss?

Not so far. Embracing voluntary simplicity does not imply that you have to accept abject poverty or that you need to reject all material comforts. Voluntary simplicity encourages you to shed anything that does not have genuine value to you. In my case, I no longer find a need to patronize Citronelle on a weekly basis, or head out to Vegas to spend a couple of thousand dollars every chance I get. I now spend money on things that bring me meaningful joy. And it just so happens that most of these things are so cheap, they are practically free.

Why did you want to become a lawyer in the first place? What were your expectations coming out of law school?

The honest answer is that I went to law school because I didn't know what else to do with my life. I had a vague sense that I wanted to work in the public interest field, but I did not know in what capacity. In the end, I was seduced by the prestige of all the law schools that accepted my application and by the opportunity to make a difference. And then the reality of incurring $120,000 of law school debt plus the allure of making a six-figure salary changed everything. By the time I left Harvard, I had already bought my first $1,000 suit.

Is there a way for you to continue on a legal career path that will satisfy your desire for simplicity?

I am definitely interested in transitioning into the public interest field. Finding a legal job that satisfies my intellectual curiosity, assuages my moral convictions, and allows me the opportunity to explore my other interests is a priority.

Why chronicle your transition so publicly in a blog? Is there something cathartic about blogging openly, or does committing yourself in public force you to stay on course?

I started the blog as a way to keep track of my progress. At first, it was just a matter of outlining all of the things that were not working in my life and figuring out practical ways to resolve them on my own. Early on, I found that interacting with other people who were confronting similar issues was another way to brainstorm and encourage simplification. There is something about anonymity that allows people to drop their guard and be open about the things they want out of life. I have learned that there is great value in sharing yourself with others, even in the shadows of anonymity.

What have you learned about yourself and what other lawyers are going through in regards to work/life balance issues?

I have learned that there are other ways to live my life and that I should follow my heart, no matter where it leads me.

I've also learned that there is something seriously wrong with law firm life. I've been blogging for five months now, and I am still surprised by the sheer number of e-mails I receive from other lawyers who are dealing with some of the very same issues I struggle with. I think there is a yearning out there for a way to reconcile the demands of a legal career with other life goals. Many lawyers feel that they have rejected important aspects of themselves in exchange for a life they no longer feel they want to live. They feel trapped because they have to pay a mortgage, student loans, private school tuition, etc. ... but have no idea how to get out.

I think it is important to emphasize that not every lawyer working at a law firm is unhappy. Some of my very best friends have thrived in that environment and are genuinely happy. If you derive genuine, meaningful pleasure from the profession and can overcome all the obstacles that this lifestyle places on your personal life, then you have it made.

Monday, October 27, 2008

Follow Your Dreams

I’ve been thinking about doing this, in one way or another, for a while now. But I was never really sure if I would be doing it for the right reasons. Not to mention how silly it sounded whenever I brought it up to people. But this weekend it all came together: the weather was beautiful, the trails were inviting and freedom seemed just around the corner. So I went for it.

This is NOT a knock against Harvard. Or a calculated criticism of legal education. Or even a rejection of elitism, per se.

Sometimes you just need to say goodbye to your past in order to move forward.

In the end, it was just a piece of paper. Nothing more. I would rather live my life on my own terms than be a person that needs a piece of paper to justify their own worth.

A special thanks to M for helping to put this video together. I think it looks pretty cool, particularly if you click the "Watch in High Quality" link right under the YouTube video. What do you think?

Thursday, October 23, 2008



This past week has been a swirl of list-making, planning, scheming and dealing with all sorts of practical minutiae that come with my new status as a “soon-to-be unemployed attorney.” With every errand done and call made, a whole new life is taking shape, one that I have been seeking, in one way or another, all of my adult life.

One of the first things I did this week is come up with a draft budget that I am hoping to put in place once the Plan is finalized. For the Excel nuts out there, you can view it here.

As you review this budget keep this in mind: apart from generally trying to not buy big-ticket items, I have little to no sense of how to truly economize. I feel a little like Bush senior when he didn’t know the price of milk in the 1992 election. The fact is that when you work the hours I do you hardly have the time to really notice the price of things you buy. Your instinct is to go into a store and get what you need as quickly as possible, put it on a credit card, and not worry about it. Ahh, the insanity of yuppiedom...


The truth is that I have been living in la la land for years and only now am I getting a taste of real life. I’m going to need some time to adjust and figure out how to get my bearings. So, please be kind. It’s not easy being a recovering yuppie:

[Cue the basement of the local community center]

Jack: “Hi. I’m Jack. I’m a Yuppie.”

Group: “HELLO JACK!”



