‘It’s time to go’: 5 sure-fire signs it’s time to quit your day job

If the figures are anything to go by, freelance writing is a side hustle for most of its practitioners.

The Freelancers for Fair Rates report released by the Media Entertainment and Arts Alliance in 2021 found that freelance income was sole source of earnings for only one-third (32.2%) of respondents.

This suggests that two in every three freelance writers are writing ‘on the side’, surreptitiously conducting research during their day job hours, conducting interviews in stolen moments, and tapping stories out in the wee hours of the night and early morning.

I should know, because I did it for years … until I couldn’t anymore.

The path to fulltime freelance writing is different for everyone. But here are the top 5 sure-fire signs that it’s time to quit your job and take the leap.

Photo by Carrie Borden on Unsplash

Your day job is sucking all the joy out of life

There is something to be said about financial security. More on that later. In the meantime, the ‘Oh please God, no!’ mindset that comes with spending all your working hours doing tasks you don’t enjoy, for people you don’t like, to bring about outcomes you don’t care about, spreads like a virus, ultimately infecting your precious non-working hours as well. Left unchecked, it will kill the joy and the playful spark that is the key to creativity.

I once wrote about how I got through the interminable hours that comprised a particularly tedious job:

Prior to every shift, I had to talk to myself in soothing tones, as though I was preparing to push out a baby.

“Come on, you can do it, you can get through this, it’s not that bad, just grit your teeth, breathe, breathe, breathe.”

I got a lot of strange looks in the elevator.

When things get to this point, it’s over. When your job is unfulfilling or emotionally draining, or especially when the environment or culture or people are toxic, it’s time to explore the options outside those cubicle walls.

You’re engaging in what psychologists call ‘avoidant coping strategies’

I developed a serious vending machine habit when working the job described above. From chocolate and chips to iced coffee and even leftover birthday cake in the staff room, I consumed anything I could get my hands on.

Compulsive eating, mindless social media scrolling, Netflix binging, heavy drinking and assorted other addictive behaviours – they’re all signs that you’re craving the fast hit of dopamine that can help you get through the eight hours of untrammelled misery that is your day job.

You might not have even consciously clocked that you’re miserable yet, because we’re culturally conditioned to soldier on. But avoidant coping strategies are, at the very least, things that should make you go hmmm …

Photo by Nathan Dumlao on Unsplash

Your day job is interfering with your writing

I didn’t set out to specialise in travel writing. But when the pandemic hit and Queensland borders closed, I started fielding calls from interstate editors who needed a scribe on the ground.

I accepted one Queensland-based assignment, then another. At some point, probably when I was on a superyacht cruising through the Whitsundays, or watching the sun rise over the red sand hills at Windorah, I realised, ‘I love this. This is what I’m supposed to be doing.’

I made a conscious choice to prioritise travel writing gigs over all other work. But my willingness to jump on a plane at the drop of a hat didn’t sit too well with the standard terms of my employment contract. I tried to juggle both, first using up all my recreational leave, then my sick leave, and then my employer’s patience. I knew that the travel writing work could dry up overnight, but I needed to back the horse I was riding. Quitting my day job thus became a no-brainer.

You’re willing to eat freelance writing’s shit sandwich

The financial realities of freelancing don’t usually stack up.

The same MEAA survey mentioned earlier found that two-thirds of freelancers (62.6%) earn less than half the average Australian weekly wage which, at that time, was around $90,000.

Barely one in ten (11%) said they were earning more than $80,000 from freelance journalism; almost seven in ten (68%) were worried about not having enough superannuation.

Those figures aren’t inevitable, but they’re hard to ignore. Then there are other challenges, from regularly coming up with fresh story ideas, writing well-considered pitches (which might be completely ignored) and attending to all the unpaid administration that needs to happen so the wheels don’t fall off completely.

Author of The Subtle Art of Not Giving a F*ck Mark Manson provided me with a moment of clarity when he posed the question: “What’s your favourite flavour of shit sandwich and does it come with an olive?” The entire post is well worth reading, but essentially, he points out that even dream jobs have their drawbacks. As he puts it, “Everything sucks, some of the time.”

When I really, truly, genuinely came to understand this, I was able to make peace with the disappointing, frustrating and downright infuriating parts of freelance journalism.

Photo by Unseen Studio on Unsplash

You must be willing to fail

For a long time, fear held me back from fully committing. Chucking in a job that provided steady income in order to spend time on an endeavour that might not pay off felt a bit like high stakes gambling. Even when I decided to go all-in, throwing myself into freelance writing full-time, there was an insistent little voice that spoke to me in my darker moments. ‘Really?’ it hissed. ‘This is seriously your plan?’

Freelance writing is an endeavour inevitably filled with rejection and self-doubt. I was scared that my writing wasn’t good enough, or funny enough, or insightful enough, or sophisticated enough. If I’m honest, I still feel that way. But writers only fail – financially, creatively, or in a billion other ways – when they stop writing.

A writing mentor once told me, “Don’t have a day job to fall back on, because you will fall back on it.” Because that’s the other thing: When you don’t have a safety net, you’re so much more focussed, dedicated and determined to make your crazy dream fly.