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Dear Culture Cultivators and Future-Proofers, welcome to the Age of Awkwardβa transitional era marked by faltering scripts, janky performances, and the weird, glitchy hiccup that comes just before cultural metamorphosis.
Itβs not a bug. Itβs a feature. In our techno-saturated present, where AI crafts our emails and avatars flirt on our behalf, we find ourselves paradoxically allergic to awkwardness. We ghost instead of confront. We text instead of talk. We design whole platforms to disappear the cringe. But hereβs the rub: awkwardness is not a malfunction of the social systemβit is the signal that the system is evolving. Hello, weβre Alice and we are always in a state of wanderβ¦
Awkwardness: The Error Message That Matters
Think of awkwardness like a network packet loss in the cultural internet. Itβs that freeze-frame moment when social scripts lag behind the reality of human complexity. You donβt know whether to shake hands, fist bump, or just nod. You donβt know if that dinner was a date or a pitch. You say βyou tooβ when the barista tells you to enjoy your coffee. But behind every awkward beat is a social infrastructure gap. The script doesnβt existβyet.
Weβre improvising in real-time, and the bandwidth gets choked. βAwkwardness,β writes philosopher Alexandra Plakias in Aeon, βis what happens when we lack a script.β Itβs the negative space where the new must be invented. Itβs the UX failure of the human operating systemβand a portal to reinvention.
Why Business Should Care: Awkwardness as Innovation Trigger
Businesses are built on assumptions: of customer behavior, employee interaction, cultural norms. But what happens when those assumptions fall out of sync with reality? Enter awkwardness as your leading indicator. The moment your hiring manager feels weird asking about pronouns? A sign your HR script is outdated. That uneasy silence after someone brings up menopause or grief in a leadership workshop? Thatβs cultural whitespace, not a flaw. When a bot says βIβm sorry,β but your gut says βick,β youβre encountering a mismatch in affective bandwidth. Again: awkwardness.
Smart businesses donβt eliminate awkwardness. They study it.
Awkwardness is where inclusion begins. It tells you where old rituals donβt scale, where new values lack language, and where meaning still needs mapping.
From Punchline to Practice: Rethinking Awkward as a Cultural Competency
The old view: awkwardness is embarrassing. Cringe. Something to dodge. The future view: awkwardness is a map to emerging norms. A design prompt for better systems. A moment of shared humanity in our otherwise over-sanitized society. Awkwardness, (if Henri Bergson were alive today and writing substack newsletters), is the laugh-track of civilization learning to walk upright in a new era. We are tripping our way into better futures.
What To Do Now
β’ Train for awkwardness β Develop team rituals for naming social weirdness. Not to eliminate itβbut to inhabit it with grace.
For example: Team Ritual: Awkwardness Bingo
Purpose: To turn social weirdness into a gameβbecause nothing says team bonding like celebrating cringe with confetti.
When: Keep it going throughout the week (or during a long meeting or off-site). At the end, crown an βAwkwardness Alchemist.β
How to Play:
Create Your Bingo Cards: Each team member gets a 5x5 bingo card filled with lighthearted awkward moments like:
β’ Talking while muted
β’ Weird silence after a joke
β’ Unintentional interruption
β’ Awkward Zoom wave goodbye
β’ Overuse of the word βpivotβ
β’ Accidental overshare
β’ The classic βuhhhhhhβ¦β
Spot It. Own It: When someone experiences a square-worthy moment, they call it out proudly (e.g., βYES, that was a triple βyou go!ββmark it down!β).
Celebrate the Cringe: First one to get BINGO must shout: βI HAVE ASCENDED THE AWKWARD PLANE!β (Yes, loudly and dramatically.) The team responds with finger snaps or jazz hands.
β’ Recode silence β Let gaps in conversation become spaces of trust rather than discomfort.
β’ Build with awkwardness in mind β Whether designing UX, HR policy, or social content, treat awkward moments as feedback loops. They're whispering where the culture is shifting.
β’ Celebrate The Snoob β That oddball silence in conversations? Itβs a shared portal. Let it open. Something real might walk through.
Final Transmission: Unmute and Rehearse
In a future defined by complexity, nuance, and emergent identities, awkwardness is the rehearsal space of empathy. Donβt mute it.
Make it policy. Make it practice. Make it sacred. Because when we lean into the awkward, we stop performing as a societyβand start redesigning it.
Yours in cringeworthy solidarity, Alice.
What else we are wanderingβ¦
π On Awkwardness
Christy Wampole traces the etymology and cultural weight of awkwardness, showing it as an ancient, embodied, and ubiquitous phenomenon. She argues that awkwardness reveals the friction between growing individualism and outdated social scripts. (via Guernica, 2015)
π Make It Awkward
Alexandra Plakias, associate professor of philosophy at Hamilton College, reframes awkwardness not as a personal failing but a collective rupture, where outdated or absent social scripts meet evolving moral complexity. She makes the case for awkwardness as a necessary portal to ethical and cultural renewal. In her book Awkwardness, A Theory, Plakias explores how awkwardness reflects our desire for social acceptance but also highlights where inclusion and moral clarity are lacking. She reveals how awkward moments can illuminate structural inequities in social systems. (via Aeon, 2024 Oxford University Press)
π§ Having Awkward Talks May Be Easier Than You Think
Leadership author Rodger Dean Duncan argues that awkward conversations are not roadblocks but bridges to deeper human connection. He emphasizes emotional intelligence as the tool to transform discomfort into trust. (via Forbes)
π The Science Of Why We Are Socially Awkward
Psychologist Ty Tashiro redefines awkwardness as a hidden strength tied to focus, curiosity, and nonconformist intelligence. He champions awkward individuals as evolutionary assets rather than social liabilities. (via Psychology Today)
π Snoob
Author Maggie Rowe introduces the concept of the βsnoobββthe awkward pause in conversationβas a moment of mindful presence. She suggests leaning into such silences as trust-building micro-rituals. (via Psychology Today)
π§ Contemporary Psychoanalysis in Action
Awkwardness can be a marker of sincerity and emotional truth, especially in therapeutic or intimate spaces. The tension it produces often signals a real moment of vulnerability. (via Psychology Today)
π Being Socially Awkward Is Actually Awesome, According to Science
Citing research linking awkwardness to high focus and potential talent, the article reframes awkward people as creative outliers often drawn to systems and structures. Their strengths are overlooked in favor of social ease. (via Time)
π§ Emotional Intelligence
Backed by psychology studies, this piece reveals that deeper, awkward conversations lead to stronger bonds and greater happiness than expected. Awkwardness is shown to be a false alarm masking meaningful connection. (via Inc.com)
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