On Being a Wandering Woman

**This is a more personal post on the less conventional ways I’ve chosen to live my life — the challenges and the triumphs.**

It’s COVID and I can no longer wander.

I spent years building up my dream business, where I’m doing work I love and can live and work from anywhere.

I even ended a five-year relationship with an amazing person — whom I nearly got married to at several points throughout the relationship — because it eventually became clear we didn’t share the same goals and dreams for personal growth, independence, and a nomad lifestyle.

When COVID lockdowns hit, I was trying my hand at living and working in Mexico, and had to make the hard choice to go home. I was mostly fine with this unexpected change in plans, embracing a go-with-the-flow mentality, and barely phased. I went back to Vancouver, enjoyed some solo quarantine time, and still managed a move to a new city (Whitehorse, Yukon) despite the pandemic.

I set up shop in Whitehorse and all was good. I planned to fly down to Vancouver when I could and crossed my fingers I could make it back to Mexico soon.

However, after months of those options being off the table, and no wandering-of-the-world in sight, some unpleasant thoughts started to hit me.

WTF am I doing with my life?

I was (and still am) living with my high school best friend and her husband, who are having a baby soon. We feel like a cozy little family and I love it, but in my insecure moments, I tell myself that all I’m doing is renting out a room in their house (which is totally lame, too old for that, blah, blah, blah).

I’m 33 years old. I don’t own a place. I don’t have a partner or a spouse. I’m not building a home or a family anywhere…

Fear and self-doubt moved in.

In the absence of being able to live the life I had chosen — a location-independent lifestyle between Vancouver, Whitehorse, Mexico, and wherever else I wanted — the deeply burrowed insecurities about how I was living my life started to emerge.

I found myself thinking…

What am I doing with my life at 33?

Other people must think I’m a totally broke loser for rooming with my friends who own a house and are having a baby…

I’m just mooching off the life my friends have built. People are probably wondering why I don’t build my own life.

Maybe I should buy an apartment, then I’ll look more put together.

Maybe I should have stayed with my previous partner and gotten married, so I would look like I have more of my shit together.


These are the exact thoughts and stories that I would call my clients on in a second. Yet there they were — screaming in my head, loud and clear.

I couldn’t believe these stories were coming up for me. I thought I’d left those thoughts behind — those thoughts I coach my clients through often, so they can stop living their life to make other people happy and do what they actually want.

Yet there they were. And let’s be honest, there they remain.

The more I learn and grow, the more I realize my insecurities and self-doubts rarely go away entirely — I just become more aware and accepting of them (which helps to dilute them as a by-product, but certainly doesn’t eliminate them).

And then, usually when life isn’t going as I hoped or planned, these insecure thoughts and stories rear their head again.

To which, in my stronger moments (when I’m not falling prey to them), I say…

“Hello, old friends. Remember, I chose this life. There are always trade-offs to our decisions. Right now, my dream life is restricted, but hey — let’s zoom out for a second here. This doesn’t mean it’s worth compromising on what you know you want. Yes, what YOU want. Not what you think you should want. Not what you perceive other people want for you (or what they think you should want). Take a moment. Tune in right now. What do you really want, just for you? Remember.”

As a wandering woman, who doesn’t want what people have traditionally perceived to be the things that fulfill a woman (marriage, children, and a home to nest in), I need to remind myself of this. And I will continue to need to remind myself of this.

Whether we’re a wandering woman or not, we all face these life decisions.

Do we live our life so that others perceive us to be happy? Or do we live our life so that we actually ARE happy?

Because often, those things aren’t the same. (Although they absolutely can be — someone could be living a totally traditional life that ticks all the traditional boxes and absolutely be fulfilled. This article is NOT for those people.)

It sounds like an obvious question, but we all see people choosing to live their lives so that they tick the boxes that make their life appear to be happy (or that they perceive are the things others think will make them happy — which is a huge distinction. Often the expectations of others are much less than we perceive in reality).

And, as I’ve shared, I feel the insecurity of not having ticked the boxes of wife, mother, homeowner, etc. at times. Sometimes my fear rears its head, telling me that to others I might look like a miserable loser (regardless of if I’m actually happy or not).

These insecurities have been brought to the surface during the later days of the pandemic and it sucks, but I’m also grateful for that. I know COVID has brought a lot of our dormant insecurities and pain points to the surface, and as uncomfortable as it may be, it’s wonderful because it gives us an in-the-face opportunity to address them.

For now, I’m letting the insecurities that come with being a wandering woman (who can’t currently wander) to be there. Because I know that no matter what path I choose, the insecurities will be there anyway — the form they take may be different, but they’ll be there.

All I have to do is remember that I chose this path, I didn’t fall into it, and I didn’t do it to make anyone else happy (or that I perceived would make others happy), and that warms me up and allows me to be ok with the discomfort I feel.

To me, it’s more important to live a life that I could write a book about, and less important to feel comfortable all the time or to live a life that avoids stepping on anyone’s toes.

Whether I’m wandering or not, that’s my choice as a wandering woman. And I’m sticking to it.


Career Coach | All-Night Dancer | Proud Introvert www.rebeccabeaton.com