Freedom hides a snake in the grass.

Like Jörmungandr of Norse mythology, freedom can eat itself. Subtly coiled within the concept is a contradiction: unchecked freedom can include the freedom to limit the freedom of others. When absolutism is taken to its limit, even our best ideas turn in on themselves. A society that tolerates everything cannot stand. A democracy that lets the majority rule unchecked can vote itself into tyranny. A platform that allows all speech—no matter how hateful or false—can become unusable for everyone else.

What sounds like a philosophical riddle from a university classroom is a daily reality. And once you start looking, these paradoxes aren’t just lurking in the grass—they’re shaping the way we live, vote, argue, and scroll.

Paradoxes

The Freedom Paradox

Freedom sounds like a no-brainer at first blush. Of course we should be free to do what we want with our lives. But friction quickly arises: my freedom to blast music at 2 a.m. conflicts with your freedom to sleep. In a completely unregulated market, someone could exploit others, manipulate systems, or build monopolies, or even just... well, hire a hitman to take out the competition—and no one could stop them.

Real freedom, paradoxically, needs boundaries.

The Paradox of Democracy

In a true democracy, you can vote for democracy’s end. It suffers from the same tension between absolutism and constraint.

Majorities can elect to strip rights from minorities or empower authoritarian leadership. That sounds uncomfortably familiar in both historical and contemporary contexts.

The Paradox of Tolerance

Karl Popper's famous insight: tolerating the intolerable leads to a society of intolerance, as the intolerant don't tolerate the tolerant. That tongue twister boils down to this: tolerance, ironically, requires intolerance of certain ideas.

Otherwise, the system dies.

The Paradox of Pluralism

Pluralism thrives when many groups with differing ideas and identities share power and space. But it breaks down when one group uses its place at the table to try and remove others. You see this with anti-pluralist ideologies that attempt to enshrine one worldview—be it religious, nationalist, or otherwise—as the only legitimate one.

Is it still pluralism if pluralism itself is undercut from within?

Modern Manifestations

Freedom → Twitter/X, Forced Speech Exposure and Disinformation

Elon Musk's purchase of Twitter was heralded as a restoration of "free speech". In practice, it's narrower: it reduces to a restriction of moderation, curation and reasoned dialectics.

Musk set out to abolish all the original platform policies and return the right to users to say whatever you want, however you want and no one was going to be able to take down your posts: a free speech absolutist's utopia. But this subtly alters a user's choice, as absolutism in this sense means no curation or moderation. In other words: the freedom to choose your experience disappears. If YouTube took this strategy (arguably they slightly do with recommendation algorithms), they would make you watch every video whether you wanted to or not. I would essentially be forced to scroll past hate speech, disinformation on top of the posts I like.

This says nothing of a company's right to choose what material they host: they are just as handcuffed if something like Section 230 were to be abolished.

Further effects are felt with an absence of guardrails against disinformation. Obviously, we have all seen the societal damage wrought by disinformation, with social media harboring a potential for it never seen before.

This free-wheeling, no-holds-barred speech severely limits our ability to rationally meet the demands that our world visits upon us: how can we reasonably make decisions in a world where people think that scientists following the scientific method chiefly lie and get things wrong or that there is a deep state conspiracy out to commit diabolical acts against us?

Absolutism with speech is cutting off your nose to spite your face, in the long run. Prudent limits would go a long way.

Democracy → Abortion Rights & Voter Suppression

Abortion laws in the U.S. are now decided by state majorities—often deeply unrepresentative due to gerrymandering or voter suppression. In states where most residents support abortion access, small, motivated minorities can still pass bans to limit that most foundational of freedoms: what to do with your own physical body. Unfortunately, the US constitution and political system is uniquely set up to to be hamstrung by a tyrannical minority.

Voter suppression laws, meanwhile, are justified under democratic rhetoric (“election integrity”) but reduce democracy itself by making it harder for some marginalized groups to vote. It's not a new phenomenon, but it certainly continues to swirl in politics, no matter if you think some of the measures might even be good ideas in principle.

The democratic system is being used to reduce democratic participation. That’s the paradox in action.

Tolerance → Hate Speech, “Wokeness,” and Weaponized Victimhood

The tension around tolerance plays out today in the realm of public discourse. On one side, some progressive spaces have grown increasingly prescriptive, leading to accusations of “cancel culture” or suppression of dissent. On the other, calls for civility or moderation are sometimes used to shield bigotry or disinformation from accountability.

This creates a rhetorical standoff where attempts to set boundaries are painted as oppression, while intolerance cloaks itself in the language of free expression. The right to offend has become a shield for some honestly abhorrent, idiotic and irresponsible behavior.

