That is a great question Born2care2001. I really have not an answer, since life is that process of discovering the answer. Let me try, yet honestly without confidence of knowing the answer.
Main question - Self esteem according to Howard Becker a social psychologist is a matter of comparing either upward or downward for a linear method of thinking. When you compare upward you may feel a loss of confidence cognitively affecting self esteem and effecting confidence.
The opposite is true when comparing downward. That self esteem may be restored and the sense of confidence restored. Caution with that method leads to what is called secondary deviancy or becoming a member of what is compared too. That is a common practice or tactic for bullying when done in an uncaring fashion as well.
The trick is to compare self to self with its many challenges. Measuring success is odd to begin with from a personal perspective. Great Athletes since before the first marathon measure their progress in workouts against their past performances not their competitors. Hard to achieve this discipline, yet it is that discipline which leads to confidence through obtainable and measurable progress. It is like the Army commercial - "Be All that 'You' can be."
Second question is I second guess myself the most here at Hubpages. However I am learning. At first I compared myself to the many, many successful here seeking emulation. What I discovered is some of those I sought to be likened to were not who I was.
I quit comparing myself to them. I stopped worrying about how many comments I received. I quit worrying about developing a following and/or meeting the demands of that following. I really have not a lot of time to invest compared to those I compared myself to. So, why compare?
I began studying my hubs and their progress. I learned. And I gained confidence in 'self.' The tools I measure with are for my entrepreneural adventure and I am successful based on those standards I determined and can live with.
An example is my score. It is directly related to views of hubs. My views are low compared to those hubs marketed heavily on the internet marketplace, yet are respectable in the confines of the Hubpages marketplace. All of the hubs I have published are featured hubs and there is not any score less than 67 the last time I checked. Those reach and/or surpass the goals I established.
Once I understand the ever changing dynamics of SEO a new adventure is entered.