The agony and the ecstasy of freelancing

And how weird it is returning to work after a massive life event.

Mike Hindle on Unsplash

An audio version of this article, narrated by me, is available below:

If a reliable office job is a smooth-running SUV, then freelancing is a honking, spluttering clown car careening down the street with its bumper hanging off. Freelancing is thrilling and terrifying, riveting and soul-crushing, lucrative and debt-inducing. I’ve been a freelance writer, editor, ghostwriter, and journalist for 14 years, ever since leaving Sugar magazine – the best job ever – when it closed in 2011. (I know, 2011 is mad because I look so young, right? RIGHT? Thanks. That’ll be the chemo.)

I’ve always loved freelancing: the freedom, the lack of office politics, the absence of appraisal forms. When work is good, I can pick and choose projects, work from anywhere, and take holidays whenever I want. I meet creative, passionate people – because, let’s be honest, none of us are in this for the riches. (Spoiler: there are no riches.) I get to become a mini-expert on niche subjects, such as handwriting analysis, forensic stepping plates, arachnophobia, hypnosis, Friends, decision-making, solo travel, hangovers, Vanessa Paradis, Joan Collins, and One Direction. That’s not even mentioning the non-niche subjects, such as mental health and wellness, which have made up the bulk of my work recently.

Yet, freelancing can be confronting. I’ll either get five jobs, all of which start simultaneously and have the exact same deadline, leaving me weeping while working into the night. Or I won’t get any of them, leaving me weeping while worrying into the night. There’s rarely a period that’s calm, steady and beautifully balanced.

No work is guaranteed. Even contracted work can be pulled or “pinned” (put on indefinite hold without payment). With new clients or day-rate work, you have to be ‘on’ all of the time – there’s little leeway for having a shitty day. Pitching is brutal with heartfelt ideas disappearing into the void. Industry downtime can foster competition over encouragement, self-promotion can be soul-destroying, and rejection is never a LOL. There’s self-doubt, self-criticism, and having to say, “Yes, that’s a wonderful idea, Graham” to the snivelling son of the big boss who’s decided to “learn the ropes” (aka “stop spanking his trust fund”).

To thrive, you must be able to embrace uncertainty and, in order to do that, it really helps if other areas of your life aren’t uncertain. It’s much easier to manage freelancing’s chaotic nature if your health and home life are stable. If they’re also skidding down Clown Car Alley, then, yeah, freelancing can feel a bit much – which became painfully clear to me last year when cancer kicked me in the teeth (or, more accurately, kicked me in the colon).

The highs and lows of returning to work

I’m tiptoeing back into work now after maternity and cancer leave. Two weeks ago, I signed a new book deal. I am over the moon about it. It’s a non-fiction mental health book that is right up my street. I’m also picking up commissions from lovely editors who haven’t forgotten about me. These are gorgeous projects to sink my teeth into after 18 months off work during which time I wondered if I’d ever work again because a) I’d either be dead, or b) replaced by AI. (Yes, Meta did steal one of my books to train its AI models and, yes, I’m absolutely fuming about it.)

This slow and steady return to work feels both reassuring and revitalising. Returning to work as a new mum is one thing; returning post-cancer is another. Returning as a freelancer in a notoriously fickle industry is the cherry on top. As a freelancer, clients are often strangers who don’t know you personally. After you’ve gone through something massive, that can feel odd. It’s not like you can open with, “Hey, guess what just happened to meeeeeeeee?!” or that you even want to. In fact, I’ve always enjoyed the separation between personal and professional lives that freelancing demands. Yet, it’s been a shock to realise how different things would be if I were returning to a long-term permanent job – somewhere familiar, with familiar work, surrounded by familiar colleagues. Somewhere a kindly HR manager would take me aside to reassure me that, “It’s okay to take things slow. You don’t have to ACHIEVE EVERYTHING IMMEDIATELY.”

Instead, I have only myself to rely on or to answer to. I have no barometer of what is and isn’t expected of me in this completely batshit situation. Am I doing too much or too little? Should I be doing less or more? I’ve climbed straight back into the driver's seat of the clown car and…

I fucking love it.

The buzz is back. I’m writing, I’m pitching, I’m throwing ideas into the void and not beating myself up about it. I’m discovering that cancer has given me a positive ‘fuck it’ work attitude that, so far, is paying off: fuck it, pitch the ridiculous idea; fuck it, post the silly video; fuck it, do the self-promotion; fuck it, up your rate to what you’re worth; fuck it, finally start that thing you’ve been putting off. There’s a recklessness that comes from dodging death that suits freelancing. Why can’t I do X, Y or Z? Why can’t I at least try? Far better to have tried and failed than never to have tried at all, right?

Conversely, I think the reason this recklessness works is because cancer has also given me a proper wake-up call about ensuring stability where I can. It’s pretty hard to be a freelancer and get sick. There’s no sick pay and no one else to do the work. To that end, I will now get sickness insurance (although I’m pretty sure that ship has sailed); I will now occasionally work in a friend’s office for company and conversation; I will now tell clients about what happened if and when it's relevant (there’s having a stiff upper lip and then there’s being a martyr). And I will now consider changing things up if the cons start outweighing the pros.

---

Thanks so much for supporting my work. If you enjoy what you read/listen to and would like to buy me a coffee, I would really appreciate it.

---

After any life-altering event or career break, reassessing professional priorities is inevitable whether you’re a freelancer or staffer. Does this still suit my responsibilities, my health (mental and physical), my finances, and my future plans? Does the job I once had even exist anymore? There’s pride, too: would doing something different mean ‘giving up’?

It’s been interesting working out which elements of freelancing I love and which I don’t – and trying to sort through whether those feelings were always there or are down to my new situation. At the moment, I’m super excited about freelancing, but I’m also much more realistic about the pros of a steady job with a regular paycheck (AND SICK PAY – imagine!). So, I’m trying to find a middle ground, propping up stability where I can so that I can lean into the aspects of my work that I adore. (Apologies for using the phrase ‘lean in’ there. *Shudders*)

If this all makes me sound like I have my shit together, don’t be misled. This week, I put teabags in the fridge, drop-kicked a new (full) wine glass into the wall, went running wearing inside-out leggings, and put some really important documents in the recycling box outside, then got stuck half-in, half-out of it while trying to retrieve them. But hey, at least I’ll have sickness insurance soon. (I must get on that.)

Just One More Thing

Is this what happens when you get older – you start keeping knackered trainers for “garden shoes” even when you don’t have a garden and thinking about stuff like stability, sick pay, pensions and fucking cancer? Is this entire post more about the fact that I’ve turned 40 than it is about freelancing? OH MY GOD, AM I JUST OLD?

---

*Exceedingly modest reminder that I have written eight bestselling mental-health books which have been translated into dozens of languages. I’ve also written a book about the TV show Friends which would make a delightful gift for any Friends obsessives. All are available to buy online or at your local bookshop.