Mac Miller wasn’t always good, but he was always trying to be better. The Pittsburgh native, who died Friday of a drug overdose at 26, developed into a wondrous rapper through a constant process of improvement that was never without its growing pains. His story has been one of resolve, of stumbling and rising and trying to stand taller than before. People recognized in him that search for the truest version of himself. It’s what makes his passing particularly devastating.

Born Malcolm McCormick on January 19, 1992 in Pittsburgh, Pennsylvania, Miller was an indie rap success story from the start. He turned a deal with a rising local rap label, Rostrum Records, and a co-sign from Wiz Khalifa into five consecutive Top 5 debuts on the album chart. His evolution into an accomplished musician, producer (under the name Larry Fisherman), and rap mentor was nothing short of inspiring.

Miller’s fourth mixtape, 2010’s K.I.D.S. (Kickin’ Incredibly Dope Shit), was pure frat-rap juvenilia. It became the cornerstone of his indie empire and induced hand-wringing from rap fanatics. (Some of it was warranted on the basis of privilege and budding talent yet to bloom, some of it harsher than necessary in response to the zeitgeist, then a booming white rapper industrial complex.) Looking back on those songs now, they seem harmless enough: nostalgic party favors from a teenager still figuring out what he was doing.

Mac’s success didn’t wait for him to find out who he was. He continued to dominate rap’s blog era with his next mixtape, Best Day Ever, and the most popular song of his career, “Donald Trump.” When Miller feuded with Trump over who deserved credit for the song’s YouTube views, he wrote off Trump’s claim by saying the track could have easily been about Bill Gates—an unwittingly damning indictment of how generic his songs were back then. By the time he released his debut album, 2011’s Blue Slide Park, Miller had built a cult following: he had the first independently distributed album to hit No. 1 in 16 years. Pitchfork infamously gave it a 1.0.

The conflicting critical and commercial responses signaled a crossroads for Mac Miller, in more ways than one. Scathing criticism, in part, turned a teenaged Mac toward drug use, specifically lean. “You’re 19, you’re so excited to put out your first album, you put it out—and no one has any respect for you or for what you did,” he told Complex in his 2013 cover story. By then, he’d already set out to snatch his respect through sheer force of will. The 2012 stopgap release Macadelic ushered stranger sounds. From that point on, Miller became harder to define and impossible to pin down. He became much better at rapping, too, abandoning the rudimentary mechanics of his early stuff for the easygoing technicality of his indie peers. Mac was always having fun in his raps but now he was fun to listen to. He started drifting through the oddball beats of Flying Lotus and Clams Casino, striking up friendships with ScHoolboy Q, Earl Sweatshirt, Vince Staples, and Da$h.