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Freelance With A Family: Advice On Making It Work From One Of America’s Top Rock Critics

Jessica Hopper on how she kept her creative dream job–and her family–thriving.

Freelance With A Family: Advice On Making It Work From One Of America’s Top Rock Critics
[Photo: Flickr user Seniju]

In the early ’90s, then-ninth-grader Jessica Hopper started putting out a fanzine to write about her favorite bands in Minneapolis. She turned that into assignments for local publications like City Pages, and then national magazines including Spin, getting her first paycheck as a music writer in 10th grade. Hundreds of reviews, features, and essays later, Hopper has one of the most well-known voices in music journalism, both in the local music scene where she lives in Chicago and nationally. This month, she releases The First Collection of Criticism by a Living Female Rock Critic, an intentionally provocatively titled anthology of her years of work (she confesses in the book’s preface that the title isn’t technically accurate, but that it is “about planting a flag; it is for those whose dreams [and manuscripts] languished due to lack of formal precedence, support and permission”). The collection ranges from A-list profiles, to an in-depth feature on the relationship between indie rock and advertising, to a landmark personal essay about emo’s inherent sexism.

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Jessica HopperPhoto: David Sampson

As of last year, Hopper now has her first staff job as a senior editor at Pitchfork and editor-in-chief of The Pitchfork Review–but for two decades, she supported herself, and then her two children, and for a time her husband as well, as a freelance music writer. While she did some PR on the side for a time, her primary source of income has always been the highly competitive, creative, and decreasingly lucrative field of rock criticism. She talked to Fast Company about how she got into the field with no experience, and how she has maintained a creative passion as a lifelong, bill-paying career. (Disclosure: I have edited some of Hopper’s work at Rolling Stone, and we’ve bonded over the challenges of being music journalists with small children.)

Learn By Doing . . . And Doing . . . And Doing

If you love to do something, cultivating your talent to a professional level still takes patience and grind. Hopper is the first to admit that she didn’t start her creative career as any kind of prodigy. “I don’t think I actually learned how to write until I was about 10 years in,” she says. “Before that, I think I was pretty much just making fun of bands. But I was really autodidactic and I thought that anything that you’re interested in doing, you just learn by doing. I was calling and leaving messages as a 15- and 16-year-old being like I totally don’t understand, I’m in ninth grade and I’ve never written professionally, but you should let me.”

While the traditional path would have been college, journalism school, and a slew of internships, Hopper skipped all of that and just kept building relationships and her voice. “When I was about 19, I started doing PR for bands, and I did that for about 10 years on the side,” she says. “But I decided I didn’t want to have five employees and turn it into some sort of lifetime hustle. What I really wanted to do was keep writing full time, and so I just took up that challenge, and for the last 10 years, I’ve just been writing full time.”

Six years ago, Hopper turned her DIY ethos into her first book, The Girls’ Guide to Rocking: How to Start a Band, Book Gigs, and Get Rolling to Rock Stardom. The book was technically to help teenage girls become active musicians, but the practical advice about tools, publicity, and how to work with others could actually be useful for any DIY creative person at any life stage. “I think you should talk to the publisher about doing another run with a different cover that shows a stressed-out, slightly overweight mid-30s mom with a dated outfit and a toddler on her hip,” reads one of the book’s Amazon reviews. “It makes me want to start a band!”


Do The Math

A lot of creative industries, including music journalism, are built on giving newcomers opportunities for exposure and experience, and very little money. For those with familial support or very few expenses, it’s possible to take these gigs to build a portfolio; Hopper freely acknowledges that her lack of college debt and decision to stay in Chicago rather than follow the majority of rock critics to New York were critical. “I could take really low-paying freelance work that I believed in, and for a very, very long time, I think I had the cheapest rent in all of Chicago,” she says. “My rent was $250 a month until I was 30 years old. I could make $250 a month just deejaying if I had to when I was younger.”

But as an adult with two children, things are much different. Both money and time are at a premium, so before she started a family, Hopper spent about a year strategizing about how to take home the most consistent pay for a limited number of weekly hours.

