Annotations (12)
“There's something illiberal in the human heart. I recently reread Orwell's 1984. What staggered me is that Orwell's of two minds. Reading it the first three times, I thought this is a liberal book about the horrors of illiberal tyranny, but Orwell is into illiberal tyranny. He almost has an erotic connection to it. In the human soul, the idea of cruelty or suppression, or maybe in gentler form, an insistence on order, that's just there, and it occasionally triumphs.”— Cass Sunstein
Psychology & Behavior · Philosophy & Reasoning · Culture & Society
DUR_ENDURING
Orwell drawn to what he critiques
“Parfit's work on the three foundations (contractarianism, utilitarianism, Kantianism) all coming to the same conclusions is profoundly liberal in his embrace of contractarianism and his search for multiple foundations for the same set of commitments. It's like Rawls's idea of overlapping consensus. I have enthusiasm for incompletely theorized agreements where people can say I like free speech because I'm a Kantian, or because it discovers truth, or because I'm utilitarian.”— Cass Sunstein
Philosophy & Reasoning · Leadership & Management · Culture & Society
DUR_ENDURING
Multiple paths to same endpoint
“Mill's book on the subjection of women is the origin of woke. It has a picture of the subordination of one group to another. It has clarity on what that does for preferences and values of both groups. It has the notion of adaptive preferences, which is potentially a liberal idea. But it can lead to illiberalism: failure to listen, dismissiveness, arrogance of the social engineer, shaming people. The woke left has gone wrong with a kind of arrogant shaming of people who are deserving respect.”— Cass Sunstein
Philosophy & Reasoning · Psychology & Behavior · Culture & Society
DUR_ENDURING
Good idea becomes bad execution
“We need to know what the speech is and what the reason for regulating it is. If there's open source stuff that is regulated, it's communication among persons. If it's producing a massive national security threat and there's no other way to reduce the threat, then it's probably okay to regulate it. If the government is trying to help economic interests of competitors, that's not adequate justification.”— Cass Sunstein
Philosophy & Reasoning · Technology & Engineering · History & Geopolitics
DUR_ENDURING
Speech plus justification test
“I saw two Russian men in their young 40s, strong, exhausted. I asked them how they were. You could see an unforgettable expression in their face of gratitude that someone was asking them how they were. I had a phrase go through my head: For the grace of God go I. With a little twist of fate or maybe Rawls' veil of ignorance, any one of us could be them. Recognition of the moral equivalence of everyone on the planet should ground our immigration policies.”— Cass Sunstein
Philosophy & Reasoning · Psychology & Behavior · History & Geopolitics
DUR_ENDURING
Rawlsian empathy at border crossing
“I saw a Trump wall, a Biden wall, and an Obama wall. I had no idea there were three walls. The people running the border said we need 3 things: infrastructure, technology, and people. They said walls are good, but people can scale walls. They said they need people and technology. If you have technology, people, and a wall that makes it very hard for people to get in illegally, there's no brutality. If I can't get over a wall, I'm just stuck.”— Cass Sunstein
Operations & Execution · Technology & Engineering · History & Geopolitics
DUR_ENDURING
Three-part system beats single solution
“Liberalism doesn't create the conditions for its own self-perpetuation. A society that is flourishing needs norms of cooperation, norms of charity, norms of mutual support. Liberalism doesn't undermine those things, but other forces can undermine them, and it's not clear liberalism has the resources to respond.”— Cass Sunstein
Philosophy & Reasoning · Culture & Society · Psychology & Behavior
DUR_ENDURING
Liberalism lacks self-repair mechanism
“I do think we need a right not to be manipulated. At the turn of the 20th century, people started to get exercised about violations of the right to privacy. That was a big step forward. We're kind of there now with manipulation. No legal system has a right not to be manipulated. We should start with egregious cases where people are losing money or time without getting adequate clarity on what's happening through hidden terms.”— Cass Sunstein
Philosophy & Reasoning · Economics & Markets · History & Geopolitics
DUR_ENDURING
Anti-manipulation as emerging right
“If you look at Philosophy and Public Affairs, it was full of Rawls and Rawls criticism. The great liberal thinkers now who are younger may be in the social sciences. Ed Glazer isn't particularly young, but he's a liberal thinker. John List is younger and a great liberal thinker. Esther Duflo is a great liberal thinker. We're not seeing a flowering of engagement with liberal thought in philosophy. We are seeing a lot of work on agency. Economists are holding the line.”— Cass Sunstein
Philosophy & Reasoning · Economics & Markets · Culture & Society
DUR_CONTEXTUAL
Economists now lead on liberalism
“Dylan's liberalism is captured in the line: He not busy being born is busy dying. The notion of self-invention of freedom is central to basically everything. His refusal to keep singing the same song, his need to do something else. Like a Rolling Stone is an anthem of freedom: How does it feel to be on your own with no direction home? Everyone felt like they were flying. Making rootlessness not be a curse, but something that is joyful.”— Cass Sunstein
