I'm not so convinced that the things listed are necessarily bad things. In the context of the letter, sure. Maybe the CIO's life was molded around things others wanted for him or expected of him.
Humans naturally want to improve and excel at what they do. I think aspiring to live in the place of your choice (address), driving an acceptable car, going the places you want to go (vacation), and doing the things you want to do (employed, self-employed, retirement) don't have to be a bad thing at all. Whether your goals are your own or based on what others want to me is irrelevant. In either scenario, you're going to be working for a better tomorrow. There's no such thing as truly doing your own thing either. Someone out there is doing the same thing. Everything is always influenced by everything else. It's funny to think we can truly escape social pressures and influences.
It just sounds to me that he realized a little too late that he was living a life that he didn't really want to be living anymore, and that's the point.