Monday, July 26, 2010

Falling Off a Cliff


Well, I’m glad that’s over.

After nearly 2 years of nearly uninterrupted exhilaration, spiritual awakening and ongoing personal transformation I suddenly fell off a cliff. Big time.

I’m not going to lie. The past couple of months have been difficult. But I’m here to tell you that all of that is behind me. And I think for good.

There are probably a dozen reasons why this happened. Here are just some of the big ones:

1. The Road Was Postponed. I had to postpone my South American trip for any number of reasons. This will probably be the subject of a future post but let’s just say that the gradual realization that I would not be getting back on the road was, somehow, too much to bare.

2. I Hit a Wall. I probably hit a wall in terms of personal development. There is only so much change you can make over a period of time. I was probably too demanding with myself. Too focused on getting to the “change” without truly appreciating the value and beauty that lies in the “journey towards change.”

3. Love. After several years doing my best to avoid a serious relationship (and reaping the exciting, yet ephemeral joys of being single) I was suddenly open to love. Real, substantial, meaningful, scary love. It didn’t take me long to realize that I was out of my element. In the end, I was undone by fear of commitment and my own insecurities. More on this later.

4. Habit. When all is uncertain, when frustration reigns, when everything that is good for you feels like hard work you embrace what you’ve known for years. In my case that means embracing my inner asshole.

There is more work to be done on the personal development front. I know that. What has changed is that I am no longer tied to some artificial schedule. My to-do lists still reign supreme but they exist in the context of a much more holistic process of “change.”

I want to take this opportunity to thank those of you who have sent emails, texts and/or otherwise reached out over the past couple of months. All that stuff helped. Believe me.

And to those in the press who have been trying to reach me, all I can say is that I am fine and that I still prefer to express myself via the blog. Not looking for publicity. Not interested in fame. I just want to continue doing what I have been doing over the past two years: challenging myself to be a better person with simple, brutal honestly.

Thank you everyone,


Wednesday, June 2, 2010

Taking Stock


Well, I’ve hit a wall. I can’t continue on this path. That much is clear. Time to try something new.

And by “new” I’m referring to a variation on the “time out” I did recently. The focus is simple: regain focus. Hopefully, this will allow me the time to examine where I am, why I am where I am, and, ultimately, how I can move forward again.

This “time out” involves the following over the next 30 days:

*Heading out with friends once a week only. Meeting up with large groups of people, all very much interested in partying and debauchery, is at the core of this current downward spiral. The idea is to limit these activities as a precursor to finding my way back to a healthier Jack.

And no, I don’t think going cold turkey on this would do much good. I would rather have access to people I trust and care about once a week than to cut off contact completely. At least I should get the chance to evaluate whether my current friendships are helping or hindering my progress.

*Limiting drinking to the once-a-week get-togethers
. I’ve noticed that drinking is clearly exacerbating things whenever I am out with people. Better to limit this as well.

And no, I don’t think I have a drinking problem. I’ve cut off drinking quite a bit over the past couple of years. Up till this past month my MO was clear: give me 2 glasses of Cabernet or 3 bottles of Sam Adams and I’ll be good to go for the night. Twice a month. At most. The problem is the combination of alcohol with my current state of mind. Need to reevaluate this as things progress.

*Limiting sexual activity, if any, to the days I meet up with friends. I think this is self-explanatory.

*Taking the time to contemplate my situation. The idea is to have enough time to really understand why I am where I am. I need to interrogate myself in a serious and honest way. There is clearly a disconnect between my actions and the person I want to be. I just have to figure out how to identify the source of that disconnect and chart a path towards safety.

I’m fully aware that there is no guarantee that this “time out” will work. But hey, I’ve learned that in life nothing is guaranteed. I’m going to give this a shot because deep down, I still believe in myself. I wouldn’t be doing this if I didn’t.

And if it doesn’t work, well, as suggested in comments to my previous post, there are other alternatives to consider.

Wish me luck.


Wednesday, May 26, 2010

I'm Out of Control


I’m totally out of control.

Those of you who follow me via Facebook probably already know what’s been going on:

-The sex has been wild. Unpredictable. Insane. Empty.
-Yoga and meditation have been tossed aside.
-Any urge to continue my internal/emotional development has evaporated.

