Conversations with Tyler

Henry Oliver on Measure for Measure, Late Bloomers, and the Smartest Writers in English

March 4, 2026

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  • Shakespeare's *Measure for Measure* is fundamentally a pragmatic play exploring the strained quality of mercy and the impossibility of individuals consistently adhering to abstract moral principles, leading to necessary, albeit imperfect, political resolutions. 
  • The interpretation of Shakespeare's works, particularly lines like Isabella's 'I did yield to him,' is highly dependent on the reader's temperament and willingness to seek controversial or non-literal readings, often complicated by the intentional ambivalence of the text. 
  • Writers like Jonathan Swift possess a unique practical intelligence demonstrated by their ability to argue complex issues—from politics to coinage—coherently across both fictional and non-fictional formats, a versatility less evident in many other literary figures. 
  • Late bloomers enjoy success more because it allows them to leave behind negative past experiences and move forward into something new. 
  • Ayn Rand's novel *Atlas Shrugged* is considered an extraordinarily good novel with exciting plot elements and first-rate B-movie dialogue, despite her controversial philosophy. 
  • When reading Shakespeare's *Measure for Measure*, listeners should decide for themselves whether to engage deeply with footnotes and blow-by-blow analysis or focus on the overall narrative. 

Segments

Listener Meetup Announcement
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(00:00:04)
  • Key Takeaway: The next Conversations with Tyler listener meetup is scheduled for Friday, April 10th, at the Vault Gallery in Chicago, Illinois.
  • Summary: The event will feature a Q&A session with Tyler, opportunities to meet the team and fellow listeners, and light refreshments. Registration is required and operates on a first-come, first-served basis due to limited space.
Introduction of Henry Oliver
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(00:01:16)
  • Key Takeaway: Henry Oliver, a research fellow at Mercatus, is the author of Second Act about late bloomers and writes The Common Reader Substack.
  • Summary: Oliver is introduced as the guest for this episode of Conversations with Tyler. The discussion is set to begin with Shakespeare’s Measure for Measure. Oliver also co-authors a new Substack on the pursuit of liberalism with Rebecca Lowe.
Measure for Measure Popularity
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(00:01:49)
  • Key Takeaway: Measure for Measure has historically suffered in popularity because its ending is unsatisfying from an entertainment perspective, often featuring rapid dialogue delivery and a lack of a conventionally happy resolution.
  • Summary: The play is considered difficult to enjoy on stage because it experiments with a comedy structure that lacks the expected marriage and celebration ending. Many modern audiences desire a happier narrative than what Shakespeare provides in this work.
Rereading and Passionate Scenes
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(00:02:52)
  • Key Takeaway: A recent reread of Measure for Measure revealed the scenes between Isabella and Angelo to be surprisingly enthralling and passionate, moving beyond its typical categorization as merely a play of ideas.
  • Summary: The intensity of the central conflict between the two characters was more striking than remembered. The play is recognized as containing some of Shakespeare’s best work in these specific interactions.
Core Theme of Measure for Measure
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(00:03:36)
  • Key Takeaway: Measure for Measure examines the strained application of mercy, picking up the theme from The Merchant of Venice, and ultimately argues that no individual can consistently maintain their abstract principles, necessitating a pragmatic acceptance of inconsistency.
  • Summary: The play contrasts Portia’s hypocrisy in Merchant of Venice with Angelo’s hypocrisy, showing that abstract ideals of justice cannot be consistently implemented by individuals. The core message suggests that attempting to live by strict principles leads to hypocrisy, and society must pragmatically ‘make it work.’
Feminist and Skeptical Readings
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(00:05:54)
  • Key Takeaway: One reading suggests Measure for Measure is highly skeptical of Christianity and feminist in nature, as Isabella receives a terrible outcome where the Duke forces marriage upon her without consent, potentially constituting enslavement.
  • Summary: Isabella’s expectations are violated as she cannot join the convent and is forced into a relationship with the Duke, contrasting sharply with Angelo’s lesser punishment of marrying Mariana. This highlights how dispensing justice based on Christian standards results in terrible outcomes for women.
Political and Erotic Resolution
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(00:08:07)
  • Key Takeaway: The play contrasts with The Rape of Lucrece by using artifice and substitution to forestall the direct resolution of political and erotic tension through actual rape and subsequent regime collapse, suggesting a pragmatic, albeit flawed, reconciliation.
  • Summary: In The Rape of Lucrece, the political order falls after an actual rape, whereas Measure for Measure avoids immediate tragedy through deceit, keeping the autocracy in power. Shakespeare questions whether this artifice, leading to forced marriages, is a better, more pragmatic scenario than widespread death.
Incest and Fertility Crisis Interpretations
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(00:11:32)
  • Key Takeaway: A less literal reading posits the play addresses a societal fertility crisis in a world rife with illegitimate sex, where Isabella’s refusal to engage sexually (even with her brother) is a defense against this pervasive environment, which the Duke ultimately forces her back into via marriage.