Philosophy & Reasoning · Culture & Society · Creativity & Innovation
DUR_ENDURING
Rootlessness as freedom not curse
“The individual claims of The Road to Serfdom are convincing and beautifully put. But the thesis that if the government starts regulating economic matters à la Roosevelt, we're on the road to something like Stalin or Hitler, that's not true. The individual claims are convincing, but the idea that if you do what the United States has been doing since Roosevelt, that we're going to end up in a place that is horrifying, that's not true.”— Cass Sunstein
Economics & Markets · Philosophy & Reasoning · History & Geopolitics
DUR_ENDURING
Micro insights valid, macro thesis not
“People should be treated as ends, not as means, and everyone has dignity. That's bedrock. What it specifically entails for immigration policy is to be determined, but that's a central liberal foundation. The wellbeing of people being deported is not a matter of indifference. These abstract foundations for liberalism don't entail concrete policies.”— Cass Sunstein
Philosophy & Reasoning · History & Geopolitics · Culture & Society
DUR_ENDURING
Principles don't dictate specific policies
Frameworks (2)
Three-Component Border Security System
Infrastructure, Technology, and People
Effective border enforcement requires three complementary elements working together: physical infrastructure (walls), technology (sensors, surveillance), and human personnel. No single component alone creates an effective system; walls can be scaled without technology and people to respond. The framework demonstrates that complex enforcement challenges require multi-layered solutions where each component addresses different failure modes.
Components
- Infrastructure
- Technology
- People
Prerequisites
- Assessment of current infrastructure gaps
- Technology procurement capabilities
- Personnel hiring and training capacity
Success Indicators
- Reduced unauthorized crossings
- Faster response times to breaches
- Lower per-crossing cost
Failure Modes
- Components implemented sequentially rather than in parallel
- Technology not maintained
- Personnel turnover
Two-Question Test for Speech Regulation
Content and Justification Analysis
When evaluating whether speech regulation is permissible, apply two sequential questions: (1) What exactly is the speech and who are the speakers? (2) What is the government's justification for regulating it? The test requires specificity on both dimensions before reaching a conclusion. National security threats may justify regulation if no other remedy exists; economic protectionism does not.
Components
- Identify the Speech
- Examine the Justification
Prerequisites
- Understanding of First Amendment doctrine
- Ability to distinguish content-based from content-neutral regulation
Success Indicators
- Clear reasoning path
- Recognition of edge cases
- Identification of less restrictive alternatives
Failure Modes
- Stopping at step 1 without examining justification
- Accepting weak justifications
- Applying wrong level of scrutiny
Mental Models (10)
Self-Perpetuation Systems
Systems ThinkingSome systems contain mechanisms that maintain themselves (negative feedback loop
In Practice: Discussing whether liberalism is self-undermining or requires external support
Demonstrated by Leg-cs-001
Psychological Ambivalence Toward Authority
PsychologyHumans can simultaneously hold contradictory attractions: toward freedom and toward submission.
In Practice: Discussing Orwell's dual relationship with the tyranny he critiques in 1984
Demonstrated by Leg-cs-001
Principles vs. Policies Distinction
Decision MakingAbstract moral principles do not directly entail specific policies.
In Practice: Discussing how Kantian dignity principle doesn't directly entail immigration policy
Demonstrated by Leg-cs-001
Empathic Identification Through Counterfactuals
PsychologyThe thought experiment of imagining oneself in another's position creates empathy.
In Practice: Sunstein's experience seeing Russian asylum seekers at the southern border
Demonstrated by Leg-cs-001
Three-Component System Resilience
Systems ThinkingSystems requiring security, enforcement, or defense often need three categories
In Practice: Border security framework discussion
Demonstrated by Leg-cs-001
Multiple Foundations Convergence
Decision MakingWhen multiple independent reasoning systems converge on the same conclusion, confidence in that conclusion increases dramatically.
In Practice: Discussing Parfit's work on convergence of ethical systems
Demonstrated by Leg-cs-001
Micro Truth, Macro Error Pattern
EconomicsA work can contain numerous valid individual insights while its overarching thesis is false.
In Practice: Sunstein's critique of Hayek's Road to Serfdom
Demonstrated by Leg-cs-001
Idea Degradation Through Overapplication
PsychologyValid insights can degrade into counterproductive practices when applied too broadly or mechanically.
In Practice: Discussing how Mill's work on women's subordination evolved into woke illiberalism
Demonstrated by Leg-cs-001
Speech and Justification Two-Step
Decision MakingWhen evaluating any restriction on communication, apply two sequential questions.
In Practice: Discussing First Amendment analysis for AI and open source code
Demonstrated by Leg-cs-001
Rootlessness as Freedom Asset
Decision MakingLack of fixed identity, location, or commitment can be reframed as an asset enabling reinvention.