The bottom line: I’ve relapsed in a major way. Simplicity has been replaced by a ferocious urge to feed my ego, to fuck ad nauseam and to generally act like a complete asshole.

I don’t know what to do.

Friday, May 7, 2010

I'm Now on Skype

That’s right, I’m now on Skype.

Not sure whether this will eventually turn out to be counterproductive in terms of my simplicity goals but I’m willing to give it a try. The bottom line is that I’m still drowning in emails requesting advice, offering speaking engagements, interviews etc...I’m hoping this can serve to answer more of your questions, even as I get to interact and learn from as many of you as possible.

If you ever want to reach out feel free to send me an email( with the following information:

1.your full name on Facebook;
2.times during the week when you can chat freely;
3.topics you want to discuss.

For security reasons I will contact you via Facebook first so we can set up a time to Skype. Note that depending on demand and availability I might not be able to respond right away.

Have a great weekend everyone,


Wednesday, May 5, 2010

I'm Getting a Vasectomy

Well, it's settled. I'm getting cut. I'm doing the old 'snip, snip'. My little swimmers will soon be no more.

I'm getting a vasectomy.


I have to admit that the decision was harder than I thought it would be. And I'm not even referring to the realities of the medical procedure.

When I first considered this option I didn't really see a coherent argument against it. None of the arguments I came across (“what if you find a person you love who wants kids;” “what if you change your mind;” “not having kids is selfish;” etc...) were really all that persuasive given my motives, my preferences and my own internal ethics.

And then something happened. I'm not sure how I can even describe it. Let's just say that I suddenly felt a twinge of existential guilt. It was almost as if the universe itself could somehow get pissed if I voluntarily eschewed a fundamental imperative shared by all living things. As much as I tried to shake it off I couldn't help but think that by getting a vasectomy I would be committing a crime against nature itself.

And then, just as suddenly, I found a solution to my dilemma that made sense to me. Why not make a bargain with the universe for the right to get a vasectomy? Surely I could offer the universe something more valuable than the chance to nurture a brood of future bike-riding, nature-loving, list-focused, sex-crazed Jacks.


Dear Universe,

I'm sure you know by now that I'm all about getting a vasectomy. Before you say anything, you should know that I've always been a very big fan and I really, really don't want to piss you off. That is why I want to make you this proposal:

let me have my vasectomy and, in exchange, I commit to spending a certain amount of time and energy every year having a direct, positive impact on children's issues. I'm also going to allocate a certain amount of money in my personal budget to help children in some way.

Now, I know I haven't quite figured out how this is going to work, but I want you to know that I am committed to this.

So, what do you think? FYI, I might make an appointment sometime next week so let me know ASAP.

Take care,


Saturday, April 17, 2010

Garden Simplicity

I don’t want to get all Martha Stewart on you guys, but I’m actually getting attached to the garden in my building. There is something about the color of the flowers and the texture of the leaves that instills in me an incredible amount of peace. It’s during these times that I regret not having a permanent place of my own where I could have my own personal garden.

I know next to nothing about gardening. The truth is that every plant I have ever had has suffered a slow, painful death under my care. There was the small potted plant on my desk in college that ended up in the garbage after 3 weeks. Another 3-4 plants died mysteriously when my folks left the country and left me in charge. And let’s not even get into the time I tried to grow spices in my apartment in NYC.
I never really understood the roots of my plant murder spree. Maybe I just wasn’t all that conscientious about watering them properly. Or maybe the cause is deeper. Maybe my plants died because I never really understood them.

After spending weeks walking by this garden I’ve noticed things that, while obvious to those who love plants and flowers, came as an absolute shock to me: plants are living, breathing, miracles of nature. Their growth and shape is determined by the contours of their surroundings. They react to sunlight, cold, warmth and rain. You can casually spot a flower bud in the morning and come home to see a beautiful fully-grown flower. Plants MOVE during the day.

Plants are ALIVE.

Friday, April 2, 2010

Reflections (7): I Am a Buddhist


Good Friday feels weird this year.

