Hannah Isaacson, the protagonist, is a complex individual. Her trials touched on many aspects of women’s lives. What are some challenges women continue to experience today.

Did Hannah make any wrong moves that could have changed her life, her options, and the outcome of the book.

Tillie, Hannah’s older sister had a profound influence on her, but she also had her limitations. How did she effectively coach Hannah. For example….

As the book opens Hannah problem-solves in a vacuum. What did she learn about the value of others in accepting help.

Among the men, who were the good and the bad guys. Have these stereotypes changed over time?

Do you think it is necessary to play the game to get ahead? What are examples of outsmarting vs veiled threats.

Transport yourself to 1900. Do you see yourself as someone who would join the suffragette movement, buck the system?

What do you see as the key societal problems in 1900 NYC and how many of those are still present in society today?

Broadly speaking, human nature is constant over time. Select a character and describe how she/he would be received today.

What was the most impactful innovation at that time and why?