In Chapter 5, Washington shares his views about how the Reconstruction Period (which he defines as spanning from 1867-1878), affected Black people in the South and in Washington, DC. He notices that many of his fellow men are “called” to become preachers as soon as they learn to read, enter government positions they are not prepared for, or become teachers even though they are not trained in academic subjects. Washington sees this as a dangerous trend. For one thing, he believes that many Black people see manual labor as less respectable than intellectual work. He also worries that if Black people gain positions of power without the necessary qualifications, they will end up looking foolish. Furthermore, he believes that many of these men are supported by white philanthropists whose only real goal is to make themselves look good.

Washington also worries about the increased dependence on the federal government that he sees among many of his peers. He understands that the government was instrumental in ending slavery and is therefore highly regarded among many Black people, but he believes that by relying on it for too much, people will lose their independence. These feelings increase when he moves to Washington, DC, to study for eight months.