Jean Chatzky
Do you have a dream job in the back of your mind that you've always wanted to pursue, but haven't? Jean talks with two professionals who went after their dream jobs—Jenn Hoffman, a contestant on the TV show The Apprentice, and David Stone, the Broadway producer behind hit musicals such as Wicked.

Just 26 years old, Jenn Hoffman has already worked as a teacher, a TV news reporter and a publicist. Her dream job, however, was to work for Donald Trump, and she got her shot to impress the real estate mogul as a contestant on The Apprentice. "I'm originally from New York, so growing up, Donald Trump was this huge icon to me," Jenn says.

Jenn made it past eight others while competing on the show, but in the end she was fired by Donald and lost out on a chance to work for his company. Jenn says having the experience aired on primetime TV wasn't exactly what she thought it would be, but she says it was an overall good experience. "You just have to have a good sense of humor about it and maintain your professionalism and maintain the understanding that it is what it is—a reality show," Jenn says.

David Stone has one of those dream jobs few ever experience. He is a Broadway producer with seven Tony Awards to his name. David says becoming a Broadway producer was a journey that started with college internships. From there, David says he learned the ins and outs of putting on a show, starting from the ground up. While David built his career from scratch, other producers sometimes start their careers as investors in a show. "There are probably only about two dozen full-time, working-all-day Broadway producers," David says. "Then [there are] a lot more billed as producers who are learning how it works by writing a check or raising money."

Getting into producing by investing in a show can be a good career move, but it is a risky investment, David says. "It is a fun way to spend your money, you get to go to opening nights and meet the cast and have house seats, all kinds of things," David says. "But as a business, it is like [investing] in start-up companies or something like that." Also, David says typical investments are around $20,000 to $100,000 per show.

Producing a musical like Wicked, from a script to a nationwide success, means being on top of all aspects of the show. "The thing I love about it is I get to do so many things every day, not just casting or advertising, but all of it," David says.