Small Stakes

Chapter 6:

To Plan or Not To Plan and White Kids Playing Spontaneous on the Other Side of the World



The electric-blue dragon of the train blotted out the horizon. It announced its approach with a series of chest rattling bleats and belched soot into the darkening Colombo sky. My three-wheeler skidded along the wet pavement, only meters ahead.

“One hour! Next time, one hour ahead!” my driver barked.

“You’re brilliant, Suress, You really are.” I smiled into his rear-view mirror. “I am going to tell everyone you can make this drive in just over fifteen.”

Suress snaked his arbutus bark lips into a scowl. He broke eye contact as we accelerated to escape a narrowing corridor of petrol-trucks. We lost ground each time the tuk-tuk hydroplaned trying to pass car. I tried to gage the distance we had to cover, squinting as the icy-rain chewed my cheeks. I could not miss this train.


To plan ahead or not to plan ahead: that’s the timeless question that plagues travelers. On one hand, the Internet has made planning easy as hell—not only is it convenient to set up your trip weeks in advance with the click of a button, but it’s almost always cheaper. Information makes foreigners feel immunized against local touts and scammers. Plus, there’s always the fear of missing out by not booking ahead.

The contra-stance is fortified by one strong argument: you never know what a foreign country will hold and to set plans based on expectations is to be boxed in by your biases. I subscribe to this approach, although I’d be lying if I said it was because of that aforementioned mantra alone. We live in a society that celebrates spontaneity and recklessness. We misuse the word freedom, repurpose latin phrases, and misquote Robert Frost. I’m sure most of us are aware of our Jack Kerouacian cheese—which more often than not results in over-nights in bus depots, excessive ATM withdrawal fees, and days spent in visa-extension lines—but that doesn’t mean we don't romanticize the idea of it. We ham up our reckless abandon every time we share a drink with someone new.


I was in Colombo less than 24-hours before I hired Suress to chase down the train. I’d spent my last two weeks in Southern Sri Lanka travelling with three friends on vacation from their teaching jobs in Egypt. I’d grown tired of the beach and they were flying out the next day. At the last minute, I decided to hitch a ride in their hired van headed toward the capitol city in pursuit of something new. I had a few numbers for people on the other side of the island. I though it might be fun to drop in on them by surprise.

“I just got on a train to Anuradhapura this morning, otherwise it would be on,” came my first response.

“I’m at work. I wish you had called ahead,” came another.

Frustrated and planless, I popped into a hip looking café to pick the barista’s brain on what was worth doing next. A well-dressed man with a face one shade darker than the espresso he pulled convinced me to head to Kandy, the arts and culture center of the Island a four and a half hour train ride north east. But leave very early, he warned. The train fills up quickly and traffic can make a 10 km drive take over an hour. I set my alarm for 6:30 a.m. and planned to catch the early morning train. I adjusted the contents of my bag and hopped a bus to a hotel to read up on my destination. But mid-way through the ride, I met a girl.


“You really like the women.” Suress’s mood lightened once we’d regained our lead on the train.

“More than reading at a hotel. More than waiting in train stations. More than waking up 6:30 a.m.”

It was 9:50 and the ticket counter for the last train that would get me to Kandy on time closed in 10 minutes.

“Why then do you not have a wife?”

“Normally those two problems go hand in hand.”

I’ve always been a miserable dater and I am definitely not the globe-trotting womanizer I’m sure my quick conversation with Suress implied. An acute phobia of commitment dictates my lack of success in the former department. A caustic curiosity and the deadpan interrogation skills of someone who has spent his past three years as a reporter means my first-impressions can feel more Sherlock Holmes than seductive. Perhaps the best way to describe my pursuits are that I ram my way into people’s lives and I do my best to make their stories part of my own. I’d spent the majority of the last six months sleeping on the couches and floors of strangers. At the Thai-Myanmar embassy two months earlier, I asked a young, kind-faced official if I could rush the application process because earlier that day I’d bumped into a girl I’d hit it off with one night in Sumatra six months back.

“I need to see her again! People call this kind of thing fate!”

We both blushed as he ushered me to the front of the line. The next day, the two of us hopped a last minute flight to Cambodia. We were together for under two weeks.


The white domed roof of Colombo Fort Station sliced through the rain. I fingered the greasy rupees in my breast pocket. I could afford to pay Suress, purchase my ticket, and maybe a samosa onboard. I didn’t have quite enough to make it to downtown Kandy, but if anything the challenge would be fun.

A few nights earlier I’d compared budgets with a Muay-Thai fighter from Portugal.

We’d spoken of scrimps and splurges—my bullet-proof four-season sleeping bag versus the night I’d been convinced to buy it after squatting in an abandoned building in Mandalay. He countered with his homeless months in South America.

“Going broke out here is the best thing you can do, man. Just see what happens. You’ll understand the world in a way you never knew!”

At first I found his philosophy tempting. Poverty pushes you into hard places—it convinces you to sleep on streets, to converse with fringe characters, and to find news ways of scrounging up enough to get by. It fuels ingenuity—is there anything more tempting as a writer? But the more I fantasized about it, the more I wondered how genuine that reality could actually be. Countless ascetics inhabit the streets of Asia. Some do so out of choice; others, out of disparity. And although they’d certainly proven it a viable existence, they inhabited a realm that I could never quite enter, even after my last rupee was gone. They walked a line with higher stakes, without the safety nets of credit cards, health insurance, and family and friends to step in if ever things got too rough. My slumming would always be a temporary state that I could end with a single phone-call or Internet transaction. I found it hard enough to stay with over-generous couchsurfing hosts; could I convince those same people that I was homeless, knowing I had a secure refuge other side of the world? I wondered if I looked just as foolish each time threw caution to the wind and flew around the world in pursuit of blonde-haired blue-eyed girls. Each time I left myself 15 minutes for an hour commute or risked stranding myself somewhere for an extra pot of coffee. I was manufacturing risks that didn’t actually exist; basking in the securities of a privilege I’d been born into and making a spectacle of my unearned invincibility on the process.


The rain had ceased once we reached the station. I tipped Suress for his reckless driving and made up the difference by travelling second class. I sat next to the doorway, gripped my camera, and hoped I hadn’t sacrificed my view of the ride ahead. Mist melted into dew-soaked mountains as we plunge northward. I let my breathing calibrate to that railroad rhythm, gazed into the green horizon, and refused to look back.