Railing against the machine

September 24 2013

"The mass of men lead lives of quiet desperation." - Thoreau

I did the Wall Street thing for 6 years before walking out one day and taking a trip around the world. I spent months dreaming about doing it. I kept asking myself, “What would it be like? If not now, when?” After suffering incredible anxiety over the prospect, I mustered up the courage, broke the news to my boss, and walked out of the office without saying a word to anyone.

One week later I was on a plane to Corsica.

I donated almost all of my possessions except my books. Books are the hardest thing for me to get rid of. My library is a direct reflection of my obsessions at any point in time. One month I was on this film noir binge and suddenly I had a Mickey Spillane section. When I discovered Mad Men, suddenly I had an advertising section. I still have this thing that whenever I see a used bookstore or a street seller I ask if they have any used Kurt Vonnegut books and buy out any Dell paperback editions from the 1980’s. I have about a hundred. I try to give them away to friends (I have a lot of friends), but I continually find myself going to as many used bookstores. “God Bless You, Mr. Rosewater” is a favorite of mine to pass along. Not only is it amazing (and way better than Slaughter-house Five), but most people have never even heard of it.

It’s been exactly one year this month since I took off. I’m thirty pounds lighter and much less anxious. I live completely detached from the market and the media circus. I’ve spent the last several months trying to find the right opportunity. I’ve got a professional job-coach that has literally re-trained me for navigating the corporate medium. I feel like a foreigner who doesn’t understand the culture or the language anymore. Just the other day I was having coffee with another Wall-Streeter. I was having trouble keeping up with the corporate-speak and it hit me how far I really was from that world.

I have a recurring dream that I’m back at my Wall Street broker-dealer and all my ex-coworkers are staring at me. The office is unfamiliar; I’ve learned the boss has taken me back as a favor to me. My suit doesn’t fit me anymore and I look extremely awkward. I sit down at my desk and stare at my hands, doing nothing.

Now, don’t get me wrong, I don’t want this to come off as a bunch of generation-y horseshit. I’m just out here trying to reinvent myself. The social pressure to settle is on its own an excruciatingly strong force. There’s a well defined, rigid societal structure in place that keeps the system going (just look at the NYTimes wedding section). I say live your life on your own terms, otherwise what’s the point? In the words of Bill Watterson, “You’ll be told in a hundred ways, some subtle and some not, to keep climbing, and never be satisfied with where you are, who you are, and what you’re doing. There are a million ways to sell yourself out, and I guarantee you’ll hear about them. To invent your own life’s meaning is not easy, but it’s still allowed, and I think you’ll be happier for the trouble.”

After helping build a successful equity derivatives strategy and trading firm in NYC, I am actively looking for startup opportunities in anywhere, USA. Feel free to send cool companies my way. Feedback welcomed.

Jonathan McLaughin
[email protected]

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