  • Summary: The prevalence of non-legitimate couplings in the play’s setting leads to questions about incestuous undertones, making Isabella’s desire for the strict restraint of a convent understandable. The Duke’s final action forces her into marriage to address the state’s need for population when the brothels are shut down.
Yielding to Angelo Ambiguity
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(00:16:41)
  • Key Takeaway: Isabella’s line, ‘and I did yield to him,’ in Act 5, Scene 1, is highly confusing, but the context suggests she is either literally admitting to yielding to Angelo or, more likely, conceding a premise in an argument with the Duke to leverage her brother’s release.
  • Summary: The Duke interrupts Isabella’s recounting of events, focusing on her phrasing, which highlights the play’s theme of language and pragmatism. The line follows her recounting of how she ‘prayed and kneeled,’ and the subsequent context implies she is describing the necessary concession made to Angelo before the substitution plot was enacted.
Connection to King James I
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(00:20:19)
  • Key Takeaway: The play was likely performed for King James I’s court, incorporating current themes about justice and self-measurement, and may have subtly flattered the King by mirroring his known views on ideal rulership, even if specific personal references are speculative.
  • Summary: Shakespeare was aware of the court audience and the contemporary interest in self-judgment as a basis for public policy. Parallels exist between the Duke’s views on governance and James I’s writings, suggesting the play offered a palatable conclusion where the King imposes the final law.
Catholic Themes Rebuttal
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(00:24:26)
  • Key Takeaway: The suggestion that Measure for Measure contains secret Catholic themes is rejected due to insufficient evidence; the presence of friars and nuns merely reflects Shakespeare’s ongoing critique of corruption within religious institutions post-Reformation.
  • Summary: Pointing to elements like friars is insufficient basis to label Shakespeare a secret Catholic, as criticizing institutional corruption was common in English literature. The play shows that Catholic systems, like secular ones, are also subject to corruption.
Anti-Girardian Reading
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(00:26:13)
  • Key Takeaway: Measure for Measure is argued to be anti-Girardian because the substitutions are intentionally fake, and characters like Isabella are driven by strong inner desires and consistency, rather than mimetic rivalry.
  • Summary: Unlike A Midsummer Night’s Dream, which fits a clean Girardian analysis, this play emphasizes individual desire. Isabella’s adherence to her own consistency forces the Duke into difficult positions, suggesting the substitutions are designed to show that one cannot measure a brother against oneself.
Favorite Lines from the Play
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(00:27:52)
  • Key Takeaway: Key memorable lines include Isabella’s denunciation of ‘proud man, dressed in a little brief authority’ and Angelo’s pragmatic statement, ‘We must not make a scarecrow of the law.’
  • Summary: The Duke’s slightly surreal line about the ‘soft and tender fork of the poor worm’ (death) is also cited as an example of Shakespeare’s peak writing when discussing mortality. The dialogue often contains slightly absurd imagery that remains dramatically effective.
Ideal Shakespeare Consumption
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(00:29:17)
  • Key Takeaway: The ideal way to consume Shakespeare is through silent, personal reading, as theatrical performances often dilute the text through overly interventionist directorial schemes, though Shakespeare certainly wrote for both reading and performance.
  • Summary: Shakespeare was aware his works would be printed and read, incorporating ‘anthology speeches’ for this purpose, catering to both the penny-paying pit audience and the educated elite. A successful production, like one directed by Jonathan Miller, focuses simply on ensuring the actors understand the words’ meaning.
Austen’s Debt to Adam Smith
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(00:32:30)
  • Key Takeaway: Jane Austen drew heavily from Adam Smith, not just for moral content but for narrative techniques, using perspective control to guide the reader toward developing an internal ‘impartial spectator’ for moral judgment.
  • Summary: Austen is considered one of the least Shakespearean novelists, which is seen as a credit to her unique voice. Smith also incorporated examples from 18th-century novelists like Samuel Richardson into his work to inform his discussions on moral evolution.
Swift’s Practical Intelligence
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(00:36:26)
  • Key Takeaway: Jonathan Swift is considered the smartest English writer (Shakespeare excepted) because he uniquely mastered addressing practical issues—like coinage or government—through both direct, polemical non-fiction and highly ambivalent fiction like Gulliver’s Travels.
  • Summary: Swift’s genius lies in his ability to maintain ambivalence in fiction, avoiding the expression of his own opinions, while simultaneously producing sharp pamphlets. Readers seeking to explore Swift beyond Gulliver’s Travels should read selections of his vicious poetry and the lively Journal to Stella.
Advertising’s Influence on Reading
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(00:39:34)
  • Key Takeaway: While advertising is generally considered a ‘diminishment’ of art, great writers like Swift were masters of lobbying and PR, effectively advertising their ideas through both direct and subtle means.
