Home » A Few Telling Signs That You’re a Freelance Writer

A Few Telling Signs That You’re a Freelance Writer


Last week I had the pleasure of spending a few days in Cancun with a handful of awesome writers (you can watch the story highlights here). We’re all freelancers, so once the margaritas start flowing (and boy did they flow…), naturally the conversation turned to all of the highs and lows of freelancing. Most of my friends IRL work regular 9-5 jobs in the public sector and while they think what I do is cool, they don’t always understand or relate to the behind the scenes stuff that goes into writing full time for a living. So, while these press trips  can be a bit logistically crazy (I was literally in Mexico for 3 days), I love that they give me a chance to connect with other awesome women writers and journalists who just get it.

Inspired by conversations I had in Mexico, here’s a few of things that most freelance writers will be able to relate to. I may just turn this into a regular series.

[Note: I realize some of these points are probably specific to sex and relationship writers/bloggers, so keep that in mind]

1. You don’t go to the dentist as much as you should.

A fellow writer friend posted a selfie that other day with the caption, “went to the dentist for the first time in 3 years! #freelancelife.” It was only once I saw her post that I remembered that I haven’t been to the dentist in far too long. I’m not talking about going to a cosmetic dentist, I mean a straight up cleaning and check-up. I have the best dental clinic — it’s in a gorgeous, easy to access area and my dentist is awesome — and yet, I always leave appointments way too long. Part of this is because of a hectic schedule. It’s also because I have to pay out of pocket for treatments (versus before when I worked at a corporate job and everything was covered by my benefits plan).

2. You have a precarious relationship with health care/insurance.

I’ve met a lot of freelance writers from the States that don’t have health insurance. The struggle is real. The only way I’m able to get away with not having insurance is because I live in Canada and the only thing I pay out of pocket for is dentistry and the occasional massage or chiropractic treatment.  Friends living in the States, I don’t know how you guys do it, but know that you’re not alone.

3. When you’ll actually get paid is even less reliable than your period.

While I have a general idea of when my anchor clients will pay me based on when I invoice them, I can’t always say that I’ll have the money by a specific date. Sometimes there are delays or a payment takes longer to clear through PayPal. It’s tricky and you always have to think ahead to make sure you have your expenses covered.

4. All of your zip drives and pens are branded.

In my case, most of my office supplies come from sex toy companies, sexy resorts and other places I’ve traveled.

Hi. I like sex and hotels and writing about both.

5. You’ve gotten hooked on an unlikely beverage or snack thanks to a press event.

There was a time in 2010 when it seemed like every PR event in Toronto was sponsored by Vitamin Water. The company even dropped off a free crate of it at my former retail job and a week later I found myself at an open bar fashion week party where all the drinks were infused with the beverage. A year later, it was Pop Chips, and after that, Starbucks Refresher energy drinks (which, I still sometimes get a hankering for — another fashion week addiction). Currently, I have a friend who is hooked on the Aperol Spritz. The last thing I became addicted to was ONE Coconut Water, which I’m not mad about because I’m pretty sure it won’t give me diabetes.

6. You re-use free items in creative ways.

While I don’t really enjoy silicone lubricant, Uberlube makes a great hair styling product. I’ve also heard it works wonders on creaky door hinges. Also, 90% of the candles in my home are actually aphrodisiac scented massage candles. I don’t have anyone to massage currently, but I am prepared for the next blackout or apocalypse!

Sex candles for the apocalypse.

7. Your work wardrobe looks less like this…

…..and a lot more like this.


If you see a photo of me on Instagram dressed up, that’s literally because it was a rare occasion when I actually wore real clothes and therefore, felt it needed documenting. While I do wear my “uniform” (jeans, a striped shirt & black leather jacket) to go to work at a coffee shop or co-working space, most of the time I’m in workout wear and wrapped in multiple long cardigans and/or a Slanket because my desk area is cold AF.

8. You frequently wonder if you should just pack it in and get a desk job.

This is something I think about at least a couple of times a month. I’ve gone through phases where I’ll apply to a bunch of 9-5 jobs, go to interviews and then something will happen — I’ll get offered a cool opportunity or I’ll secure a new client. When this happens, I interpret as the Universe telling me that I need to stay the course. While there’s definitely some downsides to freelancing, the freedom to create my own schedule is pretty amazing.

If you’re a freelancer, what would you add to this list?


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