If you’re like me, you were or are currently being pulled kicking and screaming into adulthood. There’s plenty of advice for navigating hardship (your parents likely supplied plenty of adages), but it’s often short shrift for navigating the regularness of life. All of the questions feel stupid: Can you corner your thoughts long enough to complete the task? Is there any one correct way to be? How much should you know about the things that you don’t? Are you behind? It’s dismaying, chasing something that seems within arm’s reach for everyone else yet lies just on the periphery of your own understanding. With no satisfying answers available, we make it all up as we stumble along. Mac Miller was emblematic of that ethos. Mac Miller asked all of those same questions.

His music, much like his career and his life, was an unlikely reassurance that you could always learn to be better. However long you spent wandering around in the dark, stepping on rakes, you might in time—if you do the work—find the light switch. Few artists wandered better than he did.

Not at first, which is the point: He rose to prominence in the neon-colored age of frat rap, where a bunch of dudebros in lax pinnies, snapbacks, and aviators rapped awkwardly about doing keg stands and making the night legendary, 7 a.m. freshman seminars be damned. Born Malcolm McCormick, Miller’s first tape was put out under the name Easy Mac, like the boxed macaroni. The first song on Mackin’ Ain’t Easy was called “Barz for Dayz,” on which he gleefully rapped “We playing games in this jungle, Jumanji / With bomb tree, hidden under all my dirty laundry.” He was extremely 15 years old at the time but also extremely decent for 15.

He was 18 when people began to decide that he was nice—the indie rapper coasted into a surprisingly large amount of mainstream success on the back of two mixtapes: 2010’s seminal K.I.D.S., a lot of which was standard suburban teenager fare, and 2011’s Best Day Ever, which received a commercial bump from a feud with Donald Trump. Miller was still just a goofy, grinning white kid rapping with proficiency about things parents just don’t understand, appealing mostly to other kids who looked like him. Yet Miller was always a bona fide music nerd. It sounds trite to say so, but his genuine love for the art form is ultimately what sustained him and later spurred his reinventions. (You also can’t discount his self-awareness; he was flip about his advantages at first but later developed a well-reasoned perspective about what a white rapper’s place in the game is or should be.)

For instance, he probably won’t be remembered for 2011’s Blue Slide Park. Miller showed minimal-to-nonexistent growth on his first album, but it nonetheless debuted at no. 1 and eventually, after getting savaged by critics, went gold. It wasn’t until 2013, after some very public soul-searching and a promising, introspective mixtape—2012’s Macadelic—that he won everyone over. He fully blossomed from a lovable stoner dork into something weirder on his sophomore album, the murky, genre-agnostic Watching Movies With the Sound Off. He’d started hanging out with Schoolboy Q. He walked barefoot through Brooklyn freestyling dexterously about sitting Seder with Bill Clinton. He made songs with Earl Sweatshirt. These swerves were all, critically speaking, correctives. Miller was finally an artist.

He won me over personally with “Objects in the Mirror.” It remains my favorite Mac Miller song, and if you have the time, you should watch the live version from the Space Migration Sessions.

Understand that prior to seeing this video, I had no knowledge of Larry Lovestein, the alter ego under which he released a 2012 jazz-inflected EP of love ballads. Around that time he was also working with Pharrell Williams on their ill-fated Pink Slime project, and during those sessions Pharrell encouraged Miller to sing. And here he was, in a King Krule tee, backed by the Internet, really singing. Others may mark it elsewhere, but to my mind, this is the inflection point for an artist—for a person—preoccupied with becoming comfortable within himself.

I prefer this to the recorded versions you can find on Watching Movies or 2013’s Live From Space because of its imperfections. His voice here stretches anxiously for notes just above his range. It seems like the drummer’s time is just a little quicker than he would like, not allowing Miller to linger on any one of his thoughts, forcing him to go for it. His gruffness is smoothed out by bits of reverb at the end of each line, but he’s running out of breath, which lends gravity to a song that at times can be a little cheesy. That’s the gamble with naked honesty:

Mend a broken heart, girl, if you can

I don’t expect you to be capable

You got the world right in your hands

And that responsibility is unescapable

I promise that I’ll be a different man

Please give me the chance to go and live again

I’m having some trouble, can you give a hand?

Piecing together an image of Mac after his passing makes this song and this performance feel epigrammatic. “I promise that I’ll be a different man” has stung the most over a few dozen listens these past few days. This past May brought new and profound lows for Miller, whose struggles with addiction were an open book. He had a public split with his girlfriend of two years, ran his car into a tree, fled the scene, and all of his social accounts went dark. For anyone else that could mean renewed focus or album mode—“Your mind works through the worst with the guy who made Faces, the 2014 mixtape full of ominous lyrics about hard drugs and musings on premature death,” Craig Jenkins pointed out in a Vulture profile that ran the day before Miller’s death of an apparent overdose.

What makes this tragedy doubly galling is that on the outside, nothing seemed to suggest that he was living toward that. Watch his early-August NPR Tiny Desk Concert. What do you see? A man wizened by mishaps, at something close to peace, razzing Thundercat for putting just a little too much effort into using the shaker. The lyrics were chilling—“I can feel my fingers slippin’ / In a motherfuckin’ instant I’ll be gone,” he sighs on “Small Worlds”—but Mac oozed warmth and approachability, filling in the play gaps with banter about how he didn’t know what to say.

All of which is to say that he seemed happy; the kind of happy that lies on the other side of weary. Maybe he was even hopeful. He had cause to be. He’d just released his most accomplished album and was gearing up for a fall tour with a band that floored John Mayer with all of its possibilities. “You gotta know that if you weren’t familiar with Mac Miller, you were about to be, whether you would have seen him at a festival or a friend was going to catch a show and tell everyone they knew about it (like I did),” Mayer wrote in a emotional note on Instagram. Elton John, who dedicated a recent performance of “Don’t Let the Sun Go Down on Me” to Miller, lamented both lost talent and potential.

Mostly though, if you look around on Twitter and Instagram, you’ll find fellow musicians, collaborators, and bloggers mourning the person about whom almost no one has anything bad to say. That’s telling, and worlds away from the heady days of Blue Slide Park. You don’t necessarily know more at 19 than you did at 18, but at 30, you could be a completely different person. Now all we can do is imagine who Mac Miller might have been.

He was 26.