This song finds Alesana reflecting on their career. Vocalist Shawn Milke explained to Artist Direct
: "We've always been about the art behind our music, and we care very much about the songs we write. We've had many opportunities with different labels and tours we could've done. It's like, 'Well, if you guys just do this tour with this style of music, you could get bigger than you are.' While we've had opportunities to make decisions about our band based on financials, popularity, fame, or what-have-you, our decisions always come down to what's best for the art we create. That's the reason we do this."
"It's a big reason we love what we do, and it's why we have a section of our fans that are like a cult following, because they realize we respect our art so much," Milke added. "The idea of 'Second Guessing' is, 'Was that the right decision?' It's a back and forth, left-brain and right-brain look at the choices we made."