I'm not sure you're in the minority on this one. I think that self doubt and need to please are why he can be a conman without being a sociopath or severe clinical narcissist (like nearly all of them are in real life) for a little while at least, he's doing everything he can to please somebody, even if he has to lie to do it.The false persona he builds for each con can't last forever, and the fact that it ends with him screwing the person he was pleasing over is almost incidental.

I agree with swanpride. He tends to latch on to other people and invest a lot of his self worth in how they see him, more so than is healthy. When those people disagree...