As for the budget itself, here are some observations:

*Two areas that I think I can work on right off the bat are Personal Spending and Groceries. The former, I am certain I can get down to the $300 and even the $200 range. I definitely hit a couple of bars every week with some of my buddies, but that’s not all that expensive. The amount of the latter is just a placeholder. I just don’t have any idea what I will need to spend until I start to take stock of what I buy every month.

*Miscellaneous is a catch-all category. I’ll probably expand this as I work on this budget going forward.


I am SO excited about some of things that I have planned for the next couple of weeks. One thing in particular makes me smile whenever I think about it. Stay tuned.

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.

Thursday, October 16, 2008

Bring it on!

I’m jumping. I don’t give a shit. I have been living in the dark for a while now and enough is enough. Sure, you can have tons of fun in the dark. Believe me, there have been times when the booze has been fantastic, when the partying, the women, and the meaningless self-importance of being an asshole lawyer have all been exquisite, convenient distractions from genuine happiness.

But all of that is over as of today. I have to save my soul. I can’t continue giving up bits of myself every time I walk into this office. I can’t go to sleep every night knowing that I can’t live my life for yet another year. More to the point, I can’t stand those exquisite, convenient distractions any longer.

Life is short, my dear reader. Take the time to think about this fact carefully: you, my dear reader, can die tomorrow. Now, I know you *think* you already know that, but if you would just indulge me once more, let me repeat myself: YOU (yes, you! the person reading this right this very minute) CAN DIE TOMORROW. This is a fact and not some trite Dead Poets Society slogan.

I want to live my life furiously, with tons of traveling, love, friendship, bicycling, and some serious fucking in between. I want to have the time to figure out who this Jack person really is. I want to have the opportunity to be reckless, but only in the pursuit of knowledge, experience and, ultimately, meaningful wisdom. I want to live my life as if everyday is my last day on earth.

The first day of the rest of my life starts today. No more waiting. No more bullshit. Details to follow.

Monday, October 13, 2008

Townhouse Status


So, I’m finally getting a handle on the whole townhouse issue. Last week I talked to a couple of advisers and got all the relevant info sorted out. The bottom line is that I can start the sales process at a moment’s notice, depending on how things shake out with my job, the economy and every other ball that is still up in the air. This is an awesome development and has allowed me to breathe a little easier this week. Here is a summary of my thought process on this whole issue:

As I mentioned in an ealier post, the options on the table are the following: (1) rent; (2) sell; (3) short sale; (4) deed in lieu; or (5) foreclose. At this point, it is pretty clear that it makes no sense to rent the townhouse, unless I am prepared to kick in a not-insubstantial amount to cover the mortgage every month. This wouldn’t be a problem if I actually expected to be able to sell the townhouse for some kind of profit in a couple of years. However, that’s just not realistic. Selling the house outright is probably not going to work either given the state of the market and the fact that even if I were to find a real buyer they might not be able to secure financing (banks are basically turning down people with great credit due to the credit crunch).

One option that I’ve already discounted is to just walk away and let the banks foreclose. It’s something more and more people are doing the longer this housing crisis continues. On my end, I am the perfect candidate for walking away. As I’ve mentioned before, I paid literally nothing, nada, 0, zip, to buy this place. The mortgage was fully financed and the seller paid all closing costs. All I did was put my stuff in a moving van and unload when I got there. As for the monthly mortgage expenses, let’s just say that after getting a check from my tenant and annualizing my home interest tax deduction I’m paying a ton less than what my peers pay for housing. Put it another way, since I moved into my townhouse I am actually SPENDING LESS $ on housing than anyone I know. Bottom line, I don’t feel as if I have anything invested in this house so why shouldn’t I just walk away outright?

The answer is it would be the worst possible decision. Aside from all the moral qualms that walking away from a mortgage elicits, anyone who does walk away may face a ton of tax liability, not to mention the fact that the banks may come after you to get their money back. This is stuff that I just do NOT want to deal with in any way shape or form.

Which basically leaves me with two viable options on the table: a short sale or finalizing a deed in lieu. There are some drawback to both options, but nothing insurmountable or horrendous.

So, to sum it all up, I will most likely put the house up for sale first and see if I get any bites. If not, I will just negotiate a short sale or, if that fails, a deed in lieu. Not the most simple process in the world. But hey, there is nothing wrong with facing some complexity in order to secure long-term simplicity.

