A Prayer for New Freelancers

or: what I wish I'd known in 2017

Previously: A Prayer for Debut Authors

In March of 2017 I quit my job at The Pool and I became a freelancer. No one told me outright that they thought it was a bad idea, but there were at least a couple of people who furrowed their brows. They warned me that being freelance “wasn’t easy”, and that it was an extremely precarious way to make a living, especially in journalism.

My colleagues and friends weren’t the only ones who were warning me about freelance life. As my two-month notice period slowly wound down, I began seeing more and more articles about the horrors of freelancing, the pains of getting an invoice paid on time, and the psychological burnout and moral bankruptcy that was supposedly part and parcel of the gig economy. It was terrifying, but I’d already made a big song and dance about quitting, so I left anyway. And I did ok. Actually, I’m healthier, saner and generally have more money.

In a couple of days it’ll be 2020, and I imagine at least a few of you are hoping that this year is the year you finally go freelance. The following is a list of things I wish I had known when I made that decision. I’m not going to bother with repeating all the things you’ll already have read in the many “tips for freelancers” articles already out there: you have Medium, and I’m not your mother. Invoice on time, set reminders to chase your invoices, save 30% of everything you make, blahblahblah.

Here’s the other stuff. The actually important stuff.

Try To Control Your Needy, Terrified Energy

Utilise the contacts you already have and try to strike a balance between chirpy availability and raw desperation. Get someone to proof your early emails asking for work. You will not realise how much your fear of starving to death is bleeding through into your tone, so you need a third party for that. I’m lucky enough to have Ella, and a lot of our days are still passing our laptops to one another, re-writing requests to editors. It’s funny to think how many people have commissioned work from me that was actually pitched by her, and vice versa.

Remember that your pitches function as a business card. You’re pitching yourself in addition to the work. Most of my article pitches get turned down, usually because the editor has something similar in the works already. Very often however, I will hear back from the editor within a few weeks suggesting something else. You’re not just saying “hey, I’d like to write about X”. You’re saying “I’d like to write about X, given my interest in Y, and my background in Z.”

This is tricky, because you also need to keep your pitches short. As in, under ten lines. It’s hard, and it takes practice, and hardly anyone gets it fully right.

Don’t Try To Replicate A 9-to-5

My boyfriend works regular office hours, and so it was important to me when I first went freelance that I kept to the same schedule as he did. That I woke up when he did, that I was dressed and at my desk by 9am. I would take exactly one hour for lunch and knock off at exactly 5pm.

It lasted three days.

Not only do you not need to have a 9-to-5 as a freelancer, you don’t even really need to work an eight hour day. Here’s why: think of a normal office day. You get in, you take off your outdoor stuff, you update everyone on the status of the Central Line. You turn on your computer. You look at your meetings. You make a tea. You attend a meeting that is 40 minutes long: you pay attention for thirteen of them, and you speak for two of them.

I’m not trying to imply that people in office jobs don’t work hard, but they do work differently. When you work in a collaborative atmosphere, a lot of time is necessarily given over to pencil-pushing, chit-chat, admin, meetings, birthdays, zoning out in front of your screen, leaving speeches, and someone bringing their baby in.

Rightly or wrongly, you will do very little of that as a freelancer. When I’m at my absolute busiest, I work – like actual, sitting-at-my desk work – about five hours a day. Often it’s four. I used to feel guilty about this, but after a few years of pretty decent productivity and paying my bills on time, I’ve stopped. The eight hour work day is a made-up concept and it does not make you a better person, or worker, or writer, by pretending to uphold it.

So what do you do with the rest of your time? Good question.

Try Not to Sleep, Scroll or Masturbate on Company Time

So you’ve managed to free up your afternoon with your three/four/five hour work day. Now what? When you’re not working, don’t just sit at your desk or in a cafe simulating what you think a working person looks like. I don’t want to sound worthy, but you need to cut down on aimless browsing as much as you possibly can. Your mind is like a collie, and it will find a job if you don’t give it one. Your brain will interpret your browsing as work. “She’s sure on this influencer’s Instagram a lot - it must be important. Better memorise everything about this post and show it to her later when she’s trying to sleep!”

That being said, don’t lean fully into the Seth Rogen aesthetic. Don’t be that freelancer who just wanks and sleeps all the time. You will get depression. Give yourself one couch day a month. One.

You gotta get out there, man. Volunteer, meet up with other freelancers, get a dog, or if you can’t get a dog, go on Borrow My Doggy. Walk everywhere. Cook elaborately. I got my dog Sylvie about three months into freelancing, and it has changed everything. Not just because she needs a lot of walking, but because I now have dozens of very small conversations with my neighbours and dog park acquaintances every day. It might sound like nothing, but it filled that “so have you seen The Witcher?” gap that would normally be filled by colleagues.

You Are Only Ever Seeing The Top 10% Of Someone’s Workload

Ok, so you’re motoring along fine, working five hours a day and walking your tiny dog, and then you’re hit by a bad case of Someone I Perceive To Be Less Talented Than Me Has Something I Want.

Maybe it’s a big feature in a big magazine, or a… I don’t know, whatever it is other people who aren’t writers want. You spiral, and wonder why you’re not doing that kind of work.

The truth is that they barely get to do this kind of work, or they have to work extremely hard to access it. They probably spend a huge amount of their time doing excruciatingly dull pay-the-bills work. I myself spent most of the summer of 2018 copywriting for a CBD brand and writing tweets for a holiday company. But if you looked on my social media, it looks like all I did was promote my debut novel at music festivals. I mean, I did do that! But it was like… three days of my summer. The rest was CBD and bad tweets.

The lesson here is that almost everyone you see who is doing cool stuff is also doing extremely boring stuff to pay the bills. Or, they have inherited wealth. The former don’t talk about it because it’s dull, the latter don’t talk about it because everyone hates them, and they know it.

Have A Set Time for Emails

I work better in the morning so I try to keep my emails to the afternoon. This stops you from flitting between tasks and it also stops you from falling into the trap of answering the nice emails immediately and the shit emails…. never. All the emails get done between two and three pm, regardless of what kind of emails they are.

Don’t Ever Rely On One Source For Your Money, Or Your Self-Esteem

Lastly, follow Pretty Woman’s advice: don’t fall in love, don’t kiss on the mouth. You might land a dreamy situation with an amazing client who values you and pays you on time. Maybe they invite you in for expensive lunches and tell you that “next year is going to be big for us… and we see you as a big part of that”. That company can still get their funding pulled. I should know – it happened to me twice in 2019 alone.

Diversify your income as much as you can, even if it’s with shitty little bitty jobs where the pay is so low you can’t even be bothered to invoice. Equally, diversify your self-esteem as much as you can. Don’t think you’re a big shot now because you have a column in a national newspaper. Don’t permit yourself to feel joy only when an article goes viral. This is a dangerous psychological reward system to get yourself into and you will start to emotionally self-harm when things don’t go the way you want.

Again, this is where getting a dog has been helpful. My dog likes me the same amount every day. On the days I achieve nothing, I have to pick up her shit with a plastic bag. On the days I’ve been in The Bookseller, I still have to pick up her shit with a plastic bag. There’s an equilibrium to that.

My name is Caroline and if you want to hire me you can do so here.