
Westenberg
The Westenberg Podcast offers ideas, explainers, book notes, and reflections on technology, philosophy, and the human experience. Hosted by Joan Westenberg, each episode unpacks complex topics with clarity and depth, blending personal insights with thought-provoking analysis. It’s a space for exploring big questions and fresh perspectives in an accessible format.
Latest episodes

Jul 17, 2025 • 6min
Cringe Tolerance Is a Superpower
Explore the fascinating concept of 'cringe tolerance' as a crucial skill for creators. Discover how successful people embrace imperfection, making mistakes part of their journey. Historical examples reveal that even the greatest innovators started with rough drafts. Learn why the fear of failure can paralyze potential and how sharing flawed work leads to improvement. The conversation emphasizes that the embarrassment of early efforts is short-lived compared to the regret of never trying. It’s time to accept the awkward beginnings of creativity!

Jul 14, 2025 • 8min
Why Smart People Deliberately Kill Their Status
Explore the intriguing concept of 'status death'—the intentional choice to step away from recognition to embrace authentic freedom. Discover how letting go of social standing can foster personal growth, as seen through historical and modern examples. The podcast highlights the intricate identity challenges that founders face and offers practical tactics for navigating this transformative journey. Uncover the liberating potential of embracing obscurity as a strategic advantage in the long game of success.

Jul 10, 2025 • 7min
I'm Obsessed with Infinite Leverage
Discover how intellectual property acts as a powerful lever in the digital age, reshaping productivity. The discussion highlights the evolution of ideas, from the Statute of Anne to today’s creator economy. Learn why thoughts can generate massive value, like a newsletter with just 5,000 subscribers pulling in $600K annually. The conversation also addresses the courage gap that stifles publishing and critiques traditional work ethics. Ultimately, it emphasizes the importance of turning ideas into artifacts that work for you around the clock.

9 snips
Jul 4, 2025 • 7min
The Anatomy of a Good Day
What really defines a good day? Delve into the concept that it’s not just about productivity or pleasure, but aligning with personal values. Explore insights from ancient philosophers and modern psychology that reveal the importance of presence and meaning. Learn how moments of reflection and hardship contribute to a day well-lived. Discover a rich tapestry of thoughts from Aristotle to Viktor Frankl, offering a deeper understanding of fulfillment in our daily lives.

10 snips
Jul 3, 2025 • 9min
How to Become a Time Billionaire
Discover how to reclaim your most valuable resource: your time. The conversation delves into the concept of a “Time Billionaire,” exploring how ordinary individuals can escape the clutches of productivity culture. Learn about time arbitrage, where the wealthy exploit inefficiencies in attention markets. Challenge the myth of optimization with a strategy of subtraction, and understand why your calendar is more than just a schedule—it's a moral document. This insightful discussion will change how you perceive and manage every hour.

Jul 2, 2025 • 5min
The Unbearable Lightness of Cringe
There’s a specific kind of fear that haunts internet natives.The fear of cringe.You’ve felt it. Hovering over the tweet button. Deleting a draft blog. Scrapping a podcast because you imagined what your most cynical mutual might say.Cringe is the fear of visibility. Of being caught wanting something.And if you let that fear grow, it turns corrosive. You start living at a safe, ironic distance from your own life.But every subculture, every movement, every early YouTuber and overlooked writer paid the cringe tax.The Impressionists were mocked. The punks were clowned. The first blog posts were unbearably earnest.And yet they made something.Because they didn’t flinch.This video is about how to post before you're ready. Publish before it's perfect. Make something even when you're scared of looking stupid.Cringe isn't the enemy. Silence is.00:00 Understanding the Fear of Cringe00:48 A Historical Perspective on Detachment01:28 The Cruelty of Cringe Culture02:46 The Importance of Authentic Expression03:35 Embracing Cringe for Creativity04:13 Letting Go of Cringe and Being Real