Tuesday, October 7, 2008

Biking Simplicity


[Yes, my dear reader, this is, in fact, the very first image of Jack posted on this blog]

I took advantage of a couple of cool, clear mornings to do some serious bike training this past weekend. By Sunday night I had ravaged the Mount Vernon trail, the Capital Crescent, and a good chunk of the Rock Creek trail. No way am I approaching the likes of Jill (Up in Alaska) or Nancy (Family on Bikes), but 83 miles isn’t too shabby.

There is something so elemental about bicycling. It is the most selfless way to see the world around you. There is no gasoline, no power steering, and no seat belts. You move forward as one should move through life: by sheer will and determination. Those who bicycle regularly always find a sweet, contagious rhythm that mere novices can scarcely understand. It’s a rhythm full of wind and sweat and rushing empty spaces. It is a rhythm I hope to never forget.
At one point on Saturday I ended up in Bethesda, which is apparently the third wealthiest neighborhood in the nation, behind Newport Beach and Greenwich, Connecticut. Seeing all the beautifully manicured families, trust-fund babies, and annoying yuppies made me think about my future.

Sure, I was (1) dripping with sweat; (2) wearing my 40-year-old-virgin nerd biking helmet; and (3) wearing biking shorts that screamed “seriously, I want you; no I NEED you to stare at my junk!!”


But as I walked through the streets of Bethesda no one batted one eyelid. I was, presumably, one of them. I wonder how I would be treated walking down this same street a year from now. Would I seem different? Would I act differently? Would it really matter?

As I made my way back home on my bike it all became very clear. Life was just too simple and beautiful for me to give a shit.

Saturday, October 4, 2008

State of the Blog

[Photo: Wikepedia]

Seeing as Adventures in Voluntary Simplicity (“AVS”) is celebrating its fifth month of existence I though it would be appropriate to provide the following in terms of feedback/commentary:

Comment Moderation
If you recall, I briefly considered moderating comments after a spate of questionable comments. I’ve decided to leave things as they are and let people post what they want. While constructive criticism is always appreciated, any post that smacks of unadulterated venom will be ignored. I hope other posters will do the same. My hope is to provide an environment in which people can be as honest as they want to be without encouraging unnecessary mischief. I may have to revisit this issue if I ever get inundated with spam.

Blog Structure
Over the past couple of months I’ve added several lists on the right-hand side of the blog. These include:

*“The Plan”: These posts outline my overall strategy for leaving my job and attaining my own version of freedom.

*“Simple Stories”: This is a collection of posts that focus on simple, joyful activities that, at least for me, make life such an amazing, beautiful adventure.

*"Top Posts”: These are posts that, for whatever reason, resonated with me long after I wrote them.

Blog Features
Here is where my ignorance becomes plain and clear. As I navigate through the blogosphere I always encounter interesting gadgets and programs that people have added to their blogs. Sometimes it is fairly easy to discern their utility. Sometimes not. The bottom line is that AVS is probably due for a good spiffying up. If there are any specific features that you think might complement the blog let me know. I’m hoping to add an image/video feature, but beyond that I am still a little stumped.

Photo Attribution
How embarrassing! Being a lawyer I should have instinctively realized that if I add images from elsewhere on the net I should also credit the relevant source. I will definitely do this from now on.

Monday, September 29, 2008

Progress So Far (Q3 2008)

I can’t believe I made it to the end of September. I really can’t. There have been times when the stress of work and the anxiety of waiting for this process to take it’s logical, deliberate course has been almost too much to bear. But here I am, my dear reader. I am staring at a calendar that tells me that I have survived another quarter and have moved closer to the beginning of something precious: absolute, simple freedom. :)

Now that I am here I figured it was time to check in with the Enemy and see how far along I have come:

Getting Rid of Consumer Debt/Student Loans
Start: Ongoing
End: September 1, 2009

My debt reduction plan continues unabated. By tomorrow, I will be able to say that I retired approximately 62% of the consumer debt I accumulated since I bough my townhouse. I am still on target to finish paying it all off by next September though I could always pay it off in full using part of my savings. The more I put in savings the more this becomes an attractive possibility. I think I will feel comfortable signing a big fat check sometime in the next several months. But, again, this consumer debt is parked in a 0% credit card, so it’s not as if I am incurring a monthly interest charge. I don’t have a strong incentive to pay this off at the moment, apart from the psychological boost it would provide.

The student loan debt is still humongous. I’m continuing to make minimum payments, which is annoying because I am paying a great deal towards interest. Again, I think this will not be much of an issue once I start a new public interest job. As I mentioned, my law school has a program that pays off student loan debt if you work in the public interest field. This will probably be the subject of a future post.


