"Like throwing someone into the water to see how well they swim." Itachi realized how ungrateful and grumpy that sounded and sighed. He was almost certain Hinata knew at least partially how he felt, as she was close to Sasuke.

"I'm sorry, Hinata-san." Itachi gave her a wry smile. "You're right. I've been holding my approval over his head for a while, and he needs to move beyond that. Maybe this will give him a chance to spread his wings and find his place." Somewhere not in Itachi's shadow.

Or he would crash and burn, maybe literally. Itachi predicted many sleepless night ahead. Many.