Success is rarely achieved without the grace of an epiphany. One of the earliest is the light at the end of the quarter-life-crisis tunnel. Even the most immensely successful people endure this transformative process, emerging with a clearer vision of who they are, what they want, and how they’re going to get it. The IRS had their hands in Will Smith's pockets when The Fresh Prince of Bel-Air began. By the time the show ended, he was a different type of star. No icon rises to that level without something—or several things—opening their eyes.

Twenty-six is a strange age. It’s new territory; the unfamiliar ground on the other side of 25’s creaky, transitional bridge. Jay Z—who today, at 46, is the most influential figure on hip-hop’s Mount Rushmore—was 26 when he released his debut album, Reasonable Doubt, in June of 1996, one of hip-hop’s banner years. Twenty years later, it’s almost unfathomable to imagine the moves of a man whose last studio album was a piece of branded content creating anything less than a tidal wave-like impact. But Reasonable Doubt, now celebrated as one of the best albums of all time, was relatively unheralded in ‘96. It soared over the heads of that era’s most venerated outlets, but nevertheless offered a portal into an evolving Jay Z's mind. Before the mountain of (clean) money; the Throne; the equally-successful better-half, and the bougie art sensibilities, Jay Z was mortal. Relatable, even: a twentysomething trying to transition from one phase of life to the next while completing the turn from hustler to rapper. And of all the things Reasonable Doubt captured, it’s Jay’s quarter-life reflections that remain the most fascinating and sincere.

Your 20s are all fun and games until you realize how rapidly they fade away. One day you're celebrating your legal right to excess, the next you’re halfway to 30, sparring with the value of your existence. The need for fulfillment grows with age, but contrarily (and cruelly), the window to satisfy is always shrinking. If there’s a hint of aspirational fire inside of you, there’s also a need to attain certain things as you get older. Regardless of whether you’re working a cash register, nine-to-five, or drug corner, there’s urgency. Hence why Reasonable Doubt begins with the sounds of a pounding heartbeat.

Your 20s are also marred by mistakes, pump-fakes, and false starts. Jay Z was already an underground luminary in New York City due to his drug-dealing exploits, but he was an underdog in hip-hop. The rap universe was preoccupied with the impending July release of Nas's Illmatic follow-up, It Was Written; Jay Z's long-overdue debut was largely an afterthought. He was already wary of the record industry after EMI Records fumbled his mentor Jaz O's career, and he had to shop Reasonable Doubt around because labels wouldn't give him the deal he wanted. Dwell on that for a second: Jay-fucking-Z, obvious talent and all, was essentially the guy shoving his mixtape in your face when you leave concerts. According to Kareem “Biggs” Burke, Roc-A-Fella's stoic co-founder and a Reasonable Doubt executive producer, he, Jay, and Damon Dash used their own money to promote the album. Jay Z wanted out of the streets permanently, but he was disgusted with industry politics to the point of wanting to retire after one album. He already earned high rewards via high risk; Reasonable Doubt was supposed to satisfy a creative void before he embraced legitimacy and gracefully bowed out.

Although understandably reticent about the specifics of his past, Jay Z has always been frank when explaining that rap was, initially, supplemental income. “I basically accepted that I’d be a hustler who happened to rap in his spare time​,” he said in his 2010 memoir, Decoded. In an interview with NPR about Decoded, Jay Z opened up about the true meaning of "Can't Knock the Hustle." “Who I was talking to was the guys on the street because rap was my hustle and like, at the time street—the streets was my job,” he explained. But by his mid-20s, he saw the danger in straddling the line separating legal and illegal. The intensity of that heartbeat at the beginning of “Can’t Knock the Hustle” is telling when it comes to the pressure Jay felt to make a clean break from the drug game, but more importantly the pressure to succeed as a rapper.

“Y’all niggas lunchin’, punching the clock/My function is to make much and lay back munching,” he says as the top of the final verse. Jay Z has always zeroed in on the endgame; the bottom line. However, the indicators of success he’d obtained by 26 were frivolous when put into perspective with the scope of his dreams. Jay Z is a man of impeccable vision, one who’s always seen beyond what’s directly in front of him.

