How much does it cost to house sit?

How much does it cost to house sit?

So, you’re curious about house sitting. The idea of staying in other people’s homes for free is pretty enticing…but what’s the catch? Even though no money changes hands, house sitting isn’t entirely free. Here are the actual costs that...
Do you love where you live?

Do you love where you live?

You want to know what it’s really like to live in a city, but hardly anyone has lived in enough places to compare. 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.

Traveling after a breakup and other stereotypes

Traveling after a breakup and other stereotypes

I’ve learned a lot this year about stereotypes. The moment I mention that my wife and I are separated, the conversation is effectively over. As soon as I mention an ex, every word out of my mouth is viewed from the lens of some chick flick version of a breakup....
The ultimate one-step guide to saving money on flights

The ultimate one-step guide to saving money on flights

The internet is awash in advice on finding cheapest flights. Is it about when you book? Clearing your cache? Using a VPN? Don’t forget about all the sites you should check for the best deal. And tracking prices. And the flights that transfer in your destination...
5 inspiring stories of real estate success

5 inspiring stories of real estate success

Buying a home empowers you to take control of your life, increases your self-worth, and best of all, gives you options to diversify your financial life. While it might feel overwhelming or out of reach, these women show that against certain odds or challenges, home...
The ultimate one-step guide to saving money on hotels

The ultimate one-step guide to saving money on hotels

This tip is simple and it can save you hundreds — or even thousands — of dollars.

Hotels can quickly eat away at your travel budget. A decent hotel in a city can easily be $300 a night. Even AirBnB prices climb pretty high, especially once you add in all the fees. Sure, you can save money by picking a cheap motel (at your own risk) or staying at a hotel outside of town (and dealing with traffic and parking).

There’s a way to save money on hotels without worrying about hacking your credit card points or joining every loyalty program possible or buying through sketchy third party sites. 

No, I’m not lost

No, I’m not lost

I was entirely caught off guard by the way people react to hearing about my travels. When I was backpacking in my early 20s or when I was on extended trips, people were happy to hear about my adventures. This time, meeting people can sometimes feel a bit like an...
How to create a house guide for your pet sitter

How to create a house guide for your pet sitter

It can be difficult to figure out what to include in a house guide for your first pet sitter. You want to make sure everything that might need to be in there is included, but you don’t want to overwhelm anyone! If you’re looking for a pet sitter, I highly...
United Shades of America focuses on Canada

United Shades of America focuses on Canada

Anthony Bourdain and Parts Unknown isn’t the only Sunday night show on CNN that features a Canada-centric episode. W. Kamau Bell and his United Shades of America show took a look at Canada on Sunday night. For those unfamiliar with the show, Bell travels to...
7 things Americans get wrong about moving to Canada

7 things Americans get wrong about moving to Canada

Everyone’s talking about moving to Canada, but most of the tips on immigration haven’t gotten past moose and poutine. I’m here to clear up some common misconceptions about moving to Canada. Two years ago, my wife and I decided to move to Canada. Neither of us had a...
Stop overpaying for flights

Stop overpaying for flights

The key to traveling for less is being flexible about your dates or destination. The more flexible you are, the better you’re able to take advantage of deals! This may seem like you’re compromising, but that shouldn’t be the case. There are lots of...
Gifts a traveler actually wants

Gifts a traveler actually wants

Gifts travelers actually want I know my friends and family mean well, but I usually don’t know what to do with the gifts they get me. I live out of a backpack, so that space is pretty sacred — only the absolutely essential items make it in there.  ...
Chicago’s North Side: A digital nomad’s guide

Chicago’s North Side: A digital nomad’s guide

Chicago is one of those cities I’ve been to dozens of time, but didn’t feel like I really knew at all until this past trip. I’d been there for conferences and road trips, but each time it was too short to get a real feel for the city. I spent two...
Halifax: A digital nomad’s guide

Halifax: A digital nomad’s guide

Sometimes I wonder if I could love living in a small city. A smaller, less expensive city. Where I would know my neighbors. Be able to have a meaningful impact in local politics. Buy a building with a storefront downstairs, live my main street retirement dreams. Maybe...
How to make friends in a new city

