ONE YEAR, TWO UNDERPANTS – Quitting your job and living on a bicycle


On the 5th of October 2015 I said goodbye to my relatively comfortable life in Sydney, Australia, and headed towards South America with a bicycle, a few plans, some untested gear and little else in the way of knowing what I was doing or where I was going.

My mother dropped me at the airport with an oversized, overstuffed box, and all other gear haphazardly thrown into a wheeling suitcase held together by duct tape. I shared what was sure to be my last Australian quality coffee with her as she stuffed an envelope into my hand with the sorts of words that only a mother could write. I read it past customs in the airport and my phone vibrated as I received a long message from my older brother saying goodbye and good luck, offering a few sage pieces of advice to stretch the trip out as long as possible. Notably, ‘don’t spend money on alcohol if you want to make your money last ‘, and, ‘I understand why this is something you have to do.’

I haven’t reread those messages since I left, I remember too vividly the feeling as I spoke to the security checkpoint and I know that reading them might trigger the sort of homesickness that would detract from the lifestyle I’m currently living.

Just before I left, my friends had gathered to say goodbye and good luck at one final blowout house party. My closest friend and his girlfriend gifted me an engraved compass, the sentiment not lost on me – this was about finding direction.


But how did I get to this point to begin with?

My most dense period for movement occurred from late 2007 to 2010.

When I finished school and began further study in 2006, my older brother had been spending lazy summer’s living out of a family caravan on the New South Wales south coast. A lifestyle move more than anything else, it facilitated surfing early each morning and late into the setting sun, and offsetting the cheap existence by stacking supermarket shelves in between. I’d had my share of horrible summer jobs to this point and decided that if I was going to do it for another summer, I was going to do it by the ocean, beer in hand and subsiding off toast with avocado and jarlzberg cheese.

So I packed a few small things into my late grandpa’s 1985 Mitsubishi Sigma and within a few days my life was out of a caravan. Within a week I’d landed a job slinging beers out of Batemans Bay’s local hotel and within a month I’d simplified my life to a point that I was happy with. At the end of the summer when the tourist season was tapering off I packed the car again with a few more things – an esky full of beer and my bodyboard – and set off to explore the coastline all the way to Adelaide. My days were generally punctuated with midday surf’s and ended with sunset beers before I crawled into my tent on the beach or slept in the back of the leaking and damp car. I made it South, spending time in Lake’s Entrance and Wilson’s Prom before finding the coastal route from Melbourne to Adelaide, and finally out to Kangaroo Island where I found a hidden cove and set my tent up there for a week. Afterwards I hastily drove inland and back to Batemans Bay before University began again for 2008.

A seed was sown.

I spent the first half of 2008 arguing with the various university faculties to get a bid for international exchange across the line. I bluffed the hell out of the application as to my merit and found out only a few weeks short of needing to leave that I had been accepted to the University of Toronto in Canada for 2009. Before I left I spent some time in Europe in the middle of the year generally being lost on trains and ending up nowhere I was intending to go.


On the 28th of December 2008 I bundled into Toronto in heavy snow and with my down jacket lost in transit, in short out of my depth.

It took perhaps a month to truly find my feet; at the time what I chalked up to homesickness was definitely culture shock. I’d come out of Sydney summer to Canadian winter, and people who have endured these winters can probably sympathise the difficulty they create in making friends. The trigger was when I moved out of a sterile university high-rise into a ramshackle student cooperative. I shared my house with 13 other students, and the key to my house opened up the adjacent 6 houses, each with up to 15 people.

Generally the houses were full of students from the nearby fine arts school. The mix made for a truly creative environment where you could immerse or remove yourself as much as you liked from the experience. Often what was necessary was an all in approach one week offset by sleeping for a few days. The houses had home built recording studios, rope swing’s out the back and sheds full of bicycles. Live music wafted out of some rooms and skunky marijuana fumes from others, we shared most of our meals and I made friends that I will keep for life.

In the summer I spent time WWOOFING on farms around the east coast and finally hitchhiked from Newfoundland to Vancouver Island – it was in the Rocky Mountains in Alberta that I discovered bicycle touring.

Through the east coast I had spent the time hiking in the National Park’s and forgetting the number of wild moose and caribou I’d seen. By the time I reached the mountains I was still yet to see a wild bear. In a small alpine lodge in Yoho or Revelstoke National Park I met a cycle touring couple and told them this. They laughed and when I queried they responded with:

We’ve seen 5 today, it’s hard to replicate the experiences you have from the vantage point of a bicycle, and it’s unmatched when you’re seeing the world from slightly lower and at the speed you do in a car.

I didn’t think a lot of it at the time, but when I returned to Australia 8 months later it was something I couldn’t get out of my head.


I returned to Australia in early February 2010, university was starting shortly and I wasted little time escaping the city with some friends to climb Australia’s highest peak. It kept me sane in the transition back home. Within a few weeks I was back at university finishing up 2 more courses and writing my undergraduate thesis, I occupied my free time by applying for undergraduate jobs.

Within a few months I’d landed my first job as a structural engineer, and starting from scratch I developed the skills necessary to cope in the fast paced consulting engineering sphere. I worked on some beautiful buildings around the country and travelled regionally and internationally for my work.

Bicycle Touring was still on my mind though, and in late 2012 I put a planned bike trip to New Zealand on hold for a project I was working on. The next summer I trundled over to New Zealand and rode my bike down the west coast to the fjords on the South Island, and I was hooked. A friend from home was backpacking over there at the time, and he soon developed an interest in bicycle travel too. I now had a medium to travel by and a friend to challenge me – everything I needed to validate what I’d known for year’s was the next step, something bigger.

