Ohio native Sean Flannery has been doing stand up in Chicago for almost 10 years. His one-man show "Never Been to Paris" continues to sell out in the city. The routine chronicles the multiple times he almost died: driving down a ravine in the snow, stepping off a balcony while trying to sneak into a concert.

But 'making it' as a comedian isn't so simple. Despite his success, Flannery still works as a software developer to make ends meet. You see, he has a family. Two little kids, ages 2 and 5.

"For better or worse -- really its worse," he laughs. "I have to do two jobs to be able to keep the heath insurance I need for my family."

Flannery feels like you can still make it in America but it depends on how you define it.

"If it's to be famous and have your own show? That is nearly impossible to do if you have a family," he says. "But for me I will consider myself a success if I have five really good sketches that I can be proud of. I just need to figure out how I can do this full-time."