We have mixed associations to the idea of being proud. Many people think that to be proud of yourself, is NOT a nice  thing to be, and yet we would also think badly of the person who seems  to have no pride in himself (or herself). 
On the one hand, we don't like people who seem to "like  themselves too much". And on the other hand we are taught that it is  good to have "high levels of self-esteem", or what some people call, a  "healthy ego". So the question is, "To be or not to be proud?" 
People are confused. Should I have self-pride or not?
The source of the confusion over the issue of Pride stems from  the fact that we are exposed to two competing philosophies. Christianity  and Greek thought. 
According to Christianity pride is a terrible sin
The Christians say that pride is the worst of the seven deadly  sins. To be good, you have to rid yourself of pride. You should lower  yourself and be humble. To be humble is to be virtuous. To be prideful  is to be sinful. Self-love is the worst of the sins. 
Pride:  according to the Christians interferes with the individual's reverence for the Grace of God. 
Pride according to the Christians is "the sin from which all others arise". Pride is also known as Vanity. 
The sin of pride leads to the other deadly sins of: Envy; Gluttony; Lust; Anger; Greed and Sloth. 
(I am not sure of the logic that links "Pride" to "Gluttony", but maybe there is a link that I'm not seeing.) 
So if you were raised in Great Britain, you will have been told  that pride is a bad thing. That pride comes before a fall. That you  should not take yourself too seriously, and that you should be humble. 
You should not think that you are good. In fact, you were born  as a person tainted with original sin. You are, only human. So don't get  cocky. 
On the other hand
The Greeks (Aristotle, Plato) tell us the pride is the "crown of  all the virtues". And the Greeks thought that, to lack pride in  yourself would mean that you had a "sick soul". We are told by Aristotle that pride is the "crown of the  virtues". That you should do things that would make you proud. That we  should hold ourselves to high standards and that to have pride in  yourself would be the spur to drive you on to treat others well and to  do noble deeds. 
Aristotle wrote of pride: "A person is proud if he both is and  thinks himself to be worthy of great things. If he both is and thinks  himself to be worthy of only small things he is not proud but temperate,  for pride implies greatness." 
If you are to be proud, then you must be willing to earn that pride by achieving virtue. You do that by means of being productive, courageous, reasonable and magnanimous. 
So; many people are confused. If you are too humble, then you  lack confidence and lack self-esteem. If you are too prideful, then you  are a sinner and you will be punished. Pride comes before a fall.
In my opinion, Aristotle was right, you should strive to develop  pride in yourself by developing the qualities that justify the pride. 
Pride should not be confused with arrogance. The arrogant man is  too self-centered and seeks to gain self-esteem by bragging, or by  boasting. It is interesting to note that the boaster often has nothing  to boast about. It is often true that the boaster is boasting to hide a lack of self-esteem.
By contrast, a person with true pride, does not feel the need boast
The prideful person acts in order to achieve a high level of  ability in all the other virtues. A proud man would always do his fair  share of the work. A proud man would never steal, or cheat, or fake, or  fraud, or feign. A proud woman would attend to her grooming, and her  speech and her work would be of the highest order. 
A proud person would feel good about themselves, not because  they are big-headed, but because they believe that they have the right  to hold themselves up. 
A proud person would not be overly humble. They would regard too much humility as a sign of a lack of self-esteem. 
Tensions between the two world views
There is always a tension between these two views of human nature. 
- To be proud. Pride is the crown of the virtues.
- To NOT be proud. To be humble. Pride is the worst of the deadly sins.
The choice is yours. 
Choose carefully. 
 

 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
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