How I Write with David Perell

Guest: Susan Orlean: Award-Winning Writer Explains Her Entire Process
Date: October 29, 2025

Episode Overview

In this episode of How I Write, host David Perell sits down with bestselling nonfiction author Susan Orlean to dissect her entire writing process: from tackling the blank page (or, more accurately, a mountain of index cards), to structuring narrative nonfiction, the hard-won lessons of editing, and the emotional stakes of choosing a subject you truly love. Orlean, known for books like The Orchid Thief, Rin Tin Tin, and The Library Book, shares her practical strategies but also her artistic philosophy—revealing how the craft of writing is as much about discipline, humility, and genuine curiosity as it is about style. This episode is a goldmine for anyone fascinated by how great stories come to life.

Key Discussion Points and Insights

1. Index Card Organization and Story Structure

• System of Index Cards: Orlean describes how she relies on hundreds of 5x8 index cards ("700 of these index cards" [01:10]) to catalog and later physically arrange material, ideas, and anecdotes. This manual process helps her visualize themes and structure (01:41).
  • "I use those cards... to move around and begin seeing a structure. What pieces of information fit with other pieces of information? Or what are the themes that I see coming through in the book." (Susan Orlean, 01:44)
• Chunking Information: Each card varies in size and content, from granular details to reminders referencing larger documents (02:55). The process is both intuitive and iterative.

Notable Quote:

"It's an intuitive kind of sense of what is a chunk of thought. A chunk of thought can be something very small, or it can be something significantly bigger."
– Susan Orlean [03:44]

2. From Facts to Narrative: The Art of Connection

• Building Connective Tissue: Transitioning from a thematic card stack to a narrative means constructing links—not just listing stories but weaving them into a greater whole (05:04).
• Beyond Assembling Information: Orlean distinguishes between mere factual reporting and storytelling, emphasizing the craft required to create emotional resonance.
  • "The difference between me saying, all right, now, I'm just going to read you bullet points of information versus... let me tell you this amazing story. Sit back. I'm going to spin a mood." (06:22)

3. The Lead: Hooking the Reader

• Critical Importance: Orlean stresses the heightened significance of a strong opening today, given shrinking attention spans ("The very importance of a lead has never been greater." [07:50]).
• ‘Wait, What?’ Effect: She intentionally crafts leads to elicit curiosity, confusion, or surprise—something to stop readers in their tracks.
  • Example: The opening of The Orchid Thief describing John Laroche, ending with the punchline that he’s missing all his front teeth (08:43).

Notable Quote:

"A very good reaction to a good lead is, 'wait, what?' In a way, that is almost the ideal."
– Susan Orlean [10:19]

4. Universal Curiosity and Topic Selection

• People Are Interested in People: Orlean rarely writes about inherently newsy or globally urgent subjects. She banks on character-driven narrative to convert disinterest to engagement.
  • "It relies on the fact that I genuinely think it's an interesting story, and I don't do things unless I think they're absolutely fascinating and that I'm dying to tell people about them." (11:41)
• Shared Discovery with the Reader: Orlean positions herself as a companion to the reader—offering them stories she herself stumbled into, not ones tailored by pre-existing obsessions ("I'm not a person who collects orchids... I'm in the same position as the reader." [13:19]).

5. Lessons Learned: From Young Writer to Master Storyteller

• Mistakes of Overwriting: Early in her career, Orlean admits she equated cleverness and flowery language with good writing—something she now finds overwrought and off-putting.
  • "I think the more powerful writing is writing where you pull your punches a little. You have a tone that's got a little more confidence and is a little less like, hey, look at me." (15:22)

Notable Moment:
Perell likens this to over-sauced steak, quoting Casey Neistat’s simplicity:

"A great steak is served simply. And that's what I want to do with my videos." (16:42)
To which Orlean responds:
"The meat is what ends up really hitting with readers. ... Working so hard that you're falling all over yourself, you can't say a simple sentence. It's exhausting." (17:27)

6. Transitioning to Memoir: Writing About Herself

• Challenges of Self as Subject: Used to external research and reporting, Orlean struggled to approach memoir without the 'newness' of discovery.
  • "I didn't have that adventure of going into a new world. ... I had her [a journalist friend] interview me." (21:12)
• Letting Others Guide the Inquiry: Outsourcing the questioning process helped her illuminate overlooked or undervalued details in her life story.

7. Authenticity and Book Topics

• First Book Contract Story: Orlean shares how inauthentic enthusiasm for her initial book proposal led to publisher rejections. Only when she pitched a topic she truly loved did she get a deal.
  • "She said, 'Is this the book you really want to do?' And for better or worse, I said, 'No, I don't really want to do this idea.' ...[then] I want to do a book about Saturday night in America..." (23:28–26:54)
• Lesson for Young Writers: Editors and publishers, she stresses, can sniff out inauthenticity—a lesson in the value of genuine passion over marketability.

