By Yoh Phillips for DJBooth

“Shawn Carter was born December 4th…” are the words Gloria Carter speaks to begin JAY-Z’s The Black Album, his eighth studio release. None of the seven albums that came prior start with a personal narrative or narrator, so “December 4th” stood as a conceptually uncommon introduction for Jay. If you didn’t know his birthday then, you would never forget it after.

It’s been 16 years since “December 4th” dropped. JAY-Z was a few weeks shy of 34 then, newly retired from rap, with the world as his oyster. No one knew what was next for the hip-hop superstar, and how could they? Jay at 34 had the charts and the classics; he was culture and commercial, a distinction no other contemporary rapper balanced with his effortless zeal. Other rappers have found their footing between those spaces, but not like Jay. And no one reached the pinnacle he did as they were saying goodbye.

Now, 16 years after that short but impactful farewell, another December 4th is here, and JAY-Z turns 50. Knowing how many legends hip-hop has lost in their 20s, 30s and 40s, to see Jay reach his 50s with the likes of Dr. Dre, Ice Cube, Rakim, Slick Rick, Diddy and others is truly a milestone, both for him and the culture. For younger rappers, there are few other examples that better reinforce how real longevity is possible.

To commemorate JAY-Z’s 50th year, we’ve picked 15 lessons, culled mostly from verses throughout his discography, that stand as essential life advice. Amongst the big singles and endless quotables, Jay’s nuggets of knowledge and his thoughtful outlook have made him an artist not just to study, but to enjoy. He’s paired the heart of a hustler with the talk of a teacher, and every album release has been an opportunity to go back to school. The best way to honor any teacher is to reflect on their words and remember why they matter to us.

Whatever the Cost

“My life is based on sacrifices,” JAY-Z says on “Politics as Usual,” the second track on his debut album, Reasonable Doubt. The line, recorded when Jay was in his mid-to-late 20s, reminds listeners that life before music wasn’t sitcom-perfect.

Just a stumble away from 30, different kinds of anxieties and concerns start to set in. That’s not what you hear from Jay, though. His voice isn’t weighed down by uncertainty. When he says, “By any means necessary, whatever the cost” on the last verse of “Allure,” it’s like a seven-word manifesto on how he pushed through the impossible. To build what JAY-Z has built, attitude must match ambition.

The Motto

“My motto is, simply, ‘I will not lose!’” Jay raps on “It’s Like That,” a selection from his third studio album, Vol. 2… Hard Knock Life, released in 1998. This mantra appears throughout JAY-Z’s discography, including on “Change the Game” and, most famously, in the third interlude and outro of “U Don’t Know.” He delivers the bar as if the spirit of a gladiator is speaking through his vessel. That confidence to boldly say “I will not lose!” comes from a place of unwavering self-belief. Another way to interpret this motto argues that it’s better to claim victory than to question if you can win. Don’t wonder about the outcome; just don’t lose. Ever.

Stand Back for the Perfect View

JAY-Z dedicates the third verse on “Anything,” a deep cut found on Vol. 3… Life and Times of S. Carter and Beanie Sigel’s The Truth, to his nephews. He advises them with warmth as well as brashness, in a way that only a sophisticated, larger-than-life uncle could. Jay doesn’t speak of riches or how to become famous. Instead, he offers simple coming-of-age observations. Jay’s best nugget of wisdom deals with the importance of big-picture clarity: “Standing back from situations gives you the perfect view.”

I Might Break, But I Don’t Fold

Jay’s poise has never faltered under extreme pressure—even as he’s participated in some of the most heated moments in hip-hop history. “I don’t bend, break, fold, scratch, go down,” he raps on the 2000 single “Guilty Until Proven Innocent,” a sentiment he reprised on American Gangster’s self-titled outro 11 years later: “When it all falls down, I’m like Kanye’s jaw/I might break but I don’t fold.” Life will bring pressure—that’s unavoidable—but only you determine if you crack underneath it.

Let No Amount of Money Ruin This Thing of Ours

There’s no escaping the opulence and grandiosity of JAY-Z’s lifestyle in his lyricism. Still, amid all the braggadocious celebration, he doesn’t lose sight of how money attracts the influence of greed, which can put lives and businesses in jeopardy. On “Never Change,” a fan favorite, Jay raps, “Let no amount of money ruin this thing of ours,” to no one in particular. For anyone who makes money with friends, this is an essential mantra. You can always make more money, but friendships and relationships are harder to mend.

Watch for Friend & Foe

JAY-Z turned his hustler past into Platinum plaques without losing his streetwise skepticism. The quiet corners became sold-out stadiums. “Same sword they knight you with, they gon’ good night you with,” Jay raps on the highlight-reel worthy “Grammy Family Freestyle.” The idea that every Caesar has a Brutus dates back to his debut album and appears throughout his discography (“Friend or Foe ’98,” “A Week Ago” and “Streets Is Talking”). Before Jay, Jean-Michel Basquiat wrote, “Most young kings get their head cut off.” Being cautious, even if you aren’t in the music business or a monarch of drug dealing, should be paramount. Not everyone has your best interest at heart.

