Freelance and the Feeling of Dichotomy

On wanting to be a lone wolf and part of a pack

The closest image I could find to illustrate the idea of opposites and the feeling of wanting two differing things at the same time. Rosé? Great. Coffee? Great. Together? Kind of weird, but not necessarily impossible…(Image courtesy of Dupe).

I’ve been thinking a lot recently about dichotomy, specifically the experience of feeling two opposing emotions at the same time. It’s a confusing space to be in. How can two very different things exist at once? How is that possible, and how do I know if one is more right than the other? How do I know which one to listen to?

I found myself thinking about this the other day. I had just completed my work and was closing my laptop, which is a satisfying feeling, but I felt something else – something completely opposite – nagging at me.

In many ways, being a freelancer is everything I have ever wanted out of life. It, in fact, and in more ways than one, has given me my life back.

It’s slow mornings on the couch with my dog in my lap, solving the New York Times puzzles (and cursing at Connections – if you know, you know) before I make breakfast. It’s miles-long midday walks, stretching my legs at my own pace and soaking in the sunshine (when we have it here in the Seattle area). It’s new and different projects that vary in duration, allowing my mind to move in the flexible way it was meant to. It is, in fact, what it says it is – freedom – and it is magical.

Sure, it also has its downsides. The finance aspect, for one, was a major barrier for me when I first started. I was daunted by the idea of sending and tracking invoices and filing taxes. I’m still intimidated by it, to be honest, but now that I have more of an infrastructure (and an accountant), I’m getting more comfortable. The lack of consistency and healthcare are a couple others, and it is not lost on me how lucky I am to have a spouse I can lean on in both regards.

But one thing that has snuck its way to the top of this short list of downsides is a larger-ticket item: loneliness.

Being a freelancer is wonderful, but it is also lonely.

Some people might enjoy that aspect of the job – and I do too to a certain degree – but over a year in, I’m finding myself missing the camaraderie that came with corporate.

I miss being on a team. I miss being in the trenches together with other people, working toward a common goal. I miss being a part of something bigger and watching it come to life. I miss spitballing and brainstorming and building on each other’s ideas to create something great.

I miss being inspired.

One of the hardest parts of getting laid off was leaving a team. It was having them watch me walk away against my will while I watched them move on without me. I know now, just like I tried to remember then, that it’s “just business” and that logically, it wasn’t personal. But it was painful all the same.

I love the freedom of being a lone wolf, I love dictating my own hours and choosing my own work, but I miss the camaraderie – the connection – of being in a pack. Yes, I get to know my clients and still have significant moments of collaboration, but it’s not quite the same.

It’s not like scribbling wildly on a whiteboard – whether material or virtual – with your coworkers and finally finding that answer. It’s not like exchanging dozens of Slacks and emails a day, some about projects in motion and some just to congratulate or encourage one another (complete with a GIF or two).

Perhaps I’m biased, given some of my previous coworkers have become some of my most treasured friends. Maybe my baseline is skewed and can never be reset.

Or maybe I just need a community. Maybe Freelancing 101 was Mastering of Finances, for example, and Freelancing 201 is Finding My People. Maybe “team” just looks different for me now. Maybe it’s not one built on proximity, but on passion.

I am grateful to have met another freelancer through one of my current contracts. As we’ve gotten to know one another, we’ve become not only friends, but resources for each other. We chat about what we’re working on and ask each other questions about rates and pricing (which is its own special quagmire), as well as other things going on in our lives. I was actually describing this post idea to her the other day as we were catching up, and – surprise, surprise – it got me thinking (this Substack isn’t called CEOverthinker for nothing).

What if freelancing doesn’t have to be isolating?

What if finding each other made it more inspiring?

So, my fellow freelancers, if you’re reading, I hope you reach out if you relate. Maybe it can be our first step toward connection in the solitude of our work. Maybe together we could build our own little community.

After all, we know we weren’t meant to climb the corporate ladder, we were meant to pave our own way – but it shouldn’t necessarily mean we have to do it alone. Maybe together we can bring a new connotation to dichotomy, maybe we can be independent and supported.

I, for one, like the feeling of those two already.