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When Winners Look Like Losers

What do winners look like? Are they tall or short? Black or white? Strong or weak? I guess it depends on what we mean by “winner.”

I was sucked into the story of one winner this past month as a read a lengthy, but engaging biography of Michael Jordan. The detailed account reminded me why many people’s obsession with him borders on hero worship. Many things can be said about “his airness” but nobody could ever claim he’s not a winner. Did he look like a winner before he got all those championship rings, though?

As you read the book, it seemed clear from his childhood that he would be a champion. Whether that was his outstanding play as a little league pitcher or as a junior varsity basketball player; his high school growth spurt or his game winning shot during his freshman year with UNC.

By the time I got to the chapters about his championships as a Chicago Bull, there were no surprises. The author told his story in a way that made it clear: Jordan was born to be a winner. And that’s what we know him for: winning six championship rings, five MVPs, and 14 All Star appearances…

Wait, Trip — Didn’t You Retire?

A couple months ago I surprised everyone by announcing a brand new album, “Rise.” You don’t understand how hard it was to keep quiet about it before my label and I went public. The album had been in the works for over a year, and I couldn’t wait to tell everyone — especially those who kept asking when I was dropping something new.

The response so far has been deeply encouraging. I’m amazed that people have continued to support me even though I’ve been pretty quiet for the last two years. Your love and excitement has only increased mine.

Early Retirement

One of the responses I wasn’t surprise by was this one: “Wait, I thought you retired?” This is the question that follows me around like a shadow. I’ve addressed it in interviews, tweets, and blog posts, but I know it’s still unclear to some. Let me continue to try to set the record straight: I never retired.

In 2012, I announced that I’d be “stepping away from music.” Yes, I know that sounds retirement-ish, but I purposely didn’t use that word. I kept it intentionally vague because I wasn’t 100% sure what it would…