playfulness, sincerity, and meaning-making

Modernism, with its certainty, idealism, and structure, was turned on its head by postmodern skepticism and deconstruction. The postmodernists vowed not to rest until every system and grand narrative was burned to the ground. But the flames are dying out, giving way to the constructive playfulness of post-postmodernism. Where postmodernism was destructive, post-postmodernism gives us the courage to make something new.

ModernismPostmodernismPost-Postmodernism
Time PeriodLate 19th to mid-20th centuryLate 20th century (approx. 1960s-1990s)Early 21st century onward
WorldviewEmphasizes progress, reason, and universal truthsRejects universal truths, embraces relativismBalances reason with relativism, seeks meaning in a fragmented world
Art & AestheticsClear structure, formalism, and the search for puritySelf-referential, ironic, fragmented, eclecticPlayful, hybrid, integrates different styles with sincerity and irony
PhilosophyRationalism, humanism, belief in objective realitySkepticism of grand narratives, deconstructionEmbraces pluralism, inter-connectedness, return to sincerity (meta-modernism)
KnowledgeTrusts in science, empirical evidence, and objectivityQuestions the objectivity of knowledge, highlights subjectivityBlends objectivity and subjectivity, acknowledges complexity and paradox
ArchitectureFunctional, minimalist, “form follows function”Playful, chaotic, rejects functional purityCombines functionality with aesthetic variety and innovation
TechnologyOptimistic belief in technological progressCritical of technological impacts, ironic distanceBalanced optimism, focuses on ethical and human-centric technology
IdentityStable, centered individual identityFluid, fragmented, and socially constructed identityHybrid identity, acknowledging complexity and multiple facets
Social ChangeBelief in progress and social reformCritique of progress and authority, focus on power dynamicsIntegrated approach, combining activism with personal responsibility
LiteratureLinear narratives, focus on coherent meaningNon-linear, metafictional, playful with languageReconciles narrative coherence with experimental elements
PoliticsOften idealistic, believes in overarching systemsSkeptical of systems, deconstructs power structuresPragmatic, focuses on rebuilding systems with inclusivity and adaptability
HumorSincere, often serious or moralisticIronic, satirical, absurdistPlayful, oscillating between irony and sincerity, often self-aware

terminology

The word “modern” comes from the Latin word modernus, which was derived from modo, meaning “just now” or “recently.” Modernus was first used in the late Roman Empire around the 5th century CE to contrast the present with the past, particularly in relation to classical antiquity. The sense of the term as “pertaining to the present time” or “contemporary” evolved over the centuries, coming into more widespread use in the early modern period (15th-17th centuries) to distinguish current trends from medieval or ancient traditions. By the 17th century, the word “modern” began to carry connotations of newness, innovation, and the break with past traditions, especially in art, science, and thought.

Perhaps “modern” is not a great name for a specific period of history. At any given point of time, people feel that they are in “modern” times. The term, as a historical marker, seems paradoxical since it implies a presentness that inevitably becomes outdated. This is part of why we now use terms like “early modern,” “late modern,” or even “postmodern” to refine historical distinctions.

Perhaps a more precise or contextually anchored term could have been chosen to reflect the specific characteristics of the time, like “Industrial Age” or “Rational Age.” However, “modernism” stuck because it emphasized the break with tradition and the embrace of new ways of thinking and being, which people of that time saw as defining qualities of their era.

And now we have terms like “postmodern” and “post-postmodern.” These terms aren’t great either because they’re not very descriptive. The naming scheme becomes quite cumbersome. What’s next — post-post-postmodernism?

Terms like “postmodern” and “post-postmodern” feel like linguistic placeholders rather than descriptive or evocative labels. They highlight a historical progression without offering much insight into the essence of these periods. The “post-” prefix is particularly vague, as it defines an era only in opposition to what came before, rather than on its own terms. This results in a kind of naming fatigue, as each new phase merely extends the chain of “post-” rather than articulating its unique characteristics.

