1) At the beginning of the novel, Florence is struggling with writer’s block. Why does she believe she is being obstructed creatively? How does this change throughout the story?
2) Florence envies the lives of other people and tries to mold herself to fit into the literary world in New York. In Florence’s eyes, what do Amanda Lincoln, Agatha Hale, and Greta Frost have that she does not?
3) How does Florence’s definition of “success” evolve throughout the novel?
4) Does Mississippi Foxtrot—a novel presumed to be based on its pseudonymous author’s own experiences—remind you of any real-life books? Why might an author choose to use a pseudonym?
5) Florence and Helen believe that identity is a work in progress and that it’s possible to reinvent oneself. How does this belief in “fake it till you make it” play out in the novel? Do you think people can genuinely change—or does it always involve some amount of posturing?
6) Book publishing, like many other industries, runs on mentorship and apprenticeship. How do the characters exploit this power dynamic as they mentor or assist each other? How does Florence shift this balance in her favor? Do men and women wield power differently?
7) “Ultimately, she didn’t care whether Maud Dixon was a man or a woman. She knew that whoever she was, she was an outsider, like Florence herself.” Discuss why you think Florence is preoccupied with belonging to certain spaces.
8) Andrews writes, “In a moment of rashness, [Florence] had kicked open an escape hatch from the life she’d been leading. Now that she stood outside of it, she could see how small it had gotten.” Have you experienced moments in your own life that felt this way?
9) Secrets and lies play a big part in this novel. Do you agree with Florence’s belief that “every secret contains the power to destroy something”?
10) “They were jealous, of course — jealousy being a natural corollary to ambition.” Can ambition exist without jealousy? Discuss.
11) Helen shares all types of life advice with Florence. Do you have a favorite bit of wisdom from Helen? By the end of the novel, does Helen’s worldview and lifestyle hold the same allure?
12) When did Florence’s behavior first cross the line? Does one small transgression inevitably lead to larger ones? When did Florence pass the point of no return, after which she had no choice but to stay on the path towards becoming Maud Dixon?