Meet my friend Jack.  In a lot of ways, we are very similar.

We are both lawyers.  We went to the same law school together.  We were in the same section and took most of our classes together.  We studied together, went out to bars together, and have the same core group of friends.  We both love drinking, beautiful girls, sports and humor based on dry sophisticated wit.  We even share the same birthday.

During law school, some flashes of our differences began to illuminate.  He started and sold a side business generating $100k in profit.  I partied harder, moved to a beach city and stopped buying textbooks.  He took a break from his longtime girlfriend and then got back together with her.  I broke up with my girlfriend and commenced with mass dating.  He received high grades and secured a great job at a big law firm.  I received good grades and falling short of the big firm, took a job at one a tier below his.

As with most office or corporate settings, my life began to drift towards the conventional American mold.  The natural corollary to this was that our lives started to coincide.  We both purchased homes in the same city and signed paperwork encumbering ourselves with the perceived milestone of the famed mortgage.  We both leased new cars.  I started dating a girl seriously and after a few years, Jack and I were both living with our girlfriends.

At the end of 2009, our paths that were once parallel started to shift tremendously.

Jack got married to his longtime girlfriend.  He advanced at his job and was making well over $200k.  He started buying investment property across California and some other states.  He sold his home and moved into a bigger home in a better school district, as he and his wife welcomed a new son to their family.

I also advanced at my job quite nicely, but was capped at earning low six figures.  I was required to put in “face time” at the office even if I was without work.  This was not what I wanted in life.  The partner I worked for was an extremely talented attorney, so I modeled myself after him.  Like a sponge I soaked up all his mannerisms, the way he wrote, the way he argued, the things he cared about and the things he found trivial.  Eventually, I made my first huge decision.  I quit and started my own firm.

My income went from the dependable six figures to a chaotic low fives in the first year.  My savings started to evaporate.  Having my own business however allowed me to get creative.  I took on small clients that later spawned big cases.  I bartered legal services for PR press, which landed me a published article and a subsequent deluge of opportunities.


The freedom of having my own firm allowed me to travel — and so I did.  A lot.  In the past two years, I’ve gone to Finland, Russia, Poland, Belarus, Czech Republic, Colombia, Brazil, Argentina, Bermuda, Ukraine, Germany, Sweden, Norway, and Iceland.  Slowly I began to realize what actually made me happy.  It was not material possessions, but freedom.  So I made my second huge decision — fuck convention, let me be the outlier in this mass imposed ideal of social norms.  I was not happy in my relationship, so in my early 30s I broke up with my girlfriend of 4+ years.  I found someone to take over the lease of my wonderful yet unnecessary $60k BMW.  I cut my DirecTV service.  I rented out my condo, sold my 3D Plasma TV, my projection TV, my leather couch and all my furnishings.  The remainder of my items (art, memorabilia, etc.) went into a friend’s storage.  I’m currently taking a Russian language course because, well, I can.

Fast forward to today.  Jack just quit his job and partnered up with a few other attorneys to do his own thing.  He’s happily married with a nice large house.  His wife is extremely nice and stays at home to take care of their wonderful son.  They live in a great area of suburban California and he has a few investment properties scattered throughout the U.S.  He has a great family close by to him, comes out with the boys when he can and generally seems very happy.  I have nothing but respect for him as both an individual and a professional.

My life is constantly improving.  Professionally, I’ve landed new clients via email in New York, drafted motions from Iceland, and held conference calls from Ukraine.  I fortuitously came up against my former boss in a case and beat him recently.  That client turned out to be well-connected, garnering me some substantial business from referrals.  In the past two years I’ve been recognized by a well-respected legal organization as tops in my practice.

The flip side is I have no car and no home.  I use my little brother’s non-luxury car as he’s away at school.  I find random apartments to sublease for however long necessary when I am back in LA.  And when it’s time to move again, I throw my suits, clothes and laptop into my brother’s car and drive to the next place.  I’m free from bosses, from a relationship that wasn’t right for me, and from the unnecessary luxuries and expenses that ate at my income.  But most importantly, I’m happy.

Read More: It’s Always Great To Be A Man

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