  • Summary: Most modern advertising fails because it pursues the ‘creative revolution’ of image-based mood-setting without the necessary hard-sell facts, unlike the effective Ogilvy model. The failure to target effectively means most consumers are only followed by basic, unhelpful ads, like for toasters.
Literary Overrated vs. Underrated
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(00:44:42)
  • Key Takeaway: John Milton’s Paradise Lost and Edmund Spenser’s The Faerie Queene are seriously underrated works of English literature that deserve more attention despite their length.
  • Summary: Forsyth Galsworthy’s The Forsyte Saga is considered crushingly dull and overrated, though it translates well to television melodrama. Conversely, Dickens’s Bleak House is underrated among well-read people and is considered by the speaker to be the best novel in English.
American Fiction Assessment
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(00:47:54)
  • Key Takeaway: Henry Adams’s novel Democracy is an instructive and amusing, short read relevant for those involved in Washington politics, while much of 20th-century American fiction remains overrated due to the country’s academic dominance.
  • Summary: The speaker is suspicious of many major 20th-century white male American writers who may be overrated due to the influence of outlets like the New York Times. The true lasting works from that period will only be determined by the next generation.
Late Bloomer Success Factors
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(00:51:27)
  • Key Takeaway: Late bloomers often achieve success following a dramatic external crisis that forces a complete life change, or through an internal realization that prompts them to stop delaying their essential work.
  • Summary: Grandma Moses is cited as an external-circumstance late bloomer whose artistic career only began in her 70s once domestic duties ceased to consume her time. Late bloomers generally enjoy their success more because it allows them to leave behind a previous, unfulfilling life phase.
Future of Religious Fiction
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(00:54:01)
  • Key Takeaway: Serious engagement with religion in great fiction is expected to return within the next two decades, likely driven by young converts who will provide the necessary outlet for contemporary religious experience.
  • Summary: Writers like Marilynne Robinson have recently engaged seriously with religion, but major figures comparable to Graham Greene or Muriel Spark have been absent. The current wave of religious young people suggests a literary resurgence is imminent.
Religion and Literature
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(00:55:04)
  • Key Takeaway: Literary engagement with religion, even through atheism like Martin Amis’s, remains a significant way of dealing with the topic.
  • Summary: Dealing with religion through literature, even from an atheist perspective, is a persistent theme. The speakers speculate that serious fiction dealing with religion might return in the future, possibly driven by converts or a late bloomer author. The current lack of serious religious fiction is noted.
Success and Late Bloomers
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(00:55:21)
  • Key Takeaway: Late bloomers derive greater enjoyment from success because it allows them to definitively leave behind negative past experiences.
  • Summary: Late bloomers are believed to enjoy their success more than those who achieved it early. This heightened enjoyment stems from the ability to discard prior negative circumstances and fully embrace a new, positive phase. David Ogilvy’s sentiment that men with multiple careers are enviable is cited as supporting the anti-boredom aspect of this trajectory.
Assessing Ayn Rand
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(00:55:36)
  • Key Takeaway: Atlas Shrugged functions effectively as a genre novel with exciting plot mechanics and surprisingly unclunky handling of ideas in its best moments.
  • Summary: Ayn Rand is considered a potential late bloomer if Atlas Shrugged is viewed as her singular defining work. The novel is praised for its exciting plot, functioning almost as the best genre novel ever written, featuring B-movie dialogue suitable for a Humphrey Bogart film. Her villains are noted as being remarkably true to current life, and her handling of ideas is sometimes more subtle than commonly credited.
Child-Rearing Advice
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(00:57:01)
  • Key Takeaway: Effective child-rearing involves being fun, firm, and fair, while maintaining a balance of involvement without being overly intrusive.
  • Summary: A past piece of advice for dealing with boys—fun, firm, and fair—is suggested as applicable to all children. Parents should be involved but not excessively so, ensuring children are given their own space. The core principle is allowing children the freedom to simply be children.
Reading Shakespeare’s Play
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(00:57:26)
  • Key Takeaway: When approaching Measure for Measure, readers should self-determine their level of engagement with scholarly apparatus like footnotes.
  • Summary: Listeners rereading or reading Measure for Measure should decide whether they need extensive footnotes, such as those in the Arden edition, immediately. Some readers benefit from a painful blow-by-blow analysis, while others prefer to grasp the narrative first and return to details later. Personal preference dictates the most fruitful reading method.
Closing Remarks and Recommendations
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(00:58:10)
  • Key Takeaway: Henry Oliver has multiple works in draft folders that may be published, and listeners are directed to his book Second Act and his Substack.
  • Summary: Henry Oliver is keeping his next specific project secret but confirms he has several pieces in his draft folder awaiting potential publication. The host strongly recommends Oliver’s book Second Act about late bloomers, his Substack, The Common Reader, and his joint Substack with Rebecca Lowe.