THE RISK: Leaving a Secure Job to Start Your Own Business

Kimberly Shepherd (CWR '92) doesn't like being told what to do (according to her father, anyway). This year she decided to go into business for herself, jumping head on into developing KSA Educational Consulting. How did she make the transition from dreaming to doing?

Visit the "dark side," she says. "Go right to the worst possible scenario that could happen and let it play out in your head." There are a lot of places between starting a business and homelessness, and this exercise helps you realize there are always options.

Don't go in solo. Gather your network and get them on board. If you are aligned with your goal, you'll get tons of powerful, positive energy.

Say "I'm starting my own business," (or whatever your decision happens to be) out loud to yourself until you feel comfortable. Then, Shepherd says, make it real by saying it to others.

Her other tips? Banish "perfection paralysis," do your homework (but don't be a copycat), look at your future from a place of prosperity, be honest about your motivations and be realistic about your requirements, financial and otherwise.

"I don't mention starting my own business to anyone who doesn't say 'I wish I could do that,'" Shepherd says, "but you are typically the only obstacle in your own way."

THE RISK: Moving Abroad (Without any Real Plans)

How do you know when and where to go?

Determining your deal breaker can go a long way in moving you forward. On the eve of a job interview, for a gig she wasn't particularly excited about anyway, Pund decided, "If I don't get it, I'm going abroad."

Set a departure date and surf the web to find a community that fits. Pund knew she wanted to live in a Spanish-speaking county where she could afford to live in the city and meet new friends. "I never would have come here without the Internet," she says, plus Skype connects her with family and friends on the cheap.

Having a backup plan, in this case, an emergency ticket home, is certainly a confidence booster, but an even more critical step is letting go of expectations.

"This forced me to assess how I want my life to be structured," Pund says. "I'm going to come back a much more self-aware person." [PS: She's still in Buenos Aires, where she's found a great job and a new relationship!]