I’ve been house sitting for a year now.

When I left Toronto at the end of last November I didn’t expect to be gone for more than a few months. I was going to house sit for two friends and then visit my parents.

But then one of my very first CouchSurfing hosts posted something on Facebook about Trusted House Sitters. I’d heard of the site, but I was skeptical. I’d signed up for another house sitting site a year or two before and never got any responses. I sent her a message and with her encouragement I signed up and set up my profile.

She’d warned me that it might be hard to get desirable sits right before I had any references, so I applied to several sits. I was a little surprised when I was offered a couple and had to choose between them.

I’d made my way from Toronto to Cape Breton, so it seemed obvious that my next trip should be from Toronto to Victoria. That’s not how it worked out. I applied to a bunch of sits along the route, but didn’t end up getting sits that came anywhere close to lining up in a logical route to make my way West.

I did find great sits in Chicago, Boston, and New York for January and February. Then I found a sit in Birmingham, Alabama for May, so I extended my travels.

I was planning on going back to Toronto by June, but then I saw the chance to stay with a pony. Okay, so technically Belinda is a miniature horse, but still. That just meant I got to make a lot of groan-worthy comment about how I was horsesitting.

I kept waiting for the part where I got sick of house sitting, but it hasn’t happened yet. I also haven’t made it any farther west than Chicago.

I might not have made it to the Pacific, but I have been keeping myself entertained when I haven’t been working at my “real” job:


Over the past few years I’ve had a break from the judgement you face when you’re doing something unconventional. I’ve been traveling a lot and working remotely for a while now, so I didn’t realize how being married and having an apartment was saving me from all sorts of weird comments.

Now that I’m single and don’t have a home base, I’m regularly am asked to justify my life choices. It’s so weird to have people act like I’m irresponsible and unemployed. My automatic reaction is to try to explain that I have a job, a home, and a family, but I learned pretty quickly that it’s not about facts.

The weirdness has given me fascinating peeks into what people value and their ideas about societal expectations — and why my life choices cause them distress. Are people happy with where they live? Why would someone with a college degree and lots of opportunities still spend 40 hours a week doing a job they hate? Do they feel like their family is holding them back? Why would someone live in a giant expensive house if they’re worried about money? Do people want to travel as much as they say they do? Did they realize these were choices that they made? Why are they so afraid of strangers? Why do strangers get so upset that I don’t have children?

It makes me a little sad to see how little value some people see in things that we don’t pay money for. The things that make CouchSurfing and house sitting magical — the things that make life magical — can’t be bought.

The act of paying for something changes things. This is something I’ve spent a lot of time thinking about, especially since the complicated emotions involved with monetizing the invaluable connects so deeply with my work with The Caregiver Space. The best book I’ve found on the topic so far is Debt.

While I don’t worry about dying alone and childless, I do think about how my travels impact my relationships and my community. My destinations are heavily influenced by people who are important to me and I’ve embraced spending time in both New York and Toronto even though I’m “nomadic.”

I feel a little disingenuous claiming to be a digital nomad when I’m not in Bali. I spend a lot of time in Toronto for someone who’s theoretically traveling full-time! But in the classical sense of the term, nomads were people who lacked a fixed home who rotated through the same areas.

Semantics aside, I like spending time in Toronto and New York. While traveling has introduced me to so many amazing people, most of my community is in New York and Toronto. I love meeting new people and have met so many incredible people this past year, but there’s nothing quite like visiting old friends.

House sitting makes dividing my time between two cities and new places much easier, since so many of the homeowners I’ve sat for have invited me back. I’m also lucky enough to have friends and family whose doors are always open to me between sits.

I’ve slept in quite a number of places in the last year, but the place I spent the most nights is the Blue Oyster, Sean’s sailboat. It was amazing to get the chance to spend so much time on the water and I’m so appreciative of his generosity. Now that he’s sailed south, I’m excited to live vicariously through his adventures in the Caribbean.

Perhaps I should be heading south, but instead I just pulled out my snow boots and bought a new rainproof jacket! We’ll see what the next year brings.