[Ancapistani]

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.

[devilbunny]

No kids of my own, but my niece is 16. Wife and I took her to dinner when she was ~10, and afterward she said she wanted some ice cream. Sure. We drove to the grocery store on the way home (it's an older store, not huge) and handed her a $10 bill, told her to go get whatever flavor she wanted.

She freaked out. She'd been so terrified by a litany of "stranger danger" stories that the thought of just going into a store alone - a small store with one public entrance - was alien to her. We told her she could do it herself, or not have ice cream, because we weren't doing it for her. She went.

I'm glad to hear you're pushing your kids this way.