From The Office To Travelling The World

My Office Building

15 months ago on a sunny June Friday I decided to quit my job. I still remember the moment. It was like falling in love. I walked out of the office onto the street, feeling like I’ve lost half my weight. Each step I took I felt lighter. I was walking on the moon.

15 months later, I am homeless.

I am in Kuala Lumpur. For the past 9 months, I’ve been travelling in Asia, and working on the road. In 9 months, I have saved more money than when I first started travelling, thanks to the low living cost in Asia.

It’s cheaper to travel than to stay home. I spend less than $1000 a month, all in.

I assume that you too want to travel. You have your reasons to travel. Or you may not have reasons, but only an incessant urge. I want to tell you my how I did it. Perhaps taking my experience, you can adjust it to suit the circumstances of your life.

In a nutshell: I quit my job; I failed at startup; I started doing freelancing; I made sure I could work remotely; I took care of my affairs in Canada; I handled the practical matters of travelling; finally, I took off to Thailand with a one-way ticket.

The Fear And Trembling of Quitting

The simple, if banal, truth about quitting is that “you’ll most likely be fine”. The practical problems of making enough money to live (i.e. having food, having a place to sleep) are easy to solve. The real difficulty lies elsewhere.

The decision to quit is an existential choice. I think for many of us it is not so much the steady income of a job that is difficult to give up, but the image of who we are. Our identity is inextricably bound up with what we do.

When you go to a party and people ask you what you do, it’s difficult to have a ready answer if you don’t have a job. And the questions asked in a party over amiable drinks are but pale shadows of the questions you will ask yourself when you are alone.

The real difficulty of quitting is taking up the responsibility to define who you are. Or maybe you are already satisfied with who you are. In which case, obviously, there’s no reason to quit. But if you DO decide that you want to quit, it take a lot of courage. There’s always fear and trembling before you take the leap.

The existential worries (alas, angst) of not having a job is separate from the practical worries of making a living, but very easy to confuse. You might worry about paying your rent if you don’t have a job, when in fact it is the challenge to your identity that is the true source of unrest.

Here’s a simple answer to the practical worry of paying rent: don’t pay the rent. End your lease. This is exactly what I’ve done as part of my preparation to start travelling. The practical problem is easy. The hard part is determining what to do if you don’t have an apartment, nor the job necessary to support that lifestyle.

Isn’t is weird that in modernity the core of our identity isn’t God, nation, or family, but job, and all that a job would imply.

Preparing For Change

Empty Sign. Qinghai, China

It is not possible to change overnight. Quitting, like turning 30 (or whatever), is just an arbitrary marker. It doesn’t magically, with a puff of smoke, make you a different person. You need to prepare for change.

The biggest danger with quitting is to carry on the same old habits and thinking. If so, then eventually what happens is you find another job. You shouldn’t quit today. But you should start changing now.

I didn’t quit my job then immediately was able to find contract work. I didn’t move to Asia right away and work remote, and making American wages while enjoying Asia’s low cost of living. It took 7 months before I was able to leave Vancouver.

Startup Dream. Miserable Failure.

Immediately after quitting, I started working on my project. I was building “reremind.me” with a friend. It’s a social network for people suffering depression. I envisioned it as a colloborative psychotherapy platform. Inspired by Cognitive Behavioural Therapy, and research in Learned Optimism.

I thought that if people can learn techniques that would help others, then these techniques would be precisely the same techniques that can help themselves. By helping and comforting others suffering similar problems, they gain the experience and clarity to help themselves.

It didn’t work out.

Then I worked on another idea called “jummp.in”. It didn’t work out either. By the time I was doing jummp.in, I was starting to realize “oh shit, I have no idea what the fuck I am doing”, in exactly those words. It wasn’t working out.

I learned frontend development though. I was strictly a backend Rails developer before that. After that summer I could do HTML, CSS, and Javascript/jQuery. Having these skills made me a more rounded developer, and more attractive as a freelancer.

Transitioning To Freelancing By Being Visible.

I had 6 months to go before I’d be out of cash and sleeping on the street.

Freelancing was completely new to me. I didn’t know where to find work, how much to charge, how to negotiate, taxes, or even how to give project estimate. I didn’t have a lawyer, and my mom was my accountant.

Contrary to all startup advice about being commited to my goal, I was preparing for my freelancing career while I was still working on jummp.in. I wanted to give myself plenty of time to get started.

The single most important thing you need to do to start freelancing is to be visible. One way to be visible is to have your own projects. The projects don’t have to be popular (or even useful). They just need to be there. If a potential client wants to see what you’ve done, you should have something to show. That makes all the difference.

Another way to achieve visibility (again, you don’t have to be famous or popular) is going to different meetups. It is most effective if you give talks for your local meetups. If you have your own projects, you can talk about your projects. If you don’t have a project, you can talk about other people’s project. But giving talks gives you instant credibility. I think it is the most effective way to achieve visibility.

While it is crucial to go to meetups and events, beware, though, of “networking”. I am a shy person. For me, networking doesn’t come naturally. Often I hate it so much that I just want to curl into fetal position right on the floor and hum a lullaby to myself. But because I don’t network for pleasure, it was easier for me to focus on what I wanted to get out of it, rather than just having fun.

When you are visible, you start to get lucky. You’d start getting referrals from friends. The only problem is that it takes time. Having projects you can talk about would speed up that process considerably.