In years past, making an effort to embrace my Catholic faith during Holy Week was, more often than not, just sheer and utter drudgery. To be sure, there were times when I sincerely felt as if I could literally touch the purity and sanctity of my faith. But, for the most part, the annual pilgrimage to confess before Good Friday, the requisite attendance at mass and the focus on the pain and suffering of Jesus felt rather inauthentic. Empty even.

And then everything in my life changed. Suddenly, the ground below my feet was more solid. For the first time I knew who I was, who I wanted to be, and who I would never be again.

I also began to read. Passively at first. Later, I was gripped by a furious urge to understand that surprised even me. Eventually, it took embracing something outside of Catholicism for me to come to terms with my Catholic faith.


I am a Buddhist.

I write these words with a great deal of serenity and satisfaction. This glorious, ancient practice has helped to bring clarity to my heart in ways that I still cannot comprehend. For me, it is but the logical progression of a person who has embraced the tenants of an ephemeral, yet, ever-powerful movement called Voluntary Simplicity.

If Voluntary Simplicity is my destination, Buddhism is my roadmap.

If Voluntary Simplicity is the cool, misty waters of the Pacific Ocean,

Buddhism is my Surly Long-Haul Trucker:

Let me be clear. While I have embraced the practice of Buddhism, I am still Catholic. Or, at least, as Catholic as the Church says I am. I have yet to find anything inside myself that compels me to abandon my faith. Catholicism, for all its faults and contradictions, is, and always will be, the great enigma of my spiritual life.

What Buddhism has taught me is that I don’t ever have to completely resolve this enigma. I can immerse myself in the waters of my faith, so long as I embrace the path laid out by my heart.

And it is from this path that I write these words today.

[Reflections introductory post]

Sunday, March 21, 2010

Virtual Meditation Session

Starting Virtual Meditation Session in 5 minutes.

1:34 PM Eastern

Just finished meditating. As always, the experience is immediate and personal. This time, though, there was an element of something else. I was not only connecting to a gathering of people who had long since finished meditating. I was also, in some unique way, connecting to people elsewhere who were united in a common purpose.

A truly beautiful experience. Thanks everyone.


Friday, March 19, 2010

DETAILS: Virtual Meditation Session This Sunday


As mentioned in a previous post, Adventures in Volutary Simplicity is organizing a “virtual” meditation session this coming Sunday at 1:00pm Eastern US (5:00pm GMT). The session will consist of listening to a guided meditation session conducted by Tara Branch at the Insight Meditation Community of Washington DC on December 9, 2009. You can access the session HERE.

While you guys can post comments on the blog post I will publish at the start of the session, you can always post live comments on Facebook before, during and after the session.

I'm getting really excited about this. :) I've received tons of emails from all over the world expressing interest in the project. This stuff always blows me away...I still can't quite get over how powerful this blog has become and how committed you guys are.

Whether you have pledged to participate or are just a curious bystander, I hope you all will join us for 30 minutes of relaxation and collective mindfulness.

See you all on Sunday.


Wednesday, March 17, 2010

Virtual Meditation Session This Sunday


Those of you who are regular readers know that I've come to embrace meditation. It is something that has absolutely changed my life. I feel so strongly about the benefits of meditation that I actually have no shame in recommending it to anyone and everyone willing to try it.

That's why I will be organizing a virtual meditation session this coming weekend on this blog. It will probably involve listening to one of Tara Branch's guided meditation podcasts off the Insight Meditation Community website at a set time this coming Sunday. Everyone is welcome to parcipate, regardless of experience level. Those who follow a different meditation tradition, or who prefer to meditate on their own would also be welcome. The point would be to “gather” together, at the same time, in the same “space,” in order to embrace peace, tranquility, and serenity. Just imagine: dozens, hundreds, even thousands of people from all over the world, meditating as one.

I'm also thinking of setting up an anonymous webcam with a link to the site. I would be grateful if any techies out there can recommend a user-friendly program that I can use to link to the blog.

Take care everyone,


Thursday, March 11, 2010

On Being Lonely

Well, so much for taking a break from getting laid. After some time away from meaningless sexual escapades I've been venturing back into the confusing world of dating, one night stands, and emotional turmoil.

