For Mason Jennings, finding a place to call home was more of a lesson in rock music history than a simple real estate search.

“I grew up in Pittsburgh and I dropped out of school at 16 to pursue music,” Jennings says. “I traveled around the country for a while.”

But when it came time to choose a place to settle down, Jennings says he picked a city in which many of his favorite musicians had once called home.

“I really liked Minneapolis because of bands like Hsker D and The Replacements,” Jennings says.

It’s these same Minneapolis roots that have given way to comparisons of Jennings and one of folk music’s most well-known voices — Bob Dylan.

“I can see the connection in Dylan’s earlier stuff, but his newer stuff — now that he’s kind of old — sounds sort of crazy,” Jennings laughs. “But I think it’s always a compliment.”

Unfortunately, the long Minnesota winters haven’t helped Jennings in his ability to write Dylan-esque lyrics for his songs.

“In the winter I can write music, but the words don’t usually come,” Jennings says. “For some reason, the summer is when I write all the words to my songs.”

This may be the precise reason for Jennings’ sudden change in musical style. Jennings says his most recent album, “Simple Life,” is a departure from the traditional folk sound of his previous albums.

“I was really happy and listening to a lot of Paul McCartney,” Jennings said. “I wanted to write more in a pop theme. Less folk — just melodic pop songs.

While long-time fans may prefer the grittier folk sound of Jennings’ self-titled 1998 release or his 2000 recording, “Birds Flying Away,” he says repeating the same material on his upcoming album would be a mistake.

“I try never to repeat myself. I would hate to make the same record twice,” Jennings says. “I strive on every album to try new things.”

Jennings is working on another album with new bandmates Brian McLeod on drums and Chris Morrissey on bass. Although his cold-blooded writer’s block is now in full effect, he says he isn’t worried about finishing lyrics for the project.

“For about a year I haven’t written much [lyrically], but I don’t have to worry about it because when the summer comes around, it will all come out,” Jennings says.

For many folk artists, lyrics are an integral part of creating the finished product, but for Jennings, the creative process is reversed.

“Almost all of my songs start with the guitar,” Jennings says. “Usually a couple of key words or phrases will jump out that express the sentiment of the song.

“I’ve never written a song another way — it’s always the guitar or piano first and then the words.”

Regardless of how it’s created, Jennings says a song’s sentiment is what sets it apart from the crowd.

“What makes a song good is when there’s honesty about what’s really going on — when there’s sadness, but also an underlying theme of hope,” Jennings says. “That’s like my favorite thing — when a song makes you feel like nothing else does.”

Jennings says he hopes those underlying themes of sadness and hope will translate well to the small-venue atmosphere of the Maintenance Shop Friday as it has in the past.

“I really like playing the Maintenance Shop,” Jennings says. “It’s nice because it’s such an intimate environment to play music.”