Jul 1, 2025 • 6min
Good Faith is Dead...
Good faith is dead.There was a time when you could post online and expect to be misunderstood - but at least misunderstood honestly. Someone might disagree. They might argue. But they’d try.That time is gone.Today, you’re not joining a conversation so much as entering a courtroom. You’re both defendant and surprise witness. The replies come loaded - and looking for motive.The presumption of good faith has been entirely replaced by the assumption of bad faith. Say something reasonable? You’re hiding something. Say something principled? You’re posturing. Say something provocative? You’re attention-seeking.What’s collapsed isn’t just civility. It’s the entire social contract that once made online discourse worth participating in. Context is dead. Profiles are ignored. Nuance is deprecated. And in its place: factionalism. Instant tribal sorting. The shibboleth economy.And worst of all - it’s not an accident. It’s engineered. Rage scales. Context doesn’t. And the platforms know it.This video explores how online conversation decayed into hostile performance - and how we might still salvage a few quiet corners of understanding.00:00 The Death of Online Good Faith00:47 The Collapse of Context01:52 The Rise of Factionalism02:32 Engineered Outrage03:29 The Modern Shibboleth Economy04:45 The Cost of Understanding05:22 Rebuilding Good Faith

9 snips
Jun 26, 2025 • 7min
Why The Smartest People I Know Set Constraints, Not Goals
Forget the myth of goal-setting; true innovation thrives within constraints! Dive into how limitations can spark creativity, with fascinating insights from military strategies and historical figures like Richard Feynman. Discover the psychology behind 'antigoals' and how embracing restrictions often leads to more meaningful progress. From NASA's groundbreaking solutions to the stoic philosophy of Marcus Aurelius, this discussion reveals that flexibility, not rigidity, can be the key to navigating life's challenges.

Jun 25, 2025 • 7min
How to Become a Creator-Monk
We are obsessed with virality, funnels, and growth hacks. So what happens when a creator chooses not to scale?This video explores the “creator-monk” - a path inspired by Thomas Merton’s monastic clarity and counterbalanced by the noise-optimization of the digital age. It’s for the builders who prioritize depth over distribution, continuity over content calendars, and sovereignty over scale.We’ll cover:- Why some creators are intentionally going subscale- The economic logic of building for 100 true users, not 100K- How algorithms and audience expectations have reshaped creative work- The risk of performative minimalism- What productivity looks like without visibility- And why, in the long run, autonomy may matter more than applauseThis isn’t a rejection of ambition. It’s a redesign of what a meaningful creative life can look like - slower, quieter, sharper.If you’ve ever wondered whether you’re building a brand…or building a body of work - hopefully, this one’s for you.00:00 The Silent Wisdom of Thomas Merton00:25 The Birth of the Information Economy00:49 The Creator Monk: A Middle Path01:50 The Costs of Scale03:04 The Value of Depth Over Reach05:58 The Alternative Theory of Success

Feb 19, 2025 • 7min
The Attention Diet: How to Reclaim Your Mind from Endless Noise
In this episode, I talk about the overwhelming flood of modern information and how it’s affecting my ability to think clearly. I explore why removing friction from information consumption has led to mental overload, the illusion of being informed, and how the endless stream of news and social media impacts cognitive clarity. Plus, I share a practical framework for cutting through the noise and reclaiming focus.Topics Covered:Updates on Pizza Party webcomic, YouTube video essaysThe work of Julia Wertz and Impossible PeopleThe difference between information consumption in 1933 vs. todayWhy more information doesn’t mean more understandingThe signal-to-noise problem in modern mediaThe illusion of being informedThe 90% Solution: How I curate my information dietStrategies I use for reclaiming mental clarity and focusKey Takeaways:Modern media operates like reality TV—designed for engagement, not understandingHigh-volume information consumption leads to shallow thinkingThere are only two types of information worth keeping: foundational knowledge and actionable intelligenceA strategic information diet improves decision-making and cognitive depthMentions:Pizza Party WebcomicJulia Wertz’s Impossible PeopleNassim Taleb on the ‘Rational Flâneur’Actionable Steps:Audit your current information consumption habits.Unfollow, unsubscribe, or block sources that don’t provide real value.Prioritize deep, high-quality sources over fragmented, reactionary content.Introduce regular ‘fasting’ days from news and social media.Focus on understanding, not just knowing.