Justin Alexander 3 min read

I’m 32, and Last Week I Retired – Chapter I : Musings on Money, Monotony and Madness

Random + Awesome depression four hour workweek

money and madness
money and madness

I’m 32, and last week I retired.

Maybe retirement isn’t the right word. If there’s a word that means, “I’m free to live the life of my dreams,” I’m that.

Three years ago I joined a tech startup and have been extremely busy with that. But this last year or two I’ve been struggling with a growing sense of dissatisfaction with my life. By all appearances I was an amazing success story. Here was a guy who dropped out of high school to live in the woods, became homeless for a stretch, and was now living the high life as an international businessman. We had been successful enough to provide an extremely luxurious lifestyle: 500,000 miles of first class flights around the world (for meetings), the finest luxury hotels, Michelin star restaurants, and some really fancy clothes.

The more money I made, the more ‘things’ I needed to be happy. This is the problem with ‘things’. They don’t really make you happy, and there’s always a cooler, more expensive ‘thing’ that becomes your new target of satisfaction. It’s known as the Hedonic treadmill, and it’s why there are so many miserable millionaires out there. My $5,000 (Bell&Ross) watch was great until I had the $15,000 (Panerai) watch. Next in line was a $40,000 (Audemar) watch. You get the picture.

Just writing this makes me feel like a tool. But logic gets left in the locker room when you’re running the hedonic treadmill.

I found myself caught in a stressful cycle of manic working, followed by manic partying. Every now and then I’d be standing there in a world famous nightclub, looking around at everyone having a great time while thinking, “Look at all of these hairless apes, in their expensive shoes, on full parade, trying to flaunt their social and sexual status to attract a mate.” (Did I mention that I wasn’t very cool in school?) I didn’t like the people with whom I had surrounded myself: Businessmen, socialites, club promoters, and boring models. (If you are reading this, I’m probably not talking about you) I felt trapped by this lifestyle that I bought into, and I wasn’t proud of who I had become.

Read: From Casino to Monastery: A Story of Finding Oneself

So this week I “retired” and am in the process of selling everything I own, save a Royal Enfield Motorcycle, my computer, phone, a change of clothes, a passport, toiletries, and credit card which all fit into a backpack smaller than a high school bag. I plan on traveling the world indefinitely. This is the life I’ve been dreaming about since I spent a summer in Nepal in 2005, and honestly, to truly be free, has been my dream since I was a young teenager.

It wasn’t an easy decision. This last month I spent holed away; unavailable, both physically and emotionally, to everyone in my life. Torn between the security of a high salary, and the freedom to live the life that I’ve always wanted. Security and Freedom are at opposite ends of the spectrum.

It is said that monotony collapses our perception of time, while novelty unfolds it; I couldn’t agree more. Three months in Thailand felt like a years worth of memories (fought Muay Thai, became a Buddhist monk, and was adopted by a Thai family in a rural village) while 9 months of head-down working seemed to pass in a flash. I want to unfold time and experience a life full of adventure, meaningful relationships, and countless moments that take my breath away.

People ask me what I’m running away from.

I am running from a life that isn’t authentic; that isn’t me. From the numbness that accompanies a sterile life of luxury. I’m running away from monotony and towards novelty; towards wonder, awe, and the things that make me feel vibrantly alive. I’m not breaking down, I’m breaking free; free of some very clever golden chains.

People ask me what I’m afraid of.

I am afraid of a life unlived; afraid to look back as an old man and wish I hadn’t wasted it on forgettable things or trying to be someone else. I thirst for a life that I would want to read about; an epic tale where I am both author and hero.


Catacombs in Paris. A reminder that we are impermanent.

Read Chapter 2 Here >>

P.S. feel free to creep my facebook and instagram.

This post was originally published in Dec 2013.

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