As far as I can tell, there’s no such thing as the perfect city to live in. Maybe San Diego, but even then, probably not.
Every city has its flaws and trade-offs. Every city has its relative draw and superior foods. And like finding the right partner or pet, there’s not much joy in treating your choice of city like a pure optimization problem.
But still, it doesn’t hurt to be thoughtful about it to make sure your brain is reasonably aligned with your gut and heart.
My partner and I have the good fortune of being geographically flexible, so I’ve thought about this question a lot.
In fact, I find that debating the merits of each city is one of the most common conversation topics in your late 20s. Choice really does impose the burden of agonizing.
Here are the main factors I think about when evaluating which city to live in and where to raise my future children:
- Proximity to family
- Proximity to friends/ability to create new friends
- Weather/nature
- Sense of belonging
- Opportunity for career advancement
Proximity to Family
I think I have a slightly above median relationship with my family for an Asian second generation child. I love, like, and admire my family!
And I think seeing my parents on average 1-2 per month for the rest of my life is an appropriate and good goal to have.
My parents and brother are the only bonds in life I can’t re-forge and I try not to take that fact lightly. (Yes, that one WaitButWhy graph has lived rent-free in my mind for about a decade.)
My family comfortably lives in Toronto and as such, the lowest-friction path for my life is probably there.
I have indeed thought through the logistics of moving my parents with me to a new city, but things like health insurance, visas, and breaking their existing social circles make it complicated.
The primary regret of most of my friends who moved out of Toronto is that they don’t get to see their family very often. It sucks.
Most Viable Cities: Toronto
Proximity to Friends/Ability to Create New Friends
I treasure my friends. And I feel like the “vibe” I have (self-aware, ambitious, nerdy, yet kind of emotionally soft) is uncommon enough that it’s generally hard to make good friends.
I actually find it very hard to make good friends. Without a common interest or activity, it feels almost impossible to get out of the initial phases of friendship.
By my rough estimate, you need like 50 solid hours and 3 group trips together to start feeling really comfortable with someone.
I’m also reaching the age where most people don’t want to make new friends either. They have their significant others and deeply entrenched cliques, in which I’d have to play years of catch-up to understand all of the social group lore.
The math to try and make a new good friend vs. invest into your existing friendships is pretty dicey.
As I think about this factor, it primarily comes down to where my existing close friends are or if I believe a city has enough like-minded people where I’d settle in eventually.
Most Viable Cities (based on where my existing close friends are): Toronto, New York City, San Francisco, San Diego
Theoretically Viable Cities: Los Angeles, Vancouver, London, Austin, probably a few others
Weather/Nature
For much of my life, I assumed that dealing with winter was a foregone conclusion and accepted it as a facet of my world. I now realize that is no longer the case.
I also recognize how much intrinsic happiness I receive from being in nature. Easily accessing a beach, a nice sunset, or the mountains deservedly makes your city much more desirable to live in.
Humans enjoy nice sunsets and to deprive ourselves of this innate desire is beginning to feel wrong.
It’s not like winter is unilaterally awful. It’s nice to have snow for the 2 weeks around Christmas. And from a tryhard perspective, not being able to go outside does increase your volume of work output. But in general, I’m much happier when the weather is good.
I hate to say it, but if the weather was consistently good in Toronto, it would be such an obvious no-brainer to just stay. I can deal with like 2 or 3 months of winter, but there comes a point where I just start complaining everyday and my energy sours.
Realistically, I think Toronto has acceptable/good weather between May and October, which is 6 months. That leaves 6 months of relative mediocrity.
Most Viable Cities: San Diego, Los Angeles, San Francisco
Theoretically Viable Cities: Honolulu, Lisbon, Sydney, etc. (a few others I realistically wouldn’t consider)
Opportunity for Career Advancement
I generally don’t like making geographic sacrifices for my career; it’s always felt a bit joyless to me.
For me, it’s really more of a threshold problem – I don’t want the city I’m in to actively interfere with my career options or my progress.
On the artistic front, I imagine that my music “career” would improve dramatically if I were living in Los Angeles. But there are so many musicians that succeed outside of LA that I’m not particularly fussed about this.
On the entrepreneurship front, I would probably benefit from a city with a solid “entrepreneurship” or “building” culture. Realistically, Toronto doesn’t hinder my building of Peak Frameworks, but it definitely doesn’t motivate me either.
Frankly, it’s hard finding other solo entrepreneurs at a similar scale, situation, and goal set as me. Of course there are other small business owners, but there are very few that are also lifestyle oriented and work digitally.
In my experience, it’s much easier to find driven and ambitious people in New York, San Francisco, Los Angeles vs. Toronto. There are pros and cons to this, but the brain drain from Toronto is very real.
Most Viable Cities: New York City, San Francisco, Los Angeles, London
Acceptable Cities: Toronto, San Diego, Chicago, pretty much any other “Tier 2” City
Sense of Belonging
I’m a whitewashed Asian Canadian and honestly, I think there is a limited number of cities in the world in which I’m fully comfortable “being myself”.
Even in the absence of blatant racism, it means a lot to have your culture be recognized and to be adequately represented in the community you live in.
It is a pretty funny and narrow needle to thread. On the one hand, I probably wouldn’t be comfortable in most Asian countries because my media preferences and cultural sensitivities are incredibly Western. But I also can’t comfortably live in a lot of Western cities just because I’m… Asian.
In this way, Toronto has definitely spoiled me. Multicultural friend groups are the beautiful norm in Toronto. My high school friend group borders on immigration brochure levels of diversity. Toronto elevates and embraces different cultures in a manner that few other cities even try to do.
“Panethnic groups in the City of Toronto” per the most recent census
In my experience, even if there are a lot of minorities in certain U.S. cities, racial groups feel comparatively more segregated.
As an aside, there’s also a huge disparity in the quality of Asian food around the world. I probably only eat Asian food like ~30% of the time, but the absence of good Asian food options is also a big quality of life deterrent.
Most Viable Cities: Toronto, Honolulu, Vancouver, San Francisco, New York City
Acceptable Cities: San Diego, Chicago, London, pretty much any other “Tier 2” city
Conclusion
I don’t have to decide on a permanent city for a couple of years.
My plan is still to do Toronto in the Spring/Summer and then primarily travel when it gets cold for the next few years. But I think that snowbird lifestyle becomes untenable when my (future children) are in the 4-18 years old range.
And honestly as I wrote this out, it became more obvious to me that this is primarily a family vs. weather decision. And it’s really just a Toronto vs. California question too.
Based on my criteria, I think San Diego, Los Angeles, and sort of San Francisco would all work. I will say that my most ideologically similar close Asian friends have moved to California.
So really: am I willing to trade off seeing my family 15-20 (?) times per year in exchange for 6 more months of good weather? Or am I willing to go through the challenge and risk of moving my parents with me?
Yeah, I don’t know – I’m glad I have a bit more time to decide.
