(Takes place within the universe of The Sitter with the Diamond Tiara and its semi-sequel A Dazzling School Daze. Familiarity with both is not required, aside from a little bit of context.)

Diamond Tiara has come to a realization of sorts about what her future should be and what sort of career she wants to pursue. A recent experience has convinced her to become a teacher, rather than take over her father's business.

But the young mare finds herself still plagued by uncertainty over her decision, doubts have crept into her mind about who she is and what her career path should really be. So she decides to have a talk with somepony she believes can help clear things up.

Cheerilee is quite surprised to be visited by one of her former students, but nevertheless agrees to hear Diamond out. And Cheerilee's advice and guidance might be just what Diamond Tiara needs to hear.