Hi, I’m Kelly. In late 2014, Anna and I bought our 1993 Pace Arrow, a 37 foot long motor home, and we’re setting out on an adventure.
I’m an entrepreneur and a writer (in that order, these days). As an entrepreneur, I co-founded Quiet Speculation, a media site dedicated to people who love the Magic: The Gathering collectible card game, in 2009. I’m very fortunate that my little “startup” has turned into a full-time job that allows me complete freedom of location. As a writer, I have written for Forbes.com and numerous Magic-related websites. You can see some of my writing about entrepreneurship, startups and technology on my Forbes archive.
I grew up in New York City, where my only routine exposure to nature was Prospect Park in Brooklyn. Though my family would take day trips in the surrounding area, I didn’t get to travel much, or be in the real wilderness, until I was much older.
My first real taste of travel was in college. Goucher College mandated that every student pursue a study-abroad program, so in the summer of my sophomore year I studied the German language in Berlin for a month. Sadly, ich cann nicht so gut Deutsch sprechen these days, but the trip fueled my fire for travel.
That following winter, I visited Israel for 2 weeks, basically for free, on the Birthright program (which any teen or 20-something of Jewish heritage should pursue). This really opened my eyes to what the rest of the world looked like. I walked the narrow cobblestone streets of Tzfat in the high mountains, basked in the desert sun and opulence of Eilat. Surveyed a quasi-lunar landscape after a pre-dawn climb to the top of Masada and watched a mediterranean thunderstorm crash onto the shores of Tel Aviv from a 20th floor balcony. Played flute with Bedouins at a desert encampment and of course, walked the hallowed streets of Jerusalem, an epicenter of human struggle across the centuries.
My trip to Israel really lit the fire. Another opportunity for world travel wouldn’t present itself for years to come, but the embers were glowing, waiting patiently for fuel so it might rekindle itself again.
After college, I lived in New York City again. It was not a good time to be in NYC. Everything my generation knew about the way the world worked shattered in the years between 2007 and 2010. Empty promises from corporations, schools and governments left even my most successful peers, well frankly, scared shitless for their livelihoods. Many were laid off or fired. Some would make epic come-backs. Some would not.
For my part, I was broke and living in one of the most expensive cities on earth without a job. I was stuck with a worthless college degree like so many others, and despite the “recession”, NYC was still flush with money. I’m going to paraphrase Paul Graham here, from a piece that every nomad ought to read…twice. The words below are mine, but the concept is his.
Every city has a trait force that dominates the lives of its citizens; a trait in which you almost necessarily must take an identity stake. In Boston, under the influence of Harvard, MIT and countless other institutions of the highest level, that force is Intelligence. A prevailing sense of “you should be smarter. You should really get around to reading all those books you’ve been meaning to“.
In Los Angeles, it’s Beauty and Notoriety. Nothing else would make sense in the home of Hollywood. Money is very important, but it’s usually a reward for, or a means to the end of, Beauty and/or Notoriety. If you’re rich, but neither pretty nor famous, you’re a means towards someone else’s end.
And in New York, it’s Money. There’s always someone with more of it, and they’re better than you. But it’s also Blind Ambition, a sense that you can have it all, if you hustle, and one day you’ll be the one who’s richer than everyone. The carrot is on an ever-lengthening stick, and chasing it is a fool’s errand.
All of these things have one thing in common; they’re unattainable because they’re not real. There is no such thing as Smartest or Most Beautiful; intelligence comes in many forms. Beauty fades with age. Wealth and Fame are transient; even if you’re the richest person alive, there’s always someone gunning for your throne. And besides, what do the richest people on earth do with their money? The literally give it away for free. I wonder why?
Each of these things is an Identity Stake, a convenient proxy for self-evaluation. As long as you live with an identity stake in something other than being true to yourself, you’ll be trying to live someone else’s unattainable dream. Rather than try to win a rigged game, choose to opt out. My friend, and founder of Empeopled.com, Aris Michalopoulos, calls it “costless secession”. The act of leaving a group or system in which neither the group nor the individual are any worse for the departure.
So, I opted out. I realized I wasn’t going to win the game of “be the richest person in New York”, and I knew I couldn’t keep living where that’s the prevailing priority. I moved to a small town in the midwest, where rent and groceries were cheap, and set out to figure out what was important to me. I worked various retail jobs, tried various business ideas, and slowly built up a sense of what mattered in the absence of New York’s toxic influence.
The only idea that really “stuck” was building software and online businesses. I was introduced to the work of Tim Ferriss and consumed The Four Hour Work Week at least half a dozen times between print and audio book. His description of lifestyle arbitrage struck me as a great fit for how I want to live my life. I decided to focus on learning how to write software and build modern websites; I wanted to launch an online business that sold information, not a physical good. While I was on a lunch break emailing with my business partner Douglas Linn, he asked me “why are you still working retail? You should be building something that makes you money when you’re asleep. Quiet Speculation ( my Magic: the Gathering blog) is your only equity asset. Focus on that.” So, that’s what we did. Doug and I decided to turn my blog into a full content site, complete with a paywall.
Half a decade later, the opportunity to travel came in an unexpected form. Two years into the process of building QuietSpeculation.com, Doug emailed me a link to a contest hosted by British Airways. The email came hours before the deadline, and I quickly wrote up an application. When our application was accepted, we used our website’s audience to garner enough votes to be counted among the winners. Each of the winners was invited to a 3-day conference between New York and London (and on a specially-booked BA flight in between). We got to meet Bill Rancic, of The Apprentice. Although we didn’t place in the top 3 (…a little site called IndieGoGo did ), which was worth ten round-trip plane tickets, we still got one free round-trip plane ticket anywhere in the world. It was February in the American Midwest and northern Europe, so naturally I chose New Zealand, via Sydney.
