The phrases they use are tied to their generation. My fellow Baby Boomers talk about "The Big Score." For the Silents it's "The Home Run." And, no Millennial wants "Grunt Work."
I finally figured out one reason while we're tilted in the direction of big. It's because of debt. When you carry a mortgage, and/or student loans, and/or credit card balances, hey, who can think about starting at the bottom, say as a check-out clerk in Dollar Tree. There it would be possible to learn the dollar store business, maybe move up into store management, then corporate public relations.
Had Jill Kelley not piled on the debt would she have chased all those military connections? My hunch is that she envisioned the big score, eventually. The role she had was unpaid. Without massive debt, though, she could have taken a job selling cosmetics or shoes in upscale retail and then, like Carolyn Bessette Kennedy, been "discovered" by the brass. Like Kennedy's good looks, hers would have been noticed.
The tragedy of debt is that it prevents us from starting over again. The 45% of law school graduates from the Class of 2011 who, the American Bar Association reports, didn't get full time jobs practicing law have to keep chasing the goal. With high five-figure student loan debt they can't take "grunt work" being a security guard in Home Depot and learn the loss prevention business.