Last updated: January 10, 2017

What Could Have Been…and Almost Was



I stomped on the gas pedal as the light turned green. Clutch out. The tires peeled and I smelt a faint whiff of burnt rubber and smoke. The throaty roar of the Mustang took over the cockpit. Clutch in. Second gear. 45 mph. As I exited the corner and turned on to my office street the back end came around. I jabbed the throttle harder and flicked the wheel back to the right. Clutch in, third gear. 60 mph. Fourth gear.




My office was coming up. Fast. Right foot to the brake, push hard. Clutch in. Rotate right heel to the gas; executing a perfect heel-toe downshift. Tap the throttle. Grab third gear. Another flick of the heel. Second gear.

I brought the car to a near stop as I pushed the clutch in and grabbed first gear. I rolled lightly over the curb so as not to scratch the body of my beautiful, sleek, grey Mustang. I pulled into my parking spot. Clutch in. Motor off.

Just like that the best part of my day was over.

It was fall of 2013, and on paper, I had everything.

A brand new Ford Mustang, Pony Package edition. A hotshot job as an up and coming engineer at one of the top Japanese companies in the world. A nice apartment in one of the most desired cities and neighborhoods in the world–La Jolla, California.

More money than I knew what to do with.

And best of all, I was only 21 years old. You’d think this would be cause to celebrate and enjoy life. Instead, I found myself becoming increasingly more unhappy by the day.

You see, I’d graduated high school, and gotten good grades. I applied to multiple colleges, hoping I’d get the chance. I ended up getting into the one I wanted most. I’d gone to college and graduated early. I’d escaped almost nearly debt-free, like I was supposed to. I’d then started working at a great company making a decent salary—again, just like I was supposed to. Oh, and I was beginning to look at condos to purchase, which would only increase in value as the years went on.

Again, just like I was supposed to.

You see the trend here? I was doing what was laid out for me already. A roadmap to a man’s life, if you will. This roadmap is very typical in the grand scheme of things; it’s what any and all young men are told as they grow up. You work hard in school, you work hard at your job, you meet a nice girl, you marry, you have family, you raise said family, you grow old, you retire with your 401k, you hopefully don’t crap your pants in old age, and then you die.

What kind of life is that when you already know every step of the way?

I found myself increasingly unhappy because I was playing somebody else’s game, and from what I could see, it wasn’t working out for most people. The vast majority of people in that office were overweight. They were married to wives they hated. Most of them loved their kids, but also envied me for my youth and freedom. And yet every person I talked to told me to take that next step in my life.

To buy that condo. The condo that would be a future stepping stone. It would show stability to girls so that they would want to date me. It would raise in value compared to what I bought it, so that I could later sell it for a profit. I would stop paying rent and pissing away that money, as I’d be “investing” in something. Everyone encouraged me to go that route. To buy that condo in La Jolla that I couldn’t afford.

I am grateful every day that the price rose right as I was considering it. It jumped from $185,000 up to $225,000. I balked at that. Don’t get me wrong, I had the credit score, job, and support to get the loan I needed. However, something felt wrong. It seemed like a bad path to enslave myself to well over six figures of debt.

It scared me. I stopped returning the emails and phone calls of the realtors. I stopped teasing myself by looking at the listings. I pushed other impulsive “toys” and purchases out of my mind and buried myself in writing.

(It’s worth noting that some people were also encouraging me to sell my second, economical car (a 1994 Honda Accord) and purchase a used Range Rover for transporting my sporting equipment. It was San Diego, after all.)

I went the complete other way the next year, because I took a trip that truly changed my life. I booked a week in Wroclaw, Poland, and Prague, Czech Republic. You’ve probably heard of Prague, but almost no one in American can tell you a thing about Wroclaw. I wanted the opportunity to see a city that no one knew anything about. Prague was quite a bit more touristy and known, so I picked Wroclaw to go completely off the grid.

It was one of the better choices I made in my life. I paid nearly $1,400 for my round-trip tickets. Those stubs of paper were a better investment in my life than any condo or Range Rover would have been. $1,400 seemed like a lot at the time, but was the best investment I ever made in my future self.

In Wroclaw, I realized a lot of things about life and everything I’d been told. Up until that point, I’d never really left American soil. Sure, I’d been to Mexico and the Caribbean, but those were with family and on pre-packaged vacation deals. When I touched down in Wroclaw, I was very much alone, with no working phone service and no real idea where I was going, other than that I needed to take night bus 206.

