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At least once a year, Lera Lynn considers quitting music. She says the social media obligations alone have been enough to send her packing. But it’s when she encounters a fellow artist’s particularly stellar album, song, or even video that the singer-songwriter asks herself a recurring question.

“Who am I fooling?” Lynn says. “These people are good. They should be the ones making music, not me. I think that’s something everyone can relate to. There are a bunch of different reasons why one can be discouraged.”

That Lynn,...

Donovan Woods has given his song “Truck Full of Money” an extensive overhaul, turning the cinematic track from his Juno-winning album Both Ways into an intimate acoustic ballad. This new version, premiering on Rolling Stone Country today, is the first release from The Other Way, an acoustic companion album to Both Ways that will be released May 3rd.

In its original form, “Truck Full of Money” was almost a study in contrasts — it married dramatic, sweeping production to Toronto-based Woods’ meditation on the frequently lonely, unhealthy aspects of a...