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 interrogation.

When people learn that I’ve been traveling full-time since my wife and I split up, they tend to fall into two camps.

  • People who are excited for me seem confused that I haven’t flown to an ‘exotic’ destination to have some sort of Eat, Pray, Love transformation. Or I should at least be on a beach.
  • Everyone else reacts as if I have just confessed that I am lost. And broke. And unemployed. This is when I get a lot of well-meaning unsolicited advice. I cannot tell you how many people have suggested I think about becoming an Uber driver, followed by the gentle suggestion that ‘no matter how far you go, you can’t escape yourself.’


When most people say they love to travel, they mean they love being on vacation. When people talk about traveling full-time, they usually mean they want to blow up their life and walk away. People want to figure out how to make millions while working four hours a week on the beach and sipping cocktails, but that’s not what I’m doing.

I suppose that with the popular rhetoric about quitting your job to travel, people can’t wrap their heads around the idea that I didn’t quit a job I hated, I’m not running away from something, and I’m not lost.

It’s weird that so many people’s idea of small talk comes down to questioning the life choices of someone they just met, but it does give me something to ponder on long train rides.

Stepping back into an old me

When you’re in a serious relationship, it’s normal that certain aspects of your personality are amplified and others are minimized. Shared interests come to the forefront. You discover new things together. Your priorities shift.

I got to spend time with a lot of old friends this year. It was wonderful to catch up, but it was more than that. People who I’d once seen every day still kind of view me through the lens of who I was in high school or college or when we lived together in our 20s. It was like I was rediscovering past versions of myself.

We joked about things I hadn’t thought about in years, reminisced about long-forgotten obsessions, and philosophized about dusty melodrama.

Major life shifts shake up your identity. Remembering who I had been at various points in my life was helpful in thinking about who I am now — and who I want to be in the future.

You shouldn’t have to have a major life change to think about who you want to be, though. That’s something we should always be doing.

Remembering the good times

I traveled a lot before I got married and it’s hardly as if my ex and I didn’t travel. We both work remotely and traveled for months every year. We hadn’t been home for more than a few weeks in the six months before we split. I could make the case that my shift to traveling full-time has more to do with my poor cat dying (RIP) than the demise of my marriage.

This year brought me back to several cities I’d explored with my ex. It was nice to have a reason to reminisce about happier times. During the breakup I’d spent a lot of time focusing on what went wrong in our relationship, so it was refreshing to (sometimes literally) retrace our steps and remember the beginning.

It was also nice to make new memories in old places and remember just how much I love traveling by myself.

The joys of solo travel

As much as it’s great to have a good travel partner, solo travel has its own particular joys. I find that it’s much easier meeting locals and other travelers when I’m on my own. It’s incredible how much the people I meet color my experience.

My ex and I had done a lot of home swapping and had some great experiences. However, I’d really missed the magic of CouchSurfing. Staying in a home makes traveling much more comfortable, but it’s actually staying with people that make for life changing experiences.

Traveling alone means that I’m on my own when things go wrong. It’s been nice to remember just how much I can handle on my own. I’m also amazed and grateful to the gracious strangers who seem to always appear right when I need a hand.

Breaking all of my habits

Every few weeks (or sometimes days!) I’m in a different house. Pet sitting is great for helping ensure I live a normal life while I travel, but it’s not my normal life. There’s always new pets, a new kitchen, different responsibilities, a different neighborhood. It’s certainly been a good opportunity to break some bad habits.

Just like I thought I was a picky eater until I spent a year CouchSurfing, I thought I was pretty neurotic about my housing until this year. My ex and I both had similar taste and kept a home that was basically ready for a photoshoot at any moment. Not every home I’ve stayed in has been spotlessly clean, impeccably decorated, or just so. And it really hasn’t bothered me in the slightest. Although I will admit sometimes I go to sweep up some dust and suddenly I’m washing the baseboards.

I kept expecting to get tired of house sitting. So many apartment renovations in a row had me convinced that I cared a lot about having a home that was mine. Instead, I find myself enamored with possibilities every time a new batch of house sitting listings pops into my email. 

House sitting feels a bit like stepping into someone else’s life. It’s a step past imagining what my life would be like if I moved to a different city or got a house with a yard or got a farm, because there I am actually doing those things. Sure, spending a few weeks in a place isn’t quite the same as moving there, but it’s the closest you can get to the experience without doing it for real.

Wherever you go, there you are

You don’t need to leave home to discover who you are, but sometimes it can speed up the process. We’re all different people in different situations. Watching how I behave in a bunch of different scenarios in a short span of time was really revealing.

I slip back into childish behaviors when I’m with my family. Some friends bring out certain aspects of my personality. I might bring up the same obscure topic with one friend repeatedly for no obvious reason. Sometimes when I’m staying with someone I immediately act like I live there, while other times I tiptoe around like a guest.

Paying attention to how much my behavior shifts according to the context has been really interesting. The discoveries aren’t usually flattering, but it’s better to realize these things about myself.

