I'm a Millennial, and I do something much like this intentionally. I make it a point to explicitly put my kids into situations where they are responsible for themselves and are uncomfortable because of it.

The transition to adulthood was rough for me for several reasons, and looking back I think that was one of them - my parents always did things for me, but never expected me to do things on my own.

I almost certainly go overboard with this, but that's the nature of things.