Julia,
I agree with you and Charise that a non-traditional route can often be scary and intimidating. Sometimes, I still get nervous when a student chooses a major or career that is not in demand. I have learned to provide them with as much information as I can regarding the job market and the specific major/career, as well as explore why they chose that. Passion tends to provide motivation, so I make it a priority to find what it is that they are passionate about. It helps to ask about geographic location too, such as: are you willing to relocate? Showing them the job market for that specific major/career in their desired location can be a reality check (e.g., O*NET). Ultimately, I have to remind myself that it is their decision at the end of the day; like you said, "...trust students more than I instinctively do, especially when they are motivated enough to pursue a path that requires some extra work".