I struggled with this as well. A big turning point for me was dropping entirely the notion of being entitled to anything. In reality, no one owes me anything just because I think I'm smart or because I think I work hard.
On the feeling unaccomplished part, maybe try reading a book like http://www.amazon.com/Mastery-Keys-Success-Long-Term-Fulfill.... It's sort of a "the goal is the journey" book with some practical advice thrown in.
> As a kid I used to hit the video games pretty hard, but at some point I started to realize how fake the achievements felt. I literally can't stomach playing video games anymore. It feels like taking some sort of numbing drug. I have good memories, and I don't even regret most of the weekends I devoted entirely to video games (and the costs associated).
Me too! It sucks sometimes because I want to enjoy playing a game but don't. I've found that I can't play games, like Skyrim, that are just time-based grinds. Instead, I play games for the nostalgia, the story, for creativity elements, or for the competition/skill factor. Sometimes even then I feel uneasy playing games because I feel like I should be doing something more productive.. that's a tough feeling to get over.
> I worked a job last summer teaching kids. I still visit from time to time, and the trend of positive reinforcement and lack of criticism seems to be gaining momentum in our youth. My boss would not let me criticize my own students.
I don't think these things are mutually exclusive. You can certainly criticize and be positive (or at least not negative) about it.
I have a hard time enjoying myself playing games now also.
Could be doing other more productive things and at the end of they day no one cares what you archive in a game.