Sale of Stuff
Start: July 2008
End: December 2009

One word: nowhere. After de-cluttering my townhouse earlier this year I was left with five or six items that I put up on craigslist. Maybe the prices I advertised were too high or maybe it’s just the economic times we live in but I got exactly 0 responses for all the items I posted. I will try again in a couple of months and see if I can unload some stuff. If I can’t I will just have to wait until I hold a proper yard sale before I leave the townhouse next year.


Selling the Townhouse
: October 1, 2008
End: September 1, 2009

My dear reader, you have NO idea how gratifying it is to finally start focusing on how to get rid of my townhouse. It is the single biggest obstacle to my freedom, both literally and figuratively.
Starting this Thursday I will be contacting real estate professionals, attorneys and tax advisers to try and outline all possible options. Once I get all the facts I will be in a better position to plan my exit strategy. I can’t wait to get started! :)


Leaving My Job
: December 17, 2009
End: December 31, 2009

I’m not sure when it happened, but somewhere along the way I came to terms with the possibility that I could, in fact, leave my job earlier than next December. This is actually the most significant development since I started this process and I am grateful for it. :)

From the beginning, I could justify leaving my law firm because by the time I did I would have enough cash to feel comfortable and secure for years to come. While the plan calls for having enough money in the bank to make $10k a year in interest, the reality is that I could probably live off whatever salary I get from the dream jobs I am currently researching without tapping into my savings. Bottom line, even if I were to leave my job in 6 months or even 3 months, I would still have enough in savings to make leaving my job early worthwhile.

What this all means is that the date of my departure from the law firm is no longer based on how much I have in savings. In fact, freedom for me now depends on how soon I can figure out the practicalities of getting rid of every unnecessary physical thing in my life. As soon as I can dispose of the townhouse and get rid of my furniture I will be in a position to quit my job. What a difference a change in perspective can make.


Friday, September 26, 2008

Flute Simplicity

I was biking around Georgetown the other day when I stumbled on Melchizea. He arrived in the area from Colorado a couple of weeks ago to attend a wedding in Maryland and had decided to stick around for a bit. He told me that he had been sleeping in a tent that he set up by the National Cathedral, but after about a week he had come back to find all his stuff gone. He was certain that one of the grounds people had picked it up but he did not feel comfortable confronting anyone about it.

What was amazing about Melchizea was that he seemed absolutely serene about his predicament. When I found him, he was playing a flute made out bamboo he had discovered on a bike trail in Maryland. His philosophy was that the universe has a plan for him and that his mission was to ‘listen’ closely to figure out what that plan entails.

Some of the most revealing things about Melchizea:

*He has started to make these nifty looking flutes out of that bamboo that apparently grows locally. Who knew!
*He told me that during his first week in DC he happened to meet an elementary school principal who invited him to come and speak to classes about his life, his travels and the meaning of happiness. He showed me a stack of letters kids wrote thanking him for his presentations. They were rolled into one of his flutes.

*He was actually at the Rainbow Gathering in Wyoming this past year. He had awesome stories to share.

I spent a good 20 minutes talking about how I was this self-hating yuppie who wanted to get rid of all his stuff so that he could lead a more meaningful life. He listened patiently, with a great deal of kindness. At some point, I had to move on so I said my goodbyes and without thinking about it gave him a $20 dollar donation. “See, the universe always provides,” he said as he handed me one of his flutes. “This flute will surely help you on your journey, and I can go and get a sandwich.”

Monday, September 22, 2008

New Tenant

In an effort to boost my savings I’ve decided to get another tenant for the townhouse. As of October 1st a very nice Polish student will be staying in what used to be the guest bedroom.

I’m pretty psyched about this. Having another check coming in on a monthly basis is definitely a big plus and will make the Plan that much more feasible. Also, the fact is that I’m usually not home and I hardly see my other tenant anyway. This really shouldn’t change things much. In the end, my savings account will thank me.

Friday, September 19, 2008

On Love

One of the most difficult things that I have had to face since I started this journey has been the realization that, at least for the foreseeable future, I cannot be in love. I just can’t. I'm in a place in my life where being in love would be selfish, impractical, and, dare I say, decidedly confusing.

You see, my dear reader, I, like you, long for the security of comfortable silences. I yearn to feel the familiar warmth of someone's body next to my pillow. Most of all, I crave a certain indescribable connection of body, mind and spirit with someone who instinctively understands me. Ultimately, I want to be able to tell myself: "Jack, this woman was made for you. And you were made for her. Now live your life together simply, justly, and happily."

As much as I may want love I have no choice but to push it aside. There are just too many things in the way.


The hard truth is that I've been so independent for so long that I just don't think I even remember how to be a good partner. There have been way too many late nights at bars, too many parties, too many women to count. Temptation, of all stripes, has been my friend for so long that, at times, it feels as if it is the only thing I know.

