Like a lot of talented writers, Anastasia Chipelski didn’t always see the strength in her writing that others do. While she grew up an avid journaler – someone who “had the inclination to be an archivist, to record everything that happened” – she didn’t immediately gravitate toward writing as a professional pursuit. While working in community health in Winnipeg, she would write “mini-essays” on Facebook about her experiences, which were met with comments from friends and colleagues encouraging her to keep writing. “I couldn’t see what they saw,” she told me. Based on the conversations I’ve had with writers, it seems like an inability to see one’s own talent is in fact the sign of a talented writer. Now an experienced freelance editor and writer, managing editor, and memoirist, Anastasia certainly belongs to that camp.
It wasn’t until she got a job with the University of Manitoba student paper, The Manitoban, that things started to really click for her as a writer. Working for The Manitoban “was an awesome experience in a lot of ways,” she explains, “because with two articles due every week I learned so much about my own process and procrastination.” Figuring out how she operated best and how to orchestrate circumstances to “get over the barriers” ahead of her was invaluable. It was also at this point that Anastasia was introduced to and connected with the personal essay as a genre. “My academic background is in cultural studies and media criticism, so it’s ironic that I work in media and come from a background of criticizing it,” she says. “I’m really interested in analyzing culture and mixing in a cultural critique with a personal narrative.”
Anastasia eventually moved away from community health and into editing and writing full time, working as the managing editor of the University of Winnipeg’s student paper, The Uniter, where she managed the weekly paper for four-and-a-half years. In addition to running The Uniter, Anastasia also did freelance editing for local publishers. It was at The Uniter, however, that she started writing a regular column called “Dry Wit,” where she explored issues around drinking culture and sobriety. Further pursuing this mix of cultural critique and personal narrative, Anastasia took a course at the University of Winnipeg as a means of professional development – The Rhetoric of Non-Fiction – where she was tasked with writing a memoir. The feedback she received on her work for that course, which centres around her choice to live sober, encouraged Anastasia to apply for a grant to develop the memoir into a full manuscript. She was awarded the grant, and so began the process of writing a book.
Knowing that her term at The Uniter would last somewhere between three and five years, Anastasia began planning for her move to full-time freelance work. Part of her decision to leave The Uniter was a result of coping with an illness: “I spent a year basically just being able to do full-time work and then I spent some time trying to catch up on all of that,” she explains. “But the office that I was working in was making me physically sick, so when it came to leaving, it was like ‘I just can’t be here.’” After leaving, she realized she couldn’t see herself going back to office work. “A lot of the things that had driven me up the wall about past workplaces, even that I really loved, were a built-in part of formal employment,” she says. “If I have to be at a place, at a time, just filling a seat, and there isn’t something for me to do, I get so squirrely.” Time is something Anastasia is very concise about, partly as a result of working freelance, where she learned quickly how important it is to manage yourself and your own time. “I’d rather not blend work and friendships. That sounds harsh, but if I’m going to a meeting with folks I’m working with on contract, let’s have our meeting and get it done and if we want to chat let’s chat after.” Going back to office life, complete with unnecessarily long meetings and wasted time, was, needless to say, not something that interested her. Additionally, growing up with self-employed parents – her father and stepmother own their own businesses, and her mother ran a sewing business out of their home when she was a kid – normalized the notion of working for yourself. “I have a lot of role models to see that it’s not a completely ridiculous thing to do.”
"A lot of editing happens in these secret places, and part of finding that work has been asking 'Where are those secret places that I'm needed?'.”
While it seems that more and more people are piecing together a living from freelance work – if social media is any indicator, we’ve all got a ‘side hustle’ – Anastasia finds that there’s a divide between the seemingly universal goal of gainful full-time employment and the perhaps more common desire for stable, part-time work. Finding that balance has been key to her own work life. “When I was doing interviews for The Uniter, what I learned most of all is that there’s a vast swath of creatives in the city that want a steady gig – a steady, small, flexible gig,” she explains. “But there aren’t a lot of those to go around.” And, because of the nature of editing work, a lot of it is rendered invisible. “It’s not like other creative industries where people have a product or an output,” she says. “A lot of editing happens in these secret places, and a part of finding that work has been asking ‘Where are those secret places that I’m needed?’”
Having health issues also made it imperative that Anastasia was able to create a work life for herself that didn’t involve long days in an office. Working from home allows her to both take care of herself and, in fact, be more productive. She realized she could get done in four or five hours at home what would take seven or eight at an office, without “having that noise and the potential of being interrupted.” While it certainly takes a fair amount of discipline, Anastasia explains that she has “set up a world that supports taking care of my health and not getting sick or finding some middle ground where I can still live a good life without putting all of this strain on myself.” For example, she sets a timer to force her to get up every 25 minutes for five minutes of stretching, playing with her cats, or doing little things around her house. “By the end of the day I’ve gotten a lot more done in all areas of my life,” she says. “It’s not multitasking in terms of jumping from one thing to the other, but for me it’s been a lot of learning why I procrastinate, and how I procrastinate, and figuring ways to short-circuit that, because no one is going to do that for me.” And, when you think about it, even those of us who work in an office tend to take those breaks regardless, but perhaps in different ways (like checking social media, tidying up our desks, or chatting with colleagues). “At the end of the day we only have so much time and so much energy. We have to be discerning and intentional about how we spend that, and I think I have that freedom,” Anastasia explains.
