This blog originally started out as a place where I could chronicle my thoughts while travelling and what those experiences meant to me. The irony’s not lost on me that at a time where I was actually travelling the most was when I completely stopped writing. In fact, I stopped talking to a lot of people, period. It’s been almost two years since I’ve really posted anything real or personal. To be honest, it was one of the loneliest, existential, often seemingly irrational, yet looking back, one of the most meaningful journeys that I’ve taken so far in my life.

With a new year in mind, I really want to move back into a space of vulnerability and reflection. I want to start looking at life as how it really is and not as a staged interview answer. As I get older, I find it’s incredibly difficult to stay in that honest, vulnerable space. The more I’ve seen, the more I realize that there’s still so much I have yet to learn. You’re in a way ashamed to admit you’re getting older, yet still imperfect. Shouldn’t I have it all figured out by now? While I was living this nomadic lifestyle, my friends on social media seemed to be settling into an idealistic lifestyle and maturing gracefully. Salt in the wound. Meanwhile, I was flitting around the world with no end destination in sight. As I continued to climb the career food chain, I also felt the need to appear more buttoned up.  I thought especially, as someone who has been working with startups for the last several years, where there’s often already so much uncertainty and work to be done, writing about my own personal trials and tribulations was just adding on to my weight of always living off a 12-month runway – borrowed time from investors – just by talking about it. I couldn’t bring myself to write it out.

I’m not a programmer so I feel blessed that I was able to travel and work remotely and survive (keyword here is survive) in some pretty expensive cities. (More on how to do that logistically in a later post.) It’s definitely a lifestyle more befitting of someone younger, with seemingly more time to get it right, but then again, I’ve always been a bit late to the party.

This and the following posts are really just a collection of personal thoughts that I had going into each new country. I had a different frame of mind everywhere I went. As I write this, I’m not sure if it’ll all come out with a common thread throughout, or what picture it’ll paint of me when people read it, but I’ve been wanting to get this onto a page for the longest time now.

So, I’m just going to start.

Shooting My Shot in Singapore

I originally moved to Singapore because I was seeing a big change that I wanted to be a part of. When I first started my journey in startups in 2014, the conversation was around which location would be the capital of startups and technology in Asia – Hong Kong, or Singapore? Within two years, it became very clear that Singapore would be the overwhelming winner. The access to international talent, the lingua franca of English, access to startup capital and the geographic proximity to extremely large, untapped markets were some big factors that I believe contributed to this.

I had just gone through one of the most devastating moments of my life and realizations on a career and personal level. The startup I had put all my energy into and pressure on myself had not worked out. I had just ended a string of relationships that proved there was a lot more work that I had to do on myself. At this time, a thought that I had hidden away for several years had started to also surface in a visceral way – I didn’t want to settle in Hong Kong. It was never my plan to live in Hong Kong long term. I love the city’s energy, the food, the people, but it has never felt like home to me. As a consequence, this showed up in the way that I approached my friendships and relationships while in Hong Kong, treating most people as social groups, drinking buddies, new experiences, but not as lifetime friends or partners that I could see myself growing old with. It showed up in the way that I approached my career up to that point as well, as opportunities just to get me to my next stepping stone. I was looking for some sort of permanence, a place where I could settle. I was looking in a mirror and not liking what I saw. This was due in part to my narrow way of thinking, not due to the many wonderful people I met.

While looking at opportunities in Singapore, I came across a career opportunity that at the time, I thought was the perfect job for me – working for a global music technology startup. With a background in both music and tech, I thought that it was a match made in heaven. It couldn’t have been more perfect on paper. I packed my bags and moved to Singapore with no hesitation. I believed it was my ticket to what I was truly looking for.

