[1][2] Liiv grew up in a poor and devoutly religious family and was second youngest of eight children; three of whom died in infancy, including his only two sisters Liisa and Miina.

[2] Despite their poverty and religion, Liiv's parents understood the importance of education and invested what little money they had towards their children's schooling.

Illness forced Liiv to leave school and return home, where he wrote poetry and occasional columns for the Olevik newspaper.

[3] Many readers draw a comparison between Liiv and the main character of the story, Villu, who is physically weak but strong in mind.

He variably thought he was the son of the Emperor Alexander II, the king of Poland and Estonian poet Lydia Koidula.

Many of Liiv's poems are dominated by a sense of gloom, probably brought on by his mental illnesses, poverty and lack of human friendships.