Ambition is supposed to switch on during your 20s. The switch never flips for some, but Jay Z has long been defined by the striving force of his ambition (“Acceleratin’ what drives me,” he said at 25 on a song in which the hook asks: “What’s the meaning of life?”) which, by his own admission, was “altered” by his previous career. He elaborated on the change in Decoded:

That ambition defined my work from my first album on. Hip-hop had described poverty in the ghetto and painted pictures of violence and thug life, but I was interested in something a little different: the interior space of a young kid’s head, his psychology. Thirteen-year-old kids don’t wake up one day and say, “Okay, I just wanna sell drugs on my mother’s stoop, hustle on my block till I’m so hot niggas want to come look for me and start shooting out my mom’s living room windows.” Trust me, no one wakes up in the morning and wants to do that.

Reasonable Doubt is a very honest exploration of the adjustment crisis. The mid-20s are a period of dizzying self-doubt and blind overconfidence; elation and sadness; confusion and clarity. Jay Z’s were characterized by the war between his ambition and conscience, and he accentuates the extremes with worldly insight. Stories told through a retiring crack dealer’s weary eyes are made identifiable to anyone who spent a moment of their wonder years uncertain about when the blurry image in the distance—life—will come into focus. Only one life is granted and passes for certain behavior expire in our 20s, so while we should live them to the limit, the fun is balanced by the moments when the party ends and you’re left alone with the sobering truth that it’s all temporary. Knowing that there’s more to life than the right now is why Jay Z listing his resume’s most impressive Big Willie-isms on “Politics as Usual,” drowning the bleak realities of his lifestyle in Cristal on “Feelin’ It,” or justifying his defiance on “Can I Live” is tempered by moments of reflection.

Both versions of “Dead Presidents” are about tenacious pursuit of the American Dream, but Jay Z sounds more aware of the price, risks, wrongs, and rights of his actions on “Dead Presidents ll.” The “divine intervention” that delivered him from those three shots in close quarters and implied realization that he could’ve easily met the same fate as his hospitalized friend shows an acute understanding: you can pay for material lust with your life.

According to Jay Z, a former friend fired those errant shots. Losing friends during your 20s is inevitable, but new jobs in different cities or “out of sight, out of mind” logic didn’t come between Jay and his—he lost them to the streets. As “D’Evils” illustrates, the underworld can corrode the bond between childhood friends, turning them into rivals and, on grim occasion, each other’s victims. But that malevolence takes a toll on the psyche. The game may have seasoned Jay well beyond his 26 years, but it hadn't taught him how to ignore the ghosts of past atrocities. By June of ‘96, he was about six months removed from 27 Club eligibility; he could feel his mortality stalking him. That combination made “Regrets,” Reasonable Doubt’s somber closer, a resignation from his old life. The quest for prosperity, self-actualization, and inner-peace placed Jay Z in an ethical bind. Not only did being a merchant of death trouble him, he recognized that the gains were short-lived.

Everyone wants to “die enormous,” as he says on “Can I Live,” but who wants to do it before 30? If your potential is limitless, you can’t truly “live [life] to the limit” if your profession guarantees death or jail. No matter what you do, you can’t progress without reconciling the past. So Jay Z’s angst, although shrouded by blustering, was revelatory. He emerged from his existential dilemma as an icon-to-be.

The quarter-life crisis should be metamorphic; no one should step away from it the same as they were when it began. Jay Z certainly didn’t. Superstar status didn’t arrive until he was damn near 30, but his ascent since Reasonable Doubt has been nothing short of remarkable. The self-proclaimed “immaculate conception of rappers-slash-hustlers” has left several plateaus in his wake since the late ‘90s, and it all began with Reasonable Doubt, his life-changing event. It’s the product of 26 years worth of observations and experiences, but it’s also engraved Jay Z’s quarter-life crisis into history. It’s brilliance funneled through existential plight.