To Solo Travel Or Not To Solo Travel (When In A Committed Relationship)?

As you might have seen in my last article, I am a former full-time traveler in a relationship with a man in my hometown (Toronto), trying to negotiate the sometimes messy business of traveling long-term (my biggest passion in life) and building my new relationship (which I’m also very, very excited about!).

I’ve just returned from my first extended trip (1.5 months in Iceland and France) since we started dating, which was a big learning experience for both of us, as we had to adjust to having a long distance relationship across multiple time zones. We came up with some strategies that were very successful for us (and could be for you too, if you’re contemplating doing the same) but, now that I’m home and itching to travel again, we’re faced with a new conundrum: when should I go traveling again? Should I stay home to build our relationship or should I go on the trip that I had originally planned, shortly after my return to Toronto?

I’ve lived for the last two years with one goal in mind: creating a life in which I could travel for long periods of time, almost consistently throughout the year. It has been tough; I’ve had to turn down potential clients who aren’t comfortable with me working from afar and ruined potential relationships because I was never in the same country, but it was all in the pursuit of my life’s goal.

Now, I’m dating a wonderful man, who I’m very happy with; however, the situation becomes much more complicated because of the difference in our lifestyles. I am self-employed and have the flexibility to travel anywhere, anytime, while continuing to work with my existing clients. On the other hand, he is still working full-time for a company in Toronto that requires its employees to work from the office during regular business hours.

In considering these questions, I realized that ― for the first time in recent years - I’m at the mercy of someone else’s choices and the decisions of someone else’s employer. My first reaction to this realization was anger and frustration. Almost immediately, I could see myself self-protecting, getting angry instead of trying to find a way to work it out. I started making assumptions about how my dreams would be crushed by the current scenario and then responded (to my imaginary projections) by shutting down emotionally because I was scared. I was worried that I would end up losing out on either my current love (travel) or my potential love (him), and I was feeling sorry for myself.

So, how do we move forward? My solution was this… I wrote him a long email (basically, a novella lol) that outlines my concerns and fears related to our shared long-term goal of traveling together full-time. I asked him specific questions about what his thoughts were on timelines for making it happen, what he wants/doesn’t want/is and isn’t comfortable with related to putting it into practice, etc. I am giving him as much time as he needs to think through these questions before we have a discussion about our individual plans for executing the common goal.

Interestingly enough, I sent the email and 40 minutes later, he had already read it and was ready to talk through the answers to quite a few of my questions. Because I didn’t attack him or get angry (as my first response would have lead me to do if I wasn’t working on controlling my unhealthy emotional reactions), he listened to my concerns, understood them and answered as many questions as he could right away, because he doesn’t want to upset me or make me scared about our future. We had a very comprehensive discussion that has already made me feel so much better about our future and how we are both hoping to put our goals into action over the coming months and years.

Overall, the entire experience was a very positive one that brought us closer together as a couple; however, it could have manifested in a much different way if I hadn’t controlled my unhealthy impulses and approached it reasonably and with specific “asks,” describing what I need from him to address my concerns. So I consider that a definite win!

As of yet, we haven’t sorted out our long-term travel (or life) plans but I have made the decision to push my trip back at least four months, so that we can focus on building our relationship. At first, I was worried but now I feel that this is the best possible outcome given our current situation. While I don’t like to give up on my hopes, dreams and plans for anyone (because who knows whether the relationship will be successful in the long run), it’s also important that I remember that it’s no longer just my life that is being impacted by my decisions. Now, there are two of us working to accomplish our mutual goal of working remotely and traveling the world for months at a time.

Counter-intuitively, by making this short-term concession (of choosing not to travel for a few months), I am actually one step closer to being able to live my life the way that I want with a partner who I care deeply for – which is super exciting. And in the end, I’m surprised to realize that I don’t even care that I’m going to stay home - even in the dead of a Canadian winter - because it allows me to pursue a relationship with a man who is not perfect, but who seems to be perfect for me.

Stay tuned for more of my musings on the many difficulties that solo traveling while in a committed relationship can pose. If you are doing the same, I would love to hear from you with your thoughts, experiences, questions, etc. Hit me up at and let’s talk!