Nomad in North America: What I Learned From My First Real Vagabonding Experience

I have just arrived in Manila from a 6-week trip around North America, and it was truly an incredible adventure. I have learned a lot about my thresholds for both pain and pleasure, and would now like to immortalize these lessons before the euphoria goes stale.

The trip was an auspicious combination of work and play. My 5-year graduate school reunion in Boston was slated for May 17–19 and I was the designated representative of one of my client non-profits for an international conference in Minnesota on June 17–20. The flight to Boston from Manila is 17 hrs, idle waiting time at airports not included. It does not make sense to come home only to come back again in a few weeks, so I decided to spend the month separating these two events in vagabond mode. That decision took me to New England and New York in the United States, Atlantic Canada and Nova Scotia (Moncton, Fundy, Halifax and PEI), Quebec (Old Quebec City and Montreal), Alberta (Calgary, Canmore and Banff), British Columbia (Vancouver, Squamish and Whistler), America again via the Twin Cities (St. Paul and Minneapolis), Providence, then back in Boston where I started, for a total of 18 towns and cities.

This was not my longest hiatus away from home (I spent 2 years in the States for school then work), but I was away long enough for this one while working. What might be comparable was my experience ten years ago as a stagiaire at the European Parliament, where I had called Brussels my home for also 6 weeks (I was working at a Philippine Senator’s office at the time and was invited to Brussels to add some diversity while representing my country). However, the experience was bereft of the unique vagabond element of staying put in one place for a longer time. I was 28, and just wanted to visit every European city that I could. I remember trading museum tickets for food most of the time because I did not have much money. It did trigger a lifelong passion for travel, but over the last decade, as physical energies started to wither and priorities began to evolve, I have decided that tourist city hopping and rushed itineraries are probably more suitable for younger people in their gap years.

Vagabonding, according to Rolf Potts, is long-term travel, where travelers are able to work and explore a different country on their own terms. I read this book during my recent adventure and loved it tremendously. This means, at least based on my understanding, that one can visit the British Museum 3–5 times if he wants to because it is free, because he can stay in London for more than 2 weeks, because he is location independent as a software engineer, because he is paid in US dollars so he can afford the high cost of living in the UK, and because he has a flexible work schedule that allows him to insert museum trips in the morning then check in for work when his company’s HQ in San Francisco starts work 8 hours later. In my case, I work remotely as a consultant and entrepreneur, which means I am not limited by a restricted number of vacation days imposed by traditional companies. I just needed my mobile phone and decent internet service to function professionally.

New Tools

Manila is 12 hours ahead of Boston, where I spent a big chunk of my time, so reporting for work was not as optimal. But there were several tools that exist today that were not available to me 10 years ago. These include $10/day international roaming, and WiFi on the Amtrak and VIARail Canada. There is also airborne WiFi on Air Canada, United and Cathay, but it was not cheap so I used flying time for sleeping, reading or journal writing instead. Roaming enabled me to respond to emails during idle time i.e. the 12 hour train from Moncton to Quebec, and post check-in waiting at the airports. So if your job does not require your physical presence on a daily basis (i.e. online entrepreneur, writer/blogger, web designer/developer, etc.) then vagabonding is very much possible, especially if you love to travel as much as I do.

Uber was also a much cheaper way to get around than the regular cab. They did not have that in Vancouver, but everywhere else, it was highly reliable.

Another great new-ish tool is Apple Wallet, which stored my conference access pass, my Eventbrite and Amtrak tickets, and all my airline boarding passes. No paper was wasted, it is great for the environment, and everything is stored in one place, with notifications whenever it is time to walk to the boarding gate. Sweet.

Old Essentials

On the contrary, there were certain things that existed before that no longer exist today, though there are still viable workarounds. I missed my iPod with 1000 songs and a pair of ordinary earphones. I currently use Spotify on my iPhone, and I did not download songs. That kind of fell on the wayside during preps leading up to my departure date. But my travel playlist also has at least 400 songs which if downloaded, would inevitably slow down my phone. So good music was as elusive as reliable WiFi. And my bluetooth earphones also used up so much battery.

Though obviously people still use cash to transact, there was a cafe at the Flatiron District that insisted on cashless transactions. I was using a Citibank debit card the entire time, and without my go-ahead, Citi cancelled my card due to a fraud alert: a dubious $1.10 digital payment. That took 3 days to fix, so I had to get cash from the Citi branch on Lexington Ave. The cafe refused my cash but gave me the $2 drink I had wanted anyway. Strange, and kind of snooty to be honest. But my takeaway from that is to always have cash and multiple debit/credit cards on hand. Canada prefers cards with chips.


As with anything that requires a huge time and monetary investment, planning, I believe, is everything.

At the onset, the guideposts where the final reunion and conference dates. Scheduling extraneous travel around them was the next step so it is best to have a calendar you can write on and refer back to frequently when curating a travel itinerary.

I carry a Philippine passport, so visas to both the US and Canada must be secured. These were handled as early as January-February, 2 -3 months prior to my date of departure. And because visas are rather expensive, it is recommended to take full stock of what these two countries have to offer.

It helps to scan the horizon: Who do you know in the countries you want to visit that would be worth touching base with? Where do they stay? Filipinos are everywhere, and they are genuinely hospitable to any visiting family and friends. If you are lucky, they might even let you stay in their homes which guarantees meaningful bonding and tons of savings. I was fortunate to have generous friends in Moncton and Toronto, and family in Alberta and BC, which allowed me to indulge a bit in Quebec and Montreal where I knew no one.

