Existentialism and 6 Years of Freelance Writing

Back with another personal update this week.

No writing lesson, but if you missed last week’s post on how to vary your writing voice, that’d be a great one to check out.

So what’s new around here?

Well, in a few short months, I’ll be coming up on six whole years of full-time self employment. That’s really wild.

It feels like yesterday that I graduated college and started my PR job for a local non-profit.

I was there for two and a half years, so really, that means I’ve been working on my own twice as long as I’ve worked in an office setting.

Now, there are a lot of wonderful things about working alone and from home on a freelance basis. The perks are very real, and I’m so grateful for them.

I get to set my own schedule, which means it’s often as flexible as I want it to be.
I can get up and start my day whenever I want (or sleep in a bit if needed!)
I can work extremely efficiently with zero interruptions.
I wear sweatpants most days.
I can challenge myself to earn more because I’m not on a set salary.
I get to hang with my dog Brooks and take breaks to walk him when I feel like it.
I can cook tasty lunches in my kitchen (even though I don’t very often...I’m bad at this.)

But there are also some major drawbacks to this type of work life, too.

There are no real co-workers to vent to on a rough day or to celebrate with when things go right.
Some days I go a full eight hours without talking to another human out loud.
Living and working in the same (small) square footage can get really monotonous.
With most of my work being digital, much of what I create feels intangible.
There’s stress that comes with the ebb and flow of work, which is mostly out of my control.
Sometimes not having a set salary opens the door to endless self-competition (which isn’t super healthy.)

I’ve been thinking a lot about the pros and cons of this lifestyle I’ve been living lately as I talk to friends and fellow freelancers who are now entering different life stages.

Some are having their first kids. Some are moving. Some are buying their first homes. It feels like a period of transition for a lot of people around my age right now (those of us who are shifting out of the late 20s and into the early 30s) and it generates a weird feeling.

As of right now, my life is pretty stable. No big changes on the horizon. It’s business as usual.

But I find myself wondering, “Am I doing the right thing? Am I on the right path?”


It’s really more of an existential question rather than one rooted in unhappiness or malcontent, but it’s there nonetheless. And I’ve been wrestling with it for a while.

Maybe you’re in (or have been in) the same boat before. The water is choppy. I’m feeling a little seasick (to get reaaaal heavy on the metaphor.)

I’m working on figuring out what the answer looks like for me, but I feel like it’s time for something different. An added challenge or a new goal to strive for.

I have some ideas (& hope to share some with you soon.)

Until then, remember to be nice to yourself. And keep writing.

This article originally appeared in my newsletter, A Cup of Copy. Sign up and get these free tips sent right to your inbox every other Wednesday.