It’s as if the cultural conversation hasn’t settled on precise names yet because we’re still in the process of understanding these periods. More descriptive names could draw on defining characteristics, like “Relativistic Age” for postmodernism or “Integral Age” for post-postmodernism. “Relativistic Age” captures postmodernism’s emphasis on pluralism, subjectivity, and the rejection of absolute truths, while “Integral Age” conveys the synthesis and integration of previously fragmented ideas, which is more aligned with post-postmodernism. These terms provide a clearer sense of the philosophical and cultural shifts without being tethered to the past. They also reflect a more forward-thinking approach to naming, which could make the conversation around these eras more constructive and meaningful.

it’s time to move on

The greatest contribution of postmodernism, in my view, is that it freed us from the misleading certainty of modernism. It devoted itself to a relenetless siege of the castle of modernity. Fun stuff, but at some point, you have to move on. Once you have freed yourself from the shackles of modernistic certainty, you have to do something new. And that’s where postmodernism gets stuck. It’s just corrosive and destructive in nature. It loves tearing things down, so much so that it doesn’t want anything else to be built in the place where modernism once stood.

Postmodern philosophy is a complex cluster of notions that are often defined almost entirely by what its proponents reject. They reject foundationalism, essentialism, and transcendentalism. They reject rationality, truth as correspondence, and representational knowledge. They reject grand narratives, metanarratives, and big pictures of any variety. They reject realism, final vocabularies, and canonical description… The extreme postmodernists do not just stress the importance of interpretation, they claim that reality is nothing but an interpretation… Objective truth itself disappears into arbitrary interpretations, said to be imposed by power, gender, race, ideology, anthropocentrism, androcentrism, speciesism, imperialism, logocentrism, phallocentrism, phallologocentrism, or one variety or another of utter unpleasantness.

Ken Wilber, Integral Psychology

Post-postmodernism, on the other hand, represents the creative impulse to move on, to grow, to learn from the mistakes of both modernism and postmodernism. We should keep the deconstructive forces of postmodernism in our tool belt, but keep them safely contained so they can be used when needed without stealing the show.

Moving forward, we must prioritize playfulness. We must feel free to sincerely express ourselves. We must proactively cultivate meaning in our lives.

playfulness

Both postmodernism and post-postmodernism are characterized by playfulness. But postmodern playfulness is laughing at someone, while post-postmodern playfulness is laughing with someone.

Postmodern playfulness operates from a place of superiority and cynicism, thriving on tearing others down or exposing the absurdity in their beliefs. It’s an archetypal Reddit comment: “I can’t believe that you have been taken in. Let me explain why you are wrong and I’m smarter than you because I was not gullible enough to believe in something.”

Post-postmodern playfulness embodies a spirit of inclusivity, joy, and shared experience. It’s about creating fun and laughter together, rather than at someone’s expense. It’s mischievous but whimsical and loving. It’s bubble machines. It’s confetti and fireworks. It’s dancing machine elves. It’s a psychedelic kaleidoscope of merry-making.

sincerity and authenticity

The terms “sincerity” and “authenticity” are often used lumped together, especially in discussions of postmodernism and post-postmodernism, but they carry distinct meanings.

Sincerity refers to the genuine expression of one’s feelings, thoughts, and intentions. It’s about being honest and truthful in communication, showing what you truly feel without deception or pretense. Sincerity is outward-facing—it’s about how you relate to others and whether your actions and words align with your internal emotions.

Authenticity, on the other hand, is deeper and more introspective. It refers to being true to oneself, aligning with your core values, beliefs, and identity. It’s about living in a way that is consistent with who you genuinely are, rather than conforming to external expectations or societal pressures. Authenticity is about self-alignment, ensuring that your inner life matches your outer expression.

In this sense, sincerity is about honest interaction with others, while authenticity is about honest interaction with yourself. Both are crucial in post-postmodern meaning-making because they ensure that our playful and constructive efforts to create meaning are rooted in truth—truth to oneself and truth in how we share that with the world.

David Foster Wallace was a pivotal figure in moving beyond postmodern irony and cynicism. His work (especially in Infinite Jest and his essays) often grapples with the alienating effects of postmodern detachment and the longing for sincerity and authentic human connection. Wallace recognized that the relentless irony of postmodernism was corrosive, and he advocated for a more vulnerable and emotionally honest form of expression. His emphasis on sincerity, empathy, and the struggle for genuine meaning in a fragmented, media-saturated world laid the groundwork for much of the post-postmodern conversation around authenticity.

