How do you escape a freelancing rut?

By Jason Ward
Freelance Journalist

Associate editor of Oh Comely magazine and freelance journalist whose work has appeared in The Guardian, Little White Lies, Dazed, Curzon, The Simple Things, Hot Rum Cow, White Noise and IdeasMag.

I haven’t always known stability, but now I do, I want to make sure I am not stuck in a rut.

When it’s not smothering you, conformity can be tremendously reassuring. First, you go to school and that gives you a structure for your entire adolescence; then perhaps you enter into some kind of further education and that’s another few years dealt with; eventually you manage (let’s hope) to find a job in an area that you’re passionate about, and even in an unstable economic climate, there are some opportunities to move upwards or sideways.

What happens to progression, though, if you’ve decided to strike out on your own, and you’re essentially making your career up as you go along? Stagnation happens in all fields, but outside of the framework of promotions and external job applications, it can be hard to discern a path forward. 

After you’ve survived a challenging few years transitioning into sustainable self-employment, you may find yourself stuck in a rut: I am saying this because I’ve transitioned into sustainable self-employment and have found myself in it.

I have pulled the pinbones out of salmon for a living; I’m aware that self-employment is a privilege

Stability isn't always desirable

Sometimes the ‘good problems to have’ are more like bad ones, because you feel that it’s not okay to be dissatisfied. After years of time-draining jobs that didn’t mean anything to me, I am working as a full-time writer. If you’d told me as a child that I’d be in this position, I’d be thrilled, albeit somewhat disappointed that I didn’t end up as a time traveller.

I have pulled the pinbones out of salmon for a living; I’m aware that self-employment is a privilege. The ‘good problem’ I have is that I’ve made myself too busy to seek new opportunities or take risks: the thing draining my time isn’t another admin job but the profession I always dreamed of doing.

Thanks to the relationships I’ve built with a range of dependable clients, I usually have the next few months plotted out and don’t have to look for work, but that also prohibits me from making new contacts that could lead to meaningful developments, and ultimately from pushing myself as a writer.

Everyone has different circumstances – for many, beyond the narrowness of writing, a focus on upskilling and searching for new collaborators would constitute positive movement – but here are the steps I’ve been taking to escape my cursed stability and reliable employment.

The five steps I have taken to escape the rut of stability

1) Allow yourself a break

Most importantly for me, I allowed myself a working break where I could genuinely focus on long-term planning instead of racing to meet the next deadline. As a freelancer, you end up taking much less time off, so I worked out what would be a reasonable period to not accept any paid work at all, and resolved to resist the temptation to do otherwise.

2) Learn to say no

It has taken me years – many actual years – to feel confident that turning down jobs from certain clients wouldn’t set off an elaborate Rube Goldberg machine that would result in my complete destitution. Early in my freelancing life, I found it very useful to say yes to almost everything – now I am finally learning the value of (politely) saying no. There’s a difference between loyalty and timidity.

3) Assess your progress

I undertook an honest assessment of my own progress and expectations. Beyond paying my rent, what are my actual priorities, and what gets in the way of them? Am I in the position where I’d like to be? What does that position look like, anyway?

4) Don't beat yourself up

I tried not to beat myself up, a difficult thing to avoid when you’re a click away from scores of people more successful than you. Instead of feeling dismay at the distance left to travel, I tried to work backwards from my goals.

5) Focus on the work itself, rather than the career

The line that everyone quotes from Batman is that the night is darkest just before the dawn, but I’ve always preferred the one about how when you’re freezing you should rub your chest and your arms will take care of themselves. It became evident that the central objective of my break was to remind myself what I love about writing, and to determine where I could give myself opportunities to pursue more of that.

A day in which I’ve enjoyed writing never feels like a failure

If I feel secure that I’m able make a living from all this, then maybe the bulk of my writing should be a joy to do. For me, that means carving out space for more self-directed projects, even when they don’t have an obvious path to remuneration. 

By definition, this will mean less financial stability, and to turn down paying work for others in favour of non-paying work for myself is absolutely a risk, but then I’m a freelancer: it’s not my first leap of faith.

A day in which I’ve enjoyed writing never feels like a failure, and a day in which I’ve enjoyed writing always feels like I’m moving forward.