Treat My First Like My Last and My Last Like My First

If The Black Album was JAY-Z’s retirement release, as he heralded it to be, “Treat my first like my last, and my last like my first,” from “My 1st Song,” would have been one of his last messages. Even though Jay was closing a chapter, he wanted his finale to have the same drive and passion as his debut. Given how comfort is the luxury of wealth, this approach is easier said than done. Contentment can take the place of creativity, and great art isn’t made by the complacent. So don’t forget why you started, even when you’re crossing the finish line.

Dawg, in Due Time

Trusting a process often feels like trusting a pyramid scheme. The wait can seem infinite and make you anxious, impatient, uncertain and depressed. Imagine how it must’ve felt to be Kanye West, signed to Roc-A-Fella Records, being told by JAY-Z, “Dawg, in due time!” as Ye recalls in “Touch the Sky.” Although no emerging artist wants to hear those words, Jay’s “favorite line” is invaluable advice. When the labels weren’t trying to sign Kanye, Jay waited and worked with him until they recognized his value beyond being a producer. That process took many moons to manifest, but Jay wasn’t interested in an early harvest; he knew the seeds planted would bear fruit.

Number One Rule for Your Set

The first time JAY-Z mentions living with regret is on the outro of his classic debut, Reasonable Doubt. “This is the number one rule for your set/In order to survive, gotta learn to live with regrets,” he confesses. Success, much like regret, comes with taking risks and making mistakes. As a recurring theme in his music, Jay never makes regret feel like a burden. His attitude is always to fix what can be fixed, accept what can’t be changed and share your errors so others may avoid them. “Hov did that, so hopefully you won’t have to go through that,” he famously says on “Izzo (H.O.V.A.).” In 2017, he explored this sentiment again on “The Story of O.J.,” confessing to the financial folly of buying luxury cars instead of investing in prime real estate.

You Can’t Heal What You Never Reveal

Maturity has made JAY-Z a more transparent rapper. With every post-retirement album, another layer is peeled back to share personal revelations that would usually go unsaid. The openness of his latest album, 4:44, feels like hearing the private testimonies of Shawn Carter. His famous line “You can’t heal what you never reveal” (“Kill Jay Z”) is a mantra that reinforces how time doesn’t mend the wounds that remain hidden. Nothing, including trauma, gets fixed without first acknowledging the problem.

Legacy, Legacy, Legacy

JAY-Z didn’t learn to move in a room full of vultures for a temporary job. No, his big-picture vision for music and his career was ownership. “My stake in Roc Nation should go to you/Leave a piece for your siblings to give to their children too,” Jay softly raps to his daughter Blue Ivy in the first verse of “Legacy,” the closing track on 4:44. This isn’t the first or only time Jay mentions generational wealth in his music. Still, it’s the clearest example of the opportunity ownership offers: a chance to give a gift to the future. You can’t give what you don’t own. To think and move as an owner, in consideration of a legacy, is one of the many timeless lessons found in JAY-Z’s music.

The Only Thing Worse Than Getting Old Is Not Getting Old

Aging, while painful, can be a reward. JAY-Z, who released his first album when he was 26, is now globally renowned and revered at 50. As he said on the Fool’s Paradise Remix of his 1996 single “Can’t Knock the Hustle,” “The only thing worse than getting old is not getting old.” Just look at Shawn Carter: He’s proof that one year can change your life, and 10 years can change the life of your family.

They’ll Distract You

The beef and battles JAY-Z has fought were written in hip-hop’s history books long before his 50th birthday. In competitive fields, challengers come with the territory of rising through the ranks. He fought, he rose and he continued to grow. On “Light Up,” a 2010 feature found on Drake’s debut, Thank Me Later, Jay raps, “Here’s how they gon’ come at you/With silly rap feuds, tryin’ to distract you.” Drake didn’t heed the warning, but Jay was right: Conflict is a distraction—not just in rap, but in life. Why waste time on the yelps of dogs if you lead a pack of wolves?

Nobody Wins When…

Family is never far from JAY-Z’s thoughts: the voice of his mother; the laugh of his daughter; the singing of his wife; the names of uncles, aunts and nephews, as well as other artists he reveres. On every album, Jay includes a posse celebration (“All I Need,” “Roc Boys (And the Winner Is)…,” “FRIENDS”), a record that shows but a corner of a career-long painting of camaraderie. That said, Jay isn’t a stranger to feuds within the family. He represents how we build dynasties and how they can collapse. As he said in 2017, “Nobody wins when the family feuds.”

Measure Success By…

How does one measure success? Is it based on wealth? Status? Respect? This question doesn’t have a single answer. Remember: the entrepreneur, not the customer, defines success. JAY-Z flaunts his accolades and finds pride in his accomplishments, but he’s careful not to forget what success means to him. He says it best in “BOSS,” from THE CARTERS’ 2018 album, EVERYTHING IS LOVE: “Over here we measure success by how many people successful next to you, here we say you broke if everybody is broke except for you.” Success is for the selfless, those who see being a boss as having the privilege to help others. Why choose to be a crab in a barrel when you can be the captain of a ship?