Parents of adult children face all types of challenges, even in the best of times, but the tough labor market for young people can make it even more difficult.

The baby-boomers’ kids are marching into the workplace, and look out: This crop of twentysomethings really is different. Fortune’s Nadira Hira presents a field guide to Generation Y.

Brian Kelly, Exec. Editor of US News and World Report, discusses a recent cover story, “Is College Worth It?”, and whether or not students are getting the education they’re paying for.

Katherine’s liberal arts degree from Macalester College, a private college in Minnesota, was advantageous while it lasted, but since college, she has worked as a florist, school photographer, teacher, caterer, barista, assistant, and another assistant.

Katherine currently works for Starbucks, where she says: ”I get mocha on my face and have to put on a hat that messes up my hair”. For her it’s not just a job, but a safe haven for health insurance and stability. Will she stay there through her twenties? Katherine yearns for a job where she can work with people, be creative by making things, or use her hands. But at Starbucks she does work with people: she rings up customers. She is creative: she makes lattes. She does use her hands: to clean the bathroom. She wants out. Download the film to find out if she gives up comfort for the risk of the unknown.

The Lawyer: Heather, 28 yo

Having endured stress from an 80 hour workweek at a corporate litigation firm , representing insurance companies, Heather witnessed colleagues with high blood pressure, additional health issues, and even a suicide. As a high school and college athlete at UC Davis, she was on the track team. In her working world, she learned of her competitive edge to run professionally.

Caught between 160,000 dollars in law school debt and her passion for competitive running, Heather currently works for a boutique law firm representing the little guy in workers comp and insurance litigation. However, with “part-time” hours as a lawyer she only makes 40 dollars an hour, but the flexibility allows her to work towards her dream of competing in the Beijing Summer Olympic Games.

Heather is in the red due to rent, car and mainly school loan payments. She runs daily at 7:00 a.m., arrives at work at 9:00 a.m., leaves at 6:00 p.m., and runs in the evening. This lifestyle won’t last forever; if she doesn’t make it to the Olympic Games, she will be forced to go back to a full time law job – 80 hours a week – just to pay the bills.

The Artist: Josh, 28 yo

Josh has survived as a credible fine art painter for over four years. After 2005’s Hurricane Katrina left him bound for New York and New Mexico, he found himself couch surfing in Downtown Los Angeles. He pays his cell bill when he can afford it; otherwise it shuts off; he offers painting trades in exchange for dental work; he sets his eyes on school to become a physician’s assistant, but doesn’t commit. He tries to make painting work in today’s economy, but ends up exhausted.

Josh begins his jaunt, trying to find steady employment—in anything: mural painting, “ghost-painting” for another “artist”, as a bike messenger, teaching figure drawing classes, driving a hearse, working in construction, working on a train, bartending, working for underprivileged kids… you name it, he mentions it. View Josh Talbott’s work: http://www.joshtalbott.com/

To find out if Katherine will leave Starbucks in pursuit of her passion; if Heather will be forced to return to an 80-hour work week in lieu of training for future Olympics; and if Josh will give up painting for good and what job he will end up in:

Decide. Donate. Download.