Once you have identified your stops, book all flights prior to your departure date. This allows you to get the best bang for your buck. I flew Cathay Pacific for the first time from MNL — HKG — BOS, and I loved it, at a ridiculously cheap $1000+ round trip economy fare. This ticket was purchased 3 months in advance. If it had been purchased in May, it would have probably cost $1000–1500 one way. The same rate would apply if I had chosen to land in Boston, and say depart from Providence. So whenever possible, try to pay for a roundtrip fare and then just sort out the other flights in between.

Do not forget to mention frequent flier membership numbers, because I did not do that, and realized only later that they will not be credited after travel if not cited during either the booking process or at check-in.


I like to travel alone, but cannot really be alone for too long, so it helps to set aside some time for connecting with family and friends. I did a lot of that in Boston, which I consider my second home. I have friends there that I have not seen in 4–5 years, and the conversations are of a much higher quality when shared over coffee or food. I was able to comfortably open up about my own personal struggles, and was rewarded with the same level of honesty. It was not rushed unlike the mixers at the reunion when I had to repeat what I did and where I was based more than 10 times to almost 60 people. That taught me to allot an extra day or 2 in my travels to make way for building real connections.


I was kinder to myself this time around, very likely because of age. I simply had less desire in rapidly ticking off tourist attractions unlike when I was much younger. So I intentionally traveled aimlessly, mostly by foot. Google and TripAdvisor were still handy, especially with food recommendations, but I tried to understand my new surroundings without a guide book. I was, after all, rediscovering first world environments. It was refreshing to be in places where things worked, where the ratio of parks to humans is probably 5:1, and traffic, while still present, is definitely more tolerable than Manila’s. So I ended up savoring every moment, because I knew that the fresh air I was breathing or the orange lilies I was marveling at would soon be fleeting memories. I also learned a good deal about smart urban planning and zoning for art spaces. How that wisdom could transmogrify into something useful and tangible in the Philippines remains a mystery, but will be readily shared when the right authority on the subject comes along.


I lucked out with the seasons due to my work schedule and can proudly profess that the best time to travel in the Western Hemisphere is from mid-May until the end of June (early onset of spring to the summer solstice). Not too cold (though Banff was quite the outlier at 0C) and just about to get hot. That helps tremendously with the bane of my travel adventures — luggage issues — since there was no need to pack cashmeres, thermals and winter boots.

Staying Healthy

Travel is capable of solving so many problems in the world because every extraordinary experience makes people more grateful and happy. It also teaches empathy, especially when traveling to places not as hospitable as our typically safe milieu. I caught a glimpse of the junkies lining the stretch of East Hastings in Vancouver shooting up at 7 in the morning. I could not help but sympathize with their plight, and realize how fortunate I truly am to be far removed from their realities even though I was physically close by. I could not help but think of home — not everything about Manila is bad, in the same way that not everything in Vancouver is good. It does beg the question, however: how do we improve our current situation? How and where can I contribute? Being on the move gets the mind working.

Travel is also an indulgence, a reward humans deserve to offset their hard labor. With that in mind comes the delicious eats: the lobster rolls at Neptune Oysters, burnt caramel ice cream by Toscanini’s, the burgers at Shake Shack and Five Guys, the St. Viateur bagels of Montreal, the Granville Market in Vancouver, the St. Lawrence Market in Toronto, the whiskey hazelnut ice cream by Earnest, the tiramisu at Le Hobbit in Quebec, the Tomahawk at Brigg’s Calgary, the rhubarb blueberry fritter in Providence, PEI oysters and too much alcohol. There is so much joy in eating while traveling that resistance for dietary reasons is futile.

Fortunately, I managed to keep my body weight steady, no small thanks to intermittent fasting (IF). IF permits indulgences because you can eat anything during the eating window (mine was between 1230 to 630PM). So I did all the walking in the morning to distract me from my hunger and would eat heartily for lunch and early dinner. There were, of course, inevitable adjustments (i.e. late night drinks over pretzels and calamari while rooting for the Toronto Raptors and the Boston Bruins) but I was able to prove that by consciously and consistently fasting for at least 13hrs, I could eat whatever I want and not pack in the pounds too much. That really works when visiting a city I am not sure I would be able to visit again.

Getting More Stuff Done

I am planning another extended travel in 2021, the year I turn 40, and would like it to be just as meaningful and relatively stress-free as my North America sojourn. My goal is to see as much of Asia as I could, and that means venturing into areas where things do not really work. Surely WiFi would be even more sporadic and not all public bathrooms would have toilet paper, or even proper toilets.

The next level for vagabonding is 18 months so that would entail a much longer preparation. One of the minor flaws of this last trip was not having only one person to look after my affairs back home. Bills still had to be paid, but I was relying on different people to do that. So hiring a virtual assistant would have to be considered more seriously.

I would also need more projects that can be executed remotely. My wellness business is online which is great but I would still like very much to continue my consulting practice. How can I provide value to my clients while I am away? Long-term travel would also afford me the opportunity to write and record the podcasts I have always wanted to develop, but I need to pursue something capable of funding that. It seems that for now, only a solid location independent business makes sense in turning my vagabond dreams into reality. Good thing there are now a lot of opportunities and side hustles available to anyone today.

Former presidential speechwriter, still a musician; writes about urban gridlocks. Will work full time for the planet. Harvard Kennedy School ‘14 🇵🇭

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