Susan Orlean is a longtime staff writer for The New Yorker and the author of multiple bestselling books, including The Orchid Thief, which was adapted into the Academy Award–winning film Adaptation. Her new book, Joy Ride, is a gripping and funny memoir that details her incredible writing journey, and also serves as an inspiring guide filled with actionable tips for anyone embarking on a creative project.
Orlean built a wildly original career by following her curiosity, taking big creative risks, and treating her writing like a business she runs herself. We’ve broken down her recent appearance on the How Success Happens podcast to help you apply her advice to launch your own success in three, two, one!
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Three Key Insights
1. How to Know If Your Big Idea Is Worth It
Susan says the instinct to know whether an idea is worth years of work is “probably the single most important” skill you can develop, whether you’re writing a book or building a business. When a new idea hits, she does not jump in immediately; instead she “pushes it away,” tries to forget it, and pays close attention to whether it keeps resurfacing and “nagging” at her as both a writer and a reader. She also normalizes doubt, explaining that losing faith in an idea mid-process is not automatically a sign to quit but a natural part of starting from zero and testing what you’re doing. The real challenge is learning to distinguish ordinary fear and laziness from the deeper realization that “this really isn’t as good an idea as I thought.”
Takeaway: When a new idea excites you, deliberately step back, see if it keeps coming back, and only then commit the time, money, and energy to build it.
2. Treat Your Creativity Like a Business
Even though she’s a New Yorker staff writer, Susan describes herself as “essentially self-directed and self-employed,” choosing each project the way a founder chooses what to build next. She spends months or years purely researching—interviewing, reading, and going deep—before she writes a single word, saying she must be “a student” of a topic before she earns the right to become “the teacher.” To avoid overwhelm, she types up her notes, transfers them to index cards, and then sets a strict daily quota of 1,000 words, comparing it to running exactly three miles instead of an undefined workout. That concrete metric “demystified” the work and kept her from sitting down to vaguely “write my book,” which she says is impossible.
Takeaway: Run your creative work like a business by defining clear tasks, building a repeatable system, and holding yourself to simple, concrete daily goals.
3. Editing (and Feedback) Makes You Stronger
Susan is blunt about writers who romanticize “deathless prose” and hate edits, saying people who think editing ruins their work are “probably not very sophisticated writers.” She credits good editors who respect her voice and focus on clarity, repetition, and what needs more or less emphasis, calling them “really good readers” whose confusion or questions always have “validity.” For her, being open to discussion, debate, and occasionally pushing back is part of a mature creative practice, not a threat to it. She even likens that back-and-forth to the constant testing entrepreneurs do when they hit walls and have to decide whether to adjust or abandon an idea.
Takeaway: Seek out tough, thoughtful feedback, and treat it as market insight on your ideas rather than an attack on your talent.
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Two Ways to Learn More
- Keep up with Susan through her Substack newsletter Wordy Bird, and pick up her new book Joy Ride—a candid, funny look at her career and craft.
- Check out one of Entrepreneur.com’s most-read articles on getting your writing project started — and finished: 7 Writing Hacks Every Writer Must Know
One Question to Ponder
Susan discusses the inevitable moments when you lose confidence and have to decide whether you’re just tired or truly need to walk away from an idea. What’s one project, business, or creative idea you nearly quit—but didn’t—and how did you know it was worth pushing through that doubt?
Send your answer to: howsuccesshappens@entrepreneur.com. We’ll read the best answers on a future episode of How Success Happens!
About How Success Happens
Each episode of How Success Happens shares the inspiring, entertaining, and unexpected journeys that influential leaders in business, the arts, and sports traveled on their way to becoming household names. It’s a reminder that behind every big-time career, there is a person who persisted in the face of self-doubt, failure, and anything else that got thrown in their way.
Susan Orlean is a longtime staff writer for The New Yorker and the author of multiple bestselling books, including The Orchid Thief, which was adapted into the Academy Award–winning film Adaptation. Her new book, Joy Ride, is a gripping and funny memoir that details her incredible writing journey, and also serves as an inspiring guide filled with actionable tips for anyone embarking on a creative project.
Orlean built a wildly original career by following her curiosity, taking big creative risks, and treating her writing like a business she runs herself. We’ve broken down her recent appearance on the How Success Happens podcast to help you apply her advice to launch your own success in three, two, one!
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