I think Obama is going to find harder slogging than he expects based on his experience to date. He’s going to find being chief executive a different experience than being the perpetual candidate, and I don’t see any signs he has the skills for the former.
Obama is learning that people trust what you say based on the context in which you speak. The most dramatic example of this phenomenon occurs when smooth-talking sociopaths go on trial. Such sociopaths have spent their lives using their glib charm to manipulate people who give them the benefit of the doubt. They come to believe they can talk their way out of any circumstance. When they get on the stand at their trial they intuitively assume that the same benefit of a doubt exists. It does not. The jury looks at them with suspicion and all their superficial charm and glibness do them no good. Without the benefit of the doubt, the jury listens to what they say not how they say it. They usually end up in jail.
Obama will face something of the same effect. All of his life he has been the up-and-coming ernest black man in a political subculture that fawns over such people. He’s never really had to decide and to produce. He campaigned on being himself. He campaigned on the story of being the first black president. People listened to him in the context of partaking in the story of the first black president. As president, he no longer has that context. He’s no longer the mythic story but just another politician. People listen to him with a certain suspicion. They want to know the specific whys and hows of his proposals.
Obama isn’t the inspiring story anymore. He’s just another huckster with a spiel. It remains to be seen if he can adapt.
[Update(2009-2-10-1:14pm): Some commenters seem to think I argued that Obama is a sociopath. I didn’t intend to make that connection. Rather, I simply used the failure in the context of a trial of a sociopath’s legendary glib charm and ability to manipulate people as an extreme version of how a context shift alters people’s acceptance of a speaker’s assertions.]