When Melancholy Somehow Feels Like Peace
Not every melancholy song makes me sad. Some have the strange ability to make me exhale, settle into myself and simply think. Gregory Alan Isakov’s “Mistakes” is one of those songs. Its melodies are laced with remorse, yet there is something wonderfully laid-back about the way they unfold, which is why I often play it when I want to relax—or when a deeply reflective mood suddenly convinces me that I should be writing.
Yes, this is one of the many songs I turn to while patiently awaiting the Nine Sisters to invite me into their otherworldly domain of muses. Apparently, divine inspiration keeps its own schedule. Until they arrive, Isakov’s gentle vocals and wandering instrumentation do a pretty good job of opening the gates.
Letting the Music Help Me Think
“Mistakes” also finds its way into my evenings when I want to replay the day: what went right, what went wrong, what I should have said differently and what probably deserves to be left exactly where it happened. There is something about contemplative thoughts being accompanied by the right melody that seems to guide the mind towards better reasoning. The song’s imagery feels perfectly suited to that state.
Isakov writes of being carried by a golden wave only to end up lost at sea, caught in an undertow and continuing to pay emotionally for mistakes even when moments of light begin to appear. I hear it as a reminder of how one decision can sometimes pull us farther than expected—and how regret has an annoying habit of sending invoices long after the original purchase. Yet the song never feels punishing to me. It feels contemplative: an invitation to sit with what happened, learn whatever the moment has to teach and eventually surface again.
The Farmer Behind the Daydreams
Gregory Alan Isakov is a Johannesburg-born singer-songwriter and horticulturist who was raised in Philadelphia and now calls Colorado home. His quiet, atmospheric blend of indie folk has grown across six full-length studio albums, including the Grammy-nominated Evening Machines and 2023’s Appaloosa Bones, where “Mistakes” appears as the eighth track. Interestingly, Isakov has said that “Mistakes” was actually an older song he eventually dug back up for the record.
He has also spoken about deliberately making time for daydreaming while writing—almost like entering another world and waiting to see what comes from it. Perhaps that explains why his music works so beautifully when I am waiting for my own muses to arrive. And when he isn’t cultivating songs, he quite literally cultivates the earth, running Starling Farm in Boulder County and providing produce to local restaurants, CSA members and a food bank. Apparently, some people grow vegetables and existential crises set to beautiful music. Yes, an overachiever for sure!
Want to Explore More Songs and the Stories Behind Them?
The Soundtrack of Life: Songs That Stayed With Me
This music reflection is part of my growing collection exploring the songs, memories and emotions that have stayed with me. Discover the other songs and the personal stories that made them unforgettable.
Could “Mistakes” Guide Your Next Quiet Hour?
The next time you need to unwind, write or simply make sense of the day you just lived, give “Mistakes” a listen. Sometimes the clearest thoughts arrive when we stop forcing the answers and let the right song lead us into them.
