Fail Better with David Duchovny

Episode: How Megan McArdle Became a Liberal-tarian
Date: November 11, 2025
Guest: Megan McArdle, Columnist for The Washington Post & Author of “The Upside of Down”

Episode Overview

In this episode, David Duchovny sits down with Megan McArdle, columnist for the Washington Post and author of “The Upside of Down,” to explore the contours of failure, risk, and the messy intersection of success, meaning, and happiness. The discussion delves into McArdle’s intellectual journey from her progressive New York upbringing through her embrace of libertarian ideas, and how experience, writing, and getting older have shaped her nuanced, hybrid “liberal-tarian” worldview. The conversation balances personal anecdotes, musings on technology and AI, and broader societal questions about government, regulation, struggle, and personal meaning.

Key Discussion Points & Insights

Rethinking Failure and Success

• Blurring Lines as We Age

  • Duchovny opens by noting how the more we explore failure, “the less those terms failure and success mean anything…they start to blend into one another and become part of the same experience, which is life.”
    • [02:08] David Duchovny: “I don't even understand what [Failing Better] means anymore...the more you interrogate or investigate failure, the less those terms failure and success mean anything.”

• Evolution of Perspective

  • McArdle reflects that she'd write a different book now because failure and success feel less clear-cut as she’s aged. Happiness isn’t always the chief aim—sometimes meaning is more important:
    • [03:38] Megan McArdle: “...I would probably talk more just about what it even means to succeed or fail...most people in their lives often realize that the thing they didn’t reach was a good thing and that the thing they were aiming for was not something that would have made them happy…maybe being happy isn’t all they want out of life.”

• Value of Struggle

  • The hosts discuss “struggle” as central to a meaningful life, more so than achieving peaks of happiness.
    • [05:33] David Duchovny: “Struggle in many ways is happiness...life is in the creating of these things to kind of inspire you to get off your ass and try to figure something out...it’s not the actual figuring out.”

Friendship, Kindness, and Daily Richness

• McArdle recalls a recent unremarkable-yet-meaningful vacation, reflecting on how, with age, she prizes kindness and consistent friendship over cleverness or excitement:
  • [06:16] Megan McArdle: “...there’s a great line...when I was younger, I admired people who are clever. And now that I’m old, I admire people who are kind...It’s easier to be clever than to be kind consistently.”

The Art and Nostalgia of Pie

• McArdle’s passion project: a 3,000-word essay about the history and family meaning of pie.
  • [08:48] Megan McArdle: “I wrote a long...3,000-word essay on the history of pie and I loved that piece. It was like my heart and soul.”
• She connects pie-making to lost skills as technology makes life easier but also erodes certain types of achievement.
  • [09:02] Megan McArdle: “American pie gets a bad rap because almost no one makes their crust from scratch anymore...pie, my favorite food in the world is pie made with purple raspberries...they don’t really ship well...so you basically have to grow them or buy them right where they were grown.”

Technology, AI, and Loss of Mastery

• Duchovny and McArdle debate “ease” conferred by technology and what’s lost when skills and hard-won effort are replaced.
  • [12:02] David Duchovny: “What technology offers is ease...but over the long term, ease eats away at us, I think.”
• McArdle references Walter Ong’s work on how major technological shifts (e.g., printing press) change culture—some things are lost even as others are gained.
  • [13:20] Megan McArdle: “We lost something with mass literacy. We didn’t just gain something...Culture shifted.”
• On writing and AI: McArdle says writing is “writing to think,” and AI shifts both craft and the deeper experience of engagement.
  • [14:41] Megan McArdle: “You don’t think to write. You write to think...if you’re not doing the writing yourself, you’re not having the experience.”

Relationships with Readers & Authenticity

• McArdle discusses how audience relationships are growing in importance versus anonymous, byline-less journalism. Community and authenticity matter more in the age of AI-augmented writing.
  • [17:18] Megan McArdle: “The other side...is becoming more important: to build a relationship with your audience for them to feel like they know who you are...”

Upbringing & Political Evolution

• McArdle recounts a “very liberal” Upper West Side New York childhood, with family ties to both liberal and Republican traditions:

  • [23:38] Megan McArdle: “I grew up in a very liberal milieu...as far as I knew, I didn’t know any Republicans.”

• She details her drift from “liberal to libertarian to liberal-tarian,” sparked by reading economics, self-reflection, and living amid different social worlds:

  • [25:57] Megan McArdle: “The shorthand of your sentimental education...is liberal to libertarian to what you call yourself now, liberal-tarian.”
  • [26:12] Megan McArdle: “I decided I wanted to be a writer when I was 8...I wrote a novel in one of those black and white composition books.”

• On failing as a writer:

  • [26:45] Megan McArdle: “I wrote a novel right after college, but it was like the worst novel ever written in the English language...The thing is, everyone, all writers are like this.”

Writing Process and Engaging Audiences

• Intricacies of writing, “pantsers” vs. “planners,” and adjusting to audience reaction—McArdle adapts her journalism to keep readers engaged.
  • [30:11] Megan McArdle: “...Where is the audience right now? Are they arguing with me? Are they enjoying themselves? Are they getting kind of bored...then I try to work with that.”

