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#14: Choosing where you live
a big question that people don't think about enough!
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Recently, I’ve been thinking a lot about where I should live next and the general concept of how our location shapes our lives. It’s become top of mind lately as I’ve been having more conversations with friends who are thinking about whether they should stay where they are or try living somewhere new. Deciding to move often becomes a decision with information asymmetry because staying put is well understood, but moving to a new place is filled with unknowns.
I’m still enjoying the flexible lifestyle of being able to travel often and go to wherever I want based on the seasons, but I’ve realized that this isn’t sustainable for the long run. Due to the timing of my planned travels ending in October, I’m starting to think about where I should live next. It’s been equally exciting and nerve-racking to figure out where to live on a month-to-month basis. I could probably live this way for another year or two if I wanted to, but not for five years and beyond. The greatest benefit of being nomadic is being able to see many beautiful places and sample a large variety of activities on a frequent basis. I feel like I am taking the vacations that I would take across ten years if I was still doing an in-person, 9 to 5, 40 hour / week job and compressing that into a year. On the other hand, I’m missing out on a deeper sense of community and what it feels like to live in a place long enough to know the neighborhood and the names of the people that work at your favorite cafe, bookstore, or restaurant. I don’t feel lonely at all when I’m traveling because often I’m traveling with friends or visiting friends, but I sense that there is a greater dimension of relationships that I miss out on because I’m not around for those spontaneous hangouts or random adventures.
For me today, when I answer the question “Where do you live?” I respond with where I’m physically located at the moment which might seem obvious, but previously when people asked, the answer would be where my apartment lease was signed to and not where I was in that moment. Today, the line between where you reside and where you travel are getting blurrier and blurrier. For example, if you spend six months in one place and then travel the other half of the year, then answering the question becomes less straightforward and more up to interpretation. For me, since I’m not rooted to one place in the form of ownership or a lease, where I live is the same place as where I am and I get to decide the pace/vibe.
I keep coming back to the big life question of where to live because I’ve realized from the last 1.5 years of living nomadically just how I change depending on where I live. I feel like a chameleon or Ditto (the Pokemon) - able to morph into a shape that fits the space, whether it’s big fast-paced city life in NYC or chill island life in Hawaii. I’m experiencing the paradox of choice from knowing that I can see myself living in several places with each lifestyle being distinct, but difficult to rank. I also don’t know when I even need to decide, but I have realized that bouncing around between places for short periods of time isn’t optimal in the long run.
My theory is that where you live is one of the most important decisions you can make. I also think people don’t spend enough time thinking about where to live which is understandable because until remote work became normalized, it wasn’t something we had much control over. In the last two years, that’s changed and we’ve been given the ability to decide, but it seems like this newfound freedom hasn’t come with nearly as many people actually making moves.
How we got here
Way back in time (pre-Industrial Revolution), no one really contemplated where they should live. It wasn’t something on people’s minds because it was more or less already decided for them. You were born in some medieval town and then stayed there forever, only knowing the people that were in your community, tribe, town and the occasional messenger riding on a horse to deliver some letters. Even your job was decided for you based on what your father did which is how people were named (Smith, Cook, Baker, Carpenter).
Then the next large chunk of history started with the Industrial Revolution and lasted up until recently. Technologies like airplanes, cars, trains, cellphones, computers, and TVs were invented and widely adopted. Some folks would go out of town for college and move to a big city like New York, LA, or Chicago for work, but many people still remained in their hometowns where all their friends and family remained. This was also during a time when people’s careers would be spent at one company for 40+ years.
Starting in the early 1990s, telecommuting aka remote work became possible with a large telecommuting experiment by the U.S. Office of Personnel Management and the General Services Administration. There were only 550 employee participants in this pilot study, but the benefits were clear: “reduced commuting time, lowered personal costs for transportation, parking, food, and wardrobe, improvement in the quality of work life and morale, and a better balance between work and family demands”. We all know how this plays out - the technology exists, but adoption doesn’t take off. In parallel, the interweaving of globalization, capitalism, and consumerism result in the modern corporation being formed and people caring about work a whole lot more. It becomes normal to go to college and then move away from home for your job. Families start being more spread out and split up as young workers migrate to the lands of opportunities. Cities start to pop up and have distinct flavors as they attract like-minded people and become hubs for specific industries. San Francisco is known for tech, Los Angeles for entertainment, New York for finance and fashion. People didn’t think too much about where to live because often it wasn’t a choice - you would go to where your desired job was located.
