This reading group guide for Carolina Built includes an introduction, discussion questions, and ideas for enhancing your book club. The suggested questions are intended to help your reading group find new and interesting angles and topics for your discussion. We hope that these ideas will enrich your conversation and increase your enjoyment of the book.

Introduction

Carolina Built tells the story of Josephine Napoleon Leary, a real-life American entrepreneur who was emancipated in 1865. Leary went on to build an impressive real estate portfolio that neared $10 million in contemporary value. Through it all, she maintained a marriage, cared for her two daughters and extended family, and worked in the barbershop she owned jointly with her husband. She was faced with obstacles at every turn, but never backed down from a challenge.

Topics & Questions for Discussion

1. Kianna Alexander first learned of Josephine Napoleon Leary from a tweet. Inspired and fascinated by Leary’s story, Alexander was also dismayed that, as a native North Carolinian, she had never heard of Leary or her accomplishments. So she took to writing Carolina Built, highlighting the important story of this real-life female African American real estate businesswoman living in post–Civil War North Carolina. Consider your own time spent reading the news, scrolling through social media, surfing the internet, watching television, etcetera. Is there a person, a story, or an event you’ve come across that you were surprised had missed the mainstream? What resources—books, movies, articles, shows—might be available for you to learn more?

2. From a young age, Alexander observed that the accomplishments of African Americans are too often minimized, overlooked, or dismissed entirely. Writing Carolina Built was a way that Alexander felt she could be part of the solution to fix this erasure, by shining a light on Josephine Leary—a woman whose story has sat on the margins of history until now. Discuss the absence of figures like Josephine Leary from mainstream history. Why do you think Leary’s story hasn’t been well known for so many years? If it weren’t for Kianna Alexander writing Carolina Built, do you think Leary’s legacy would still be relatively unknown?

3. Though Alexander had myriad resources to study the historical facts of Leary’s life, a novel requires a structured narrative arc with dynamic characters, dialogue, inner monologues, and conflict, among other things. Considering the real-life subjects of this book have been dead for generations, Alexander was left to rely on her imagination and historical research to bring Leary and her family, friends, and acquaintances to life on the page as characters in the novel. In your opinion, was Alexander successful in producing a compelling novelization of real people and events in Carolina Built? What do you think would be the biggest challenges of writing a historically accurate biographical novel? If you were to write a book on a historical figure, would you choose to write a nonfiction biography or a biographical novelization?

4. After she was emancipated in 1865, Josephine Leary went on to build an extremely valuable real estate portfolio—she was a true real estate magnate at a time when it seemed all the odds were against her. Leary built her portfolio, wealth, and legacy while maintaining a marriage, running her barbershop business, raising children, and caring for her extended family, which included her grandmother, mother, and brother. As a Black woman in the late 1860s, Leary was faced with obstacles at every turn, but she never backed down from a challenge. Today, which barriers to success would Josephine still face? Which ones have become obsolete in contemporary society?

5. As Josephine begins her free, newly married life with Archer Leary (Sweety) in Edenton, North Carolina, she is quick to set her heart, mind, and focus on building her and her family’s legacy. Discuss the role of legacy in Carolina Built and in Josephine Leary’s life. Why is legacy so important to Josephine? Does Sweety assign the same importance to legacy that his wife does? Why or why not?

6. Josephine’s biological father is a white man, Colonel Lamb, who impregnated Josephine’s mother, Jeanette, when he visited the plantation where her family was previously enslaved. This was a common practice at the time, as Josephine acknowledges: “I know the colonel is the stern-looking, dark-eyed man who sired me, then denied me. I suppose he’s simply doing what other men of his status do, but I try not to think on him too much (page 4). When Josephine marries Sweety, who is also of mixed race, she mentions the difference in their complexions: “My husband possesses a fair enough complexion to pass; I do not. It’s a mere coincidence, a trick of fate. Yet wherever we go, people assume he is white and that I’m Negro” (page 13). Discuss this notion of “passing.” Do you think the events of Josephine and Sweety’s life in Edenton—including their purchasing land, building a house, opening a business in town—would have been different if they weren’t of mixed race, or if Josephine had been the one between them who could “pass,” while Sweety was considered “colored”?

7. Discuss Josephine’s very first real estate purchase, and the interaction between the newly married Learys and the proprietor, Mr. Charles, who demands the full price of five hundred dollars up front for the lot they’d like to purchase instead of half the price, as had been advertised. He says to Sweety: “I had no intention of selling my land to anybody associating with coloreds” (page 13). Josephine steps in and offers the full five hundred dollars from money sent to her as a wedding gift from her biological father. Mr. Charles relents, and reluctantly sells them the property. Within this scene we see Josephine’s ambitious, bold character and natural business acumen come to life. Discuss the nature of Mr. Charles’s racism in the context of Josephine’s observation that “his greed outweighs his prejudice” (page 15). Do you think Josephine took this fact into consideration going forward in business dealings? Do you think this observation that greed outweighs prejudice contributed to her eventual wealth and success in the real estate business? How else did Josephine use social observations and her own interpersonal skills to her advantage?

