Songfacts®:

• In this acoustic ballad from Dawes' seventh studio album, lead singer-songwriter Taylor Goldsmith sings from the perspective of a young man from a working-class Florida family who takes comfort in his childhood memories of his hometown as he approaches adult responsibilities.
  
  "'St. Augustine At Night' is a song about one's relationship to their hometown," Goldsmith explained. "But also is a song about the varying degrees to which we all watch our lives pass us by."
• Goldsmith grew up in Southern California but St. Augustine gave him the hometown vibe he was looking for in the lyrics. "I have relatives who live in St. Augustine, Florida, and every time we go on tour, I visit," he told Magnet Magazine in 2020. "We go fishing and have a fish fry. We hang out at the local bars, and everybody knows everyone else. I've never lived anywhere but LA, so there's a romance to that. I like the idea of finding solace in a hometown. Wherever you come from, no one else can interrupt that relationship - even if you never go back."
• The band sought Nashville producer Dave Cobb, known for his work with Chris Stapleton, Brandi Carlile, and Jason Isbell, to helm Good Luck With Whatever. Under Cobb's guidance, they didn't have the chance to second-guess their instincts. "He forces the whole experience to move at the fastest pace possible - and that sounds uncomfortable, which it is," Goldsmith noted. "I think that's why he's so effective. We'd sit down on the couch and play him a song, and we'd do these little adjustments. Then we'd cut it live - all four of us, with me singing the lead vocal. Typically after the second or third time, he'd say, 'Great, that was it. Let's go back to the couch and do the next song.' He makes it so an artist can't overthink."
• Prior to releasing this album, Dawes embarked on a tour to celebrate the 10th anniversary of the release of their debut album, North Hills.