White-collar folk with Jason Pilling

Jason Pilling is a singer-songwriter who draws lyrical content from a lifetime of being a regular nice-guy with a math degree, a nice little nuclear family, and 20 years of white-collar career experience. “I celebrate the nuance of a normal life,” Jason likes to say, by which he means he doesn’t do love songs. Genre-wise, it’s mostly folk, but Jason likes to tinker. What comes out reflects the tools on hand. His 2004 album “Ambidextrous” was guitar/vocal driven because that’s what he had. The 2019 album reflected the explosion of what one person could do with guitar and a laptop. Since finally quitting his day job in 2020, sounds have been built, sampled, synthesized, and collaborated to release three EP’s and fifteen singles. Jason performs around Toronto, and is in the middle of recording two more album projects in 2023.

Jason shared his song Protect the Cubs. Download the lyrics to follow along.

We talked about:

• Jacob Moon and his Looping Master Class sessions at Long & McQuade
• The passing away of David Crosby of Crosby, Stills, Nash, and Young
• Finding the structure and schedule to do songwriting that works for you
• How Jason made short video “vignettes” that spawned full “grown-up” songs
• How Jason was able to use a common experience with a friend to focus the idea for Protect the Cubs
• The role of the guitar rhythm in a lyric-focused song
• How to incorporate abstract lyrics in your songs, like Gord Downie
• Ways to set apart your chorus
• How there are hardly any songs from a parent’s point of view
• Jason finds that deep learning of a cover song is the best way to learn about songwriting