Libertarianism and Healthy Skepticism

• The meaning of being a “liberal-tarian,” and how McArdle’s libertarianism is rooted in skepticism of centralized power, not blind faith in markets or deregulation.
  • [42:30] Megan McArdle: “I’m not that kind of libertarian. I’m a libertarian who is skeptical of government power in a number of ways...I just lean on the side of what if government did less stuff...”
• On government regulation, idealism vs. reality, and the messiness of policy.
  • [43:46] Megan McArdle: “One thing that I think people do is...look at real problems...then they kind of imagine an ideal government solution and then they compare the ideal solution to the real world thing. But the solution you’re going to put in place is not going to look like your ideal system.”

Tech Culture, Ego, and Risk

• On tech moguls, hubris, and the blurry line between admirable risk and tone-deaf ego.

  • [45:45] David Duchovny: “It does seem to me that they're infected by this idea that because they were a success in one area that they know everything about everything else.”
  • [47:09] Megan McArdle: “Anyone who does anything that’s unique and takes the kind of risk taking and intensity...they took a lot of risk, they put it on the line and they made it work.”

• Should government take more risk? On science funding, vaccines, and the COVID response—how risk-taking can sometimes deliver huge public benefits.

  • [49:02] Megan McArdle: “In some ways I do want the government to be more of a risk taking entity...We could do more of that with our science funding.”

Struggle, Ease, and the Search for Meaning

• The danger of choosing ease over challenge in life and culture.

  • [51:19] David Duchovny: “...We're just so addicted to our ease again...But that’s killing us soulfully, I think.”

• The importance of chosen struggle and craftsmanship for happiness and self-worth.

  • [52:47] Megan McArdle: “...we don't have to struggle against the land, we don't have to struggle against...How do we maintain our struggle?...that is what’s valuable about it.”

Concluding Thoughts: Debate, Openness, Civility

• Duchovny commends McArdle for her ability to debate herself and model how ideological conversations might become more productive in society:
  • [54:14] David Duchovny: “...to watch you debate yourself is exemplary, you know, it’s an exemplary way to see how the debate might happen because you are at home, home on both sides in some ways...hopefully modeling how we can have, start to have this discussion in this country.”
  • [55:06] Megan McArdle: “Well, it’s very kind. Thank you for having me on. This has been an amazing discussion and really enjoyable.”

Notable Quotes & Memorable Moments

• On Meaning & Contentment:
  • [03:38] Megan McArdle: “Some of them realized that maybe being happy isn’t all they want out of life. Right. They want some higher meaning or they want to feel like they're struggling in a great cause.”
• On Kindness:
  • [06:16] Megan McArdle: “...when I was younger, I admired people who are clever. And now that I'm old, I admire people who are kind.”
• On Pie & Tradition:
  • [10:00] Megan McArdle: “…my favorite food in the whole world is purple raspberry pie.”
• On Writing and AI:
  • [14:41] Megan McArdle quoting Derek Thompson: “You don’t think to write. You write to think.”
• On the Value of Struggle:
  • [05:33] David Duchovny: “Struggle in many ways is happiness...life is in the creating of these things...”
• On Growth Through Failure:
  • [28:49] Megan McArdle: “...you have to be comfortable with the fact that your work’s not going to be very good a lot of the time and that you have to take the not very good work and make it better.”
• On Finding Joy in Creation:
  • [33:30] David Duchovny: “Whatever words you want to put on that feeling, I would put joy on it...because you love thinking about it, talking about it, writing about it, knowing about it...”
• On Struggle as Human:
  • [52:47] Megan McArdle: “...it’s not just something that makes us human, it is something that makes us happy.”
• On Bridging Political Worlds:
  • [54:14] David Duchovny: “You have traversed the spectrum in many ways...to watch you debate yourself is exemplary...and open.”

Timestamps for Significant Segments

• The Fuzziness of Failure and Success: [02:08-05:33]
• On Friendship, Kindness, and Maturity: [06:16-08:47]
• Pie, Technology, and Lost Traditions: [08:48-14:41]
• Writing, AI, and Experience: [14:41-17:37]
• McArdle’s Upbringing & Political Journey: [23:30-28:49]
• Failure in Writing & Creative Process: [28:49-33:30]
• Engaging the Audience: [30:03-33:30]
• Liberal, Libertarian, and "Liberal-tarian": [38:38-43:28]
• Tech Culture, Ego, and Government Risk: [45:45-51:19]
• Struggle vs. Ease; Modern Malaise: [51:19-54:14]
• On Civil Discourse: [54:14-55:06]

Tone & Style

The conversation is introspective, candid, wryly humorous (especially around tales of baking or ideological faux pas), and intellectually adventurous—both Duchovny and McArdle model curiosity and gentle skepticism, encouraging listeners to ask themselves why they believe what they do, and how “failure” might be reframed as a vital engine of growth, connection, and meaning.

This summary captures the essence of the episode, providing clear entry points and context for listeners and non-listeners alike.