I think herein is the issue. Generally, people tend to have a particular perception of who they should be; I should be witty, I should be intelligent, I should be attractive, I should be popular etc.
Low self-esteem tends to come into play when in a person's mind, those perceptions do not meet the reality (these perceptions, more often than not, are extremely misconstrued). "I'm not very witty, I'm not particularly intelligent, I'm not popular... well, why not? What am I doing wrong?" - These questions, typical of those with low self-esteem, tend to manifest doubt, frustration, and even in more extreme cases, self-hatred.
Low self-esteem, and its accompanying distorted perspective, tends to make it problematic for an individual to give themselves an accurate appraisal. It can be difficult for them to assess their strengths and weaknesses - because to them, their weaknesses are all-encompassing. They feel inadequate because another person is wittier than them, because another person is more intelligent than they are, because someone else has more friends than they do etc.
I think that once they cease to focus on what everybody else has to offer, it becomes much easier for them to see that they have just as much to bring to the table. Self-doubt is the antithesis to confidence. Once a person is able to accept that they don't need to be this 'perfect model' of everything that's 'desirable' in another human being, and that they are perfectly okay just the way that they are, doubts tend to dissipate and confidence will skyrocket.
ChickenGuy, from what I've seen from you on JUB, there is absolutely
nothing wrong with your personality. I think you're very intelligent, and I'm sure I've left you
more than a handful of comments laughing at your witty puns. I think you're an extremely likable guy, and I don't think it's your personality that's the problem here - but your distorted perception of it.