Table of Contents
At the 29th season of Winter Words, hosted by Aspen Words, legendary journalist and author Susan Orlean sat down with moderator Christine Benedetti to discuss her storied career and her latest work, Joy Ride. Known for her tenure at The New Yorker and her best-selling books like The Orchid Thief and The Library Book, Orlean has built a reputation as a writer who uncovers deep meaning in the seemingly mundane. During this wide-ranging conversation, she shared insights into the transition from observer to subject, the changing landscape of the magazine industry, and the "elemental" nature of curiosity that drives her work.
Key Takeaways
- Curiosity as a Professional North Star: Orlean credits her career to an innate openness to the world, a trait she inherited from her father, who believed he could have been a writer had circumstances allowed.
- The Art of Curation: Writing a memoir is less about recording a life in real-time and more about the editorial judgment of what to leave out to keep the narrative compelling.
- The Evolution of Media: While the "glory days" of print advertising and metropolitan Sunday magazines have waned, the digital expansion offers new, albeit different, entry points for aspiring journalists.
- Student vs. Teacher: Orlean views reporting as an external process of learning (being a student) and writing as the internal process of translating that knowledge for others (being a teacher).
The Genesis of a "Story of Stories"
For years, Susan Orlean insisted she would never write a memoir. However, the unique conditions of the COVID-19 pandemic and a realization that it had been 25 years since the publication of The Orchid Thief prompted a period of deep reflection. What began as a project about the craft of writing eventually evolved into Joy Ride, a book she describes as "the story of my stories."
Turning the Lens Inward
Accustomed to observing others, Orlean found the prospect of being her own subject daunting. To overcome the awkwardness of self-examination, she hired a journalist to interview her over several months. This provided a third-person perspective on her own life, helping her identify the narrative arcs that were previously hidden in her memory. She also had to navigate the physical remnants of her past; Columbia University had recently acquired her professional papers, forcing her to book time in their library to access her own notes, drafts, and even the occasional accidentally archived tax return.
"What I’m good at is noticing the world around me. How can I notice myself? It felt really like a challenge."
The Discipline of Narrative Curation
A central theme of the discussion was the necessity of editorial judgment. With a career spanning eight books and hundreds of articles, Orlean had to choose which milestones to feature in Joy Ride. She ultimately focused on three major magazine pieces—including a profile of a ten-year-old boy for Esquire and a story on a gospel group—to illustrate the broader evolution of her career.
This curation process is what Orlean considers the "great art" of writing. By focusing on specific milestones, such as The Orchid Thief, Rin Tin Tin, and The Library Book, she provides readers with a sense of the long arc of a creative life without overwhelming them with unnecessary detail. The goal is to provide compelling, telling details rather than a chronological log of every moment.
Navigating a Shifting Media Landscape
Orlean’s career took off during an era of "titans" like Tina Brown and Anna Wintour, a time when metropolitan newspapers and alternative weeklies flourished. She acknowledges a certain nostalgia for this period, noting that many of the publications where she got her start no longer exist. However, she avoids a purely pessimistic view of the industry’s digital migration.
Advice for the Next Generation
When asked about advice for young writers, Orlean is candid about the current challenges. While the barrier to entry has lowered, the economic stability of the profession has shifted. She suggests that while print pages are shrinking, digital platforms are expanding and offer space for those who are enterprising.
"It’s never been easier to get published. It’s never been harder to get paid for it."
She emphasizes that the most valuable asset a writer can possess is a good story idea. Rather than simply wanting "to be a writer," she encourages novices to develop a practice of looking at the world with curiosity and advocating passionately for the stories they find. Orlean believes that editors are always hungry for a great idea, even if it sounds unpromising on the surface.
The Mechanics of Discovery
Orlean’s most famous works often started with "weird" or "unpromising" premises. The Orchid Thief began with a small news item about a man arrested for stealing orchids in a Florida swamp. The Library Book was born from her realization that she didn't actually know how libraries functioned, despite their presence in her life since childhood.
She argues that a writer must allow a story to change during the reporting process. If the final product matches exactly what the writer imagined before they started, the story likely lacked depth. This willingness to be surprised—and to follow the story where it leads—is what separates a standard report from a piece of narrative non-fiction.
"If a story is turning out as you expected it, it’s not a good story."
Finding the "Ending"
The conversation concluded with a discussion on the elusive nature of "done." Orlean admits that no piece of writing is ever truly finished; instead, a writer eventually feels they have completed a "circuit in the storytelling." For a memoir, this is particularly difficult, as the only true ending would be the end of the author's life.
In Joy Ride, she resolved this by writing about the craft of writing endings. By slowing down the tempo and bringing the reader to a comfortable settling point, she found a way to tie off the narrative arc of her career thus far. Even as she continues to work on new projects—including a story for National Geographic and a new book—Orlean remains committed to the same curiosity that has defined her work for over 30 years.
Conclusion
Susan Orlean’s career is a testament to the power of staying open to the world’s "bristling" potential for stories. Whether she is exploring the intricacies of a massive library fire or the life of a ten-year-old boy, her work is grounded in a deep respect for the subject and an unwavering commitment to the craft of storytelling. As the media landscape continues to evolve, her focus on curiosity and narrative integrity remains a vital blueprint for writers and readers alike.