It hasn't been easy. I think for the first time in a long time I am absolutely prepared to give a piece of myself to another person. And maybe that's the reason I have found things so difficult this time. Suddenly, physical beauty, availability, and the willingness of a woman to pretty much do anything I want is no longer enough. Suddenly, I want HER. I want the person I see inside to be mine. Or maybe what I really want is for the person inside of me to be hers.

Either way, I honestly, truly, sincerely have no idea what I'm doing at the moment. One minute I fall hard for someone with a beautiful smile, only to retreat emotionally after making love. Half the time I am convinced the person I am caressing as they sleep will be unfaithful to me. The other half I spend trying to convince myself that what I really need is to get laid with just about anyone else.

What a mess.

The truth is that after years of doing my best to avoid being in a truly serious relationship I've come to realize that I am profoundly alone. And not in the I'm-at-home-on-a-Friday-night-and-noone-wants-anything-to-do-with-me-sort of loneliness. No. It's more of an existential loneliness, one that constantly laments not being able to share the essence of a new-found life with another like-minded soul.

Maybe this is just part of the transition. Maybe I'm just feeling my way through a dark room for a bit...until I find the light switch.

I hope so. Wish me luck.

Tuesday, March 2, 2010

State of the Blog: Back from Sabbatical


Every once in a while it just makes sense to disconnect from everything. I tend to do it when I'm feeling overwhelmed. Or when I'm contemplating significant life changes and need the time and space to think and focus. And, sometimes, it's a little bit of both.

All I can say is that I'm no longer overwhelmed and that I found the time and space to think things through. It's good to be back.

Tuesday, February 16, 2010

I Love the Law Again


I had a pretty strange experience yesterday. As a favor to a friend I found myself in a conference room surrounded by a bunch of business guys eager to get legal advice on a number of corporate matters. My adrenaline started pumping as the trickle of legal concepts and strategies I presented became a torrent. I found myself excited, indeed intoxicated, by the magnificent edifice that is the law. And you know what? I enjoyed it.

Or did I? Maybe I've become so averse to opening any door that could let in the Jack of old that what I felt was not joy but relief. The bottom line is that, for the first time in a long time, I found myself enveloped in the exciting machinations of corporate law without all the baggage I felt back in the day. There are several reasons why this happened. It probably helped that the business guys in question run a company that isn't stuffy and that is ethically honest. It's also not lost on me that the progress I have made over the past several years has outfitted me with an impenetrable shield against all the BS I faced every day back at my old law firm.

But probably the most important reason is that I wasn't providing advice as a Big Law attorney. And I think that's why I might have felt relief during the meeting. I had always believed that my problem with Big Law was not Big Law itself but the tendendy of Big Law to encourage a lifestyle that was antithetical to my core beliefs. Suddenly, this belief was transformed into fact and I was free to love the law again, without having to reprise my role as an egocentric asshole lawyer.

Let me be very clear: I have ABSOLUTELY, POSITIVELY NO INTENTION of going back to corporate law. That being said, I consider yesterday's realization an unexpected gift.

Sunday, February 14, 2010

I'm happy

I'm happy right this very second. These moments are precious. I will always be grateful for moments like these.


Friday, February 5, 2010

Marijuana Simplicity


I don't think I'd be exaggerating if I were to admit that I was one of the biggest potheads in college. It's true. I had tried weed on and off back in high school but it wasn't until my crazy, sex/beer-filled freshman year that I fell in love with the pure, mellow joys of marijuana

My routine at the time was pretty simple: for each lecture/seminar I would only attend the very first class in order to pick up the syllabus and course schedule, and thereafter only show up for quizzes, midterms, and finals. Aside from a massive 2-week cramming session at the end of each semester, I had virtually the entire academic year to hang out with buddies, be with my girfriend(s?) and, or course, smoke some bud.

I only had one rule: I could smoke as much as I wanted so long as I got As in all my classes. (The irony is that the more I smoked, the easier it was to get those As. Go figure.)

And then came law school and the sudden realization that I was entering a profession with legit rules of ethics and professional responsibility. By that point, weed had lost its luster. Inhaling smoke, of any kind, seemed like an unbelievably stupid thing to do. The spiritual component that had originally drawn me to marijuana had long since been replaced by an urge to party. Suddenly, it made sense to hang up my bong.

