How I Write: “My Top 10 Writing Lessons from 2025”

Host: David Perell
Date: December 3, 2025

Episode Overview

This special solo episode of How I Write has host David Perell reflecting on the most powerful writing lessons and conversations from interviews with acclaimed writers throughout 2025. Drawing on clips from previous guests, David distills ten core insights about the craft, mindset, and purpose of writing—ranging from nurturing wonder and ambition, to breaking through barriers of convention and self-doubt, to the practical methods and rituals that underpin great storytelling.

Perell walks listeners through vivid stories, memorable lines, and diverse perspectives, illustrating how unique each writer's process can be, yet how universal many of their challenges and discoveries are. Throughout, listeners are encouraged not just to write, but to see, to live, and to strive for true originality by standing on the shoulders of literary giants.

Key Lessons and Discussion Points

1. Retain Your Sense of Wonder

(Guest: Alain de Botton, 02:25–03:34)

• Wonder is “an essential survival skill”—it’s “jaw dropped…poisoned by the miracle of the world.”
• Rainbows as the “charismatic megafauna of wonder”—each person’s experience of wonder is unique and “utterly bespoke.”
• Quote:

  “If you’d stepped a yard to the right and become a different person, you’d have seen a different rainbow. So that’s wondrous.”
  – Alain de Botton (03:24)

2. Writing From Felt Sense, Like an Impressionist

(Reflections on Robert’s Writing, 03:34–05:28)

• Writers like Robert “write with a deep emotional or even spiritual connection,” rendering their felt experience rather than factual reality.
• Comparison to Monet and Impressionists: it’s about capturing “a combination of light, water, and shadow,” not every architectural detail.
• Writing that starts with, “What does this make me feel? And how do I put that onto the page?”

3. Embrace the Mystery: Following Memory Into Meaning

(Guest: Jane Ann Phillips, 05:28–07:51)

• The power of “what we don’t forget” as a clue to identity and values.
• Writing as surrender—“I’m inside the work, following the sentences themselves deeper into the material.”
• Quote:

  “If the writer can pull you in deeply enough, you are experiencing that voice, almost as though it’s happening to you.”
  – Jane Ann Phillips (07:13)

4. Dare to Be Great—Risk Ambitious Art

(Guest: Paul Harding, 10:47–13:15)

• It’s okay—even necessary—to aim to create work as powerful as your greatest heroes.
• Evolve from being “self-conscious” (afraid of judgment) to “self-aware” about your ambitions.
• Reverence for the craft and those who’ve come before, learning by studying the best.
• Quote:

  “You’re only a jerk if you say you did it…but I’m not trying to write a crummy book. Melville was just trying to write a book as good as Hamlet.”
  – Paul Harding (11:46–12:14)

5. Study the Greats and Steal With Meaning

(Discussion with Dana Gioia, 16:38–23:13)

• Insights from Gioia on Baudelaire (“the greatest poet of having fucked up your life”), Marshall McLuhan, Bob Dylan, Steinbeck (“the dignity of the outcasts”), Cheever (“a fabulist”), Tolkien (“the English version of War and Peace”), Tolstoy, and Dostoevsky.
• Collaboration (the Beatles), rhetoric (MLK), and performative power.
• On originality:

  “So much originality is born out of a deep understanding of people who’ve come before…”
  – Host (23:13)

6. Observe Reality: “Don’t Think, Look.”

(Guest: Henrik Carlson, 25:06–26:42)

• Approach writing as a painter approaches a still life—constantly checking your words against reality.
• Don’t get lost in manipulating words; stay grounded in the thing itself.
• Quote:

  “Wittgenstein has this line…‘Don’t think, look.’”
  – Henrik Carlson (26:42)

7. Break Free From Industrialized Thinking

(Guest: Alain de Botton, 28:12–29:51)

• The news and culture can “industrialize our inner lives.”
• Free thinkers celebrate knowing less about what “everyone” knows, keeping mental space for themselves and their art.
• Quote:

  “You are not really a responsible adult until you don’t know certain significant things that people around you think of as very important…congratulate yourself.”
  – Alain de Botton (29:14–29:46)

8. Write With Your Voice, Not Corporate Speak

(Guest: Lulu Cheng Masservi, 32:27–33:23)

• People are “allergic to inauthentic corporate speak.”
• Let personality and authenticity shine, imperfections and all.
• Quote:

  “It’s better for it to be bad and honest…than to release something that’s dead and boring and stale and stiff, because that is just not going to break through.”
  – Lulu Cheng Masservi (32:27)

9. Storytelling: Lightness and Speed

(Guest: Mitch Albom, 34:44–39:48)

