Caillat explained to the Associated Press why she titled the album Breakthrough
: "I have been struggling for years with stage fright, and finally I woke up a couple of months ago and I knew I had a lot of preparation for this new album coming out. I was going to be going on tour again and I had to find ways for me to love it, and breakthrough my fears and my insecurities and be comfortable with myself as a young woman... Sometimes I would be having a great show and having fun and the next night I would be terrified and almost cry before I go out on stage. It was just inconsistent. I think it has to do with being comfortable in your own skin and finding out how to do that."
Caillat added that she felt pressure from the expectations of her sophomore album after the success of her debut release. She said: "I felt pressure from the beginning when I had to write for this record because after I had been on tour for a year and a half and when I was writing on tour I was writing these sad songs about missing home and I was just worried that I was going to have this depressing album. Once I decided to let go of that I went to Hawaii in January with my friend Jason Reeves
and Kara DioGuardi. We were there for three weeks and we had this house on the beach and just were writing songs and talking about experiences and love and break-ups that we all go through and really having like this therapy session of everything that we go through in life, and how we can write about it and how we can have people relate to it."