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.