The job-shifters: people who reinvent themselves mid-career

"In New York, we didn't play cowboys and Indians. We played tenants and landlords," he quips to an audience at the Emelin Theatre in Mamaroneck, N.Y. "In Times Square today, I saw a cop on a horse on a cellphone. There's something unsettling about seeing a horse on a cellphone."

After 20 minutes of banter, he turns over the stage to two more comics, who were also booked and marketed by Mr. Eli's company, Ivy Stand-up. Since Eli hasn't become the next Jay Leno yet, he has found it easier to sell a full show of comics rather than just himself.

His business venture is what reinvention experts would instantly recognize as a melding of passionate interest with previously learned skill. Until 2009, Eli was Shaun Eli Breidbart, Wall Street banker.

Although he began faxing jokes to "The Tonight Show" on a freelance basis some 20 years ago, what really sparked his transition to comedy was a friend who persuaded him to try stand-up. He signed up for classes and found a niche in so-called clean comedy. Eli began setting up gigs, and got busy enough that he quit his banking job in 2009. Since then, he's averaged about three major shows a month – usually in the New York City area. He also recently performed in Maryland; Washington, D.C.; and northern California.

His earnings have plunged from the "low six-figures to the mid-five figures," he says. "But I'm getting stronger and stronger." He hopes 2012 will bring his breakthrough: the year he performs on television. "I'll begin sending videos of my performances to bookers of TV shows – realizing, of course, that I'll just get one shot at their attention."

Many people who have had success reinventing themselves don't stop with just one career change. They keep going. Blair, the gang member-turned-high-tech executive, had worked his way up to where he was making more than $100,000 a year. Yet that wasn't satisfying enough. He wanted to start his own company.

So his boss at Logix became his business partner, and 24/7 Tech, a technical-support firm for medium and small businesses, was born. Blair then sold the company to launch SkyPipeline, a wireless broadband provider, which he later sold for $25 million.

Now, he is chief executive officer of ViSalus, a weight-loss and fitness direct-sales company based in Troy, Mich., and Los Angeles, which last year saw sales skyrocket to $231 million, up nearly seven times from 2010.

"I would dream about my life, like a movie," he says, when asked for his top tip to would-be career-changers. "If you can visualize ringing the Nasdaq bell or writing the bestselling novel or whatever it is, you will really start to train your subconscious." And "start today," he adds.

As a successful entrepreneur and speaker, Blair was asked in 2010 to give a talk to a megachurch in Detroit. As he prepared to speak, that memory of reading the Bible to an imaginary audience in juvenile detention came back with full force. "I was amazed and in awe," he recalls. "I just believe that when I created that dream, my mind absorbed it."

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