Chicago singer-songwriter Tanner Dane has shared his new single ‘Hardest Lessons Learned’, out now via Easy Does It Records.

Following ‘Gotta Love Somebody’, the new track finds Dane looking back on the end of a relationship with a little more distance. It is a song about the kind of growth that arrives too late to save what has already gone, but still leaves something useful behind. Rather than turning the lesson into easy comfort, Dane lets the song sit with the loss itself.

“This was written during a period of reflection after a breakup, when I came to understand that personal growth sometimes comes at a painful cost,” Dane says. “The song explores the realization that becoming a better person can happen too late for the relationship you hoped to save, leaving behind lessons that were earned through loss.”

Dane wrote the song with fellow singer-songwriter Levi Foster in Nashville in 2025. It was engineered and mixed by Ziyad Asrar of Chicago indie band Whitney.

The single follows a busy period for Dane, who has been building a local following in Chicago with sunset performances on Lake Michigan, as well as more informal shows outside the usual venue circuit. He is also preparing for a second Backyard Tour, built around non-traditional spaces such as backyards, garages, rooftops, lofts, alleys and parking lots.

Dane first became known as the frontman of Chicago band Hollyy, before moving into his solo work with the 2025 EPs ‘Cut Me Loose’ and ‘Pull Tabs’. His writing still carries some of that band energy, but ‘Hardest Lessons Learned’ puts the focus on the song itself: direct, reflective and made for anyone trying to find some use in heartbreak.

Tanner Dane is set to play an official Lollapalooza after party at Lincoln Hall in Chicago on July 30.

‘Hardest Lessons Learned’ is out now via Easy Does It Records.

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Easy Does It Records Website / Facebook / Instagram / Bandcamp