In Practice: Discussing Bob Dylan's philosophy of constant reinvention
Demonstrated by Leg-cs-001
Connective Tissue (2)
Orwell's dual relationship with tyranny in 1984
George Orwell's 1984 operates on two levels simultaneously: as a liberal critique of totalitarianism and as an exploration of the human attraction to order and control. Orwell himself demonstrates ambivalence, showing both horror at and fascination with illiberal systems. This mirrors the psychological reality that humans are drawn to what they intellectually reject. The literary work reveals that opposition to tyranny and attraction to it can coexist in the same mind, suggesting liberalism must contend not just with external threats but with internal psychological forces.
Discussing why liberalism is fragile; Sunstein rereads 1984 and recognizes Orwell's psychological complexity
Evolution of privacy rights in early 20th century
At the turn of the 20th century, legal systems began recognizing a right to privacy that had not previously been codified. This represented a society-wide recognition that technological and social changes (photography, mass media, urbanization) created new forms of intrusion requiring new protections. The evolution from no explicit privacy rights to comprehensive privacy doctrine took decades but transformed legal systems globally. This historical precedent illuminates how emerging technologies can create novel harms that require conceptual innovation in rights frameworks before legal systems can respond effectively.
Discussing the need for a right not to be manipulated; drawing parallel to privacy rights evolution
Key Figures (13)
Bob Dylan
4 mentionsMusician, songwriter
John Stuart Mill
3 mentionsPhilosopher, political economist
Friedrich Hayek
3 mentionsEconomist, political philosopher
Derek Parfit
2 mentionsPhilosopher
John Rawls
2 mentionsPolitical philosopher
George Orwell
2 mentionsAuthor, 1984
British author whose novel 1984 both critiques and is drawn to totalitarianism.
- Orwell was of two minds in 1984, simultaneously horrified by and drawn to illiberal tyranny
Catharine MacKinnon
1 mentionsLegal scholar, feminist theorist
Thomas Scanlon
1 mentionsPhilosopher
Immanuel Kant
1 mentionsPhilosopher
Edward Glaeser
1 mentionsEconomist, Harvard
Esther Duflo
1 mentionsEconomist, MIT (recently moved to Zurich)
John List
1 mentionsEconomist
Sendhil Mullainathan
1 mentionsEconomist, behavioral scientist
Glossary (2)
incompletely theorized agreements
DOMAIN_JARGONConsensus on outcomes despite different underlying reasons or principles
“I have enthusiasm for incompletely theorized agreements where people can say I like free speech because I'm a Kantian or because it discovers truth.”
adaptive preferences
DOMAIN_JARGONPreferences shaped by circumstances of subordination or constraint
“It has the notion of adaptive preferences in it.”
Key People (13)
George Orwell
(1903–1950)British author of 1984 and Animal Farm
Immanuel Kant
(1724–1804)German philosopher, categorical imperative
John Stuart Mill
(1806–1873)British philosopher and economist
John Rawls
(1921–2002)American philosopher, A Theory of Justice
Edward Glaeser
(1967–)Harvard economist, urban economics
John List
(1968–)Economist specializing in behavioral economics and field experiments
Esther Duflo
(1972–)Development economist, Nobel laureate, experimental approach to poverty
Sendhil Mullainathan
(1973–)Behavioral economist, co-author of Scarcity, works on AI and agency
Derek Parfit
(1942–2017)British philosopher, sought convergence of Kantian, utilitarian, contractarian ethics
Thomas Scanlon
(1940–)Philosopher, contractarianism, influenced Parfit's convergence work
Friedrich Hayek
(1899–1992)Austrian economist, The Road to Serfdom, spontaneous order theory
Catharine MacKinnon
(1946–)Legal scholar, feminist theory, sexual harassment and pornography law
Bob Dylan
(1941–)Concepts (8)
self-perpetuation
CL_SCIENCESystem's ability to maintain itself without external support through internal mechanisms
Kantian liberalism
CL_PHILOSOPHYLiberal philosophy based on treating people as ends, not means, and human dignity
veil of ignorance
CL_PHILOSOPHYRawls thought experiment: design society without knowing your position in it
contractarianism
CL_PHILOSOPHYEthics based on hypothetical agreement among rational agents under fair conditions
utilitarianism
CL_PHILOSOPHYEthics based on maximizing overall happiness or wellbeing for greatest number
overlapping consensus
CL_PHILOSOPHYRawls idea that different philosophical traditions can support same political principles
adaptive preferences
CL_PSYCHOLOGYPreferences that form in response to constrained circumstances, especially subordination
right to privacy
CL_LEGALLegal protection against intrusion, developed in early 20th century responding to new technologies
Synthesis
Synthesis
Migrated from Scholia