I don't agree with how you have portrayed this as a matter of 19-year-old immaturity. Every sentient adult who saw what was happening in the early 2000s and yet

I don't agree with how you have portrayed this as a matter of 19-year-old immaturity. Every sentient adult who saw what was happening in the early 2000s and yet assumed the NSA would not have access to (say) call records was being naive. People who assumed they would have access to call records have seen that assumption vindicated. Internet companies suffer major compromises on such a regular basis that it is pretty foolish to have 'privacy expectations' about your use of the internet, even if the NSA did not exist at all.