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Chapter 2 starts off saying that Ivan's life was the most simplest, the most ordinary, and the most awful. Why is a simple life awful?

"The second part of ‘‘The Death of Ivan Ilych’’ describes the life of Ivan Ilych while he was healthy. It can be summed up in the opening line, which states, ‘‘Ivan Ilych’s life had been most simple and most ordinary and therefore most terrible.’’

Ivan Ilych's life is simple because it is devoid of any real emotional connections or feelings.  His life is driven by what is proper, by social order, by how things look to others.  It is superficial and empty, therefore it is terrible.

He picks his friends by social class, not a desire for true friendship.  He marries his wife out of a sense of propriety.

"Praskovya Fedorovna and eventually marries her, not for love but because it seems the proper course of action at his stage in life."

His life is a constant struggle to attain material wealth and recognition in his profession so as to climb higher in the social strata. 

Ivan Ilych's life is not real, it is artificial, therefore, a life lived like this is characterized as terrible.