Early on in Parker McCollum’s career—before he had a career to speak of, really—his brother Tyler gave him a challenge. Parker had been in Austin, Texas, half going to college and half writing songs, but mostly doing nothing. “Floatin’ through, skatin’ by,” he told Apple Music in his Up Next interview. “No direction, no hustle.” So, his older brother says, how about you go play 30 shows in 30 days, just to see if you can. Parker had always trusted Tyler: They’d fallen in love with music together, learning guitar in the family barn while absorbing George Strait and Willie Nelson, The Judds and Jerry Reed. So Parker went out and played a show—just an open-mic-type thing at a bar. Then he played another, and another. “And I’ve been playin’ ’em ever since.” Born in 1992 on the outskirts of Houston, McCollum is a kind of hybrid figure: on the one hand, a baseball-hat-wearing guy who captures modern Nashville’s casual, rock-friendly sound; on the other, a songwriter whose interest in the Americana of Townes Van Zandt and Steve Earle puts him into quieter, less commercial territory. Part of it’s age (his breakthrough song, “Pretty Heart,” didn’t hit until was he 27), but part of it’s temperament: Not only did he want to work on his own clock, but he never felt all that young to begin with—a bittersweetness he captures in “Young Man’s Blues.” “I wanted to do it the hard way,” he said. “I really wanted to earn it.” The 30 days—that’s where it started. Where it’s going, he’s proud to say he’s not quite sure.