There is a basic problem we need to address concerning self-esteem.
To some extent it seems clear that a person who has good self-esteem (self-respect) and who thinks highly of herself will have the internal motivation to work toward the Good Life. Conversely, a person full of self-loathing, who hates herself and thinks she is a bad person may not think herself worthy of the happiness the Good Life can bring and so she may have no motivation to work toward betterment.
On the other hand, we know that Virtue Ethics argues that we should work to be as objective as we can when assessing our own character -- the list of vices and virtues that comprise who we really are. People who really are good, who exhibit excellence in virtues should feel proud of themselves. And, people who don't possess many virtues and who instead possess vices should probably not feel so good about themselves.
So, we have a bit of a paradox here. It seems we need self-esteem in order to be motivated to work toward virtues but maybe we don't deserve to have this self-esteem until we have achieved virtues. But, if we hold off feeling self-esteem until we have earned it, we may never earn it because we lack the self-respect to care enough about ourselves to do the work.
You can see the practical impact of this conundrum in our society today. Some argue that we should instill self-esteem in all children by any means necessary. That is, we should not expect children to earn self-esteem by their behaviors, achievements or attitudes but instead we should just encourage all children to love themselves no matter what. This philosophical viewpoint leads to things like the banning of dodge ball and the game of tag since these activities can make kids feel bad about themselves. Honor rolls and other honors such as special recognitions for high achieving athletes are seen as negative since those kids who don't get on the Dean's List or who don't get the large trophy will feel bad. All children should have an equally VERY HIGH level of self-esteem and one way to do this is to make sure that nobody is treated as 'better than' or special.
Of course the opposing view is that offering special honors for high achievers is a way to motivate children to strive for excellence. Kids want the honor of the Dean's List and they want the special recognition of getting the lead in the school play or being named First Chair trumpet in the band -- and so they will work hard to achieve these honors.
What do you think?
Eric
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