taste testing cities
living somewhere for a little bit makes that place a part of your world
The best thing I've ever done was move to San Francisco completely alone when I was 20. It was a little scary, lonely, and nerve-wracking at first, but it was one of the periods in my life where I experienced the most immense personal growth.
Going there wasn’t a straightforward decision at the time - I had no close friends moving there so I roomed with random strangers from Facebook Marketplace in a tiny room, and the start-up I was interning at was so early we were working out of their friend’s apartment as a makeshift office.
SF was one of the places that felt very far out of reach for me as a Canadian, and a place I’ve always wanted to go to, especially after hearing about it and seeing it on shows like Silicon Valley. But after I went there once for the first time, I found myself coming back three more times in the span of six months - two for weekend events I was invited to, and the third time for another internship. The flight from Toronto to SF didn't feel as far after all, and I never would've gotten the opportunities to come back there if I hadn’t taken the leap to see what it’s like there for myself.
Same with New York - it was a city I’ve always admired, but never got the chance to spend much time in. I ended up squeezing a short VC internship at a growth fund and kind of overloaded my summer, and despite realizing I didn’t love growth VC as much, it still ended up being a win because New York became a second home to me through that experience.
7 weeks of New York living with a stranger pushed me very much out of my comfort zone to meet new people and get acclimated to the tech and creative scene here quickly. Similarly within six months of my time to New York, I found myself returning to New York three more times to support different shenanigans and events, including a women founder’s retreat, the New York Steakhouse, and hosting the Personal Computing Hackathon - all things that I wouldn’t have been able to do if I hadn’t lived there once before.
If you see a place for 2-3 days, that’s window shopping cities. You get to see a lot of the sights, local food and attractions, and inspiration to come back the next time.
Living in a place for at least two months is taste-testing cities, where you experience what it’s actually like to live in a place on a day-to-day basis and build friendships with the people who live there.
Once you’ve done that, gathering friends and bringing communities together in cities becomes much easier. Taste-testing cities is truly an unlock for making a place that seems so far out of reach become a part of your world. You start making friends, discover your favourite cafes and day plans, and find many excuses to come back.
I tweeted this a while ago about imagining yourself as a little node on a graph but each year your worldview expands even more to what's possible as a function of what you learn, the people you meet, and the places you get exposed to. Three years ago I was so afraid to get on a plane alone. Now, I feel like I can take on anything.
some rapid fire tips to make this possible
Of course I wanted to end the article on a more poetic note, but I also wanted to be realistic for those reading this and wondering “so… how can I actually do this?”. I think to myself sometimes that maybe if I knew these tips before and checked out San Francisco when I was in high school maybe I would have been exposed to things a lot earlier, but alas I did not have the financial means, confidence or the knowledge I have now to make it happen.
get an internship! cold email startups (yc work at a startup is a good place to start) and find unique ways to pitch yourself. A 3-4 month internship is a perfect amount of time to really experience a new place, and will make it financially possible to try it. I’m always in the mantra that experiences + growth > material things when saving.
scour for housing on facebook marketplace, discord, and airbnb. I found pretty cheap housing on FB marketplace and facetimed my roommates and landlord to make sure it was legit. Sometimes it’s actually a blessing in disguise to opt for a smaller room because it forces me to go outside and work in public spaces, where I naturally bump into people.
don't be afraid of living with people you don't know. I’m actually really glad that I found cheaper housing in NYC by living with the airbnb host (who I also facetimed beforehand!) instead of getting my own apartment - she ended up being a good friend and showed me a lot of great new york spots. I think everyone should experience a bit of the lower east side charm in their 20s.
take advantage of budget travel opportunities. for all the times I returned to the places again, I used credit card points or cheap airlines to book my flights, or luckily came back for vc sponsored events! For my shorter trips I’m incredibly grateful to have friends host me (thank you Arielle, Jaclyn, Twinkle + Leslie, Rainia + Saleh ❤️)
It goes both ways! My old roommates joked that my room in SF was literally a mini airbnb, because I always had friends either coming from South Bay or elsewhere crash on the weekends. I’ve also housed some friends visiting Socratica at Waterloo.
And now to actually end this off on a poetic note, it couldn't be more fitting to end it off with a quote from Dr. Seuss - oh the places you'll go!
~ Mathu