Credit: <br/>Illustration by Jason Wyatt Frederick

Massive newsroom job cuts and a populace in isolation helped drive the upsurge in single-operator newsletters in 2020. The number of active writers on Substack doubled between March and June alone, and Mailchimp and Medium also reported increased activity.

Chicago music journalists—including the three Reader contributors quoted in this piece—have contributed to that boom. Ernest Wilkins, who writes about the business of culture on Office Hours With Ernest Wilkins, describes newsletters as a “necessity-built thing” that arose in the mid-2010s when the demand for highly curated content outstripped the resources that traditional publishers devoted to the specialized writers who could create it. Trust in newspapers also declined, with plenty of help from the Trump administration. “So we’ve got to figure out a new strategy to touch people,” Wilkins says. “‘If I don’t trust this newspaper, maybe I trust this columnist.'”

The accessibility and flexibility of newsletters allow for a limitless variety of approaches. Joshua Minsoo Kim has built the increasingly popular experimental-music newsletter Tone Glow around a tight-knit community of contributors, rather than writing everything himself. “Everything’s always more fun when it goes beyond yourself and your own interests,” Kim says.

David Anthony launched Former Clarity in 2019, but after he developed a serious illness, it stopped being a music newsletter and started being a newsletter about music, navigating the healthcare industry, and “finding clarity,” as he puts it. He says his work has fostered deep connections between him and his readers. “People are willing to open up a bit more because they’re just replying to an e-mail that only I’ll see instead of sending a tweet out into the world,” he says.

Wilkins doesn’t think the market is saturated yet—he’s confident there’s more room for Chicago music writers to succeed with their own newsletters, provided they’re willing to put in the work. “What I see happen, especially in our city, is that people keep sitting and doing things, expecting someone to descend from the sky and tell them that they are valid and worthy,” Wilkins says. “Anna Wintour does not live here. You’re not going to get chosen. So you have to do it yourself.”