Big Sean can easily imagine an, even more, bizarro reality. In this scenario, he never freestyles for Kanye at that radio station in Detroit and never signs to G.O.O.D. Music. He doesn’t invent hashtag rap or collaborate with Nas, Eminem, or Lil Wayne. There are no platinum plaques. There aren’t two No. 1 albums. He doesn’t drop 10 singles that crack the Billboard Top 40 or accept trophies from BET or MTV. Someone else nabs those four Grammy nominations too.

Sean Anderson certainly wouldn’t be at Drai’s Nightclub for a special Drai’s Live Residency on a broiling May Saturday night, rapping on this rooftop aerie overlooking the neon archipelago of the Las Vegas strip—before a frenzied and swaying audience of 4,000 adoring fans who have memorized every syllable.

Being a professional rapper was all Big Sean ever wanted to do, and now he’s one of the most famous rappers on earth. Oh, and he dates Jhene Aiko—who he describes as a cross between Aaliyah and Sade. Who am I to contradict him?

But every time Sean squints, he glimpses the alternate route: a conventional 9-to-5 job anonymously toiled at for a half century, the disappointed wife, the litter of kids who lacked a proper role model—the quiet desperation that Thoreau lamented. Big Sean might not have written Walden, but he did write “I Don’t Fuck With You,” which takes a different route to achieve similar ends.

Lingering neuroses about that thankfully bypassed outcome concerns much of his latest album, February’s Gold-certified, I Decided. It opens with an elderly voice lamenting a wasted life. It concludes with a life-affirming conversation between Sean and his mother, celebrating his ability to elude deadening existential complacency.

“For a few years now, I’ve really felt that this was my second chance to get it right,” Sean says in a luxury suite at the Cromwell, the hotel attached to Drai’s.