8. Discuss the nature of Josephine and Sweety’s relationship. Josephine is ruefully aware of her eccentricities as a woman in the context of her time: “Society has deemed men the breadwinners and women the caretakers, and Sweety and I are a part of that society. But to send me off to do chores as if I’m a child? Or the cleaning lady? That just beats the Dutch” (page 35). Is there an argument to be made for Sweety’s feelings of shame and emasculation in the context of history when his wife earns and spends money on herself and their family? Did you notice a distinct moment in the book when Sweety’s dismissive treatment of Josephine as a woman goes from troublesome to damaging? Why do you think Josephine stays with Sweety? What can we learn from their relationship about compassion and forgiveness?

9. Josephine has two beloved daughters, Clara and Florrie. Many times, Josephine alludes to her desire and determination to give them an easy life. She devotes herself to her daughters’ development as strong, educated, and independent women, almost as if they too are investments in the portfolio of their family’s greater legacy. In what ways does Josephine encourage and tend to her daughters’ curiosities, interests, and growth that might have been considered a break from the status quo of mothering? What parenting practices of Josephine’s might have set her apart from other mothers of her time?

10. Discuss the scene at the Edenton Ladies Auxiliary meeting where Josephine presents on “the societal roles of the modern woman, and how we might act and speak in ways that will increase our levels of success and satisfaction in life” (page 162). Josephine’s words are received with mostly bewildered and scandalized reactions. Why do you think the women in the Ladies Auxiliary react with such shock and suspicion to Josephine’s idea of financial independence? Why do you think Alberta reacts with defensive anger? Discuss the differences in the expectations of women in the 1860s. Is Josephine far ahead of her time, presenting new and unorthodox ideologies? Or are her thoughts on the role of the modern woman part of an established school of thought? Who would have been Leary’s feminist contemporaries?

11. Josephine Leary and Rosa Jackson are immediate kindred spirits, despite that Josephine is Black and Rosa is white. Josephine observes, “There’s something about Rosa, be it her easy manner, ready smile, or unconventional dress, that makes me think we’ll be fast friends” (page 24). Discuss Rosa and Josephine’s fast and easy friendship, considering Rosa is the daughter of one of the wealthiest landowners in the county. What do you make of Rosa? Why do you think she treats Josephine as an equal, while other white men and women in Edenton do not?

12. Discuss Josephine’s reactions to instances of racism in the book. When two white women attack Josephine with racial slurs, she calmy writes it off as a “lack of breeding” (page 131), choosing instead to ignore them even when they continue their racist provocations. Then there is the climactic scene at the Juneteenth festivities when three former Confederate officers drunkenly ride their horses through the celebration, hurling a wag of rotten tomatoes. After Sweety goes to the sheriff, who is willing to address his concerns because of his light complexion, the sheriff concedes to punish only the ringleader of the group, but only with a “stern talking-to” (page 241). Sweety is disappointed, but grateful for any repercussion nonetheless. What do you make of Josephine’s and Sweety’s reactions to the racism that they encounter in Edenton? How does their treatment and lack of justice make you feel?

13. The book ends with Josephine’s decision to rebuild on the lot that has burned down instead of her selling it. The closing lines suggest a long road of work ahead, and Leary’s enthusiastic intention to continue building her business and legacy for years to come: “Where I was lost, I now have direction. I have my brother, and my ancestors, to thank for that. And now that I have my heading, there will be no stopping me” (page 301). The epilogue brings us to the celebratory grand opening of the J. N. Leary Building. What questions are you left with? Do you feel there were any important questions about Leary’s life left unanswered, or is there a piece of the story you would like to know more about?

14. For Josephine, a central aspect of the legacy that she sets out to build has to do with financial security and independence for herself and her daughters—the first generation of her family born into freedom following emancipation. Unfortunately, the assumption that now-free African Americans could ascend the economic ladder and catch up with the country’s white population in terms of generational wealth has not been a reality. Eight generations later, according to a 2019 Washington Post article (see https://www.washingtonpost.com/outlook/2019/06/19/why-racial-wealth-gap-persists-more-than-years-after-emancipation/), a typical Black family in America has one tenth the wealth of a typical white family. Why? Author Ta-Nehisi Coates has coined the term “the quiet plunder,” referring to a system in which the people in power perpetuate racial discrimination and disadvantages by creating new ways to marginalize the Black population, and do so by concealing their intentions with their own narratives of freedom and civil rights. Discuss the concept of generational wealth and race in America today. What are ways that racial oppression has morphed through the years from the Civil War to today?

Enhance Your Book Club

1. Review the bibliography (page 313) and choose a text from the list to read as further reading. Discuss your choice(s) with the group.

2. Legacy is a central theme in Carolina Built—it is a primary motivating factor in Josephine Leary’s persistent business and financial ambitions. What do you think constitutes a “good” legacy to Leary? Now think about your own life. What does “legacy” mean to you? What is your idea of a good legacy, and how can you achieve it?

3. Discuss other female figures in American history who have had impressive business success. Do you see patterns in their success stories? What lessons can you apply from their experiences to your own life?