As I play more I'm slowly getting into more of the roleplay aspect of the game, thinking of how I would be in a certain situation, trying to think like a person instead of a video game character. I try as best I can to imagine myself in these situations when I need to make a decision.

One idea to contend with is death. When you first start out, assuming you take the prison start, it's never really stated that you've killed a man before, perhaps just light rat and crab hunting at best, or maybe nothing at all. As your character progresses you'll probably have to kill more creatures, and certainly other humans. Every major quest lines involves killing people, except maybe the thieves guild. Did you imagine it to be a big deal when your character killed someone for the first time, eventually getting used to it, then not being really bothered by it?