#998 - Zack Telander - Everything You Want Is On The Other Side Of Cringe
In this Modern Wisdom episode, Chris Williamson and Zack Telander explore how the fear of being labeled "cringe" can prevent people from expressing themselves authentically online. They examine the relationship between sincerity and criticism, discussing how maintaining an ironic distance can serve as a defense mechanism while hindering meaningful engagement with ideas.
The conversation delves into the nature of "coolness," supported by research on traits like extraversion and autonomy, and the challenges of balancing ambition with present-moment appreciation. Williamson and Telander share insights about content creation, including building resilience to public judgment and maintaining equilibrium between productivity and personal well-being. They also discuss the differences between online and in-person interactions, and strategies for finding joy in daily experiences while pursuing long-term goals.
This is a preview of the Shortform summary of the Sep 25, 2025 episode of the Modern Wisdom
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1-Page Summary
Authenticity, Sincerity, and the Fear of "Cringe"
Chris Williamson and Zack Telander explore how authenticity is received online and the impact of being labeled "cringe." Williamson discusses how expressing sincere beliefs makes one vulnerable to criticism, particularly from those who maintain an ironic distance. Telander adds that while irony can serve as a defense mechanism, it prevents meaningful engagement with ideas.
The hosts examine how the fear of being labeled "cringe" can discourage people from pursuing their interests and expressing themselves authentically. They note that despite these concerns, there remains an inherent appeal to those who present themselves genuinely.
Balancing Ambition with Present Moment Appreciation
Telander describes his approach to life as being both "dream-pilled" (intensely pursuing future goals) while practicing "gratitude maxing" (finding joy in present moments). He shares practical examples of staying present through sensory experiences, like enjoying meals with friends or observing nature.
Williamson reflects on his desire to make an impact while acknowledging the challenge of not getting lost in future-oriented thinking. Both hosts discuss strategies for maintaining this balance, with Telander sharing his running philosophy as an example of harmonizing goal-setting with present-moment enjoyment.
The Nature of "Coolness"
Williamson discusses a study of over 5,000 participants that identified key traits of "cool" people: extraversion, hedonism, adventurousness, openness, power, and autonomy. The hosts explore how authentic coolness emerges naturally rather than through conscious effort, with Telander noting that trying too hard to be cool often backfires.
They examine the tension between coolness and goodness, observing that while "cool" people intrigue through their unpredictability and autonomy, "good" people earn respect through reliability and traditional virtues.
The Reality of Online Content Creation
The conversation turns to the challenges of being an online creator. Williamson describes how fear of public judgment can limit creative expression, while Telander shares insights about building resilience to criticism. Both hosts emphasize the unique value of in-person interactions compared to online engagement, and discuss the importance of maintaining a sustainable balance between productivity and personal well-being in content creation.
1-Page Summary
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Counterarguments
- Authenticity and sincerity might not always be met with criticism; in some online communities, these traits are highly valued and encouraged.
- Irony isn't inherently negative and can be a sophisticated form of communication that allows for nuanced expression and can engage with ideas on a different level.
- The concept of "cringe" is subjective and culturally dependent; what is considered cringe-worthy in one context may be celebrated in another.
- The appeal of genuineness may not be universal; some audiences or individuals may prefer personas or entertainment over authenticity.
- Ambition and present moment appreciation might not be at odds for everyone; some individuals may find their ambition is what brings them present moment joy.
- The traits associated with coolness are not universally accepted and can vary greatly across different cultures and social groups.
- The pursuit of coolness, even if conscious, can be a form of self-expression and personal growth for some individuals.
- Goodness and coolness are not mutually exclusive, and some individuals may embody both sets of traits simultaneously.
- Online creators may find that public judgment enhances their work by providing diverse perspectives and constructive feedback.
- Resilience to criticism, while important, should not lead to a dismissal of all criticism, which can be a valuable tool for growth and improvement.
- Online engagement can sometimes offer support and community that are not available in person, especially for those with accessibility issues or social anxieties.
- The balance between productivity and personal well-being can be highly individual, and what works for one content creator may not work for another.
Actionables
- You can create a "Sincerity Journal" to practice expressing your authentic thoughts and feelings without fear of judgment. Start by writing daily entries about your experiences, focusing on being as honest and genuine as possible. This private space allows you to become comfortable with your authentic self, which can eventually translate into more sincere interactions with others.
- Develop a "Present Moment Reminder" system to balance ambition with appreciation for the now. Set random alarms throughout your day with labels like "Take a deep breath" or "Notice something beautiful." When the alarm goes off, pause whatever you're doing to engage in a brief mindfulness practice, such as deep breathing or observing your surroundings, to ground yourself in the present.
