Introduction Life is very interesting because it has many spheres. Wherever people come from, or the challenges they have faced to reach their current position is of less significance. On literally looking at Barack Obama, the president of the United States, one would think his childhood life was on a silver platter. The same applies to the famous author, Frederick Douglas, who was a famous human activist during his time (Weidt 63). Barack Obama and Frederick Douglas have one thing in common; they are both black people who encountered many challenges in their struggles to live with the whites. The two individuals passed through many difficulties in their childhood and career life. Times had changed in the twentieth century, and one could think that racism was a thing of the eighteenth century. However, that is not the case since a lot of racism was evident in the twentieth century, and Barack Obama was one of the victims. Many authors have written books, poems, and other literary works in their attempt to portray racism in different ways. However, narratives based on personal experience are so insinuating because they depict a real life experience. To express his personal struggles, Barack Obama wrote his book, Dreams from my father, while Frederick Douglas wrote the book entitled, Narrative of the life of Frederick Douglas, an American Slave . From the narrations in the two books, this paper gives a critical analysis that compares the challenges that being black created for Douglas and Obama. Challenges during Obama and Douglas’ early years of life On his birth in 1818, Frederick Douglas was known as Frederick Augustus Washington Bailey. Frederick was born and raised as a slave, and thus, he worked as a slave in Maryland for a long time during his childhood. Slave children had no right to access education, and although Frederick desired to read and write, he never had that opportunity during slavery. Frederick suffered from beatings and physical torture during his childhood (Douglas 942). After a series of sufferings, Frederick finally managed to escape from slavery, and headed to New York before eventually settling in New Bedford, Massachusetts. Barack Obama was born to Ann Dunham of Kansas, and Barack Obama Sr., a PhD student from Kenya, in Honolulu, Hawaii. Obama was luckier than Frederick was because slavery had reduced during his birth. He never suffered from beatings, physical torture and other cruel practices as Frederick did in his childhood slavery. However, in his daily life Obama experienced considerable instances of racism. Obama lived in the neighbourhoods of the whites and white’s children could repeatedly bully him. Challenges during Obama and Douglas’ education life During his childhood, Frederick Douglas remained enslaved in the farms while the white children were in good schools. The white farmers took advantage of the powerless blacks, and made it difficult for their children to access education. Douglass and other black children had to work on the farms and this made them very ignorant. The children of the whites went to the best schools to gain knowledge, which would establish and improve their future careers. Frederick only received self-education whenever he encountered some educated and freed blacks. He only lived with the hope that someday he would get a chance to learn how to read and write. Obama did not receive such challenges because education was a primary right during his time of birth. Slavery had long been abolished, but Obam