Freelancer Matt Elliot sits on a bench with his laptop, outside a legacy newsroom building, which only has a few lights left on. In a thought bubble that appears to his right, we see that his laptop screen shows the “Substack” logo.

The Substack Dilemma

A longtime music journalist, Michael Barclay began writing on Substack during what he calls a “mid-career crisis.” After working for Exclaim!, Maclean’s, CBC, and other outlets, he launched That Night in Toronto, a newsletter focused on music and culture.