Chet Baker sings “Everything Happens to Me” as if misfortune were an old flame he can’t quite bring himself to leave. Billie Holiday sings it as if she has already forgiven the world for every slight it has handed her and would like it to know she noticed each one. In both hands the song turns bad luck into something close to a romance, a run of calamities told with such tenderness that the listener starts to envy the person they keep happening to. That is the trick of the old torch songs. They let you be wry and wounded in the same breath.

Miles Jenson took those two renditions as the seed for “Against My Best Interests”, and what he grew from them is a confession of a more modern kind. The hard luck in his song is something he hands himself. By his own account, getting better has never arrived for him without some vice still sitting in the passenger seat, along for the ride. He can be doing more good than harm on balance and still be doing harm, chasing progress with one hand while the other keeps reaching for the thing that undoes it. Plenty of us know that arithmetic. Few songs bother to do the sum out loud.

What I find most generous in the song is its refusal of the tidy story. Pop likes its arcs clean: the fall, then the rise, or the rise followed by the spectacular crash. Jenson won’t accept that those are the only two endings available. He sets up camp in the long grey middle, the stretch between blossoming and imploding where, as he sees it, most of us spend far more of our time than either extreme would suggest. There is no redemption scene here and no ruin either. There is a man still trying, still slipping, and singing honestly about holding both at once.

Jazz is the right language for that, and Jenson knows exactly why. He describes the music as having a bittersweet throughline that lends itself to self-sabotage, and anyone raised on Holiday will nod at that. The standards were built to carry contradiction. A melody can lean towards the sun while the harmony underneath it darkens, and the singer can smile through a lyric that is quietly falling apart. Going by how Jenson frames the song, rather than any blow-by-blow of its bars, “Against My Best Interests” works in precisely that tradition. It is built on classic jazz-standard structures and dynamics, with sophisticated modulations doing the work of shifting the ground beneath the listener. A romantic, sunlit melody pulls against a sinister undertone, and that pull is the song’s subject made audible. The brightness is the self-improvement. The shadow is the vice that rides along with it. Neither cancels the other out, and the song would be dishonest if it let one win.

Vincent Ott arranged and produced it, and his orchestral setting gives that tension room to breathe. Strings and the wider ensemble lend the song the scale of a classic ballad without smoothing away the ache at its centre. Ott does the same for its companion, and the pairing of a singer this steeped in soul with an arranger working in this cinematic register feels like a meeting of temperaments rather than a set of instructions.

It matters, too, that the song isn’t dressed in irony. Jenson could easily have made a knowing joke of his own backsliding, and the torch tradition would have permitted it. Instead he treats the subject with the same seriousness Baker and Holiday brought to their misfortunes, which is to say with affection for the person suffering them. He has said that what he wants most is for someone to hear his music and say “I always have struggled to name that feeling and now it has a name”, and this song names a feeling most of us carry around unlabelled: the suspicion that we are improving and sabotaging ourselves in the same week, sometimes in the same evening.

“Against My Best Interests” sits on the EP ‘North Star‘, released on 14 August 2026, and it is a quietly brave piece of writing from an artist readers may not yet know but ought to. Where this song turns inward, its title track turns its gaze outward to the country around him, the necessary counterpart to a song about the fights we pick with ourselves.

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