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As much as the general freelance wisdom is to try for every assignment possible, Hopper focused her pitching and relationship building on higher-paying regular work, even if it meant saying no to more fun one-off assignments. “I wrote regularly for GQ, which paid a lot more than everything else,” she says. “I got columns, things I knew would give me a paycheck every single month. I focused on places where I had good relationships with editors. I made sure had a full spectrum of work where I had weekly work, I had daily work, and I was working for monthlies. I really diversified what I was doing so my eggs were never in one basket.”

She also says the calculus wasn’t just about what paid the most, but also what fed her creativity, rather than sapped her energy. “I don’t want to say I had a hierarchy, but I found gigs that actually meant something to me so that it never was draining,” she says. “I was excited about doing the work. When people asked me, ‘You have six regular gigs, how do you do it?,’ I was like, ‘I’m really psyched every single time I crack open my computer.'”

This was particularly important with children–because self-employed workers don’t get paid family leave, Hopper made a deadline six days after giving birth to her first son.

Find Your Niche

To get consistent work as a freelance creative in a competitive field and command the rate you need, you have to be more than good at what you do–you have to be in a position to do something that few others can, and make sure everyone knows it. In addition to cultivating a unique voice, one thing that Hopper did on this front was turn her physical location outside the center of the music journalism universe into an asset.

“Because I was in Chicago and I wasn’t going to travel to do stories, at least until my kids were older, I looked for big stories that were in town that nobody outside of Chicago would know about or be able to report to the same depth,” she says. One of those was a 2013 feature for Buzzfeed about the artist-friendly executives in Chicago’s advertising industry that helped turn around the business of indie rock.

“I was like, what is an industry here that isn’t necessarily the same elsewhere?” she says. “We have a huge ad business and I have a lot of ins, so I reported that for a year. No place would have sent a reporter out somewhere to document stuff and report stories. I just strategized about what’s in front of me that I can be the expert on, that I have the advantage because I’m in Chicago, how can I make it work that I’m not in New York? The ended up being one of the biggest stories of my career.”

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Get To Know Your Creative Clock

Like many working parents, Hopper now has a hard stop time when her kids are home, and puts in a second shift after bedtime. Managing this well is particularly important when you’re your own boss, doing work that is almost entirely creative.

“One of the ways I managed to get a lot done is that I recognized the times of days when I was most clearheaded and capable, and I made sure that those were the times of day where I had childcare, or when my husband I were splitting our work and kid time 50/50, both working from home, that I could have that time slot, so to speak,” she says. “Also, once I had kids, I just got realistic about how much I was ever going to get done, or the quality of work I could get done at the end of a long day or work and parenting, and just let myself off the hook and made sure what I had slated for that post-bedtime hour–or three–was never heavy lifting intellectually. I started doing a lot more multitasking–making sure I had the records I was reviewing on CD in the car for whenever I had a spare 15 minutes to myself to dedicate to that, making sure I always have a way to make notes, as things occur to me, so that I would have the bones of a piece before I even sat down to start cranking on it. I no longer had the luxury of sitting there and toddling through my lede.”

When All Else Fails, Keep the Lights On

Not long after Hopper had her second son, her family went through a six-month period when her husband, who had been in law school for much of their earlier marriage, was setting up his law practice and not working regularly. When she was suddenly her household’s sole support as a freelance rock critic, all the careful planning and time budgeting flew out the window. She could have looked for an unrelated job with a steady paycheck to fill the gap, but she knew she didn’t want to sideline her main passion until things stabilized.

“It was a really exciting and at times frightening challenge to think, okay, two kids. . . How do I support four people on a freelance income?” says Hopper. “I just gunned for it. I tried to never miss a deadline and I hustled every hustle I had. That was totally frightening. I was doing three columns at once, and any single record that mattered at all to me, any festival I could possibly cover, any angle I could have, I was pitching it. For that period of time, there was no grand plan. It was just keep the fucking lights on.”

About the author

Evie Nagy is a former staff writer at FastCompany.com, where she wrote features and news with a focus on culture and creativity. She was previously an editor at Billboard and Rolling Stone, and has written about music, business and culture for a variety of publications.

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