Songfacts®:

• In early 2020, Rascal Flatts announced they would be disbanding at the end of the year following one last tour. Unfortunately, their farewell concerts were canceled due to the coronavirus pandemic, but they still released a final EP. This is the title track.
• The upbeat song finds Rascal Flatts singing about making the right life choices.
  
  Did you make 'em laugh or make 'em cry
  Did you quit or did you try
  Live your dreams or let 'em die
  What did you choose
  What did you choose
  When it all comes down
  It ain't if, it's how they remember you
  
  As this is the lead single from Rascal Flatts' final record, there is a parallel meaning of the trio reflecting on their legacy.
• Marc Beeson, Josh Osborne and Allen Shamblin wrote the track. Rascal Flatts' Jay DeMarcus compared the first time they heard the song to their first time listening to "Bless The Broken Road." "It's a timeless message that will inspire people, and it's about what kind of mark you leave behind when you leave this world," DeMarcus told The Boot: "What kind of legacy do you have? And, for me, when I heard it, I first went, 'What are people gonna say about me when I'm gone?'"