You have said it all @starstrings01 and @iskafan
It's really difficult when one has a low self esteem
I think first for such a person is to build his confidence level, courage and determination not considering the amount of failures and pains yet looking up at the goal .

The goal has to be a burning desire of that person perhaps an aspiration or a dream or a role model
It has to be something he/she can see that will keep him standing.
There are negative WEs also... changing circle and environment can also help