- Initiate a "Coolness Reflection" exercise to discover your natural cool traits. Spend a week noting down moments when you felt effortlessly cool or received compliments for just being yourself. Reflect on these instances to identify patterns in your behavior or qualities that resonate with others. This self-awareness can help you embrace your unique version of coolness without trying to conform to external standards.
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Authenticity, Sincerity, and the Perception of "Cringe"
Chris Williamson and Zack Telander delve into the nuances of how authenticity and vulnerability are received online, and how the fear of being labeled "cringe" can affect our willingness to be sincere.
The Correlation Between Authenticity and Vulnerability
Chris Williamson discusses the exposure and vulnerability one faces when honestly expressing beliefs, particularly those open to challenge. The act of being sincere carries a risk, as it can make one a target for distant, ironic criticism which avoids the expression of sincere beliefs. Williamson acknowledges the inner critic that might discourage us from enjoying simple pleasures by deeming them "cringe."
Sincere Beliefs Seem "Cringe" Due to Online Distance and Irony
Williamson comments on how being truly authentic and sincere in a public space, especially online, is considered exposing because of the prevalence of irony and distance on the internet. The use of the term "cringe" is seen as a form of non-engaging criticism that avoids the expression of sincere beliefs and instead opts for a detached form of judgment.
Irony as a Protection Against Vulnerability
Ironic Speech Avoids Engaging With Ideas and Accountability
Williamson elaborates that when people use irony in speech, they create distance between themselves and their words, allowing for criticism without the engagement of personal beliefs or accountability, effectively avoiding sincerity. Zack Telander adds that irony serves as a defense mechanism and an attack form but prevents true progression because nothing substantive is proposed. Ironic speech can serve as a protection, forming a shield against being the focus of others' scrutiny.
The Challenges of Navigating the "Cringe" Landscape Online
Criticism and "Cringe" Accusations Can Discourage Authenticity and Interests
Zack Telander discusses how the concept of "cringe" is often linked to the pursuit of hopes and dreams, with critics labeling such pursuits to discourage them. He implies that critics may have abandoned their own dreams and deride others who continue to chase theirs. Williamson voices his concern about how the constant potential for ...
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Authenticity, Sincerity, and the Perception of "Cringe"
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Counterarguments
- Authenticity and vulnerability online can sometimes be performative rather than genuine, with individuals curating their vulnerability to gain attention or sympathy.
- The term "cringe" may not always be used to suppress sincerity but can also serve as a social check against behaviors or expressions that are disingenuous or inauthentic.
- Irony and satire have long been effective tools for social commentary and criticism, and their use does not necessarily preclude sincerity or the progression of ideas.
- The fear of being labeled "cringe" might sometimes act as a healthy social mechanism that encourages individuals to reflect on their public behavior and align it with social norms.
- Critics who label others' pursuits as "cringe" may not always be projecting their own failed dreams but could be offering legitimate critiques of unoriginal or overly idealistic endeavors.
- The advice to be sure of what you want to say and to understand your topic well before speaking, while sound, may not always protect against criticism, as even well-informed opinions can be controversial or subject to ridicule.
- The internet culture's focus on hypocrisy can be se ...
Actionables
- Start a "Cringe Journal" to document your authentic thoughts and feelings without the fear of online judgment. By writing down your sincere beliefs and ideas in a private space, you can become more comfortable with your authenticity before sharing it publicly. For example, if you're passionate about a hobby that others might find unusual, write about why it matters to you and how it makes you feel, which can help solidify your confidence in your interests.
- Create a small, supportive community group where members encourage authenticity. This could be a book club, a hobby group, or an online forum where the focus is on sharing genuine interests and ideas without fear of being labeled "cringe." Within this group, practice expressing your sincere beliefs and support others in doing the same, fostering an environment where authenticity is celebrated.
- Challenge yourself to sh ...
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Balance Between Pursuing Goals and Appreciating the Present
Zack Telander and Chris Williamson discuss the significance of balancing the pursuit of future aspirations with a deep sense of gratitude for the present, examining the essence of what it means to lead a fulfilling life.
The Duality of Aspiration and Gratitude
Achieving Future Goals, Content With Present
Telander describes himself as being "dream-pilled," a state of being ambitiously driven toward future goals, particularly in his passion for music, which he pursues "harder than ever before." Concurrently, he finds profound contentment in moments of daily life, indicatively practicing "gratitude maxing."