How to make friends in a new city

Moving to a new city can be pretty intimidating. Most people made friends in school, when you practically had to go out of your way to not make some BFFs. Unfortunately, it’s rare for people to actually know how to make friends. It just happens, right? Even if you...
Birmingham, Alabama: A digital nomad guide

Birmingham, Alabama: A digital nomad guide

None of my friends could quite understand why I decided to go to Birmingham, Alabama. The only thing we remembered about Birmingham from school was the civil rights movement — which hardly makes it sound like a great place for a digital nomad to land. Birmingham...
How to travel for months (or years) without going broke

How to travel for months (or years) without going broke

Here it is: the obligatory how I afford to travel post. People think traveling is expensive, but it doesn’t have to be. Most of the time I spend the same amount of money each month when I’m on the road as I do at home — or less. The obvious way to save money...
The story of Toronto’s St. James Town

The story of Toronto’s St. James Town

When we first moved to Toronto, I quickly became fascinated by St. James Town. While most of Toronto’s highrises are brand new, these ones hailed from an earlier age. Clearly one that didn’t catch on. The low prices and easy subway access were pretty tempting, but...
My time with Jesus People, USA

My time with Jesus People, USA

My experience with JPUSA (Juhpoozah) started with a search on CouchSurfing. Jane had so many references, wrote a bunch of books, has gone on epic bike trips, and lives in an intentional community. Obviously, I wanted to stay with her.  Sure, I may be traveling in my...
Retirement planning for digital nomads

Retirement planning for digital nomads

There are lots of articles out there telling you how to cut costs and save money. That’s great, but where do you invest that money for retirement when you’re a digital nomad? The remote worker with a pension plan — or even a 401k — is few and far between....
Buying a condo in Canada

Buying a condo in Canada

You hear it all the time: Toronto is way too expensive to buy anything! In fact, houses downtown are over a million dollars! What’s wrong with this statement? The idea that you need to live in a house right downtown. No one talks about buying houses in Manhattan or...
I went personal item only for 6 weeks

I went personal item only for 6 weeks

and survived to tell the tale When I booked a United Basic Economy ticket there was a little popup message warning me that my ticket tier was personal-item only. Even though a carry-on was a tiny bit more money (was it $5? it was something insignificant) something...
Renting an apartment in Toronto

Renting an apartment in Toronto

You’re finally moving up! Here’s how to find your new home in Toronto, from where to look for listings to what to expect in your lease. If you’re coming from a small town, renting in Toronto is probably going to seem really unpleasant. If you’re coming...
How to find a sublet in New York City

How to find a sublet in New York City

In an era before AirBnB I was a habitual subletter. I managed to live in New York for seven years without ever signing a lease, hopping from one sublet to another and crashing with friends (or my parents) in-between. Finding a sublet in New York is more difficult than...
Setting up your apartment in Canada

Setting up your apartment in Canada

Once you’ve signed a lease or bought a condo, it’s time to turn your empty place into a home. Before you move in, you’ll need light, heat, water, internet, and furniture.   How to move to Canada Utilities Insurance Furnishings Utilities Unless you’re okay with...
9 reasons to love home swapping

9 reasons to love home swapping

I spent five months traveling in 2017 and am set for at least another five months on the road in 2018. How do I manage without a trust fund? A mix of pet sitting, home exchanges, and couchsurfing. It’s more than just making travel affordable, though. Traveling...
Toronto neighborhood guide

Toronto neighborhood guide

Neighborhoods of Toronto The neighborhood you live in has a huge impact on how you experience the city. Before you rent your first apartment or buy a condo, you want to make sure you’re choosing a place that fits with your lifestyle. Toronto is a big city with...
Managing birth control while traveling

Managing birth control while traveling

When people talk about getting ready for a trip, they rarely talk about birth control. If you plan on having the kinds of sex that can result in pregnancy and want to use some sort of contraceptive besides condoms, it can take some planning ahead of time. IUD The...
Looking back at 2017, looking forward to 2018

Looking back at 2017, looking forward to 2018

Every year seems to come with big changes and 2017 was no exception. Casey and I started the year by renovating the kitchen in our condo. As soon as we finished, we found pet sitters for our two cats and left for Europe. We didn’t exactly retrace the route of my...