Question for Joel: How do you take the next step when you're not sure what it is?

I was talking with a friend/colleague yesterday who has been in the healthcare industry for about 20 years and is currently a Director for a privately held company.

She wants to do something different and mentioned doing something with either medical technology or working with a cancer organization. As you know there is a big push within the industry to automate medical records and other tasks so at least in theory, there should be a lot of opportunity for her in the future. However, she lost three friends to cancer this year and is thinking that she might want to work with a cancer organization.

She enjoys her current job and specifically the freedom of working from home when she's not traveling and the training and speaking elements of her job. She wants to semi-retire in about 7 years and start a consulting practice.

Given what you know about her and her goal of retiring in 7 years, what should she do? Should she try something new? And if she should do something new, how can she go about figuring out what she should do?