Years later, bathed in the light of my trusty laptop, I take a long, smooth drag from a makeshift bong made from an aluminum can. The taste is still sweet. I just want to feel pure and mellow one last time.

Sunday, January 31, 2010

Reflections (6): On Being a Guy

Walking by a beauty salon the other day I stopped dead in my tracks. Turns out it was some sort of day spa for dudes. For a fee of over $100 a guy can enjoy a pedicure, a manicure, a lucious mud bath and complementary bath oils and soaps. Full-body massages are extra.

What. The. Fuck?

I don't know about you, but after spending almost three months “showering” in McDonalds' bathrooms all of this metrosexual bullshit pisses me off. I understand that Simple Living can mean different things for different people, but I can't help but feel sad at the current state of heterosexual guydom.

In the great tradition of Edward R. Murrow here's my own This I Believe short essay:


I believe in Moday Night Football, pickup basketball and sweaty gyms.

I believe in shaving only when I feel like it.

I believe in making love to beautiful women.

I believe in drinking good beer and embracing occasional hangovers.

I believe in never shaving my chest.

I believe men can be considerate, loving, open and honest with their partners without turning into total pussies.

I believe half-naked chicks riding mechanical bulls are hot. Yeah, I said it. Again.

I believe I would rather get punched in my balls than watch The Notebook.

This I believe.

[Reflections Introductory Post]

Monday, January 25, 2010

GUEST POST: An Alcoholic's Perspective


The following is a Guest Post written by my friend R, the subject of a prior post on alcoholism. I think it speaks for itself.

An Alcoholic's Perspective

I am R.

Jack invited me to read and contribute to this article a few days ago. When I finally read it, I was extremely touched and also awakened. I guess the main message I would like to communicate here is that a disease such as alcoholism--as with any other infliction--is extremely difficult to truly understand unless one experiences it first-hand. I know I'm a great was mentioned by Jack, successful, traveled, educated, all of that. But I have this evil little devil sitting on my shoulder at all times. I hate this part of my life and wish there was a way to just hit the "off" switch. But through personal experience and extensive research, I've learned that there is no easy fix. It takes time, determination, support and constant adherence to daily goals.

To draw an analogy: it is like trying to convince yourself to not drink get thirsty, then thirstier, then even worse...and you finally convince yourself that you need to drink water in order to survive. Well, granted, water is in fact necessary for survival, and alcohol is not, but in the mind of an alcoholic it is.

Another thing about this condition is that alcoholics often don't even realize what is happening when they are drunk. They don't comprehend reality in the same fashion as others. Hence they make irrational decisions, such as prolonged drinking. Sometimes when I am drinking, I find myself having a dialogue in my head, "I don't want to drink, but I will anyway. Why? I don't need to. I know it is destructive. There is absolutely no reason for me to drink. But I will anyway."

This is an example of irrational thought that pervades my mind. So in an effort to combat this, I set little daily goals and stick to them. For example, I will not allow myself to have a drink before X time of day. I will limit myself to X number of drinks. I've found that I cannot go without alcohol completely, but if I set little goals like this and regulate my drinking, I am OK from day to day.

And also here I must mention my indescribable appreciation for Jack and his selfless graciousness. He hauled my butt to the hospital more than once when nobody else was around. Who knows what might have happened if he hadn't. Not only has he done this, but, through conversations (a kind of informal counseling), he has extended a whole world of insight and compassion for me to embrace. On the surface, it's friendly dialogue between two friends about a problem. Deeper, it has had a profound effect on me and my outlook on life. Thank you for this Jack -- it is appreciated more than you will ever know.

In closing, I guess I would just like to extend this entire blog post and responses to others who suffer from the same infliction. Just remember that life is too beautiful to let oneself slip to such lows. And, as one poster here mentioned, sometimes it is necessary to hit rock bottom before recovery. I feel like I'm pretty much there currently, so I'm looking forward to a big rebound. I have many great things in my life right now, and I look forward to getting back to enjoying them.

Wednesday, January 20, 2010

On Alcoholism


Those of you who follow me via Twitter and Facebook probably noticed a couple of rather strange-sounding status updates over the past several months. They all, in one way or another, referenced several trips to the ER and being there for friends in need. I think I'm about ready to talk about it. If only because it has taught me valuable lessons about how difficult life can be when you are no longer in control.

