In the Autobiography of an Ex-Colored Man, there were three main dilemmas. According to Webster's dictionary a dilemma is a situation that requires a choice between options, usually equally unfavorable or mutually exclusive. In other words, a dilemma is a problem that presents a difficult choice. In James Weldon Johnson's book, his character faced many similar problems that African Americans faced all over the country at this time.
The story is about a young man born in the southern state of Georgia, but was raised in the northern part of the country, which is frequently referred to as "Negro friendly". When he is young, he loses his mother to death and for the first time faced with his first real life dilemma. This dilemma was the one of were and what was he to do with his life. This was a time of mourning when a person tends to lose site of rational thinking, and decision making becomes a chore. He had to figure out what he wanted to do with his life. His mother had left him some money that and with that he decided to fulfill his long time dream of pursuing college and with money he had been left he could pursue at least two years at an Atlanta college rather a short stay a Harvard or another New England school.
Soon after he decided to go south in his quest for education, he came upon some turbulence. Despite seeing the racial tension and discrimination, he was subjected to be robbed by a fellow tenant at an overnight boarding house he had been staying at. This posed a real problem. He had already visited the president of the university and made plans to attend the school not knowing his funding was no longer available. Now his chances of entering school were significantly shortened and once again he had a dilemma on his hands as to how he could overcome this situation. He had no money, no where to live and no plans. He soon recovered and found himself in Florida working with a group of Cubans in a factory as a "stripper".