My 10 Year Plan To Become Homeless

In less than 21 days our apartment lease will expire, we will pack up everything we own, discard an embarrassingly high volume of college IKEA furniture, move our belongings into storage and accomplish something I have dreamed of for over a decade — true location independence.

My family and I will set off to San Pedro, Belize for six weeks, and we will be legitimately homeless.

For some, this might be a scary proposition. The consumption habits of American suburbia compounded with a doom and gloom 24–7 news cycle crushes the will and means to travel for many. Half of my peers are deathly afraid of Zika anywhere South of Denver. The other half are locked into mortgages, car and student loan payments sapping much of their liquidity.

The idea of being able to travel the world, unbound from a desk job has been a virus in my mind, infected by the Godfather of lifestyle design, Tim Ferriss. I was 24 when I discovered his book, The 4-Hour Workweek, and a new world opened before my eyes. Tim shared tales from his adventurous life and weaved together a model for anyone to make money online and leverage their wealth to explore new corners of the globe.

As a third-generation Arizonan, and someone who grew up in the desert, the idea of global travel supported by an online business fascinated me. I had an experience rich and fantastic childhood, just not one that took me outside American comfort zones. By the time I started my own business, my entrepreneurial experience was a mashup of employment from very traditional companies like Apple, LG, and local advertising agencies with 50+ years tenure in the Phoenix Valley. Both my parents, as well as my wife’s family, pursued very established professions, namely in education and manufactured goods.

I was the least likely candidate for the means, experience or support to chase a location independent career and life, yet I could not shake the thought and would come back to Tim’s book at least once a year.

I had my first daughter at a young age. While I was eager to kick off an online 4HWW (ad)venture, ushering in a life of beaches and piña coladas, I couldn’t muster up the courage to do so. I was insanely fearful of anything that might risk my ability to provide for my daughter and future family.

Six years would go by down a much different path. Six very hard years.

During this time, my first business, a branding agency called Keane Creative, struggled. I was young and not equipped with the experience and courage to balance life, leadership, and family. I drank heavily, a habit that rarely has positive outcomes.

In 2011, I capitalized on an opportunity to partner with two amazing people in Argentina and found myself with a new business, NSB/Keane, and this time an opportunity for travel. Perhaps my location independence dreams could finally be realized! Soon I was off to Buenos Aires, a city I fell in love with and oddly enough a city Tim Ferriss romanticized in 4HWW.

With incredible music, around the clock espresso, polo lessons and ample opportunity to practice my awful Spanish, I loved my time in South America, yet I still felt empty. Every trip was a whirlwind of work, and I was forced to leave my family behind. The late dinners and the wine — the great wine — would ultimately come to an end. After warm goodbyes coupled with many kisses on each cheek, I would find myself alone and drunk in my hotel room full from the night’s incredible meal, yet depressed and empty with the life I was living.

At the age of 30, I hit a major turning point and made a decision that would forever change the course of my life. For me to recognize my true potential, there was a lifestyle change I had to make. I needed to get sober and quit drinking once and for all.

My sobriety started October 22nd, 2013. At that point, the world became a very different place. I worked as hard as I could inside NSB/Keane for almost another year, but the writing was on the wall. I knew my current business could never grant me the freedom or wealth to grow beyond Phoenix, AZ.

In August 2014, my partners and I mutually agreed to close NSB/Keane. On September 1st, 2014 I was unemployed.

In hindsight, it is easy to see how the decision to close my agency would lead to the liberation and space needed to create something even greater. At the time, however, I was freaked out of my mind.

For moral and mental support, I frequently consumed the podcast The TropicalMBA, a weekly podcast dedicated to the location independent entrepreneur, headed up by Dan Andrews and Ian Schoen. They ran a private forum called the Dynamite Circle, a place for entrepreneurs to connect and support each other.

Again — excitement struck. Perhaps, finally, six years later, I would crack the code and achieve location independence.

Here is an excerpt from my very first post, ever, on Medium, 14-days after I closed my business:

I’ve been lightly involved since I joined a few weeks ago — absolutely love the content being put up here — but as the forces of the universe will have it I’ve suddenly been thrust into a position needed to make some quick decisions on where to put my energy and focus.

Long story short, I have been running a fairly successful advertising and branding agency for the last 10 years, the most recent 3 with a partner. In 2013 we broke 3mm in revenue, with virtually no profit. Quite a grind. Last week we agreed to call it quits — however, in doing so I have also ended my primary revenue stream.

It’s a bit like jumping into the freaky deep-end of the middle of the Pacific, but that is what’s fun about this, right?

I was humbled by this years later when I appeared on the TropicalMBA. Dan and Ian were gracious hosts and read my first post aloud, triggering a wave of emotion. Thinking about the journey, it made me very grateful.

For the last two years and seven months, I have painstakingly engineered my personal and professional life to support location independence. The journey has not been simple. I doubt any significant life changes are easy or fast to maneuver. To achieve what I really wanted, required me to burn everything I had to the ground, and start from a clean slate both professionally, personally and mentally.

Oddly enough, our flight to Belize is on April 10th, just a week after the ten year anniversary of the 4-Hour Workweek’s original publish date. My whole family is coming, we’re homeschooling our kids for the rest of this school year, I’ll be running my businesses remotely, and adventures are inevitable.

Thank you to Tim Ferriss, Dan & Ian, Garrett White, and the entire DC and Wakeup Warrior community for inspiring me every day.

Thank you to my amazing wife Mika Perry for never giving up through the insane twists and turns.

And thank you to God for really kicking ass.

I’ll most certainly be sharing more.

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