writing > Nomad Chronicles > Place-people
Last Updated: Mar 2018
12 minute read


In December 2013, I left San Francisco to begin my life as a digital nomad. For the next 2 years, I lived out of airbnb listings, mostly in Asia, while I continued to work remotely for my startup, BitGym.

That time has changed the way I see and interact with cities forever. When I don’t go out much or find the town’s vibe discouraging, I lose my sense of drive and purpose. On the other hand, being in a city filled with life, vigor and passion boosts my motivation, energy and happiness.

About half the days during my nomadism were spent without speaking on any personal level to another human being face to face.

During these days, I came to realize there was still always one reliable source of company and comfort – the city itself.

The Company of Cities

I’m not alone in this city – I’m alone with this city.

It was mostly inevitable given my circumstances much of that time – my work was on isolated tasks that I had full ownership over, confined to my laptop. I would fly into a city where I knew literally noone, and plan to stay for 1-3 months. Usually I couldn’t speak the language at all. Other times by choice, I intentionally avoided human contact from the exhaustion of going through reintroducing myself, making the same distant small talk with each transient encounter.

My friends were often surprised that my next leg was going to be 3 months in a city without a single personal contact, let alone a close friend. At first this was probably because I didn’t know what I was doing, or had some simplistic approach to choosing a destination like “I hear Seoul has really good internet.” Eventually I realized why I was not just okay with this, but sought it out.

Everything I saw, did and experienced was not just me in a vacuum. If you’ve traveled alone without much of a schedule, you’ll know what I’m talking about. When I was out and about, the city suggested activities, provided the sights, presented me with food options. Which I proceeded to choose from and interact with. This consciousness became the place-person, and the time I spent with it our conversations.

This is easiest when alone with a city, but at times I consciously converse with cities even when with other humans. Just like with people, the conversation can range from grand topics to seemingly trivial matters, and there’s no telling which will prove more profound and meaningful.

Place-people Conversations

One of my favorite things about conversations with Place-people (if you truly listen) is that they speak purely with their actions, and as a corollary their actions are true to what they say. They put their money where their metaphorical mouth is, so to speak. The city offers encouragement and inspiration by showing you honestly and openly what it cares about.

Conversations with cities aren’t anything specific. In fact, I have a hard time describing what is and isn’t a conversation with a city. Sometimes it’s talking to people, sometimes it’s just overhearing conversations. If I don’t have the leisure to learn their language, I try to learn the connotations, contexts and literal translations of common phrases. There’s a reason why “how to swear” is one of the first things we learn casually in a new language – In my experience, they’re the most common expressions in most languages, and yet are context-rich, information-dense and full of subtleties about the local culture and what is offensive, mocked or appreciated. Sometimes it’s being an outsider, sometimes it’s pretending to be a local. Sometimes it’s attending a central cultural event, sometimes it’s just watching rush hour traffic from a cafe window. Sometimes it’s about the laws and policies, other times it’s about what isn’t a policy. Sometimes it’s just noticing the looks on the faces of people watching other people – or yourself – do the things people do.

Grand Topics

I have a hard time talking about cities without circling back to Paul Graham’s essay on cities and ambition. His essay covers what I consider the grand topics of conversation you can have with a city.

Cities suggest and inform your ambitions and support your passions with all the subtle messaging: Paris loves you as an artist. New York can commiserate on your desire to be richer. Silicon Valley goads you to acquire more power. LA encourages you to seek fame. This is on the grander end of the spectrum of conversation one can have with a city. The whispers of these cities come in a choir of a thousand voices – what you overhear in a coffee shop, advertisements, evident economic stratification, employment sectors, celebrated pastimes, the list goes on.

PG argues that we as mere humans cannot fight the Pavlovian conditioning for the values of the place beyond a certain extent, no matter how sheltered, stubborn or individualistic we may be. As a corollary, we can never be as passionate about X as someone surrounded by values that inspire them to pursue X, all else being comparable.

A related essay of Paul Graham’s showcases the differences in how places talk about the Grand Topic of ambitions and innovation – Why Startups Condense in America. Tens of cities or countries every year vocally promise to be the “next silicon valley” – whether that’s a worthwhile aspiration is a separate topic – via “startup” and “tech” grants, a coworking space and a few statements from the mayor and some local tech CEO. However, an engineer-entrepreneur listening closely, aka, tries actually living in one of these while building things, can quickly cut through the marketing noise and hear the true voice of the city. If it inspires, welcomes and encourages them, and honestly just makes what they do easier, more rewarding, and a pleasure – that is the true promise. The place will resonate with a history of having done this or at least a willingness to do this for decades, and it will use many voices to say this.

The Grand Topics are unsurprisingly important to think about and share with your city. Other such things (not mentioned in PG’s essay) include the dichotomy of individualism vs communalism vs collectivism. The cultures surrounding openness, restraint, conservatism, freedom, and so so much more. But what I oftentimes find myself further absorbed with are the trivialities.

Trivialities, or what seem trivial

Almost every city will quibble and gush about the quaintest little things too. I love this aspect as much as, if not more than the conversations on Grand Topics.