Back in September I met R, a guy who lives in my apartment building. R seemed intelligent, interesting, well short, a pretty nice guy. R and I hung out a few times and as I got to know him I realized we had tons in common. I'm not going to get into any substance, but let's just say that he seemed just as damaged as I was in some pretty fundamental ways.

A couple of weeks after we met, as I was hanging out one Friday evening in my place, R knocked on my door. He looked absolutely terrible. He was sweating profusely, his eyes were dilated and he could barely walk. He told me he had always suffered from some mysterious illness that prevented him from sleeping for days on end and made eating difficult. Even as he slurred his words I made the executive decision that he needed to head to the ER immediately. I grabbed my keys, grabbed my wallet and slowly walked him downstairs to a cab.

At the ER, everything was pretty routine. They took blood and urine samples, gave him an IV and after 4 hours told him that they could not figure out what the problem was. Heading back home R was more himself. We even joked about a couple of smoking hot nurses who had treated him.

Sometime in late December R showed up at my door looking even worse than back in September. Again, I dropped everything and took him straight to the ER, where, for the first time, an inkling of what was really going on began to emerge. “Have you been drinking?” the attending physician asked. “No,” was R's response.

Up until this point, I had assumed that any drinking on R's part was merely exarcerbating whatever affliction he suffered from. After the nurses and doctors were gone I pressed R a bit. “Dude, when was the last time you drank?” “Jack, I'm an alcoholic,” he said with some seriousness. After he was discharged we walked back to the apartment building in silence.

Early the next morning, several people in our building walked into R's apartment to find him catatonic. He was seated in a chair in a daze, arms raised to shoulder level. There was a nearly empty bottle of rum on his desk. It took three of us to carry him downstairs to a waiting taxi.

R spent 15 hours in the hospital and was released early the following morning, only to continue drinking for several weeks after that.


I think I've learned several things from my friendship with R.

First and foremost, it is clear to me that, whatever my demons might be, there are people who are struggling with far worse. I think back on what I have accomplished over the past several years and wonder if I could have gotten this far if I had started out as damaged as R is. Somehow, I doubt it.

I've also learned that alcoholism, like any other addiction, can affect even the smartest and most capable of all of us. R is still a great guy. I still respect him greatly. I just wish he would slay his demons so he could be free as well.

Good luck R. I believe in you.

Saturday, January 16, 2010

Yoga and Meditation are Awesome


I just had an awesome Yoga-guided meditation session! I just can’t believe I ever lived my life without yoga and meditation. They have become a a part of me in ways that I could not have imagined a year ago.

Definitely encourage everyone to take a couple of yoga classes just to see what it’s all about. Those of you curious about meditation can start in the privacy of your own home. I highly recommend the online podcasts run by the Insight Meditation Community featuring Tara Brach. She has a wonderful gift for guided meditation.

Take care everyone,


Thursday, January 7, 2010

Inspiration: The Alchemist


I know I might be preaching to the choir with this post, but I have to say that reading The Alchemist was a transformative experience for me.

I first read the book back in college, at a time when getting laid, drinking with friends, and “finding myself” were very much priorities. Looking back, I have a feeling that the real message of the book was probably muddled by a good deal of post-adolecent angst and a perverse (naïve?) confusion only a classical liberal arts education can generate.

Some years later I reread the Alchemist at a time when getting laid, drinking with friends, and “finding myself” reemerged as priorities. The experience was completely different. Coelho's narrative was now crisper, mode defined, and less allegorical. I no longer saw a boy tending to his flock and traveling the world in search of a treasure he has only seen in his dreams.

Suddenly, I understood what I had to do. Where I had to be. And, more importantly, who I didn't want to be.

Tuesday, January 5, 2010

I Love You

I can´t stop thinking about you. And there is so much to think about…

Your long, flowing hair.

Your knowing eyes.

Your easy smile.

Your love of literature, film, and art.

Your courage.

Your capacity to love.

Your capacity to understand.

Your independence.

Your sense of adventure.

I just have two questions for you: (1) Who are you, and (2) When will I finally meet you?