The meager income Richard earned was quickly eaten away by "the endless expenses at home".

Living with his grandmother and his invalid mother in Jackson, Mississippi, Richard's existence is a constant struggle against poverty.  In the summer before his eighth grade year, he is too small and slight to get a job at the brickyards, but manages to secure a position as a water boy there, an exhausting job that pays only a dollar a day.  He later gets a job that pays a dollar and a half a day at the same location, picking up damaged bricks and wheeling them over onto a wooden scaffold from which he would dump them into a pond.  His earnings are summarily used up in support of the people in his household, and when Richard is bitten by a dog, he has no money to see a doctor.

The brickyard eventually closes, and Richard works as a caddy for a short time.  He is disgusted by the meager wages offered, and frustrated by his inability to earn more.  When school starts, he manages to get a job working mornings and evenings for three dollars a week.  It is at this point that Richard comes up with the idea of trying to sell one of his stories to the local Negro newspaper.  The paper prints his story in three installments, but does not pay him for it, and Richard receives nothing but criticism for his work from his family and from his school.  Although he loves to write and in his wildest dreams aspires to be a writer, he receives absolutely no encouragement, and continues through school frustrated, angry, and unfulfilled (Chapter 7).