If you want to learn about success, talk to a successful person. If you want to learn about failure, talk to a very successful person. In his new book Fail Up, TV and radio host Tavis Smiley offers lessons on how to turn life's setbacks into success.

2011 marks Smiley's 20th year in broadcast — and that anniversary got him thinking: "The way I arrived at this place [of success] was failing my way — all the way," he says. The book is sort of a Top 20 Worst-Of list: It details the 20 biggest mistakes of Smiley's life.

Some of these mistakes were news even to Smiley's close family. Before the Fail Up manuscript arrived at his parents' house, Smiley called home to tell his mother and father they were about to read things they'd never heard before. Smiley was the first person in his family to go to college — but when he marched across the stage at Indiana University to get his diploma, he hadn't really graduated. It technically took Smiley 16 years to get his degree; during college, he had been arrested and sent to jail for check fraud. "I couldn't bring myself to tell my parents that I'd gone to jail while I was in college," he says. "[Or] that I didn't have a college degree."

He thinks as a young man, he couldn't have truly comprehended the concept of "failing up." There are certain things, Smiley says, that you simply have to learn the hard way. "I've got great mentors, great family, great friends," he says. "I have a deep and abiding faith. But there are some things you can only learn via experience."

A Presidential Poster Child

Smiley isn't the only one who has learned to fail up — he also gives examples of public figures who've had their fair share of both failure and success. Believe it or not, President Obama is "the poster child for failing up," Smiley says. Back in 2000, Obama couldn't enter the convention hall for the Democratic National Convention. "He couldn't get the hookup to even get inside the building ... [he] didn't have credentials," Smiley says. "In 2008, he's sitting in the Oval Office as the leader of the free world. If that isn't an example of failing your way up, I don't know what is."

Smiley hasn't been shy about criticizing then-candidate and now-President Obama — and that didn't always sit well with his audience. "It is a very difficult thing to go from being celebrated to being persona non grata almost overnight," Smiley says. "I understand that after 400 years black folk wanted — by any means necessary (forgive me, Malcolm) — to see Barack Obama in the White House. I get that."

But as a member of the media, Smiley says, his job was to hold elected officials accountable, and he took that task seriously. "Then this black man shows up," Smiley says, "... and I'm not supposed to talk about accountability?" He stands by his decision to challenge Obama's policies in the same ways he says that he challenged President Bill Clinton's and other public figures'.

Confidence Vs. Cockiness

When you hit a point in your life where your success-to-failure ratio starts to balance out in favor of success, that's when you start to learn the hard lessons about humility. Smiley rejects assertions that he is arrogant, or has a big ego. Everyone in the media, he says, must have confidence.

"There is a distinct difference between confidence and cockiness," he says. "And it always troubles me — it makes me laugh actually — that when you're a black man with confidence — you own your own radio show, you own your own TV show, you own your own publishing imprint ... then you don't have confidence, you have ego."

He says his work speaks for itself — as does his track record of breaking down barriers of race at NPR (which aired The Tavis Smiley Show from 2002 to 2004) and other broadcast organizations.

At the end of the day, Smiley says he'd like to see failure redefined as "preparation." He thinks Babe Ruth said it best: "Every strike gets me closer to the next home run."

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