Why where you live matters so much
Everything in your life flows downstream of where you live including who you hang out with, what you do in your free time, what you eat, and even what you care about. This is obvious if you pause for a sec and reflect on your current situation. Sure you can always Facetime, but it’s a lot more fun to hang out with friends in person. If your friends all work out at Equinox in NYC, then you’re more likely to sign up. If you live in Hawaii by the ocean, you’ll probably end up trying to pick up surfing. If you move to Denver, you’ll inevitably pick up skiing even if you’ve never tried before.
I’ve seen firsthand how much location shapes how I live from noticing how different of a person I can be based. When I was living in Hawaii from April to July, my mindspace was occupied with with prioritizing health, surfing, and chilling. Relatively speaking, I was free-spirited, open-minded, and internally oriented. By internally oriented, I mean that I was more focused on making myself happy, cared less about socializing or meeting new people, and also cared less about making a difference / saving the world in some lasting way. Last summer in NYC was quite the opposite. I was focused more on work, going out, and socializing. I stayed up later because I would go out on the weekends, but also during the week, people prefer to hang out at night rather than during the mornings. People in NYC are more likely to care about their work or are working on a startup or personal business, so the topic of work comes up more often in conversations even in casual settings. In NYC, there’s a much higher density of restaurants and apartment kitchens are smaller so you end up cooking less at home and eating out more. It’s subtle, interconnected characteristics that compound to result in vastly lifestyles.
Everything is interconnected based on where you live. Your friends are determined based on all the possible people that you cross paths with. The conversations you have with your friends influence what you care about and how you spend your time. There’s no right or wrong and it comes down to what you want at a particular time. When I was recently living in Hawaii, it was refreshing to meet people and never bring up the dreaded question “Oh so where you do work?” and to this day, I still don’t know what some of my friends do for work. That’s in contrast to living in San Francisco where work/tech/startups can often be the primary topic of a conversation at an actual party.
It might seem paradoxical that remote work enables us to choose where to live, but then also influence what we actually do for work. For example, if I were to live in Hawaii, I’d be more likely to want to start a small business like a cafe or work for myself as a freelancer because I would value lifestyle and freedom more. If I were to live in SF or NYC, then perhaps I’d be more likely to start my own company or work at a startup. However, if I lived in Seattle (where I currently am) then maybe I’d gravitate to working a big tech company like Microsoft or Amazon. This all ties into mimetic desire (what we end up valuing is based on what others around us value) and Paul Graham’s essay on Cities and Ambition that I’ve referenced before.
I’m finding myself caring a lot about this question of “Where should I live?” because:
I’ve realized this is a question I need to actually answer. I can’t keep bopping around from place to place forever.
I understand how important of a question this is from observing how different of a person I am when I’m in Hawaii vs. NYC vs. SF vs. traveling between small ski towns.
I’m in a position to actually answer the question and then move since I don’t have a lease and have a remote job. (I think a lot of other people are also in a similar position as me.)
How to figure out where you want to live
Given how important it is, deciding where to live can often feel overwhelming, complicated, and impossible to make. That said, with remote work, online communities, and short-term stays, it’s never been easier to test out living in a place. In order to actually answer the question of where to live, there are a few things that need to be put into motion:
To start out, fully grasp how important where you live is and how everything from friends, values, lifestyle, interests is intertwined with where you live. If you don’t think this is super important, it’ll be hard to actually figure out where you want to live simply because of the inertia of staying put.
Find a way to sample living in different places. This step includes anything from finding a remote job to quitting your job to be funemployed for a little bit.
Go try living in different places while being observant of who you spend your time, how you spend your time, and what you end up valuing. This step is the actual Doing and can seem daunting, but there are a few ways to make this less intimidating:
Get rid of your furniture. You simply can’t travel with a ton of stuff and it’s not worth keeping things in storage thinking that eventually you’ll return. “Every thing you own, owns a piece of you.”
Have a home base. In most cases, this would be where family lives. This simplifies things by having a mailing address, place to store extra belongings that you didn’t get rid of in Step #1, and it’s also important to have a place of rest in between trips. Traveling back to back is exhausting and it’s also impractical to carry all your belongings with you.
Start easy. Visit places that you know people in. Crash on friends’ couches. Stay in cheap Airbnbs. If you don’t where to go, then make a list of what you want to learn or experience and then go to the places that are known for those things.
Commit to one place. Based on:
Goals: Is this place an enabler or impediment for what I want? Does it accelerate or decelerate progress towards my goals?
Community: Do I feel like I belong here? Do people care about the same things that I care about?
Lifestyle: Can I pursue my hobbies here?
Family: Is staying close to family easy here?
Cost of living: Can I afford to live here permanently?
Where do I want to live?