Singapore is a pretty incredible place. In a world that seems increasingly black or white, poor or rich, red or blue, democrat or republican, conservative or liberal, capitalist or communist, you have a country in Singapore where almost every religion is recognized, every culture is living together to create a true representation of ideas, customs and culture. When I think of this, it’s no wonder that Singapore has become an important international hub. In many ways, it feels like the Europe of Asia. In an hour you’re physically connected to Thailand, Vietnam, Cambodia, Malaysia and many other places where everything is different. Food in Singapore is probably a great representation of this. It isn’t “dumbed” down to fit a certain palate as you find in many countries where you want to try something different but it’s often altered as to not offend the local established taste buds. Singapore is as close as I got to better understanding positive Muslim culture as someone who has been perpetually removed from any positivity provided by Western media where we only feature the bad and not the good of the religion.

Living there, I also noticed many things that I had a difficult time with. A pint of beer was $20 bucks. The weather is 32 degrees. Every day. Big brother is around every corner, telling you to have more kids or to fit a certain mould. The city is being built at a rapid clip by underpaid, marginalized minorities. A big question I always had was, how do you get so many different cultures to play nicely together? In marketing, I saw a dark answer to my seemingly innocuous question. In many ads the conversation was often around how to squeeze as much “diversity” into our ads as possible. It’s not a secret – Singapore has been trying to find the answer to this for awhile now. One Chinese, one Indian, one Malay was often the imperfect and unpalatable answer.

As for my job, it started out like a dream. I got to work on products that would help predominantly Asian artists make their music. Something that growing up, I always felt was out of reach to me as a minority in Canada. I got to meet like-minded people who wanted to work in music not for financial gain, but to really help make products that would make a difference for musicians. I dug further into the Singaporean music scene – young talents like Gentle Bones, Gareth Fernandez, Shigga Shay, The Sam Willows… no matter what genre you’re into, the level of production and quality in Singapore is pretty incredible.

Unfortunately, it didn’t last long. Without getting into the details or slagging off anyone (but happy to share over a drink or private conversation), I was fired, for the first time in my professional life. I spent the next several months mulling it over. Singapore is an incredible place save for a few flaws. But something still didn’t feel right, so I continued my search.

Back To Hong Kong… Somehow

I had left pretty abruptly just 6 months earlier, so it was a surprise to many when they started seeing me at regular Hong Kong haunts again. I was surprised myself. Many commented that they knew I’d be back. I wasn’t so sure. I had landed a regional role at one of the hottest startups in Southeast Asia and while I had applied to a role based in Singapore, they wanted me to come back and work at the regional headquarters in Hong Kong. I wasn’t so sure this was the right move for me, but since it was such an incredible opportunity, I didn’t want to pass it up.

At the time I had been working in a consulting capacity for several startups, mostly at the seed stage. I had learned in a trial-by-fire way how to help early stage startups get up and running, however this next job involved a Series B to C startup, helping a product launch in markets to reach over 500 million people.

Once again, it felt like I was learning everything all over again – and I had to learn fast. It was challenging, but extremely exciting. At the same time, I started to realize what I was still lacking in my current skillset. The amount of data that we received as organization was staggering and all in real-time. I started to see the holes in my skills that would keep me from fully succeeding at the organization. I also started to draw a distinction from what I saw as true leaders and bosses from what I witnessed at the organization. Leaders inspire action and are never truly defined by a title. A boss commands action and often only from authority.

I spent a lot of my free time reading and consuming different viewpoints on management theory (short answer: I don’t think there’s one right way to lead – it has to be aligned with your authentic style) and learning more about the ways data-driven tech marketers in later stages succeed. Whenever I’d pick up a new book or article, whether it was by Andrew Chen, Brian Balfour, Eric Ries, John Doerr, one common thread kept popping up – they were all doing it in Silicon Valley.

At the same time, Hong Kong felt exactly as it had when I left for Singapore. I had a great job in most respects, but I still didn’t see how it was going to get me to where I wanted to be. I spent months fighting to find my decision. Little did I know that a short year later, Hong Kong itself would be fighting a much bigger fight.

I made up my mind that I was going to stop getting second-hand information from books and try and get it straight from the horse’s mouth. So, I packed up my bags.

A song by Scott McKenzie came on late into the night on a cab ride home after way too many contemplative drinks in Hong Kong on my situation. How fitting.

I was going to San Francisco…

More to follow on dodging feces in San Francisco, karate bar fights and porn stars in Tokyo and the beginnings of Vancouver.