Personalization vs. Differentiation

After reading your posts, I couldn't help but think of this image.

My follow-up questions are:
1. Who else is in the car?
2. Does it matter where they are sitting?

I ask this because I started to label the seats...and then realized that I couldn't decide who was in the car and where they should sit. Should it be teachers? School Counselors? Parents? Other students/peers? Community members who can provide real-life, authentic learning opportunities?