For Anastasia, life these days involves managing Prairie Books NOW, a publication dedicated to promoting books by Prairie authors and publishers, along with both writing and editing work for freelance clients, all while working on completing her memoir. While she’s done freelance work for a number of years, the biggest change in moving to full-time self-employment is managing the balance between working on your business and working in your business. “A lot of folks will start out just working in it and not building it or developing it,” she says. “So, I’ve been trying to get my head around doing those two things simultaneously, because honestly the dork in me would work on my business full time – I love that stuff.” A lot of that balance involves recognizing those invisible or behind-the-scenes parts of freelance writing and editing that are important and valid, like reading, researching, and working on your own word-based projects. “You have to be doing your own professional development, your own marketing, reaching out to new clients, and then keeping things going,” Anastasia explains. “And then if you want to do anything creative on top of that, you need space.” Creating and maintaining that momentum has been a challenge, but not unmanageable. “When I started freelancing, I told myself I would make the memoir a priority and set aside two afternoons to work on it,” Anastasia says. “There’s the balance between writing when you feel like it and setting aside a time. … I have to argue with myself that it’s still worthwhile.”
Writing a manuscript, especially for the first time, is no easy feat. While at first she approached it as a series of essays, Anastasia now sees each essay as a piece of a larger quilt. “I make a little square, and I make another a little square, and then I have to take all these quilt pieces. … I look at it as an editor and say, ‘How does this fit together? What do I have, and what do I need?’” This also means allowing for her focus to shift and evolve. “I didn’t want to write a memoir because I wanted to write about myself,” she says. “This was supposed to be a sobriety memoir about why I got sober, but it doesn’t actually answer that question, I’m realizing, and that’s actually also okay because there weren’t and there still aren’t narratives around sobriety that aren’t tied to the addiction narrative, the 12-step narrative, the rock-bottom narrative. … I wrote it because this is what I wish I had.” While there are more varied viewpoints around sobriety being published these days, we still live in a world dominated by drinking culture. “The point of art is to illuminate society and connect people, and I think it’s essential that writing do that. I’m also fascinated by how it can do that best. To do something well and simply in any discipline basically erases the work that’s gone into it.”
“The point of art is to illuminate society and connect people, and I think it’s essential that writing do that. I’m also fascinated by how it can do that best. To do something well and simply in any discipline basically erases the work that’s gone into it.”
Being an editor first has been paramount to her success as a writer. “When I finally got around to making my business cards, I intentionally called myself an editor and writer instead of a writer and editor,” Anastasia says. “Not because one is more important than the other, but because everything I’ve learned in editing now informs how I write. I feel like writing is maybe a sexier thing to say that you do, but editing is honestly magic. And being an editor has made me a better writer because it’s made me ask from the very beginning, ‘What am I saying and why?’” Being an editor first also means that she doesn’t dread being edited, but rather welcomes it. She also recognizes the vast amount of back-end work that goes into both writing and editing, like reading other writers’ work, thinking critically about what she wants to say, and trying not to be “too precious” with her words. It’s clear, though, that Anastasia loves editing. “It’s a beautiful thing. … It’s like polishing your boots versus not polishing your boots: you really shine. I can see when I’m reading things if it’s been touched by an editor or not. It’s pretty evident.”
Anastasia’s advice for new writers or people interested in working for themselves is two-fold: acquiring and maintaining some kind of regular writing practice, and balancing “the ideal and the real.” Writing for The Manitoban was invaluable practice for Anastasia because it taught her the discipline and importance of “doing something consistently enough that you can figure out what your own patterns are and what works for you.” That also means learning how to push through procrastination and being critical with yourself, especially “when you’re sitting at the page and you’re like ‘I don’t want to do this.’” Working for yourself also means learning what kind of working life is realistic for you and your goals. Anastasia says it perfectly: “You think everyone’s got their shit figured out, and they don’t.” Balancing work with marketing yourself while keeping the lights on isn’t for the faint of heart: “You have to be psychologically and emotionally ready to deal with precarity. You have to figure out how not to panic, but you also have to figure out the point at which you do need to panic.” Learning when you need to “start printing out resumes” takes some serious self-reflection. But while the advice floating around online explaining how to best be “ready” for freelance work can be helpful, Anastasia recalls that she wasn’t ready in a lot of those ways when she made the move. “I didn’t have a website, I didn’t have business cards, I didn’t have savings. But I was also super ready because I’ve been doing this for a long time. You don’t have to wait for everything to be perfect, because it’s never going to be perfect and there isn’t one way to do it. Try not to buy into the middle-upper-class Instagram vision of success. It’s a lie.” In addition to navigating that balance between being ready and just biting the bullet, it’s important to recognize that none of us can do this alone. “Talk to people who are in similar boats or different boats or younger than you or older than you. … As much as editing work and writing work are invisible, the networks that sustain it are also invisible, but so essential.”
"Try not to buy into the middle-upper-class Instagram vision of success. It’s a lie."