My favorite thing is listening to the streets. How long do the “walk” signals last to cross major streets? In downtown San Francisco, you can cross Market Street approximately every 45 seconds and have 30 seconds to do so. In downtown Madison, WI, I had to wait precisely 3 minutes to cross E Washington Avenue after hitting the “Press to Cross” button, and had the same 30 seconds to get to the other side. It speaks to the social strata of automobiles compared to pedestrians in these cities. In India, it’s a free-for-all – you just hope to not come into contact with another traffic entity at too high of a speed, a kind of natural feral law, favoring the physically larger entity.

In Taipei the walk signals are a quaint animated LED display instead of a bulb through a static transparency like in most other places. It turns out to be a cultural affinity to invest in making official information appropriately adorable, something you can find in other Asian countries to varying extents in street signage. In London, there are many kinds of crosswalks including what the Londoners call Zebra, Pelican, and Toucan. We can all guess why the Zebra is called so, but even most of the Londoners I asked had no idea why the others had the names they did, and had some pretty funny guesses. You can look up where each of them got their name, but what amuses me rather than their origin story is the overarching penchant to zoomorphize street crossings. Did the rest just follow because Zebras? Is it perhaps that London, august and proper on the day-to-day, loves to bring up animals that are a tad silly when crossing the streets to showcase there’s more to them than drab and class?

In Japan, one of the most notoriously OCD cultures in the world, trash/recycle bins are pretty hard to find on the streets. How strange! Especially given that several streets had more vending machines in the open than people. True, vending machines are typically accompanied by the appropriate recycle bin for the leftovers of what it dispenses, but just as often they weren’t. Curious, I started asking locals what the deal was. They had various plausible answers.

It turned out to be a nuanced, simultaneously conscious and subconscious outcome – The most prominent factual reason was a “trash-based” terrorist attack by a doomsday cult in the 90s. They wrapped newspapers in plastic bags filled with the chemical-weapons-grade ‘sarin’ gas and dispersed these in trash cans and in the open in a major train station. However, this technically only resulted in reducing garbage receptacles at train stations.

Others told me that a realization of the collective Japanese OCD consciousness was “rubbish begets rubbish.” The streets used to have more litter and stray trash, diffusing outwards from well-meaning garbage bins being used by well-meaning folk. Removing them acutely reduced the trash by recalibrating everyone’s expectations and methods of dealing with trash, and the cultural agreement was to reduce what you generate on the streets, and to carry whatever little you generate with you and dispose of it responsibly and intentionally.

Over the course of my time there I noted nobody ate or drank on the go in Japan. Eating on public transit is not even prohibited – just noone does it. Later conversation with locals clarified that it’s considered embarrassing/disorderly to consume food on the streets. I later put 2 and 2 together, and realized this meant they eliminated the primary source of garbage generation on the go, reducing the need for bins! This mindset and the purging of garbage disposal seem to have a chicken and egg relationship, as none of the locals I asked had an idea which caused which, or if they’re even directly related. I also saw locals often when using a vending machine, finish their drink right there and discard the can in the associated bin. Meahwhile, people walking out of a convenience store with an onigiri or a candy bar would patiently take their sustenance to their destination, unlike my impatient self who would always pop it open as soon as I’d paid for it.

I could talk endlessly about little eccentricities of each and every city I’ve built a variety of relationships with, almost as easily as I could talk about the strange quirks of my (human) friends.

Places are Dynamic

None of these traits are static. Just like with your best friend, their quirks and talents developed over time from their interactions with the world around them, with their family and teachers and friends, and with you. I get deeply uncomfortable when people treat places as static, immutable entities without feelings or personalities. A dot on a map, a certain number of miles or hours away, the source of some specific kind of goods, aribitrarily the hub of some activity. They’re all roughly the same, and seemingly the only explicit reasons we choose one over another is its basic geographic relationship with our life – distance from our job, our family, friends, and allowed legal presence where it applies. But real cities are so much more.

“I’ve seen Vietnam, I want to go to Cambodia next”

At best people treat places outside where they live like an average book or movie – something that may have some depth, but once you’ve been through it you’re done and never need go back to it, unless you feel like you “missed something” or want to “relive it”. Is that how you treat the people you meet and get to know? Once you’ve had coffee with them once, you cross them off your list, occasionally mention to friends how you once had coffee with a person, remember nothing of their feelings or emotions in that conversation, and never think of them otherwise, except on some rare occasions where your experience was so magical you go out of your way to see them for another coffee?

Awkward silence as we both realize I just described online dating, the shallowest and most harrowing social experience of our generation

A city is the growing, shifting values, food, language and architecture, across hundreds of generations, funneled through their weather and geography, multiplied by the variety of cultures and events that collide with it. It will have flaws, setbacks, pride and pain that is constantly changing, sometimes at odds with the things the city loves. They can be welcoming, diverse, stoic, rude, creative, hesitant, energetic.

I won’t presume to tell you what to do or not do when you go out into a city. Just this: Talk to cities. When you come back home, ask yourself if you felt like you had honest conversation with the city. Not with its tourism industry or with its top reviewed destinations, but with the soul of the city.

You may find an interesting friend. A friend different from the ones you have. A friend who may teach you something new, things you never expected to learn. A patient, badass friend who has the wisdom of a hundred generations, the might of a million voices, the size of a literal city.

But most importantly, a friend who will remember you long, long after you’re gone, and share your story as part of its own to all its future friends.

cross-posted: on Facebook