Sandy's Guide to a New City

September 19, 2018
Confidence: likely

So I’ve been in Ottawa for about a month now. Without a doubt, it’s the best place I’ve ever lived. While I’m sure some of that is Ottawa’s fault—after all, it is the best place to live in Canada—more important has been my attitude towards the move.

At this point I’m a little bit of a connoisseur of jumping into cities and getting set up quick. After all, this is my 19th move in eight years (shock! horror! dismay!) That’s not to say I’m an expert by any means, but I definitely seem to be getting better at it.

As it happens, home is where your people are, and so no surprise, it’s pretty important to hit the ground running on that front. Here are the things I’ve been consciously keeping in mind.

1: Who Do You Want to Be?

Moving to a new city where you don’t know anybody is strangely exciting. It’s a chance to reinvent your image, since after all, nobody knows any better.

Because people know similar people, there’s a huge founder effect to be wary of. Your first few friends in a new city are going to snowball and introduce you to people like them. Which is to say that you’re probably going to end up in a filter-bubble of people similar to the first people you start hanging out with. Assume your social circle in six months will be full of people like the ones you hang out with in your first month.

All this goes to say that you shouldn’t just spend time with the first people you meet, if you’re not genuinely excited about them. Or even if you are, but they cluster along personality lines that you don’t necessarily want to foster in yourself.

I’ve made this mistake in the past—especially in Denver. I made some really great first friends there, but they were not particularly good at meeting new people. As a result, they didn’t introduce me to anyone who could introduce me to anyone, and my social life stagnated.

So! Make a list of qualities that you really admire in people, and then strive to meet people who embody those. It’s hard to overstate just how important this is. The first few friends you make will drastically shape life in your new city, so choose wisely.

2: Location Location Location


I said it once I’ll say it six times. Location, my dudes, is of key-importance. The goal here is to be central to a city’s action. It doesn’t really matter what kind of action, so long as there’s exciting things happening within walking distance of you.

You don’t need to necessarily live in this hella-central location long-term, but it’s a good place to be for your first couple months.

The idea is to make it so laughably easy to get out and do things that you really don’t have any excuses not to. If you’re anything like me, your rationalization process goes something like this:

  • “There’s this cool event happening tonight that I want to go to!”
  • “But I don’t know anyone there and it’s far away”
  • “Do I REALLY want to go to this?”
  • “Oh hey, look, there’s a new season of Narcos on Netflix!”

This is a dangerous spiral to fall into. Even though I knew it was bullshit rationalization, the activation energy of taking public transit for a bunch of time to go to a thing I wasn’t convinced I’d like was too damn high.

Instead, consider what happens when this thing is happening literally down the street.

  • “There’s this cool event happening tonight that I want to go to!”
  • “But I don’t know anyone there. Maybe I should just stay in.”
  • “Well fuck it’s only a block away. I’m not really THAT lazy am I?”
  • “OK fuck it I’ll go but I’m not going to have any fun”
  • ???
  • “Wow what a great time I’m so happy I went out my life is awesome great work Sandy for suggesting I live somewhere central.”

3: Always Say Yes

I have a “secret” rule whenever I move somewhere new. For my first six months there, I am only allowed to say yes to invites. It’s my one-hundred-percent-yes policy. Satisfaction guaranteed.

Part of being somewhere new is opening yourself up to the microculture of your new place. Cities have their own vibe and their own things that their denizens consider important. In my experience, the only real way to key-in on these things is to just jump into the deep end and see what happens.

It’s also a great first impression to make. Not only are you going to get out and do cool things outside of your comfort zone, but people are going to be genuinely excited about you. If they feel like they can reliably count on you to go do weird things with them, you’re going to get invited to a lot of weird things—and as a result, you’re going to make closer and faster friends.

Obviously sometimes you have to say no, due to scheduling conflicts or exhaustion or what-have-you. In these circumstances I really harp on how sorry I am to have to miss the thing, and I try my best to follow up with that person within the same week to get up to something similar. It doesn’t always work, but if your enthusiasm is genuine, people will take notice.

4: Be Vocal

You’re new in town! That’s super fucking cool.

Did you know that most people have relatively boring lives? Not to pass any judgment here, but it’s a thing you tend to notice when you spend a lot of your life traveling. Even if you’ve spent the last six months gallivanting through sixteen different countries, been through four relationships and gone skinny-dipping in the Baltic ocean, you’ll be surprised to realize just how normal things are when you get back.

Getting back is always weird. Nothing has really changed. The people you know are for the most part still in the same jobs, doing the same hobbies, in the same relationships, and complaining about the same things they always have been and always will be.

Stability is nice, but excitement is great too! And being new in town puts you in a uniquely exciting position.

Keep this in mind as you go about meeting people in your new city. Be loud and proud about being new! Most places are sleepy enough that you’ll be surprised at how popular you’ll be as someone new in town.

5: Take the Initiative

Just because you don’t know a lot of people doesn’t mean you need to be passive about getting up to things. Start doing things, and shamelessly invite people to come along with you. More often than not they’ll say no, but that’s kind of a good thing. The best relationships are those in which the people involved make one another a priority.

By aggressively inviting people to spend time with you, you’re effectively filtering for the ones who want to. And those are the people you really want to be friends with.

You should also look around for existing groups to join. Branch out. Get into things you haven’t done since high-school, but liked back then. Be strategic about the groups you join—the goal is not in-and-of-itself to join these groups, but to diversify the people you know. When faced with time constraints, choose the activities that are going to make people scratch their heads and say “wow, I never would have guessed you did THAT too!”

A corollary to all of this taking the initiative stuff is that you’re going to be a busy beaver for a little while. Aim to be out five+ nights a week, doing diverse things with diverse people. I’m naturally quite an extrovert, but my god is this exhausting.

It’s worth it though. You can slow down when you’ve got a good map of the territory. When you’re still a fresh-eyed young buck in a new place, you’ve got enthusiasm and energy on your side, so take advantage of it. It’s only going to get harder the longer you wait, and so live by the eternal motto “I can sleep when I’m dead.”

At least for a month or so. Sleeping is pretty great too.

6: Be Punctual about Following Up

Most people I know express a bit of a lament: “it’s hard to make friends as an adult.” Until recently, I’d always agreed with this sentiment. As children it was easy, and in university the shared context went the distance. But as adults it seems like too often the only option is alcohol. Which sorta works, but it seems to optimize for lots of drinking.

If there’s one great piece of advice I’ve gotten in my life it’s that I don’t look very good in green.

But if there’s two great pieces of advice I’ve gotten, it’s that I don’t look very good in green, AND to always follow-up with people you met. My friend Ellen put it like this:

The secret to making friends is to see someone twice in one week. Humans can’t resist being friends if they see one another that frequently.

At the time I thought she was just being glib, but wow. Making friends as an adult really is this easy. It sounds too good to be true, but give it a try. If you run into someone you like, invite them to hang out again sometime in the next week.

It’s like MAGIC.

So that’s what I’ve got. Six RADICAL TIPS for diving into a new city. Of course, I’m only one data-point, but my god do these things seem to work. What’s even cooler is that most of these don’t actually require being new in town. If you feel like you could just a little shake-up in your life but aren’t keen to leave town to make it happen, try adopting some of these principles and see what happens.

I bet you’ll be pleasantly surprised, and have your toes tickled in the process.