Songfacts®:

• This ballad features harmony vocals from James Taylor. "I've loved his voice forever," beamed Amy Grant to Billboard magazine. "I said, 'I hear James Taylor on these lines and I'd love to ask him if he'd sing on this.' He worked from home and he really spent some time stylizing it. He sent me a really sweet email afterwards saying that he'd spent the last several days with my voice in his head and hoped I was pleased."
• Amy Grant recorded "Don't Try So Hard" for her 2013 album How Mercy Looks From Here, which she dedicated to her mother, Gloria Grant, who died in April 2011. Gloria was living with Lewy body dementia, but shortly before her death, she gave Amy a simple request that echoed through the entire record.
  
  During one of their final visits before Grant left for a tour, Gloria looked up with a smile and asked, "Oh, you sing?" When Grant confirmed she did, her mother offered one piece of advice: "When you walk out on that stage, sing something that matters."
  
  Grant told Hope 103.2 that those words remained "whispered in the back of my head" throughout the recording sessions, but she connected them most deeply to "Don't Try So Hard." Built around themes of grace, self-acceptance, and letting go of the need to prove your worth, the song acts like a personal reminder. The message is something she has to "sing to myself all the time."
• Unlike albums conceived around a single concept, many of the tracks on How Mercy Looks From Here were written years before her mother passed. Grant and producer Marshall Altman (Natasha Bedingfield, Matt Nathanson, Kate Voegele) only gradually realized how cohesive the collection was becoming.
  
  Grant described the album's creation to Songfacts as like making soup by "digging in the refrigerator, digging in the freezer, looking in the pantry" and throwing together whatever was on hand. It was only near the end of the project that she realized the songs had bonded into something far deeper than she or Altman had planned.
  
  That realization lands squarely on "Don't Try So Hard." Instead of striving to achieve more or push harder, Grant sings about releasing the pressure to earn love and acceptance in the first place.