• Tell “the slow parts fast and the fast parts slow.”
• Strive for engaging, human-centered stories—less worry about exhaustive detail, more about emotional truth.
• Memorable Story:
  Mitch recounts the 1992 Olympics, a runner’s injury, and the father carrying his son, revealing the power of crafting a tale around feeling and meaning:

  “…when he was a little boy, I taught him how to run. I put his feet on my feet, and that’s how I taught him…I remembered that, so that’s what we did.”
  – Mitch Albom (38:52–39:48)

10. Poetry Should Be Lived, Not Just Analyzed

(Guests: Dana Gioia, David White, 40:25–45:13)

• Poetry was once central and joyous—“badly taught” but beloved—until overanalyzed.
• The secret to loving poetry is to experience, memorize, and perform it, not only dissect it.
• Quote:

  “My sense of teaching poetry is fairly simple. Students experience it…they memorize it. And then, once you’ve done that, you can do some analysis. But analysis is very secondary to what poetry is.”
  – Dana Gioia (41:31)

• David White: Poetry is “a secret code to life”—a well-memorized poem can sustain and guide through life’s trials.
• White’s recitation of Mary Oliver’s “The Journey” exemplifies this:

  “…there was a new voice, which you slowly recognized as your own. That kept you company…determined to save the only life you could save.”
  – David White (44:00–45:13)

Memorable Closing: Life, Love, and “The True Love”

(David White, 46:56–50:46)

• Writing is ultimately a prism for exploring life—love, grief, wonder—beyond the page.
• David White shares the story and reading of his poem “The True Love,” connecting biblical narrative, Hebrides tradition, and the personal quest for reverence and courage in love.
• Quote (poem excerpt):

  “There’s a faith in loving fiercely the one who is rightfully yours…So that when you finally step out of the boat toward them, you find everything holds you…and if you wanted to drown, you could. But you don’t…You’ve simply had enough of drowning, and you want to live and you want to love.”
  – David White (47:54–50:46)

Additional Highlights & Techniques

• Impressionism in Writing: Both Robert’s and Monet’s approaches teach writers to translate subjective experience, not merely external fact.
• Diversity of Process: There is no single “right” way to write; surrender to the book or rigorously structure it—each approach is valid if it leads to truth.
• Learning by Memorizing: Host’s anecdote about memorizing poetry lines in a Portland bar—a way to make poetry personal and alive again.
• Breaking Convention: Good writing doesn’t need perfection—Reddit threads or text messages can pulse with authenticity if truly felt and well-observed.

Timestamps for Key Segments

• 02:25 – Alain de Botton on wonder
• 05:40 – Jane Ann Phillips on memory and immersion
• 10:47 – Paul Harding on writing ambitiously
• 13:55 – On influence and finding your “canon”
• 16:38 – Dana Gioia on literary and artistic lessons
• 25:25 – Henrik Carlson on looking at reality
• 28:12 – Alain de Botton on mental horizons and the media
• 32:27 – Lulu Cheng Masservi on authenticity in writing
• 34:44 – Mitch Albom on storytelling and family tales
• 40:25 – Dana Gioia on poetry’s purpose
• 46:56 – David White, “The True Love”

Notable Quotes

• “Wonder is an essential survival skill.” – Alain de Botton (02:25)
• “It’s strange what we don’t forget.” – Jane Ann Phillips (05:40)
• “You want to evolve from being self-conscious about your writing to being self-aware about your writing.” – Paul Harding (11:14)
• “Baudelaire is the greatest poet of having fucked up your life.” – Dana Gioia (17:23)
• “Don’t think, look.” – Henrik Carlson, quoting Wittgenstein (26:42)
• “You are not really a responsible adult until you don’t know certain significant things that people around you think of as very important.” – Alain de Botton (29:14)
• “If the writing is bad, it’s better for it to be bad and honest…” – Lulu Cheng Masservi (32:27)
• “Tell the slow parts fast and the fast parts slow.” – Host (36:00)
• “Poetry was always something that I felt was a secret code to life.” – David White (43:26)
• “…you will walk across any territory, however fluid and however dangerous, to take the one hand you know belongs in yours.” – David White, “The True Love” (50:43)

Tone & Final Reflection

Throughout the episode, Perell is warm, anecdotal, and thoughtful, gently encouraging experimentation and self-discovery. The conversations range from the poetic to the pragmatic, but always circle back to the central idea: Writing is about revealing the world as you feel it and see it. The episode ends on a note of reverence for the art, showing how writing, when honest and deeply seen, becomes a prism for all of life.

For Listeners

If this episode resonated, Perell encourages you to share it with a fellow writer or anyone striving to express themselves more fully—and to join the conversation with your own takeaways and lessons.

[Advertisements, intros, outros, and technical segments have been omitted. All content above is focused on the substantive writing lessons and insights shared in the episode.]