Transition Planning... what do you do when the student has unrealistic post secondary goals?

Another issue that comes up when teachers are helping students to plan for life after school is that some of these students have very unrealistic and most likely unobtainable goals. At some point you will have the student that has the goal to be a Doctor or the next Taylor Swift.  It is not our place to tell this students how unrealistic these may be but we are obligated to assist them in looking at breaking these overall goals down to find something that is related directly to their goals.  For instance, I have some of those students who just know they are going to be the next big hit in the music industry.   I sit down with these students and do some job exploration including web searches to look at jobs related to the music industry. I talk to them about their ultimate goal and then I encourage them to have back up plans to work toward first.  Many of my students start to think about other jobs or ways that they can do things that have to do with music.  The other day I had one of these students say that they think maybe working in a music store might be a good backup plan. 
It is difficult at times to know exactly what direction to look in depending on the post secondary goals that our students have in mind. I think that a big part of the transition process needs to be exposing these students to many different job opportunities through work based experiences and instruction.  Many special education teachers could benefit from traning to help direct them in assisting students to plan for transitioning into post secondary schools, training, work and living situations.