Going Swimming

If you're new to this blog, first let me say welcome!  Thanks for visiting!  This post was the first one I wrote, published about 4 weeks after I started my journey.  If you're now thinking 'What journey?' or 'Why even take a journey to begin with?', then read on!  (If you're not thinking that, you may want to click elsewhere.)


1.  Which Way to the Pool?

Time: 6:30pm
Date: September 2015
Location: 30,000 feet over Virginia
People: Me and an attractive young woman seated to my left on the flight to Philadelphia

With another week of consulting travel in the books, I found myself sipping a Diet Coke and picking at free Delta pretzels en route home to the City of Brotherly Love.  While attempting - and failing - to come up with a witty icebreaker for the woman, I decided to read one of my favorite books, "The Art of Nonconformity."  I soon came across a section in the book in which the author, Chris Guillebeau, recommends performing a "Perfect Day Exercise." It’s easy enough: all you do is write down what your perfect day looks like.  Similar to the classic "write down what you did today" productivity trick, which attempts to weed out inefficient behaviors through forced visualization and self-reflection, this exercise acts as a wake-up call to those who lead decidedly non-perfect lives.  Here's my average day, compared to what I came up with.

The incongruence between the two leapt off the page.  On some days, only working out, eating, and sleeping made it from my perfect day to my regular one.  Making matters worse, my mental state during a normal day routinely bounced between stress, boredom, and aggravation, while my perfect day had me calm and satisfied throughout.  I knew I needed to change something, but how?

(Oh, I never did talk to the woman.)

2.  Approaching The Pool

For most people, the “perfect day” exercise doesn't actually spark any action, and I don’t blame them.  It’s not really a surprise that normal days don’t look perfect.  “You’re living in fantasyland,” someone told me.  “I need to pay the bills, I can't run off to Fiji on a whim, and I have to support my family.  This is real life we’re talking about!”  There’s another common response: “Besides, I take a vacation every year where I DO live my perfect day 7 days in a row, and when I retire everyday will be perfect!”  Me?  I wasn’t ready to accept that line of thinking.  (I’ll detail why in another post.)  Here’s what I did.

1.) Listed out the obstacles preventing my perfect day activities from permeating my normal day. Most were simply societal constraints that existed, unacknowledged and tacitly accepted, in the background of my life:

- Availability of Creature Comforts (hot water, A/C, fast WiFi, drinkable water, sewage systems, reliable cell phone reception, etc.)
- Necessity of Moderate-to-High Income
- Predictability and Opportunity of Career Advancement
- Possession of Material Goods
- Proximity to Friends and Family
- Similarity of Life to Those of Others (this one was especially comforting…and limiting)

2.) Realized I could pick and choose which constraints govern my life.  A simple, yet incredibly powerful, epiphany.

3.) Decided to intentionally remove some of the constraints blocking my perfect day.  I figured I could handle it, but wanted to play it safe initially….

3.  Dipping My Toe in the Water

I figured two tests would sufficiently prove if I could handle life outside society’s comfort zone. Each time, I removed as many constraints as I could.  


Experiment 1: Solo Trip to Mexico, November 2015

Looking into the Pacific from the yoga platform. (Click to enlarge.)

Looking back at the bungalows from the yoga platform. (Click to enlarge.)

Summary: Over Thanksgiving Break, I traveled to the Present Moment Retreat, a tiny enclave of eight beachside bungalows in Troncones, Mexico.  The marketing material billed it as an escape from everyday life – the town itself has only 600 residents – and yoga, meditation, and massages helped guests nama-stay in the present.

Result: The place definitely lived up to its billing, but perhaps a little too much for me.  The rustic environment shocked my system; with no A/C, WiFi, cell phone, or laptop plus tons of bugs, only four other guests, and not much to do outside of yoga, meditation, and the beach, I found myself struggling.  I spent the first couple nights wide awake, my mind racing.  What am I doing here?  It’s so freakin’ hot.  I don’t know any Spanish.  Mosquitos are ravaging my body.  What are my friends and family doing?  How do I need Senekot and Immodium at the same time?  I was determined, however, not to let my thoughts interfere with my reality.  I kept up my yoga and meditation, ate cocoa and journaled every day, and devoured soul-soothing books like Thoreau’s “Walden” and Eckhart Tolle’s “A New Earth.”  It worked: I eventually mellowed out, learned to embrace the solitude and present, and found peace….right as the vacation came to an end!

