In this regular feature, Story Board asks Canadian writers to share a few details about their work habits and their strategies for navigating the ups and downs of freelance life.

Sharon J. Riley got her start in journalism as an intern at Harper's magazine. Researching and fact checking for the publication gave her a foundation in journalism from which to start writing her own feature stories.

Her writing has appeared in publications such as The Walrus, Maisonneuve, The Tyee, and Harper's itself, among others.

Her recent Walrus feature Rise of the Robots included interviews with two dozen truck drivers from across North America about the development of autonomous trucking technology and what it might mean for their jobs.

Sharon took the time to speak with Story Board recently about the pains of pitching, the importance of finding a freelance community, and the self-imposed challenges that come from being a freelancer without home wifi.

A lot of your projects are big and ambitious. How do you keep yourself motivated when you're trying to get a new feature underway? It's tough. I get a lot of motivation from finally having a pitch accepted and knowing someone else cares about the story.

I do find that I often try ideas out on my friends. So I'll go to parties or whatever, meet people and start talking about something that I'm interested in writing about, to see if people have that wide-eyed expression. Like "oh that is shocking" or "oh that is interesting." And that's my cue for whether or not I've latched onto something that might be a good idea. That keeps me motivated.

But pitching is hard for me because I want to be really well prepared by the time I have a pitch to send in. And it's hard to figure out exactly how to pitch something before you've done all the reporting.

I feel like most of my pitches could run as short news stories or even short features. Because I try to write them the way I'm going to write the piece so that the editor can see what they're going to look like. And I have a good sampling of the characters that I want to include. It ends up being an enormous amount of work. So at that point I'm so attached to it that if it doesn't land I would be crushed.

How many features do you try to pitch per year?

It varies. I've been in journalism since 2013. So that's five years. I started mostly fact checking. I was an intern at Harpers Magazine and they asked me to keep fact checking after I was done the internship. And from there I got many other fact checking gigs.

So that was my crash course in journalism. That's how I learned how to report, how to write, how to interview people and how to research. I've been trying to move more and more into my own writing in the last couple of years. I'm trying to increase the number of features that I pitch a year. But really if I can land a couple of big projects I'm very happy.

It consumes my whole life when I'm working on something big. So I will be entirely obsessed with wildfire for six months and then all of a sudden I'm entirely obsessed with truck drivers. I'll drive down the highway and every truck stop I see I'm thinking about what I'm going to write about it. And then for that just to be done and to publish it... it's weird to jump ship so quickly.

I haven't really ever pinpointed an exact beat. So when people ask me what my beat is I get little flutters of anxiety because my beat is things that I'm very interested in. I have an environmental background so my stories often are related to that but not always.

Do you feel like you need to develop a beat? 

No, I don't think so. I think my background has been varied enough that I feel pretty comfortable in a variety of subjects and so as long as I feel confident that I can actually tell the story and I know enough about it to not just be someone who's parachuting in, then I don't think I need to have a very specific beat.

I find it exciting to dive into a whole new topic. I don't want to get to the point where I'm always recycling my own material and my own findings. I feel like it can get a bit stale at some point when you're always covering the same thing, if you don't keep that fresh perspective.

What's the best thing you've ever done for your professional development? 

I applied on a long shot to an internship at Harpers magazine in New York. It was a total long shot. I just knew I was really obsessed with Harpers. And I would read the magazine front to back, I just loved it. And it wasn't as though I had never considered journalism. I recently was going through some of my old papers from when I was a kid and I had written that I wanted to be a photojournalist when I grew up.

So it's always been something I've been interested in. But I applied for that internship and I got it. I think they just kind of thought that I was the weird "let's give her a try" character. Which turned out really well for me. It was the start of a career in journalism.

You told me earlier that you don't have internet access at home. How can you possibly be a freelancer without access to the internet at home? 

I actually think it works really well for me as a way to balance out work and life, which is something I struggled with for a long time as a freelancer. It's impossible to unplug. And so my partner and I decided to just not have internet at home anymore.

Now we have to both make a conscious decision to go out and get internet and that helps me weigh my priorities a lot more. Because I get emails, I can check my email on my phone. And then if I need to reply in any detail, I have to decide: is it worth going to the library or a coffee shop, or not? If it's not, maybe it didn't need to be answered at 10 o'clock at night anyway. So that's been really important for me.

What do you think is the most pressing issue facing Canadian freelancers? 

I feel like it's been said so many times, but journalism jobs are disappearing and people don't have stability in their work. I definitely have seen it in many different places -- that magazines and news outlets take advantage of the fact that people will take low-paying work just so they can have something. And there's always going to be someone who's willing to work for less.

So I guess I would say the biggest issue is coming together collectively to not let that happen as much. I feel like I've been guilty of that, too. In my twenties I would do anything that came my way for any amount of money, because I just wanted to get my foot in the door.

But I do think we could band together and fight for our rights. Right now we all live in our own little worlds and we have no idea what other freelancers are doing -- or at least that's my experience.

You're a member of CMG Freelance. What do you think is the most important thing a union can offer to freelancers or other precarious workers? 

I think it's community, definitely. There are lots of tangible benefits to joining the union -- you get access to health care plans and things like that. But that's not why I joined. I joined because I wanted to meet other people who are facing the same sorts of choices.

It's not necessarily a struggle for everybody to be a freelancer, but you're always making the same kinds of trade-offs. Do I say yes to this project or not? Do I negotiate on this or do I just take it because I don't want to be left behind? I feel like connecting people together as a union to talk about those issues is super important.

 

You can find more of Sharon J. Riley's work on her website, and you can follow her on Twitter at @sharonjriley.

*This interview has been edited for clarity and length