Over the following year’s I worked harder and longer, on bigger projects with more at stake. I changed employer, hoping that maybe it was the key to enjoying what I was doing. There were two questions I couldn’t get out of my head, and I think they’re questions we should all be forced to answer if we want to know what we’re doing is right for us.

One of the engineering buzzwords I heard on a daily basis was ‘added value’, how can we add value to this project for the client? This concept of adding value is great from the perspective of someone who is paying the bills, and great if you want to market yourself as the best at whatever it is you’re doing. But a better way to phrase this question is to ask about the added value to society as a whole. Was I adding value to other people’s life? Probably yes, but not in a way that was meaningful to me.

The other idea that occurred to me was the balance of societal goals versus personal goals. Surely this idea of adding value to other people’s life couldn’t exist without a fine balance in looking after you. People probably exist all the way along this spectrum, looking out for only themselves or only for others, or more likely somewhere in the middle. Trying to figure out where I sat on the spectrum and whether it was too heavily balanced to work was as simple as asking the question, Am I proud of the work I’m doing? I found out the answer was personally yes, but that it was more often overwhelmed by added stress.

When I changed employer I didn’t necessarily know the answers to the questions above, but the change was enough for me to realise I was dealing with a bigger problem than who I was working for. It was becoming more apparent that there were other things I had to explore before I could satisfy myself I was doing what I should be.


So this brings us back to the start, for one year now I’ve lived on my bike in South America. I’ve traced a meandering route north from the southernmost city in the world with no real direction further than a few weeks ahead.

I began the journey with the friend from the New Zealand trip but this was as far as our plan together went. We spent one week riding together at the beginning, enough to confirm that our riding style was different and then we went on our own way, crossing over briefly for Christmas in Northern Patagonia and then again in Bolivia. All up we’ve ridden less than 2 weeks together and generally gone our own way.

I needed little confirmation for this lifestyle, it’s a perfect marriage of always slow and sometimes lonely that stimulates me – in truth I haven’t felt quite so introspective since hitchhiking across Canada in 2009. It’s afforded the free time and free thought to accomplish some of the things I’ve wanted to do for years but never found the energy between work and sleep.

When I was living in Canada I took the time to learn some very basic French. Afterwards I never used it, but it has served as a solid foundation to understand Spanish and its structure. My older brother is fluent in French, and until I had taught myself Spanish I’d never completely understood when he opined the value of having a second language.

What it comes down to is that different cultures offer different opportunities to understand and explore the world. On a personal level of course we’re all unique, none of us experience the world in the same way, but on a broader cultural level it’s impossible to truly understand a place without having a firm grasp on the language. My Spanish is now at the point where I can hold political conversations and take a keener interest in the people and places I visit, it has opened up far more doors than I could have expected and has become a point of pride. I beam every time someone asks me where I’m from and then tells me my Castilian is very good, I’m almost sick of explaining that I’ve been here for a year now, and that it’s sufficient to get a grasp of it. They laugh at my forced modesty.


Over the last 12 months I’ve traversed mountains, shivered in my tent, caught boats and slept in strange places. I’ve rekindled my understanding that vulnerability and lack of security is sometimes the best way to meet people and enjoy places – after all, it represents a key commonality in the human condition. A smile goes further than a bike can take you and the best way to look at a trip like this is to understand that the last one across the finish line is the winner. It’s impossible to maintain a lifestyle like this with a schedule and the further I’ve come north the more important weather has become in my plans.

A Brazilian friend I rode with intermittently has recently returned home, one of the last things she said was that when she began cycling a year ago she would ride for 6 days straight and rest for 1, and after a year on the bike she found she was cycling for 1 day and resting for 6.  She discovered the joy of stopping and spending time with people and the bike became the mechanism to do it. I think it’s a nice and restorative way to be and a perfect model for the sort of bike touring I enjoy.

At times I’ve ridden alone and relied entirely on local interaction, and at other times I’ve ridden in larger groups. I’ve made good friends and ridden with people from Brazil, France, Australia, Germany, the USA, Uruguay and many others. I’ve battled the wind alone and with friends and found beautiful landscapes in both formats. I’ve been hungry and thirsty in wild places and climbed mountains on bike and on foot, swam naked whenever I could and often when it’s so cold that I shouldn’t.

The intention was loosely to find out what I wanted to be doing, the answer I’ve found is what I’m currently doing, at least for now. When the money runs out I’ll reassess, and I’ve developed the confidence to know that the decision will be an easy one at the right time. I expect one year may turn into two.


Until today I’ve ridden almost 11,500km by bicycle through almost 4 complete countries, to the North lies at least another 4,000km of windy mountain climbing through Northern Peru, Ecuador and Colombia – what people promise me are the steepest roads they’ve encountered in South America. After that lies the treacherous Darien Gap between South and Central America and I expect that I’ll find a collection of boats somewhere in the north of Colombia on the Caribbean which can traffic me across the border to Panama and the next stage of this journey.

I don’t really know what to expect further than that, but I’m sure the weather will play a part, I know the people will play a part and perhaps the money will play a part. Ecuador is currently still devastated by the recent earthquake and if my engineering skills are of any use there then this is an option. I’ll buy a snorkelling mask when I get to Central America and I expect there might be a lot of resting on the beach, coconut or rum (more likely both) in hand between swimming in crystal clear cay’s and doing more of what I’ve been doing now. If I make it to North America I expect I’ll ditch the snorkelling mask and replace it with a fly fishing rig – something I’ve always wanted to learn to do.


It’s getting close to 10 years ago that I lived in Canada, so about that long since I started moving about a lot. I wrote something down in my notebook all those years ago which I’d forgotten about until just recently, which is that

life is mostly about occupying time, and finding some level of contentedness in whatever way you’re occupying it.

At least in that capacity I feel like I’ve picked up where I left off all those years ago.