Tolerance becomes a tool used against itself.

Subtler Renditions

NIMBYism and Popper in the Suburbs

I recently read an excellent article in the Atlantic on the quiet loss, over the past 50-ish years, of America's unique freedom to move and reinvent yourself. The ramifications are quite keenly felt today, yet are often lain at the feet of "housing shortages", "wage stagnation" and "hollowing out of the middle class". The article is worth the read, as is the book it talks about (Yoni Appelbaum’s Stuck: How the Privileged and the Propertied Broke the Engine of American Opportunity), but lurking in the shadows of this analysis of reduced American mobility was a subtle rendition of the paradox of democracy.

To use the article's pithy summation:

"A nation that had grown diverse and prosperous by allowing people to choose their communities would instead empower communities to choose their people."

A self-interested group of urbanists collared the open systems of mobility that they themselves benefitted from, statically preserving their own interests over the benefits such a system visits upon all. What seems like a staple of American life to my generation: neighborhood-level guaranteed freedoms to vote on our own zoning, codes, development projects, etc, wasn't always so, I was shocked to find out.

The current name for this movement is NIMBYism, an especially pernicious political phenomenon given that most of its purveyors subscribe to ideals in direct opposition: those of inclusion and social equality.

The Populist Paradox

Some modern populist movements position themselves as defenders of freedom and tradition—yet they often advocate for policies that restrict those very things for others. They may decry “government overreach” while supporting bans, surveillance, or ideological litmus tests. They speak of “democracy” but question elections that don’t go their way. They celebrate “free speech” but oppose the teaching of ideas that make them uncomfortable.

This isn’t unique to one political movement or nation, but it’s a potent example of how paradoxes are exploited: using democratic language to justify anti-democratic outcomes. It’s a tension between the rhetoric of liberty and the realities of power.

The Seduction of the Paradox

These paradoxes aren’t just academic quirks or footnotes to democratic theory. They’re very real. They offer the comforting illusion of coherence: that we can be totally free without consequence, or totally tolerant without boundary, or protect democracy while hollowing out its core. That’s where moral psychology and social contract theory come in.

Humans are tribal, moralistic(ish) animals. We’re wired to prioritize in-group cohesion and to judge fairness through the lens of “us vs. them.” This is why many of these paradoxes thrive in the political wild: they exploit our innate need to feel morally justified while still protecting self-interest.

This is how systems get manipulated. When long-standing privileges are challenged, some respond not with introspection, but with indignation—claiming persecution in order to protect power.

• Progression to new educational theories, frameworks and lenses are reframed as “indoctrination.”
• Requests for religious neutrality in public life are interpreted as attacks on faith.
• Efforts to diversify communities and broaden the systemic benefits are seen as threats to self interest

These aren’t just contradictions—they’re stories people tell themselves to preserve power while believing they’re upholding virtue.

As Wilhoit’s Law puts it:

Conservatism consists of exactly one proposition, to wit: There must be in-groups whom the law protects but does not bind, alongside out-groups whom the law binds but does not protect.

Even if you don’t fully endorse Wilhoit’s framing, the point remains: the social contract cannot function when protections and obligations are distributed unevenly.

The Design Dilemma: Building Systems to Limit the Paradoxes

Cool, now we have identified some philosphically paradoxical ideas, notions and actions. Philosophers often stop here. We don’t have to. But then, what do we do?

These paradoxes don’t mean we abandon freedom, democracy, or tolerance. But they do mean we can’t afford to be lazy with them.

We must design systems that limit their extremes and thence, one group or individual's ability to zero sum life's games. Constraints-as-design limit the subjective logic of things like gerrymandering, christian/sharia law, NIMBY-ism and the madness of bad actors and destructively riotous crowds. For Pete's sake (whoever he is), can we please implement independent bodies for voting districts and housing/zoning? Come on, y'all. Clamp the damn snake's mouth shut so it isn't even tempted to eat its own tail.

That’s the trick: a strong system doesn’t give you the illusion of freedom—it gives you boundaries and limits that protect it. Like seatbelts. Like fire codes. Like content moderation. Like disinformation regulation. An invisible hand needs its own invisible hand.

Thinking in terms of these limits gives you consistent ethics, it doesn't tear them down. These aren’t infringements on liberty: they’re what make liberty possible. To build society without them is to build a house of cards.

Freedom hides a snake in the grass. But if we know where it slithers, we can build a fence. True freedom—like true democracy—isn’t a free-for-all. It’s something we have to build, maintain, and defend from its own excesses.