Rather than immediately starting work on a new album once, Jimmy Eat World had finished their tour cycle for Damages, the band decided to take a year off. This song was inspired by that sentiment of refusing to be tied by work-related goals but instead taking the opportunity to try out new things. Frontman Jim Adkins explained to Rolling Stone: "'Sure and Certain' sums up the idea that if you're cruising with blinders on and are just goal-driven, it's limiting because you're missing out on what's immediately around you. If you're unwilling to open up and say yes to things that might seem scary, then you're just missing out on so much."
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