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Freelancers Need Community, Too: ‘1099’ Events Aim To Empower, Connect Chicago Gig Workers

Music and culture writer Ernest Wilkins wants to bring better resources to city freelancers. And no, he doesn't mean ping pong.

Ernest Wilkins is teaming up with Logan Square's Pilot Project Brewing on the event series.
Courtesy of Samantha Parquette; Facebook
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LOGAN SQUARE — Chicago-based music and culture writer Ernest Wilkins is launching an event series he hopes will make life easier for people like him — freelancers.

This past winter Wilkins went full-time freelance after 10 years of freelancing on the side while working full-time jobs at companies like RedEye, Reverb and Red Bull.

Wilkins said when he made the shift he was struck by how few financial resources and community-building opportunities are available to freelancers across all industries — not just writers.

He said he was especially frustrated because freelancers make up a lot of the American workforce nowadays: 35 percent as of October 2019, according to Fast Company.

“I’m pretty depressed about how freelance culture hasn’t really been catered to outside of the faux-WeWork bottomless coffee or beer culture that brands have worked with over the last five or so years,” he said in an email.

Determined to change that, Wilkins decided to launch 1099, an event series named after the tax form freelancers use. The goal of the events is to bring freelancers together so they can learn how to better navigate the world of freelance and have some fun in the process.

Wilkins has teamed up with friend and former coworker Dan Abel, co-owner of Pilot Project Brewing, on the project.

All of the events will be held at the Logan Square brewery incubator at 2140 N. Milwaukee Ave. The first one is set for 7-10 p.m. Feb. 20.

For the first event, Wilkins plans to bring in a couple of speakers to talk about the financial ins and outs of freelancing. For example, he wants experts to talk about the slow months in various industries.

“If it’s going to slow down for the summer, a lot of budgets you’re pitching are dead starting in August — it’s being able to communicate that information,” Wilkins said.

Wilkins said he’s also interested in bringing in some cannabis companies to talk about freelance opportunities.

“I want to make sure that people who attend can take something away that they can activate immediately,” he said.

If the first event goes well, Wilkins hopes to host the events on a quarterly basis.

Wilkins emphasized that 1099 isn’t just for freelance writers — it’s for freelancers across industries who need questions answered and want to build community.

“I understand that people like Facebook groups, but I really think we need to create opportunities for people to interact in person,” he said.

Wilkins is perhaps best known for his five-year gig at the once-daily newspaper RedEye, where he wrote about popular culture, music and nightlife.

He has gone on to work for various companies, both in the news and marketing industries, but he still primarily writes about music and culture.

With a laugh, Wilkins said of his new venture: “Instead of me trying to find you a fun place to go, now my job is to help people find work so they can survive.”

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