50 Cent says: Make a vision board. Do it tonight, when you get home. Open your laptop. Create a new folder. Think about the things you want for your future. "I want you to Google pictures and put everything you want in this folder," 50 Cent says. "Everything. All right?"

He’s wearing a Yankees cap and a snug, fatherly argyle sweater with horn buttons that keep getting snagged on his various enormous muscles. His beard is like the line a surgeon draws before he cuts. His office in Midtown Manhattan, where we’re sitting, is spare. On the table in front of him is a deck of playing cards with the "I <3 NY" logo on them that he periodically picks up and shuffles and a white squash ball that he periodically picks up and squeezes.

All right, I reply.

50 Cent thinks for a minute. Actually, he says, my girlfriend—the one I just mentioned, the one I’d just moved in with? 50 Cent would like her to make a vision board, too. Then we’re going to compare. "Take things out of your folder and things out of her folder to create a folder that has everything," he says. "Now the vision board is no longer your personal vision board for yourself: It’s a joint board." That joint board will represent what we have in common. It will be a monument to our love.

But there will be some leftover unmatched photos, too, in each of our folders. And that’s what the joint board is really for—what it’s designed to reveal. "The things that end up on your vision board that aren’t in hers are the things that she has to accept," 50 Cent says. "And the things that she has that you don’t are the things that you have to make a compromise with." In a healthy relationship, he explains, your differences are really what need talking about. This is how you go about making that conversation happen.

"See?" 50 says, smiling. "Now, they ain’t gonna tell you to do that in no book."

There were good reasons why I asked 50 Cent—the same 50 Cent who named his dog after Oprah, and not in a nice way—to become my life coach. He has seemed, in the decade since his first record came out, like a person with wisdom, or at least savvy. He’s published a couple of self-help books—The 50th Law, a best-selling meditation on fear and the impossibility of trust transfigured into a set of boardroom commandments; last year’s Formula 50: A 6-Week Workout and Nutrition Plan That Will Transform Your Life. In his office hangs a poster of the movie he starred in opposite Robert De Niro, Righteous Kill—a testament to an improbable second career on-screen that continues this month with his new drama series on Starz, Power. He invested early in Vitaminwater and earned $100 million. His new album, his first in nearly five years, is called Animal Ambition; maybe he’d be willing to impart some of that ambition to another man.

It was sort of a stunt, the life-coaching thing, and in the beginning I treated it that way. I liked the notion of becoming a better person. Who wouldn’t want to become a better person? But I’d also become fascinated with the ways in which 50 Cent had failed—over the course of his long career but especially lately. He was ubiquitous, sold an unfathomable number of records, and then suddenly he wasn’t and he didn’t. He was said to live alone in an eighteen-bedroom Connecticut mansion that formerly belonged to Mike Tyson, wore a bulletproof vest every day for five years, traveled in a bombproof car. He abjured alcohol. His life in 2014 seemed lonely and impossible. He was a living example of someone who had entirely captured the attention of the culture and then watched the culture speed right by. I thought I’d go to him, ask leading questions, present what I perceived to be his problems as my own—I’m 31, I’ve had some success already, but now I fear my best days are behind me, what should I do, 50 Cent?—and in doing so get him to talk about himself, about the existential predicament of what comes after success so large it can never be repeated.