In his famous essay E Unibus Pluram: Television and U.S. Fiction, Wallace critiqued the postmodern reliance on irony, particularly in how it dominated American culture and media. He argued that irony, while useful for critique, had become a default mode that hindered deeper human connection and stifled genuine creativity. He called for a new generation of writers and thinkers who would have the courage to step away from the safety of ironic distance and embrace sincerity, even at the cost of seeming vulnerable, uncool, or naive. He saw this as a way forward, beyond the postmodern tendency to tear down, and toward creating something new and meaningful. His vision was for a culture that could balance both self-awareness and authentic engagement with the world.

Courage is indeed needed for those who wish to publicly express themselves in today’s atmosphere. The prevailing culture of deconstruction means that any attempt to create or express something authentic can feel like opening yourself up to harsh critique, often from a place of superiority or cynicism. Publicly expressing sincere thoughts can be seen as either naive or reckless, leading many to either develop a thick skin or retreat into silence. This pervasive fear of being torn down creates a defensive culture where people hold back from taking creative risks or expressing genuine feelings.

Then there’s other people’s fragility and hypersensitivity, which make it difficult to speak without walking on eggshells. People are so wary of causing offense that they end up self-censoring to the point of sterility. This results in communication that feels corporate, bland, and devoid of any real emotional or intellectual depth.

Everyone runs their thoughts through their own kind of personal HR filter. People are self-reporting their thought crimes to themselves.

Catherine Shannon, Everyone is numbing out

These dynamics stifle sincerity and authenticity. Overcoming this requires not only courage but also a cultural shift toward valuing vulnerability, constructive criticism, and a more compassionate engagement with differing perspectives. We need to cultivate an atmopshere where sincerity is met with curiosity and respect, rather than immediate deconstruction or overreaction.

meaning making

Post-postmodern meaning-making represents a shift from the skepticism and relativism of postmodernism, where meaning was often deconstructed or seen as entirely subjective, to a more balanced and constructive approach. In the post-postmodern framework, meaning is not discarded or endlessly questioned, but rather cultivated with intention. It acknowledges the complexity of reality and the diversity of perspectives, but seeks to build something cohesive from those fragments.

Whereas postmodernism emphasizes the instability of meaning, post-postmodernism recognizes that we still crave meaning in our lives. It allows for sincerity and authenticity, even within the awareness of subjectivity and the limitations of certainty. In this context, meaning-making becomes a playful, creative act—something we actively engage with, knowing that it’s not fixed or universal, but still deeply valuable.

In essence, post-postmodern meaning-making is a deliberate and participatory process, balancing skepticism with the impulse to construct new frameworks, narratives, and connections that enrich our lives, even if they remain flexible and open to revision. It’s about engaging with life as an unfolding process of discovery, bringing sincerity, playfulness, and community into the act of creating meaning.

What would it look like if this approach to meaning-making were widely adopted? I would love to see a proliferation of communes, whether in meatspace or virtual reality. Social experiments. People living together, in community, with a shared goal of meaning-making. These kinds of communities provide a space where people can explore alternative ways of living, outside the constraints of conventional society. By coming together with shared values and intentions, individuals could experiment with new forms of meaning-making, grounded in collaboration, playfulness, and authenticity. Communes could become microcosms for testing and refining ideas and values, fostering environments where people actively engage in creating shared meaning and purpose.

These communes could be fertile ground for the birth of new religions, philosophies, psychotechnologies, and social or economic models. Free from the traditional structures of society, people could experiment with alternative ways of thinking, being, and organizing. New religions might emerge, not in the dogmatic sense, but as flexible spiritual frameworks focused on meaning, connection, and growth. Philosophies could evolve organically from lived experiences, while psychotechnologies like meditation, contemplation, and collective rituals could be explored and refined in real-time. Economically, these communities could pioneer cooperative or decentralized models that prioritize sustainability and collective well-being over individual profit. It would be a dynamic, evolving ecosystem of ideas and practices—a living laboratory of human potential.


In reflecting on modernism, postmodernism, and the emerging ideas of post-postmodernism, we’ve explored how each cultural phase responds to the one before it. Postmodernism, with its skepticism and irony, liberated us from rigid truths but often became stuck in its corrosive nature. The need now, as we transition into post-postmodernism, is to reclaim sincerity, playfulness, and meaning-making—embracing the lessons of postmodernism without letting them dominate. As David Foster Wallace suggested, this will require courageous pioneers willing to be authentic, even at the risk of seeming uncool. Moving forward, we need to create spaces where sincerity thrives, where playful, constructive creativity can flourish, and where new forms of living, thinking, and meaning-making can take root.


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