Whenever I visit a place, I pay attention to how the locals live to see if I could see myself living there. Ideally, most places end up falling into one of two buckets: amazing place, but wouldn’t live there and amazing place and would live there. Some of my favorite places to visit that I wouldn’t live long-term in are Mexico City, Bali, Chiang Mai, Hoi An, Lake Tahoe, Denver, and Salt Lake City. Within the category of places I would want to live, there’s a further breakdown between places I would live in right now and places to settle down in the future. When I’m older with a family, I’d want to live in Hawaii or San Diego where I would have a sense of community and have a balanced, healthy lifestyle. I could also see myself enjoying Bend, Oregon or Jackson, Wyoming, but sense of community might be harder to find.
When it comes to the next immediate place I would want to spend a couple years in, it becomes less obvious. I think in the next 6 months I will want to switch modes. If this current chapter is themed around exploration in all ways - where I live, what I’m doing, who I’m with, then the next chapter will be centered around focus - staying put in one place, putting a lot of time into only 2-3 things at a time, and having a fewer, tighter relationships. New York City is currently at the top of the list for me because (despite record high rents of $4k) the city is attracting hoards of young, ambitious people. I’m sure part of this NYC frenzy is driven by FOMO and hype, but I have noticed that the brightest, most driven people I know are moving to NYC right now. By the time I’m ready to lock in and stop exploring, I think I’ll be okay with putting a pause into the nature-filled travels. Instead of seeking out the best places to visit, I’ll be looking to surround myself with some of the best people.
Where you live should ultimately depend on what your goal is which change from time to time. I think that icebreaker question “Would you rather live in the mountains or by the beach?” is kinda dumb because I like both and also don’t think I have to make pick just one or the other. I also think that the big city vs. small town debate is a false dichotomy. Someone can be equally interested in both types of locations and on the other hand, someone could be completely apathetic towards where they live. For example, I want to be around young, ambitious peers and having accessibility to a rich variety of food, culture, etc. but also love the mountains and the ocean. I think there is a person who might not really care about either. They’re ambivalent because maybe they don’t value their environment as much. Maybe they’re a Twitch streamer and spend ten hours a day staring at a computer screen or just haven’t given it enough thought.
Regardless, I think more people should adopt this view that environment plays a big role in who we become because if not, then we’re all just going to spend more time staring at screens. This is going to be reality because technology is enabling the digital world to become increasingly more entertaining while the real world is moving a lot slower. Fast forward twenty years and I think society will unfortunately resemble WALL-E a lot more with the majority of time spent sitting, starting at a screen, and getting fat. Imagine a life today that involves staring at a computer screen for 8+ hours a day and eating all of your Doordash’d meals behind a desk without much free time. It doesn’t take much imagination to go from that to a dystopian future where you spend all your time in VR and get sustenance from an IV drip tube that supplies all the calories, water, minerals, and vitamins that you need for your physical body to survive. That’s scary to me.
Relatedly, I think about Reality Privilege a lot. It’s the idea that eventually, the majority of people will basically live online (Ready Player One vibes) because their digital life will be far more enjoyable, richer, fulfilling than their offline life. It’s an outcome driven by two forces heading in opposite directions. On one hand, the best places to live in the world are getting more expensive and exclusive. These desirable places with beaches, mountains, forests, lakes, etc will only become more unaffordable. Real life is fun when you can walk outside surrounded by beautiful nature or play in the ocean. It becomes less fun when the only restaurants in your small town are McDonald’s and Wendy’s and you can’t even get fresh produce at your grocery store besides bananas (food deserts are a real problem). In the digital space, video games are getting exponentially more fun, immersive, and addicting. Atari invented Pong in 1972 and that doesn’t seem that fun to real life things, but nowadays kids are literally spending all of their free time playing Fortnite which might actually be more fun than real life. Movies and TV shows are cranking out content and never running out of ideas. Reality Privilege is a dystopian concept because if and when it happens, we’ll continue to see rich people skiing in cozy mountain towns or watching the sunset by the ocean, but the rest of us will be living in our dilapidated homes staring at screens all day in a sprawling town that’s been hit badly by climate change.
How does choosing where you live tie in with Reality Privilege? I rationalize it by thinking about this ability to choose where I live is a huge privilege. Not everyone has the ability to move and even if they can move, there’s often financial barriers among others that limit their options. Soon, a lot of people are going to find their online life more appealing than doing stuff in the real world. It’s already happening as time spent on TikTok exceeds 90 minutes per day. Having experienced both extremes of the spectrum with how dope the real world stuff is (skiing, hiking, surfing), but also the other end of playing the video game League of Legends for six hours a day back in high school, I can confidently say that the real world is a lot more fun, but also healthier than the digital world. The problem is that the great joys of the real world are not as accessible as it should be. If you have the privilege to choose, you shouldn’t waste it.
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