Since moving to Toronto I have had this conversation approximately a thousand times:

Me: I just moved here.

Them: Oh? That’s great. Where’d you move from?

Me: Brooklyn.

Them: [Some variation of WTF is wrong with you, but in a passive aggressive Canadian way, followed by them explaining why they love New York for an uncomfortably long amount of time]

It’s not a great small talk experience.

Generally, Canadians are very polite. Except for when they’re telling me that:

• I am an idiot for spending months of my life and thousands of dollars immigrating to Canada
• Canada’s largest city is an overrated, overpriced shithole
• They feel powerless to be a grownup and actively make choices about their life

First I tried to convince Torontonians to appreciate what they have. Canadians did not like that. Then I explained how it’s possible to move from Toronto to New York if that’s what they want to do. There are plenty of countries they could move to.

You might think hockey is Canada’s national past time, but actually it’s complaining. I enjoy kvetching as much as anyone, but I also love creating the life I want.

You get to decide where you live

The thing is, if you don’t like living in the place you’re living, you can do something about that.

Sure, finding a new job and a new place to live and uprooting yourself is a hassle. If that’s the case, you’re making a decision that there are enough things you love about your current home that it’s worth staying.

Sometimes it’s worth it to stay in a place you don’t particularly care for. Making an active decision to stay and make it work is a lot more fun than pretending it’s all out of your control and bleeding out your unhappiness with your life to strangers at networking events.

Perhaps you are ready to make a change, but you don’t know where to go.

How do you pick a new city?

It can be really challenging to choose a new place to live. What would your commute be like? How hard is it to find a job in your industry? Who else lives there? What’s the housing like? Would you be happier there than where you live now?

Most people have only lived in one or two places their whole lives, so it’s not easy for them to compare.

Someone who’s lived in one city will know it like no one else, but they lack the context of knowing what it’s like to live in another city. Moves often come with major life changes. Comparing life in Halifax as a broke college kid to life as a successful professional in Calgary to parenthood in Hamilton isn’t very helpful.

Flying around checking out every city isn’t feasible for most people. Plus, how well can you get to know a place in a few days? I visited dozens of cities around the world before falling in love with Toronto. There were quite a few weekend trips before I was confident enough to put my old place on the market and start planning my move.

How can you be sure you’re making the right choice?

Someone who’s actually lived there…and can compare

It’s rare to find someone who’s lived in multiple cities in a short time, which is where I come in.

As a house sitter, I have the opportunity to actually live in cities around North America. I run errands, hang out at the local spots, and go in to offices for meetings. As a CouchSurfer, I meet locals and get a wide variety of perspectives on each place.

lbh that the world doesn’t need more travel guides. Moving forward, I’ll be providing information you can’t get anywhere else — what it’s really like to live in Toronto, Brooklyn, Manhattan, Boston, Chicago, Kingston, Raleigh, and other places I’ve gotten to (temporarily) call home.