Telander and Williamson delve into the common struggle of enjoying the present amidst the relentless pursuit of what's next. This often leads to a preoccupation with the future, overshadowing the capacity to savor the present. Williamson emphasizes his personal desire not to merely coast through life but to leave a substantial impact in his wake.
Using Senses to Appreciate the Present
Noticing and Deriving Joy From Small, Everyday Experiences
The art of appreciating the present comes through in Telander's shared moments with friends, like the simplicity of going to Nando's and delighting in the "wonderful nectar" from a drink machine. He also cherishes evenings with his partner, savoring Mexican food and margaritas while watching classic movies, affirming these moments verbally by exclaiming "this rules" or "this is it."
Telander advocates the practice of using one's senses to stay grounded in the moment, such as the time he aided a North American swallowtail butterfly. Moreover, he highlights the joy in appreciating the flavors of sushi or the marvels of modern technology, acknowledging the effort behind these conveniences.
Strategies For Maintaining Balance
Pursuing Goals While Practicing Gratitude and Presence
The conversation turns to the need for harmonizing the journey toward goals with the art of being present and grateful. Although these aspects may seem at odds, engaging in this balance is a constant battle worth waging.
Telander conveys ...
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Balance Between Pursuing Goals and Appreciating the Present
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Counterarguments
- While pursuing goals with gratitude is ideal, some may argue that excessive focus on gratitude for the present can lead to complacency and hinder the drive necessary for achieving ambitious goals.
- The concept of "gratitude maxing" might not be universally applicable, as some individuals may find that their circumstances make it challenging to practice gratitude.
- The balance between goal pursuit and present enjoyment is not a one-size-fits-all approach; what works for Telander and Williamson may not be suitable for everyone, as individuals have different values and life situations.
- The strategy of using senses to stay grounded in the present might not be effective for everyone, especially those who may be struggling with sensory processing issues or who find mindfulness practices difficult.
- The minimalistic approach to running and goal-setting described by Telander may not resonate with or be practical for everyone, particularly those who are goal-oriented and thrive on structured progress.
- Williamson's struggle with productivity and seeking a varied life might imply a dichotomy that doesn't exist for everyone; some individuals may find routine and productivi ...
Actionables
- You can create a "Gratitude Soundtrack" by compiling songs that evoke a sense of thankfulness and presence, playing it during your daily routine to remind yourself to appreciate the moment. For example, include tracks with lyrics that celebrate life's simple pleasures or instrumental music that helps you focus on your surroundings.
- Start a "Joy Journal" where you jot down one simple pleasure you experienced each day, like the taste of your morning coffee or a funny text from a friend. This practice can help you become more aware of the small joys throughout your day and cultivate a habit of gratitude.
- Develop a "Sensory Minute" routine where you pause for one minut ...
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Nature of "Coolness" and how Achieved
Telander and Chris Williamson delve into what it means to be "cool" and the challenging balance between coolness and goodness.
The Psychological Profile of "Cool" People
Chris Williamson discusses a study involving over 5,000 participants from 12 countries who evaluated individuals they considered cool or not cool, and good or not good. The study identified cool people as consistently being described as outgoing and social (extraverted), seeking pleasure (hedonistic), taking risks and trying new things (adventurous), being curious and open to new experiences (open), having influence or charisma (powerful), and doing things their own way (autonomous).
Extraverted, Hedonistic, Powerful, Adventurous, Open, and Autonomous
Williamson breaks down the attributes associated with cool people as extroverted, hedonistic, powerful, adventurous, open, and autonomous. He explains that these personality traits signal to others that someone is capable and confident enough to carve their own path.
Role of Authenticity In Being Perceived As Cool
Telander and Williamson discuss the necessity of authenticity in maintaining coolness. They suggest that trying too hard can undermine coolness because it appears inauthentic. For example, George Heaton discontinued the "owner's club" range of his clothing company Represent due to concerns overexposure might negatively impact the brand's coolness. Previous research indicates that efforts to appear cool usually don’t work and may result in a loss of status in the eyes of others. Genuine coolness comes from being true to oneself and unconcerned with societal norms, not from attempting to fit a certain image or trend.
Trying too Hard Undermines Coolness
Telander points out that if one tries to be cool or something they're not, it often comes across as inauthentic, suggesting the importance of being true to oneself. Williamson mentions cases, like the Rizzler, where behavior that initially seemed genuine became contrived, such as engaging in dance videos or brand partnerships for the sake of maintaining coolness, which can often backfire.
The Tension Between Coolness and Goodness
Williamson and Telander ...
