[jordo37]

It seems like this would also change per application, in which case A/B testing could really help you understand how users are thinking about and interacting with your program / tool / application. I think both of the paradigms that Dustin brings up in his article are good and there are applications I use that fall into both camps. Just as an example, SimpleDNS is a tool where I work on my stuff. Facebook is a social network where I got to interact with lots of stuff and the Your feels more appropriate there*

* Interestingly enough, it seems like most of the major platforms have moved away from using either "my" or "your" altogether, eg Facebook and Twitter both just have Friends, Followers, Tweets, Photos, etc.