Just like you don’t need to travel to learn about yourself, you should always be striving to be the best version of yourself. No breakup or passport required.

You don’t need to go far to experience cultural differences

I wanted to stay close to my family and friends this year, but sticking around North America hardly means I escaped encountering cultural differences. I like to imagine that spending so much time in New York and Toronto means I experience a lot of the world, but I’m still in a bubble, even if its a fairly large one as bubbles go.

While I didn’t have to worry about learning a new language (or making do with hand gestures and Google Translate), I still found myself in worlds that felt incredibly foreign. I stayed in a Christian commune. I explored a bit of the American south. I tried to wrap my head around Quebec. I was hosted by CouchSurfers from around the world. I got to know other people’s families. I shared multiple meals with Trump supporters.

When I was texting friends about some of my more challenging experiences, they didn’t seem to understand why I kept staying with people I didn’t have anything in common with. But that’s the whole point! I wanted to push myself out of my comfort zone and CouchSurfing made that easy. All of my hosts were wonderful and I’m grateful they were willing to welcome me into their homes. Even when we didn’t have anything in common. Especially when we didn’t have anything in common.

When the news is so awful, it’s nice to have real reminders that there’s no “other side,” just people who are probably really lovely to get to know.

Seeing things differently doesn’t always mean you disagree. There are often many right answers and correct ways to do things. There were a lot of opportunities for me to remember that in my travels.

Practicing my elevator pitch

As someone with a masters in communications, I should really be better at introducing myself and explaining what the heck I’m doing with my life.

While I’m not one of those people who makes up stories when they’re out with strangers, it’s been really interesting to see how people react differently to the ways I introduce myself. When you’re distilling your life down into an introduction there are a virtually endless ways to do it.

It’s so easy to take your own work for granted. Have you ever updated your resume and ended up feeling impressed with yourself? Sometimes my job feels like I reply to unsolicited emails and manage some Facebook groups, but then someone asks what I do and I remember that, oh yeah, I run an international nonprofit. And I wrote two books this year on topics that make other people’s brains explode.

I feel like an underachiever because I haven’t made a medical breakthrough, sold a startup for millions of dollars, written a bestseller, won a Fulbright, or made it to the top of a conglomerate. I’m not in a band touring around the world. I don’t even have a private jet.

There was one night I was proud of myself for the awesome nachos I’d made and then one of my high school classmates was in the news for leading a march on Washington. My nachos were really delicious, even if they didn’t save lives.

Meeting people from all walks of life has been a reminder that my former classmates and friends are outliers.

And, even without a private jet, I can’t think of anything that’s missing from my life.

Seeing my reflection

Sometimes, no matter what you say, people will hear what they’re expecting to hear. When most people travel they’re on vacation. It’s a break from real life. Pair that with the fact that people assume I’m a decade younger than I am (because who backpacks in their mid-30s?) and you end up with the assumption that my life is in a holding pattern.

I can tell people that I work as a consultant and they hear I’m unemployed and maybe pick up jobs on Taskrabbit. Plus, a certain number of people assume that pet sitting is my job. I’ve had more than one person ask if my parents are disappointed. Seriously!

I joked with a host about how the sailboat I’d been staying on doesn’t have AC so I’d been loitering at the yacht club to stay cool. Humblebrag much? A few minutes later she commented to her husband about how tough it must be for me to have nowhere to go.

At first it irked me to have people assume I’m a broke backpacker. But then I realized they always pick up the tab. And that they’re usually the same people who are unhappy with their own lives. They aren’t criticizing me so much as projecting their own fears onto me. If they didn’t have a giant house would people look down on them? If they chose a job that was meaningful, would they ever be able to retire? If they went away for a few months, would their friends forget about them? If they didn’t have kids, wouldn’t they die alone and unfulfilled?

Weird comments are usually followed by someone sharing how they feel trapped in their jobs and fear they’ll never pay off their mortgage. They see me living out of my backpack and assume I live a life unencumbered by paperwork, annoying clients, and bills. If only!

They can’t imagine a world that involves both traveling and having a career, so they discount anything contradicting that storyline.

And then they ask me for tips on how to set up a website.

On meandering

It feels like more than a year has passed since my wife and I split up. I’ve done so many things, my life with her already feels like another lifetime.

Somehow the more I travel, the fewer travel stories I have to tell. Is it because traveling with a cell phone reduces the serendipity of my first backpacking experience? Is it because I’m old enough to know that things that are new to me are old hat to everyone else? Is it because having an open-ended trip and not paying for accommodation means I can slow down my pace?

It might just be that I’m not really looking for an adventure. I’ve been to more than my share of dance parties and have had a lifetime’s worth of fancy cocktails, but more and more I find myself stopping what I’m doing to watch the sun set or staying up late talking with an old friend. Last summer I was a frenetic burst of pent up social energy. This summer I’m paying more attention to what matters to me.

Sure, I’m just meandering. I don’t have a route planned out, I’m lining up house sits and visits to friends and family. I’m easily swayed by an interesting house or a cute puppy. But who says I need a destination? No matter where I go, there I am.