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

Nicholas Hune-Brown is a Toronto-based magazine writer whose long-form journalism has been published in such outlets as Toronto Life,The Walrus, The Guardian, and The Globe and Mail. 

His Toronto Life feature “No Fixed Address,” an exploration of Toronto’s homelessness problem and its causes, is the winner of the 2019 Dave Greber Freelance Writers Award.

Nicholas took the time to speak with Story Board recently about long-form magazine writing, building your reputation as a writer, and developing your freelance superpower.

Q: How did your Greber Award-winning piece come about? 

A: My editor came to me with that story. For those sort of broad subject stories, Toronto Life is usually doing the assigning.

It had just been a rough winter in Toronto and they thought “how about we start thinking about this now so that we’re not just reacting to the predictable thing that happens every January when people are outside in the cold. Let’s think about this all summer and have something smart to say about it when it gets cold again.”

So they brought me the story. And I think it was as broad as “homelessness.” It became my job to figure out what that story actually looked like and try to find an angle.

Q: It’s a massive piece. What were the biggest challenges in writing it? 

A: For this one it felt like the challenge was just understanding the subject well enough to make some arguments and describe what’s happening in an authoritative way. It was a question of learning about decades of housing policy and learning how the system itself works. It felt like a lot to digest.

And then the huge other challenge was that for a long time I was hoping to find one central character that could carry you through the story. I think those are, in some ways, the kind of stories that I like best and that can be the most effective.

But I was interviewing dozens of people and in the end it was impossible. It felt like it would work better with multiple voices because there’s no quintessential homeless experience. And also it was just hard to find that specific character who could embody a lot of the themes and things I was seeing on the ground.

It was a challenge — you don’t want to weary readers by constantly introducing another person and another person. But hopefully we found the right mix in the end of sharing enough stories.

Q: When you’re pitching your own ideas, how do you decide you’ve found a subject you want to spend an extended period of time on? 

A: I don’t have a beat at all, I’ve written all sorts of different pieces on different subjects. I usually have some vague idea and I’ll do a little research and I’ll either find that it’s been written about a million times and it’s not as interesting as I thought, or maybe I’ll find that there is an interesting story there and I can imagine spending a couple months with it.

What strikes my interest is hard for me to say. I do write about social justice issues sometimes. For Toronto Life I seem to write about difficult moral questions, that’s the beat that they seem to have me on. They’ll ask me to write about end-of-life legislation or about sex ed protests.

And the thing that interests me is when it’s not so straightforward. I guess that’s something that I’m attracted to is when the issue is complex enough that it demands the longer form and some nuance and thoughtfulness.

I’m not really a polemical writer. I think I try to approach stories with some sort of sympathy for the different people I’m speaking with. So I guess moral complexity is one thing I’m interested in, but then I’m also interested in more quirky stories.

One of my favourite stories I’ve done recently happened after I was on the subway looking at one of those Shen Yun posters for the Chinese dance troupe. I just was thinking I need to know more about the story behind this. And people had written about it here and there but I really went deep on it and had a lot of fun telling a story that’s a bit quirky but also brings some bigger themes to the table.

Q: How have you made freelancing work over the years in terms of being able to earn enough income? 

A: At the beginning I made very little money. I lived in a big house with a bunch of people. We were sort of artists more than professional humans. I played in a band and did plays and freelancing and I lived really cheaply like a student for a lot of years, picking the long-form magazine pieces that I wanted to do and not really thinking of myself as a journalist but more as a writer or an artist. 

I was exclusively freelance from 2005 until just last year. Over that time I got better at writing, and got to know editors and eventually people start coming to you with pieces.

And for a while now I’ve had a few regular gigs, which are really important for a freelancer. I had a column for Hazlitt, and a column for Canadian Business for a while. I still have a column for Sharp Magazine.

Just knowing once a month, or once every two weeks, or whatever it is, that you’re going to have a paycheque and you’re going to have to write this thing… you’re not just completely tetherless in the world.

And then building enough of a reputation that people come to you with stories is hugely important. Because coming up with enough pitches to sustain a living is definitely tough.

For the last two years I’ve had part time editing work at this new publication called The Local. It’s pretty interesting, it’s funded through a couple foundations. It’s been fun to edit some of the best magazine writers in the country and it’s also given me even more stability. Now I get a regular monthly paycheque and I’d never experienced that before. It’s a revelation.

Q: What keeps you freelancing? 

A: It’s the only way I can write the stories I want to write. There are a only handful of jobs in Canadian media. I mostly like writing and I think freelancing is the way to do it. I love the freedom of it.

I’ve never done an office job and I don’t really want to. I like being able to make my own hours. And I like being able to tell the stories I want to tell. I think that’s the biggest benefit. It’s the only way, really, to tell these kind of stories.

Q: What does it mean to you to win the Greber?

A: I’m so grateful to the Greber that they’re actually supporting specifically freelancers. Because you go to something like the National Magazine Awards and it’s true that so much of the best magazine journalism in the country is done by freelancers who are all kind of scraping and scrabbling.

So I’m really appreciative that this prize exists to support people like that. I was thrilled to win it.

Q: How do you schedule your week so that you can fit in everything you want or need to do?

A: Whenever I read these Q&As people have such good structures. But I’m completely structureless and I don’t think it’s something I’d recommend to anyone!

I work from cafes, I work from my bed, I work from wherever I can. I work to my next deadline and kind of structure it back from there. So you have periods of intense crazy work and then it loosens up a bit. That’s still something I’m hoping to develop — just structuring work-life a little bit better.

But one thing is to try to definitely have a number of pieces in the pipeline and arrange your deadlines well. I always have one long feature that’s due months from now that I chip away at. I have a column due two weeks from now that I chip away at. I have a short feature due a month and a half away.

And I try to keep that balance so I’m never just faced with nothing to write at all and have to scramble around and find new stories.

Q: What advice would you give to someone thinking about getting into freelancing?

A: Even in the time I’ve been doing this everything has changed so much that it’s hard to know what to tell a young freelancer starting out.

As you’re doing your hustle and you’re writing a million pieces of whatever you have to write — short pieces, commercial work, whatever it is — if you want to do feature writing, try to find a publication that maybe doesn’t have a giant high profile and maybe pays a little bit less, but that will edit the hell out of your piece and take care with it.

Do one feature piece as a loss leader to hone your skill and get that clip under your belt. Do it for one of those slightly smaller publications to build your profile. Because often it’s hard to write the story you really want to write for the places that pay the best.

Q: Any other advice for freelancers just starting out?

A: The most common thing I’m asked is how I get my ideas, which I think is the most important thing for a freelancer starting out. You’re nothing without your pitches because nobody knows you.

I tried to force it for a number of years. I’d read a bunch of studies and try to do a Malcolm Gladwell-y kind of thing, or read small town newspapers.

In the end, I found that the best way was reading a bunch of features and thinking intensely about them. And suddenly something switches in your brain and you start recognizing the stories that you want to tell. You just start to recognize what that piece would look like and what would interest you about a piece like that.

When you’re bartender and you talk to someone, or you talk to someone at a party, or you’re reading a story and you notice this tangent that no one’s explored yet — that’s kind of the superpower that you gain after you’ve spent a lot of time thinking about how magazine features work.

You can find samples of Nicholas Hune-Brown’s work on his website and follow him on Twitter at @nickhunebrown.

*This interview has been edited for clarity and length

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