I started letting my friends know that I was looking for freelancing work in mid-August. I started my first project in mid-October. The second contract started in early November. The third contract started in late November. The fourth one in middle of December (having finished one contract by then). Two were remote, and two were local in Vancouver.

Getting Ready To Go

Sunset at Tofino

As I was picking up freelancing gigs, I got serious about travelling. Roman Snitko told me that he was going to live in Thailand for 6 months, and invited me to go. When he was there last time, he rented a new vacation condo unit for $450 a month. The building had a roof top swimming pool overseeing the ocean, and a gym. He said that in Thailand he could easily live for less than $1000 all in. That blew my mind. In Vancouver, I was paying $1200 in rent alone. I was very interested, but I wasn’t sure if I could actually work from a different country. How about timezone difference? How good is the Internet in developing countries?

Of the first two clients I had, one was in Seattle and one was in New York, so I already had experience with remote clients. The only problem was that I always worked from home, where I had total control over my work environment. I’ve always needed a very quiet place to work. The least bit of noise distracts me. I can’t, for example, work listening to music.

If I were to travel, I had to make sure that I can get work done on the road. As an experiment, I decided to visit Tofino for a week. Tofino is a busy resort town in the summer, famous for its surfs. In the winter though, it’s a perfect getaway. There really wasn’t much to do there in the Winter.

I met some interesting people there. People who go to a surf town in the dead of Winter are by that selection bias pretty weird. There was a divorced man seeking new life. He also lost his business. There was a retired programmer who did Cobol for living. There was also a woman who was a life coach. One breakfast she was teaching a tough looking, bouncer type of guy how to listen with more empathy. Two geologists from the Univeristy of Alberta were crazy enough to have gone surfing in winter’s bitter cold water. And there was a German guy who travelled across Canada for 2 months. He couchsurfed all the way, and the only two nights he paid was to stay in the hostel in Tofino.

During the day I explored Tofino. I worked in the evening, and sometimes in the afternoon when it rained. I averaged about 4~5 billable hours of work each day. So the experiment went well.

The solution to the noise problem? Earplugs.

Taking Off

In December, I ended the lease to my beloved apartment, and moved back home. Living with my parents, I thought, would give me the extra motivation to move on with my life. Indeed, it was dreadful moving back. I was ready to do everything I could to get the hell out.

After the New Year, I started to prepare for the trip itself. I bought a one-way ticket to Thailand. I renewed my passport, and got the visas for China and India. I informed my credit card company that I’d be out of country. I bought travel insurance. I got an international driver’s license. I changed my ATM card’s PIN from 6 digits to 4 (some country’s ATMs can’t take 6 digit PINs). I sold my iMac. I sold my stocks at a significant loss. I got my taxes ready for the year.

I bought the stuff I needed to travel. I wanted to travel light. I had a 25L backpack into which I had to fit everything I need. My packing rule was that I’d leave out anything if I wouldn’t use everyday. If I wasn’t sure I’d need something, I’d leave it out. If I could get something locally, I’d leave it out.

Two weeks before the flight, I was putting in extra hours for my clients, so I could take a week off to adjust when I got to Thailand.

On Janunary 25th, I took off.

On The Road

Plank Walk at Mount Hua. I waz there!

In 9 months, I’ve been to Thailand, Hong Kong, Cambodia, China, Korea, and Malaysia. The pace of my travelling is slow compared to others. A couple I met in Korea who also travelled for 9 months had also visited India, Nepal, Laos, Vietnam, and Australia. I took my time.

I scheduled three days of work for every one or two day’s travelling. When I had to travel by bus or train to another place, I’d take the next day or two to work, and rest from travelling. In effect, I was alternating between work and travel. When I was tired from working, I’d go see things. When I was tired of travelling, I’d work on things.

This system wasn’t foolproof. It failed me when I travelled to Siem Reap to visit Angkor Wat. As I was especially tired from the trip to Siem Reap, I took the first three days to work. I booked a guide to take me to see Angkor Wat starting on the fourth day. Unfortunately on the third day I got a nasty skin inflammation. I was going to tough it out and stay for two more days to see Angkor Wat before going back to Bangkok. But by that night the inflammation was hurting like hell and spreading. So next morning I left Cambodia, before I had a chance to see Angkor with my own eyes.

Been there, didn’t do it, but got the postcards.

The Schrödinger’s State of Being

To be sure, getting to this point wasn’t as smooth and planned as this narrative might suggest. In reality, I met many dead ends, and went into detours. I was fraught with doubts, and endlessly exploring different opportunities. Much of what happend was ad hoc and opportunistic.

What I didn’t tell you in this story is that while I was doing all this, I was also interviewing for jobs. I was actively sabotaging my own plan to travel. Luckily, I didn’t get lucky with job hunting.

It seems miraculous. Life, to a great extent, cannot be planned or predicted. Much of it depends on chance. Had I found a job, I would’ve been in San Francisco busting my ass for a startup. My plan to travel would’ve come to naught.

Was I lucky or what?

Maybe the lesson isn’t that I was lucky enough to fail to get a job. The real lesson, rather, is a stoic appreciation for whatever life has in store. Whatever happens to me, I should make the best of it. It is a sort of optimism. Life always seems to work out fine in the end, one thing leading to another.

In this godless age, with the absence of providence, this is perhaps one sort of faith we can have. Have faith in life, that it would turn out alright. Que Sera Sera.

Discuss on Hacker News

If you like my writing you should follow me on Twitter.

Comments