Musings in Montréal

I had the pleasure of swinging by Montréal recently and a thought dawned on me: it had been quite a while since I visited a city that was truly new to me. I had gotten stuck in a routine of repeat visits to cities and countries I’ve been to before (all which I loved) – but I had forgotten what it was like to dive into a place where I had no idea what to expect and no pre-conceived notion of its history or culture.

I have to admit, the prospect of a whole new playground to explore gave me quite the rush. And not just because it was in Canada. 😉

As is tradition when I visit major destinations for the first time, I present this documentation of my exploration in superlative form. Locals may not agree and this list is definitely not comprehensive, but it is what I’ll remember from this latest trailblazing effort in Montréal, the “Paris of the North”.

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Notable quotes from The 4-Hour Workweek

People sometimes tell me that I should follow in the footsteps of author Tim Ferriss, given my penchant for travel and remote work. I have a couple of qualms with this:

  1. In my opinion, Tim Ferriss often comes off as a douche – in both speaking engagements and in writing. I’m sure he has good intentions to help people – but his delivery of advice is a mix of humblebragging (look at all this cool shit I’m doing) and light condescension of people living “normal lives” (what you can’t pull this off?). I was looking for a clip of him speaking that exemplifies this, but I think this will do:

    I know I can be pretentious at times, too – but at least I try to catch myself and would hope I never get to Tim Ferriss’ level of aggrandizement.
  2. Tim Ferriss advocates for a world where no one actively works on building or maintaining anything. He would have you create something once and passively sell it forever, thinking as little as possible about improving it or creating new products. All while outsourcing your tedious tasks to some poor folks in India.

    This bothers me mostly because I am a product manager – and no half-decent PM would release a v1 without some sort of long-term vision or roadmap for where the product should go. I am also a very hands-on PM, so the idea of letting someone else manage my inbox makes me nervous.

Continue reading Notable quotes from The 4-Hour Workweek

On travel withdrawal and returning home

So I’ve just resettled back in San Francisco after living and working 5 months in Sydney and 7 months in Ho Chi Minh City. It has definitely been a challenge to readjust to life at “home” and I’ve struggled to accurately convey this to folks who have asked about it. Some common sentiments that are shared:

  • “It must be nice to be back after so long!”
  • “Did you miss life back here?”
  • “Your family/friends must be so happy to see you!”

To all these well-meaning sentiments, I’ve only been able to respond with a hesitant, “Well, yes and no…”. Here I’ll try to shed some light on what it’s like to come back to a place after extensive time abroad.

Everything is dull in comparison

Especially if you’ve been travelling to places with cultures much different than your own, there is a very real “crash” when your exposure suddenly stops. You get bored extremely easily. Nothing excites you anymore. Food tastes bland. All buildings start to look the same and blur together. Even within the most beautiful cities in North America (e.g. Vancouver, San Francisco), you can’t help but get the sense that there’s nothing interesting going on anymore.

It’s all in your head, of course, but that’s what this “reverse culture shock” feels like.

You feel like it was all a dream

As memories of your time abroad start to shift themselves into the long-term part of your brain, you start getting the sense that they could have all been manufactured. The places you went, the people you met – were they real? Did you really live like that for so long?

Looking at pictures helps, but only so much. Those fond memories seem like a world away – and in a way, they were.

You want to leave, but then you don’t

It’s common for frequent travelers to report a “travel bug” they get if they stay at home too long. It’s this wanderlust that drives some to continue travelling for years on end. (Everything being dull on their return certainly contributes to this.)

What is not so commonly reported is that extensive travel has some real downsides – and if you’ve felt them before you’ll stop and think twice before committing to another round so quickly. You’ll remember that the lifestyle includes isolation (a.k.a. “crippling loneliness”), a lack of routine that the body craves (including exercise), and a longing for familiarity that serves as the cruel antithesis of the boredom you’ll feel when you return.

This conflict of feelings may be enough to put you into analysis paralysis – when you realize you can’t be happy at home and you can’t be happy abroad either.

No one fully understands your story

When you try to tell your friends and family about all this, they are most likely going to respond with blank stares or platitudes on how great it must be to travel all the time. And you really can’t blame them – most people think of travel as infinite upside and are unaware of the downsides.

It’s rare to find someone who can truly relate to the entirety of your experience. You’re more likely to be perceived as spoiled or entitled, as this sketch clearly shows:

And it’s a completely fair perception. The lesson here is that it’s important to not take your experiences for granted and do more internal reflection rather than expecting others to understand everything that’s going on.

You’re more alone than when you started

Extended time away from the people you love means that you will start drifting – there is no avoiding it. Despite your best efforts to arrange visits or draw them into your world, the fact is that most people will assume you are “gone” the minute you declare your outbound flight. (They may not even be aware when you return!) You will most likely be left off invite lists to birthdays, housewarmings, etc. as the operating assumption is that you will not be able to make it – and that’s totally fair. But it also results in fewer and fewer opportunities to stay caught up between friends, which ultimately makes it harder to reconnect when you return.

Do you even know what is new in these people’s lives? Not everything is posted on social media. When you meet up again, how much of their story can they catch you up on without omitting the colorful details that make the memories stick? Be aware that your relationships will be reset – most of them shallower as a result.

This is unfortunate, but there are exceptions to be found – notably with those you hold the deepest relationships with. Old, lifelong friends are those that you can meet up with and continue as if you were never away. Hope that you have some of those waiting for you.


I believe it’s important to share these experiences, despite them being incongruent with the typical glamorous thought pieces about travel. My hope is that highlighting these challenges will help me overcome them myself, as well as encourage others (like Charlie Guo) to share their own. Feel free to share your thoughts here as well.