Why would anyone choose this?
Answer: Most of us don’t, except maybe Meg Wilcox (but at least she can tell you how to make the flaming tire fire that is capitalism-born freelancing more tolerable).
If you read the last edition of How to Actually Like Freelancing then you know that I fell into this line of work at best accidentally, and at worst begrudgingly - and which one of those it is depends on the day. There are still some weeks where I ask myself why on Earth I chose this (this happens to be one of those weeks). But to me, that’s still a big upgrade from my old way of thinking - which was that I didn’t choose this. Being forced to do something against your will because you didn’t have any other options will always, always feel worse. Maybe I’m fooling myself a little bit about this…but even if that’s the case, embracing freelancing is the path I’ve chosen.
A lot of the freelancers I speak with fall into the same camp as me: I don’t know that this is what I wanted, but I’m here now and I’m making the most of it. But there’s another type of freelancer - the ones who did choose this line of work because they like it. I aspire to be this kind of freelancer (that’s kind of where the premise for this newsletter came from), but in the meantime, speaking to one of these elusive creatures is the closest I’m going to get.
Cue Meg Wilcox.
“I got into freelancing because I was interested in doing a lot of different things, and I was trying to build up a portfolio,” says Meg. “ Now I have a permanent full-time faculty job that in many ways feels like a freelance job, but I have the stability and salary. That’s something to keep in mind - freelancing doesn't have to be forever.”
In her former life as a full-time freelance journalist, Meg spent nearly a decade travelling the country as a reporter, producer, and host for broadcasters that include CBC, iPolitics, CTV, Banff Centre Radio, and CKUA. She’s now the co-director of the Community Podcast Initiative and an Associate Professor in the School of Journalism at Mount Royal University, while also working as a freelance podcast producer and consultant. Meg literally wrote the book on freelancing: The New Journalist's Guide to Freelancing: Building Your Career in the New Media Landscape (even for a seasoned freelancer, it’s a great read).
Even though Meg hasn’t been a full-time freelancer for a few years now, she still spends a lot of time thinking about how to make freelancing better. So, I asked her to chat with me about why people choose freelancing…and how we ended up in this sort of dystopian work landscape where it often doesn’t feel like there’s much choice.
“We spend a lot of time thinking and talking about what got someone into freelancing,” says Meg. “Like, I was freelancing because there either was a job I wanted that I couldn’t get, or the jobs I wanted didn’t really exist. But I think the more interesting discussion is once you are freelancing, what keeps you there?”
According to Merriam-Webster’s article on the history of the word of freelance (yeah, I’m using this very trite framing method BECAUSE IT WORKS OKAY), “When freelance first came into English in the early 1800s, it was used to refer to a medieval mercenary who would fight for whichever nation or person paid them the most.” It was literally a person with a lance who was free for hire. The meaning has obviously expanded in modernity to mean someone who works outside of the world of soldiering, but that’s not the only thing that’s changed: many contemporary freelancers have lost the ability to take the highest pay cheque, and instead feel like they have to settle for what they can get.
I’m not an economics expert in any way, shape, or form - and you don’t need to be one to be a good freelancer (lord knows you have enough on your plate). But I think knowing why you weren’t able to get the job you wanted or why it doesn't even exist anymore really helps to take the sting out of being a freelancer. And this knowledge can help you leverage some tools you might not be fully utilizing as a freelancer.
“ We know that more and more Canadians are working gig economy jobs - that could be anything from driving Uber to running your own freelance production business,” says Meg. “In Nicole Cohen's book Writers’ Rights: Freelance Journalism in a Digital Age she talks about how employees are more expensive to companies because you have to pay their benefits, pensions, and all those other things. That doesn't mean that you can't work around that and negotiate it in other ways for yourself as a freelancer, but overall we know from the numbers that unions have a way higher success rate for improving things like workplace quality, salaries, benefits, etc. As soon as you're outside of that system, you're automatically going to be at a disadvantage compared to someone who is an employee. So, there's kind of this weird tension between the idea that by working freelance, we're technically helping companies be bad employers. But on the other hand, if we weren't working freelance, we probably wouldn't be working in the field at all.”
Depressingly, it can feel like we’ve entered a vicious loop: companies realize that employees are expensive, so they restructure to have less of them. But people have bills to pay, so they agree to work as freelancers and swallow the expenses themselves that were previously the responsibility of the company - and most people quickly find out that what they’ve signed up for can be a lot to handle.
“Freelancing can be really hard at times,” Meg admits. “You’re working alone, and having to figure out your own stuff. Maybe the client you pitch falls through, or you have a couple of months where you're not making much money, and it's really easy to blame yourself for it. It’s easy to say, ‘Oh, the reason this is failing is because I didn't do enough, or I'm not enough.’ But when you do that, you’re not acknowledging that maybe that client that you pitched to just lost one of their sources of government funding and it has nothing to do with you. Or think about the institutionalized systems of racism, sexism, and so, so many other of these colonial systems - I mean, it’s probably not great to live your day every day blaming colonialism and just rolling over, but on the other hand, I think not acknowledging these systems and how they influence us….it’s a big deal, we can't just ignore it.”
Being a freelancer can feel pretty dour and hopeless, especially if you feel like you just kind of ended up here. But that’s part of the problem - there are things that you can do as a freelancer to mitigate some of the issues that keep the cycle spiralling towards unsustainably low pay rates and the loneliness that many of us have a hard time managing.
“When we're cut off from tools like collective bargaining, it also means that we’re losing context to make our decisions,” says Meg. “That is where as individual freelancers, we are going to be at a disadvantage…but that doesn't mean that we can't organize collectively. And I’m not talking here about making a union, because that doesn't really work in these cases, but I think we're seeing other forms of developing community and supporting each other to work around these challenges. The Canadian Freelance Guild offers memberships for $150 CAD per year, and some of the support they provide is looking over contracts, or they can give you advice on things like how to negotiate. There's also networking events and practical skills training. Information and connections help any worker do better, whether it's figuring out what you should be charging, or emotional support as you're trying to figure out how to do your taxes for the first time, or how to work out a schedule when you're mostly working from home and on uneven hours and days. None of us were meant to work in a vacuum, so I think it's about finding a way to create those networks. What I do feel has changed for the better is that now these kinds of organizations not only exist, but there are more of them and they are growing.”
Maybe you’re like Meg and you picked freelancing because you like the freedoms it gives you over your time and contracts - or, maybe you’re also like Meg and you picked freelancing because that’s what was available. Either way, knowing why freelancing is so prevalent—and that most freelancers are facing the same struggles—can make the experience feel a little less isolating. And that’s a step toward making it better.
x Jess
Meg’s menagerie of coworkers when she works from home (husband not pictured.)
Further reading:
The New Journalist's Guide to Freelancing: Building Your Career in the New Media Landscape by Meg Wilcox
Writers’ Rights: Freelance Journalism in a Digital Age by Nicole Cohen
“The Surprising History of 'Freelance'” - Merriam-Webster