Since the conference terminated in London, I decided to spend some time in Europe before my flight to Australia and beyond. It was wonderful to see old friends, but on an overnight bus out of Paris I got a vicious stomach virus that put me out of commission for days before my flight. I landed in Sydney drained (both literally and emotionally) and jetlagged.
The next morning, I woke up feeling a thousand times better. I had all day to explore, so I decided I wanted to go on a long meandering walk around the city. After a lengthy relaxing brunch of writing, strategizing and note-taking, I left everything but my wallet and a notebook at my hostel and set out. During that cathartic brunch of fruit and yogurt, one thought came to me with the utmost clarity. I realized what I wanted in life; the freedom to explore any whim that came my way. To pursue any idea I wanted, to go wherever I wanted. That wasn’t going to happen while working a retail job in the Midwest.
I know nothing about Sydney, Australia. I barely looked at a map. I just walked. At each intersection, I would choose the direction that most interested me. What followed was the single most amazing afternoon of exploring I’ve ever experienced. I started out in the Potts Point neighborhood, where I eventually came upon the idyllic Victoria Street. The street was lined with hostels and camper-vans, populated by skinny shirtless men with scraggly hair and guitars. Almost every van had a for-sale sign on it. I dreamed up a scenario where they had just crossed the whole outback in a tiny little caravan, and were now ready to sell the van to set off on their new adventure. Maybe it was blind luck, or maybe I was just “primed” to see it, but it struck me as odd that I was suddenly in the midst of people who shared my newfound desire to go with the wind, free to explore. The image of these lost, self-sustaining souls, lost by their own active choice, in their tiny caravans, planted itself somewhere in my brain and never really let go.
I continued my meander down Victoria Street and decided to turn into a back alley on, what else, a whim. About 100 yards down the alley, I was met with a fence. And 112 old stone stairs leading steeply and sharply straight down a cliff. When I took my eyes off the dead drop I was (apparently) about to descend, I looked up to the single most magnificent view I have ever seen in my life. In front of me was a 180 degree panorama of Sydney. The Opera House nestled in the Royal Botanical Gardens served as a foreground to a majestic full skyline view of the city, Harbor Bridge and all.
This was my reward for wandering and following my whims. My brunchtime epiphany was cemented in that moment. I wanted this, and more of this, forever.
The rest of my day was spent wandering further in reflection. It ended in an anti-climax. I got some fries and a coke at a McDonalds near the Opera House so I could use their wifi, checked my flight, hopped on a bus, and zipped off to New Zealand.
I looked forward to two weeks in paradise, recuperating, reflecting on my newfound clarity of purpose. I expected serenity. Instead I got hell. 3 days after I arrived in Christchurch, a 7.3 magnitude earthquake devastated the city.
The previous quake had left the city vulnerable and this one finished the job; the city’s infrastructure was crushed. Major monuments fell. Even the city’s titular Church of Christ was shattered. The streets were flooded from broken water mains and liquefaction (in which mud and silt and sand mix with water and are forced to the surface by vibrations in the ground). It was a mix of rubble, water and quicksand. To see the extent of the damage, just look here.
I was sitting on a park bench next to a small stream, two blocks from Cathedral Square, reading Richard Branson’s autobiography when the quake hit. The sound was unremarkable at first; Growing up in New York I knew what a truck crossing a metal bridge sounded like. I looked up at the bridge; no traffic. Then it got louder. Growing up around trains, I knew that sound too. No train tracks. The sound of trains was replaced by the sound of screaming and shattering glass. I had been warned of this; the region had been experiencing “aftershocks” from its last quake. I secretly had hoped I’d feel one. I was thrown off my bench and multiple feet in the air; higher than I can jump on my own.
A Filipino woman was on her knees, crying, about 20 feet away. I ran to her, thinking she was injured. Thankfully she was healthy and whole, but her daughter was at kindergarden across town and all the phone lines were down. She was panicked and didn’t know if the school was intact or her child alive. I couldn’t reach my host in the suburbs to arrange for a ride out of town, so we decided to make our way through the ruined city to find her daughter.
After slogging through kilometers of quicksand and rubble (and I am not exaggerating; the liquefaction was brutal), carrying two women across a flooded street, and being detoured around unstable buildings by firefighters, we reached the school. The building next door was a heap of twisted metal, but mercifully, the school was intact. Mother and Daughter (and soon, Father) were tearfully re-united, and I was rewarded with a few small triangles of Marmite Sandwiches for my trouble. (Marmite is a bizarre condiment in the same vein as Vegemite. I do not suggest it unless you are very hungry and there is nothing else to eat. This was the case, and I was legitimately grateful for the food).
Eventually, phone service came back up and I was able to get out of the city. In the coming days, I would learn that the book store where I bought Richard Branson’s autobiography was probably gone forever, the mall I had just shopped at was in shambles, and the noodle shop where I had dined about 30 minutes before the quake had been crushed. The family that operated it was thought to be dead. I had decided to go read my book outside rather that stay in the food court, and that decision likely saved my life. It wasn’t even nice outside.
I returned home during a brutal winter, shellshocked and determined to make changes. That was 2011. Four years later, these changes have finally come about.
In late 2014, Anna and I bought our 1993 Pace Arrow, a 37 foot long motor home, and we’re setting out on an adventure.