In the video for his 2020 single Miss Andry, Sydney pop artist Flowerkid sits slumped in the corner of a boxing ring. Drenched in red light, he’s scratched, bleeding and spent, fighting demons both invisible and ever-present. “Who’s to say that you still think of me?” he laments: “I’m just weak and miserable and only five foot three. How do I compare?” It was for songs like this – deeply personal stories of identity, mental health and familial trauma, wrapped up in slickly produced bedroom pop – that Flowerkid (real name Flynn Sant) was pegged as one of Triple J’s Ones to Watch, and caught the attention of Billie Eilish’s manager, Danny Rukasin, who signed him for the US. At just 20 years old, Sant can already look back on the early phase of his career with the nostalgia usually reserved for people much older. “When I’m listening to my music, I feel like I’m time-travelling.” Released on Wednesday, his debut EP – Everyone Has a Breaking Point – features songs recorded over the past three years, a period that began when he came out as transgender. It captures his voice incrementally deepening and moving into a lower register – a side-effect of taking testosterone. “It’s like documenting the journey as I go,” Sant tells me over Zoom. “To be honest, I don’t realise how much it’s changed unless I go back and listen to the first tracks that I made. It’s crazy. I love it. I love hearing the change.” Sant began making music at an early age, figuring out how to play an old Yamaha keyboard he was given by an aunt. “I was born into a Catholic family, so, you know, I had my communion and reconciliation, all of that,” he says. “All of that” encompasses the guilt and shame Sant believed was his due inheritance, burdens he carried in secret and now channels into his music. On I Met the Devil at 4 Years Old, he raps over distorted synths and sirens: “Someone came up to me with faith and hope / Saying I sinned trying to hang myself from the rope / So I told her … God was a no show.” “I was so little and all I could think was that I was a sinner. I was going to hell,” he says. “I tried praying and I tried to submit myself to God and every time these bad things kept happening … I just couldn’t make sense of it. I thought, ‘Am I a bad person? Is that why my prayers aren’t being answered?’ And that continued for a long time.” By high school, Sant identified as “a bit of an atheist” (“I didn’t really believe in anything because I thought … I’m not getting any blessings here”). But by then he was exposed daily to a new kind of oppressive structure: teenage boys, whose private, Catholic school uniforms granted them a free pass to torment and intimidate. “In year 10, I came out as liking girls. It was before my transition and [my girlfriend and I] got a lot of shit. The culture of what masculinity is supposed to be, it was disgusting. And it was in my nightmares, it was in everything I thought of. “I had these thoughts like, ‘I think I’m transgender’, but they were in the back of my head.” He “kept them back there” until he left school, after completing year 10 in 2017. “If I stayed in school, I wouldn’t have come out at all. It was such a hostile environment. Once I had that space, I was like, ‘oh, that’s what’s going on’.” As Sant began to understand his changing gender identity, his rage and distrust towards men mutated into what he describes as feelings of inadequacy: did he hate the confident, broad-shouldered boys around him, or envy them? These are the questions he grapples with on Miss Andry: “I never hated you, I don’t even hate them, I just hate myself,” he sings. “Taking shit out on you was never right.” The song – Flowerkid’s break-out – resonated with other men, who reached out to say it had articulated their own complex feelings about masculinity. Feedback from fans is validating, but as he’s grown in popularity, the line between “Flynn” and “Flowerkid” has become finer – and more vital. “Why I started Flowerkid was to help people, and to give them a universal language that they can mourn to, heal to – whatever,” he says. “Something that I’ve battled with is having this overwhelming sense of responsibility for people to … to be well. Which can be very burdening and heavy sometimes. It’s hard separating from Flowerkid; it feels like it’s me.” The song Vodka Orange Juice is the tender and nuanced heart of Everyone Has a Breaking Point. On the surface it’s a recollection of a high school party. As the social dynamics play out with the help of sickly boozy concoctions, Sant floats above, narrating as the tall boys (of course they’re called “James”) exert their dominance, the girls yield to them, and the kid with the scrawny arms seeks the safety of the corners of the room or the privacy of the bathroom. That’s where he stares at his reflection, resenting what he sees. “Maybe it’s the way that I act / Or it might be the way I look,” Flowerkid sings. “I can’t help the way I am / I didn’t sign up for this life, but I’m doing the best that I can.” Everyone Has a Breaking Point is out now