The Bible Background says:
Luke's word choice for "squandered" is "dee-as-kor-pid'-zo" which in Greek literally means to "toss it up in the air, scatter it." The same word is used to describe separating wheat from its chaff.

This definition reminds me of a memorable experience when I was teaching this story several years ago. (Names changed for privacy)

The model I use for my classes is learning centers. After we share the story together, students are invited to respond in a variety of stations, some of which are based on the rotation model. After spending time with the Prodigal Son story, students were invited to create wire sculptures depicting the father and the son. Zoe chose to only sculpt the son, and we noticed that the money bag was a prominent feature of her sculpture. She then went to the journal center, but instead of writing about the story, she tore a piece of paper into numerous tiny pieces.  Our curiosity was piqued. Next she went to the puppet theater and soon all those pieces of paper were flying into the air.  We assumed it was confetti for the party celebrating the return of the son, but when we asked her to tell us about her puppet show, we learned that the paper was money and she was depicting the son squandering his money.

It turns out that at the time, she was living with her single mother and grandparents, all of whom were unemployed and in the midst of job hunting. Zoe was struggling with the concept of the son squandering his money.  This was what she needed to address in the story at that time in her life.

Sometimes, I think we need to trust the Holy Spirit at work in the lives of our students.