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Nature of "Coolness" and how Achieved
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Clarifications
- Cool individuals are often seen as outgoing, adventurous, and autonomous, valuing traits like risk-taking and independence. On the other hand, good individuals are typically described as reliable, warm, and conscientious, embodying traits associated with traditional virtues and agreeableness. While cool people may attract attention for their unpredictability and autonomy, good individuals earn respect for their reliability and adherence to societal norms. The distinction lies in how coolness emphasizes uniqueness and independence, while goodness focuses on reliability and adherence to social expectations.
- The trait of being capable is highlighted as a common factor between individuals perceived as both cool and good. This capability is essential as it empowers individuals to assert thei ...
Counterarguments
- The association of coolness with traits like hedonism and risk-taking could be culturally biased and not universally applicable.
- The definition of coolness as being autonomous and unconcerned with societal norms might overlook the importance of social responsibility and ethical considerations in one's actions.
- The emphasis on authenticity might ignore the complexity of human behavior and the fact that people often play different roles in different contexts, which is a normal and sometimes necessary part of social interaction.
- The dichotomy between coolness and goodness could be overly simplistic, as individuals can possess traits from both categories simultaneously, and the traits themselves are not mutually exclusive.
- The idea that efforts to appear cool often fail may not account for the success of marketing and branding strategies that effectively cultivate a cool image.
- The suggestion that good individuals are more likely to earn lasting respect could be challenged by the notion that respect can also be garnered through innovation, change, and challenging the stat ...
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Experiences and Challenges Of Being an Online Creator
Telander and Williamson dive into the complexities and paradoxes of life as online creators.
Perceived Vs Actual Gratification From Online Content Creation
Telander discusses the fear of being labeled as "cringe" and how one builds resistance by facing it repeatedly. He indicates that many aspiring creators face discouragement from critics who delegitimize their work as cringe-worthy. Williamson further elaborates on how the fear of public opinion and judgment can constrain creators, leading them to miss opportunities due to overly cautious decision-making.
Disconnect Between Creators' Impact and Gratitude Received
Williamson touches on the sensitive nature of online reception to perceived grifting or shilling, suggesting that creators are often constrained by the fear of misjudgment. Telander shares his own struggles, implying that he’s felt a personal disconnect while trying to convince others of his authenticity.
The hosts discuss the vulnerability of creators online, pointing out that despite their impact, they may not always receive due gratitude or recognition. Williamson remarks on the regular nature of online feedback and the potential for creators to undervalue individual comments due to their routine occurrence.
Williamson also talks about the misconceptions among aspiring content creators regarding the level of gratitude they expect to receive compared to the reality they face upon entering the online creation space. He compares this to being in a band, where the external appearance of success might mask a lack of gratification internally.
The Importance of In-person Interaction and Feedback
Telander and Williamson discuss the unique value of in-person interaction. Telander describes receiving gratitude from a bartender—an interaction that symbolized a meaningful acknowledgment he had not experienced online. Williamson recalls live performances on tour as being more impactful than digital interactions, and they both agree that live experiences with audiences provide a different, irreplaceable connection.
The Need t ...
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Experiences and Challenges Of Being an Online Creator
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Counterarguments
- While facing criticism is a common part of being an online creator, not all creators may experience the fear of being labeled "cringe" to the same extent; some may be more confident or indifferent to such labels.
- Critics who delegitimize work as cringe-worthy may sometimes offer constructive feedback that can help improve the quality of content, even if it's harsh.
- The fear of public opinion can also serve as a motivator for creators to improve their work and strive for higher quality content.
- The perception of misjudgment and grifting can be mitigated by transparent communication and building a trustworthy brand over time.
- Some creators may find that the disconnect between their impact and the gratitude received is less pronounced, especially if they have a niche audience that is highly engaged and appreciative.
- The routine nature of online feedback can also be seen as a positive aspect, as it provides consistent engagement and can help creators stay connected with their audience's preferences and opinions.
- Misconceptions about the level of gratitude expected versus reality can be addressed through mentorship and education for aspiring creators, helping them set realistic expectations.
- Digital interactions, while d ...
Actionables
- You can build resilience to criticism by sharing your work with a small, supportive community first. Start by joining or creating a private group on social media with friends and family who encourage your creative endeavors. Share your content with them to gain confidence and constructive feedback before exposing it to a wider, potentially critical audience.
- Develop a personal gratitude practice to counterbalance the lack of recognition. Keep a journal where you note down every positive comment or piece of feedback you receive online. Regularly review these comments to remind yourself of the positive impact your work has, even if it's not always acknowledged publicly.
- Sche ...
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