8. Editing: Be Brutal, Be Patient, Read Aloud

• Growth as an Editor: Moved from protectiveness over ‘every word’ to embracing ruthless self-editing, aided by technology and methodical process (30:28–32:56).
• Primary Editing Tool: Reading aloud exposes weak spots, redundancy, and poor rhythm—her “first line of editing.”
  • "Sometimes when you're reading out loud and you get a little bored, that's a sign that it's maybe a little boring." (32:56)
• Love for Editing: Orlean delights in incremental improvement, seeing editing as creative and satisfying, not tedious.

9. Craft Issues: Bad Habits and Description

• Passive Constructions: Flags overuse of “would” as weak and unnecessary ("It's sort of passive in a way, and when you remove it, it's really striking." [37:29])
• Adjectives and Strong Imagery: Advocates for potent, vivid, singular description over piling up adjectives. Too much detail dilutes impact.
  • "Rather than stringing a million adjectives together... pick one really strong image and hit it hard." (39:29)

10. Choosing Topics with Depth and Dimension

• Three-Dimensional Subjects: A book needs not just breadth (“width”) but depth—topics that serve as a prism for multiple themes, eras, or cultural currents (43:09).
• Example—Rin Tin Tin: What seems a narrow topic unfolded into a century-spanning history of Hollywood, animals in war, American pop culture (44:00–47:20).

Notable Analogy:

"Ideally you can take it and turn it in many different directions and go, oh, I'm now seeing it from this direction. ... They’re all part of the same story."
– Susan Orlean on finding a ‘prism’ subject [47:39]

11. Process, Discipline, and Daily Quotas

• Phased Approach:
  • Research & Reporting ("three or four years of research" for The Library Book [50:57])
  • Processing & Structuring (index cards, never starting to write before digesting the material)
  • Writing: strict daily word quotas (usually 1,000 words per day, 5–6 days/week).
    • "I look at it as a task. My task today is to tell you a thousand words of this story." (53:50)
• Discipline Feels Liberating: Contrary to myths about wild, chaotic inspiration (a la Kerouac), Orlean finds structure liberating for creativity and prevents procrastination (55:58–58:39).

Notable Quote:

"It was immensely liberating to give myself these deadlines. ... Instead of looking at the void, feeling this is overwhelming, my response used to be: I'll go organize my knife drawer."
– Susan Orlean [56:38]

12. Editing and Writing Analogies

• Editing and Running: Perell and Orlean compare marathon training to book writing—success comes from incremental, achievable goals and psychological pacing (60:49–62:27).

13. Libraries: Memory and Permanence

• Central Theme of The Library Book: Libraries as bastions of permanent memory—even more meaningful given the ephemeral nature of human life and individual memory (62:32–65:19).
• Modern Libraries: Orlean pushes back against the idea of decline, seeing libraries as vibrant, adaptive public spaces that evolve along with culture, technology, and public need (66:03–69:08).
  • "They have become these public portals to information, and libraries just have evolved with each change in the culture admirably. ...They see them as kind of community centers for knowledge, however that may be conveyed." (68:28)

Notable Quotes & Memorable Moments

• “A very good reaction to a good lead is, ‘wait, what?’ ...Because when we're saying 'wait, what,' you're saying, I'm gonna read a little more." (Susan Orlean, 10:19)
• “I wasn't having that adventure of going into a new world. I had to try as much as I could to create some version of that ... I had her interview me.” (21:12)
• “I think the more powerful writing is writing where you pull your punches a little. …A tone that's got a little more confidence and is a little less like, hey, look at me.” (15:22)
• “You should write how you find works for you. Whatever rhythm works for you.” (57:25)
• “Each description you use should be a real punch. A really strong punch of visual imagery.” (39:29)
• “[Libraries] have become these public portals to information…” (68:28)

Timestamps for Key Segments

| Timestamp | Segment | |------------|----------------------------------------------------------------------------------| | 00:37 | Orlean’s index card methodology for research and structure. | | 06:00 | Difference between factual reporting and narrative storytelling. | | 07:25 | The critical importance of a great lead. | | 08:43 | Reading the opening of The Orchid Thief; crafting irresistible leads. | | 14:40 | Lessons Orlean would give her younger writer self (avoiding overwriting). | | 18:10 | Transitioning from writing about others to memoir—challenges and solutions. | | 23:28 | The (inauthentic) triathlon book proposal and the eventual, authentic breakthrough.| | 30:28 | Learning to self-edit ruthlessly and the fluidity technology enables. | | 32:19 | Trick: reading work aloud to catch flaws and redundancy. | | 37:29 | Common writing bad habits: overusing "would", adjectival overload. | | 43:09 | What makes a book subject right: dimensionality and depth. | | 49:31 | Orlean’s day-to-day process for book-length projects: research, then writing. | | 53:50 | On daily word quotas and how structure enables creative focus. | | 62:32 | Libraries as vehicles for memory and permanence. | | 68:28 | Libraries adapting and thriving despite perceptions of decline. |

Final Thoughts

This episode provides an intimate, practical, and inspiring window into Susan Orlean's rigorous-yet-playful approach to writing. Her blend of discipline, empathy for her readers, ruthless editing, and deep curiosity can inform and energize any aspiring writer or storyteller. The episode is a masterclass not just in process, but in why stories—and the places we store them, like libraries—matter so enduringly.