Only recently have I started to work my way out of this maze. And there is the rub. I just don’t know how long it will take me to get out. About the only thing I know is that I will occasionally stumble along the way. And that is not a good foundation for love.


The reality is that I just don’t know where I will end up next year. I have a couple of ideas floating around in my head, biding their time until the practicalities of the Plan are resolved. But I just don’t see how I can get close to anyone when I don’t even know where this journey will be taking me.


Embracing simplicity can fundamentally rearrange the contours of the dating world. At least for me. I can just picture my profile:

“Hi, my name is Jack. I’m an ivy-league educated lawyer working at a big time law firm here in DC. I earn a great salary and live in a fantastic townhouse. I enjoy traveling, wine, and gourmet food. In fact, I’ve been to most of the best restaurants in DC and NYC. And let’s not forget that I’ve traveled extensively in Europe, North Africa, North and South America. Believe me, if you take me home to meet your parents they are going to LOVE me. They are going to take one look at me and they will see a multimillion dollar house in the suburbs, 2.3 grandkids, a couple of Mercedes, several trust funds, etc…

But just so you know, over the next year or so I plan on (1) getting rid of my possessions; (2) getting rid of my townhouse; (3) quitting my very lucrative job; and (4) embracing a simple life. I hope to hear from you soon.”

My journey thus far has been an exhilarating, at times painful, mostly joyful experience. In the end, I just hope that this process can add meaning to my life and that it brings me the clarity and the certainty to love someone simply and completely. We shall see.

Tuesday, September 16, 2008

Day in the Life (part 6)

Jack leaves the office in a hurry. He wants to get home in time to catch a netflix movie on his laptop.

Not so long ago, he might have left his bike at the office for a chance to indulge in the wonders of alcohol consumption with some of his lawyer friends. Sometimes it was at a bar in Adams Morgan. At other times, Chinatown did the trick. If it was warm, the Georgetown waterfront was the place to be. Regardless, there was nothing like drowning away the evening with a glass of beer in your hand, good conversation and hot chicks all over the place. And there was nothing like indulging Monday through Saturday, if at all possible.

But that was before Jack’s big epiphany. After a couple of years indulging in all things excess, Jack began to feel that something was very wrong. At first he couldn’t quite put his finger on it. He was making tons of money, had a bunch of ‘friends’ he could count on, and he was as promiscuous as his free time allowed. “What else could I possibly want?” Jack asked himself.

His first reaction was to indulge even more. He went to more bars, slept with more women, partied until all hours. One day he found himself on a bathroom floor reeking of tequila. Looking up at the ceiling he realized what had been bothering him for so long: he was horribly unhappy.

It was such a simple but powerful epiphany. It was as if he had been using his bare hands to dig sand out of a hole, only to find a shovel at the very bottom. In time, he would come to discover the beauty of simplicity and the happiness that comes with a simplified, deliberate life.

But that’s a story for another day.

Wednesday, September 10, 2008

Park Simplicity

As the days start to get shorter and dusk begins to sting my face with a slight northern chill I start to get very protective of what is left of summer. I feel as if my time to enjoy this life is limited and I must do everything possible to experience the beauty and simplicity around me.

Just the other day I spent an entire afternoon by myself at a gorgeous park in the middle of DC reconnecting with my inner 9-year old. I walked barefoot. I picked grass. I laid back and stared at the clouds above me. I smiled.

It was one of those days when you realize that however much you might yearn for a nice house, an expensive car and exotic vacations, what we are really searching for is the certainty and simplicity that only a 9-year-old would understand.

Saturday, September 6, 2008

Day in the Life (part 5)

Jack picks up the phone and jumps right into the belly of the beast:

“Jack, listen, client Big Brother is, once again, intent on taking over the world. Could you please do X, Y and Z to see if we can help them out? Definitely appreciate it! Oh, and by the way, could you do it yesterday?"

This pattern is repeated over and over again throughout the day. Jack listens for instructions and does his job as best he can, all the while hoping that it is enough to keep the phone calls away. Inevitably, stacks of paper start to pile up on his desk and begin overflowing onto window ledges and floor space. At times, Jack feels like he is floating on a vast, endless ocean of paper, screaming at a torrential storm of pens, legal pads and overwhelming responsibility. He knows the sad, inevitable truth: the law firm is a ferocious, starving beast that can never be satisfied.

By the time the clock hits 8pm the splitting headache that started during that 2pm conference call has settled into a more manageable throb. He changes clothes, dons his bike helmet and waddles through a sea of paper, ready to fight the cabs again.