Those three days there (spent with a great friend) showed me that I wasn’t living the life I wanted to live. I didn’t want to be stuck in a cubicle, I wanted to explore. I wanted to be the prize in the dating world, not be left with table scraps. Most of all, I saw a lack of material items in Wroclaw. Nobody had cars, but the tram and bus system was simple. Nobody had expensive houses, everybody lived in small, reasonable flats. The small apartment I split with my friend had a music system in the bathroom, but was devoid of crazy, debt-inspiring luxury items: 80-inch TVs, expensive furniture, etc.

When I got on my plane back to San Diego I knew I needed to return. I just didn’t know how.

Within a calendar year I had significantly downsized my life. My four racing bicycles turned into two. The Mustang had been sold, and my $375 monthly payment eliminated (plus $200 insurance). I nearly cried. I’d moved out of La Jolla where I was paying $1,400 a month rent to North Park, where it was a far more reasonable $800. The apartment resembled much more of Wroclaw’s Old Town Square than 2015.

While I had the weight lifted off of my shoulders, I also was grappling with a new sense of the world. You see, it’s not easy to have life turned upside down of you. Since stumbling across a specific article about what to do when a girl says “we’re not having sex”, my life had been turned upside down. I’d discovered that everything I’d been told, from high school to college to career, was what everyone was being told. I’d done everything perfectly in the top 1%.

Yet my growing unhappiness was proving to me it was a scam.

However, dealing with learning the realities of women, career, and other aspects of life was a lot for a 22-year-old kid to handle. While I now had the knowledge and the desire to escape the spiral, I didn’t have the balls. My entire knowledge of the world had been reshaped within a year and a half. It was as much as I could handle.

Later that year, the career path got worse. Despite being the youngest and (probably) the sharpest engineer, I got passed up for several promotions I’d deserved (and one which I probably didn’t, but tried anyway). The reason?

I was too young. The Japanese promote seniority and loyalty. They didn’t see someone my age as worthy of being a Senior Engineer.

And again, I am thankful every day that they passed on me. Because, I was so disheartened I took another job with another solid company, this time in Los Angeles. I left my “college home” of San Diego, all of my friends, and my girlfriend (though that fell apart later) behind. I moved to a new place where I knew no one.

I hated every single day there. There was not a day that went by that I didn’t dread and despise walking into that office.

A year after my first trip, I took my second jaunt to Europe. This time to Budapest, Hungary, where I spent 10 days partying and meeting the locals. It was the time of my life. Again, I had the desire to get out of my corporate job and see the world, and still…couldn’t.

It wasn’t until I went to Colombia later that year (this is November 2015), and met some digital nomads. Guys who were living in Colombia, dating the local (stunning) women, and just having the time of their lives. They were freelancing and making $1,200, but seemed a lot happier than I was.

I had the blog at the time, and it was doing okay. A few days after I got back in Los Angeles, I sat down for an entire afternoon. I looked at where I wanted to go in the world. I looked at my bank account and deduced I had enough money to last me a year and a half if I didn’t make a single cent.

I decided I would go all-in.

So far…it’s worked out okay.

PS: This is an excerpt from my upcoming book. In the meantime, my current book is pretty darn good.

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    1. No idea really, can’t seem to find something that’s comparable at this point. I’d guesstimate over $250k but less than $300k.

  1. The American Dream is like a pit of snakes disguised as kittens in a basket.

    It’s always good to hear the stories behind someone’s transition. I hope more and more young men break free of what their told to do – and instead doing what they truly want to do.

    1. “The American Dream is like a pit of snakes disguised as kittens in a basket.”


      Made me chuckle. Might even put that line in the book itself…

  2. Good article. I’ve enjoyed your blog and found it a lot more thoughtful and interesting that the ‘how to bang chicks in Turkmenistan’ kind of thing that you often get. I think you are doing exactly the right thing seeing a bit of the world before you commit to anything irrevocable. As a European, I have particularly enjoyed reading your impressions of the various bits of Europe you have taken in. Anyway enjoy and keep writing!

    1. Sean, thanks very much! Glad you are enjoying the content.

      Where in Europe are you? Give me a shout if we can touch bases.

  3. Very interesting journey you went through. Thanks for sharing.
    It fascinating once you realize the many possibilities that lie beyond the bland corporate lifestyle.

  4. Kyle when did you start nomading?
    Also I haven’t left the USA since the inauguration. Last time I left was this Jan, I was in Estonia for a job interview. Do you get a lot of questions being an American about Trump? Most normal questions I would get from local people would be “have you been to NYC? Do you know my cousin there? Will Trump win? Other questions depending on year, guns, snowden, etc.

    1. Last year, March.

      Not really. People want to talk about it, but we rarely agree so I just change the topic (usually).

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