Final Verdict: Touch and go for a little bit, but ultimately a success!  


Experiment 2: Solo Trip to Thailand, December 2015

The southwest side of Koh Phangan, Thailand

Summary: Almost immediately after returning from Mexico, I started planning my next experiment.  During my research, I came across an intriguing group of people: digital nomads.  These are people whose jobs afforded them the luxury of working anywhere with WiFi.  Usually getting paid in US dollars, digital nomads ingeniously gravitate to places with low costs of living and weak local currency.  Taking advantage of this “geo-arbitrage” allows nomads to work significantly less hours while enjoying a standard of living equivalent to, or exceeding, the typical American.  To top it off, many of the digital nomad hotspots are located in tropical destinations by the beach.

Now with a Northern Star of sorts, I quickly found one of the top digital nomad cities in the world: Chiang Mai, Thailand.  In fact, all of Southeast Asia serves as a digital nomad paradise, with extremely low costs of living, friendly people, strong WiFi, and comfortable climates.  After a couple clicks, I booked a round trip ticket to Bangkok over the Christmas holiday.  Unlike Mexico, I reserved a hotel for the first two nights and intentionally left the rest of my itinerary blank.  I ended up spending time in Bangkok, Chiang Mai, and Koh Phangan, the location of the infamous Full Moon Party.

Result: My Thailand adventure warrants a separate post, but suffice to say it proved a lot more challenging than Mexico.  On the other side of the globe from my friends and family, I could barely speak the tough Thai dialect and, well, didn’t have an itinerary.  On at least two occasions I found myself facing (perceived) enormous adversity and thinking all hope was lost.  The gods ultimately smiled down upon me, and I made it back to the US alive and sane. 

Final Verdict: Touch-and-go again, but successful nonetheless.


In early 2016, with two experiments complete, I tallied the results.  I knew I could survive – even thrive – without the constraints of modern life, which in turn meant I could achieve my perfect day.  Time to run the biggest experiment yet!

4.  Diving In Headfirst

Actually, the final step could be “sink or swim,” but let’s give the jury time to deliberate on that.  While the objective of my first two experiments simply was to “see if I can do this”, I now wanted to get a bit more specific.  You can probably guess my main objective.

Primary Goal: Achieve my perfect day (including traveling the world, living in tropical destinations, and finding calmness in everyday life)

If you noticed in the notes section of my perfect day, I touched upon “fun productivity” and “finding my passion.”  Here’s what I wanted to do:

- Learn Spanish
- Teach English (passion?)
- Learn to surf
- Start remote work (web development?)

Now came the easy part: picking a place to go.  I say easy because I had, in effect, placed a new set of constraints (oh no, not again!) on my life, which narrowed the possible locations for the first leg of my journey.  For example, I couldn’t learn Spanish in Bali, nor could I learn to surf in Prague.  I also knew I wanted to stick with digital nomad hotspots, not only to satisfy the “Start remote work” goal, but also to make my budget go farther.  After some Googling, I came up with a starting point and a rough itinerary.

Unless I do something crazy, I don’t expect to spend more than $1,000 per month, all in, including travel. As you’ll see in later posts, $1,000 may be a significant overestimation, and remote work income will help offset some of my expenses. 

As for the timeframe, I’ve told people I expect to travel for 18 months, which is a completely arbitrary number.  In reality, I’ll travel for as long as I want.  I’m taking life one day at a time; my friends at Present Moment Retreat wouldn’t have it any other way.


Experiment 3: Solo Trip Around the World (Removal of All Constraints), April 2016 - ?

Planned route around the world.

Summary: Quit Job, Sell/Donate Possessions, and Travel the World

Result: In-Progress

Final Verdict: TBD

In future posts, I’ll fill in all the details, including what items made it into my backpack, monthly expenditures, my current home, additional reasoning behind quitting my job, and more.

Thanks for reading, and I’d be glad to receive your questions or remarks.  Feel free to leave a note using the comment function below (which will be public) or email me.