I guess I'm just jaded because I've been through so many cycles of 'this will automate your security needs' followed by 'every system can be gamed' a couple of years later - much as Phil Zimmerman commented The natural flow of technology tends to move in the direction of making surveillance easier, and the ability of computers to track us doubles every eighteen months.
Nowadays I worry less about my privacy on the assumption that it's probably hopelessly compromised anyway, and more about being able to hold an unpopular position or opinion without official interference. For example I think it's far more important that gay people enjoy full civil rights, be able to marry etc. than they had better privacy tools that would allow them to remain in the closet indefinitely.
That's like saying that having 100% uptime and zero failures is more important than having backups. Sure the former would be ideal but in reality that answer doesn't cut it. Sure civil rights and free speech and personal autonomy are ideal, but over here in the real world there are a lot of people who still have to hide to avoid bad stuff happening to them.
I also don't think you can use 'automate' and 'security' like in the previous paragraph and expect good results.
I know perfectly well, from experience, that I could vastly increase my privacy (or reduce the huge volume of information that I choose or passively accept liability for sharing, eg by having a FB account and not logging out of it every time I go to another tab etc. etc.). But how much of my time do I want to spend on opsec?
I don't want to be in a defensive posture for the rest of my life, hiding from bad actors and constantly worrying about some overlooked chink in my digital armor. Frankly, if the future is endless low-grade cyberwarfare I'd rather be on the offensive and steal other people's data for my own advantage than be endlessly upgrading my door locks.