What Really Makes a Good Day? | Philosophy, Psychology & the Quiet Art of Living

Most people don’t know a good day until it’s over. No disasters, no dread, just a faint sense of ease that only shows up in hindsight.

But when we ask what makes a day good, we’re really asking something deeper:

How do we measure our time? And what do we think life is for?

In this video, we explore ancient philosophy, modern psychology, and everyday experience to unpack what a “good day” actually means. Not in terms of productivity or pleasure—but in terms of alignment, presence, and meaning.

From Aristotle’s eudaimonia to Epicurus’ quiet pleasures…
From Stoic resilience to Mihaly Csikszentmihalyi’s flow…
From Viktor Frankl’s search for meaning to Montaigne’s bowel movements and essays…

Not a self-help checklist. A slow meditation on what it means to live well, even briefly.

Becoming a Time Billionaire: Taking Back Control of Your Hours

There are no markets for time - no ETFs, no futures, no indexes. And yet, every institution in modern life operates like a time exchange: buying your hours cheap, renting them out high, and keeping the spread.

This video is a manifesto for reclaiming control over the scarcest resource you have: your attention, your agency, your hours. We talk about the concept of the “Time Billionaire,” explore the hidden mechanics of time arbitrage, and show how founders, creators, and even small-town carpenters are quietly opting out of the attention economy’s worst trades.

Inside:

Why productivity culture has hijacked your calendar

How time arbitrage works (and how the quiet rich use it)

The myth of optimization vs. the strategy of subtraction

What it really means to own your time

Why the calendar is a moral document

If you've ever felt time-poor despite earning well… if you've ever wondered where your hours go… if you crave autonomy more than hustle - this might be for you.

Becoming a Time Billionaire doesn’t mean working less. It means owning the stack: what you work on, when, how, and who for.

00:00 Introduction: The Mispricing of Time
00:23 The Illusion of Time Ownership
01:01 Reclaiming Your Time: A Manifesto
01:17 The Economics of Time: An Auction Analogy
02:25 Time Arbitrage: Exploiting Attention Market Inefficiencies
03:38 The Myth of Optimization
04:43 The Concept of Time Wealth
06:57 The Calendar as a Moral Document
08:20 Conclusion: Becoming a Time Billionaire

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 Cringe
00:48 A Historical Perspective on Detachment
01:28 The Cruelty of Cringe Culture
02:46 The Importance of Authentic Expression
03:35 Embracing Cringe for Creativity
04:13 Letting Go of Cringe and Being Real

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 Faith

00:47 The Collapse of Context

01:52 The Rise of Factionalism

02:32 Engineered Outrage

03:29 The Modern Shibboleth Economy

04:45 The Cost of Understanding

05:22 Rebuilding Good Faith

Why Goal Setting Is Overrated: Embrace Constraints Instead

The 1953 Yale goal-writing myth has long misled professionals, suggesting clarity of ambition leads to success. This video challenges that notion, arguing that true innovation stems from working within constraints, not rigid goals. Examples from John Boyd's OODA loop to Richard Feynman's playful problem-solving illustrate how constraints foster creativity, adaptability, and meaningful progress. The stoic philosophy of Marcus Aurelius and the career paths of successful creatives further underscore the power of self-imposed limits over fixed goals. In navigating life’s ambiguous challenges, setting constraints can often be more effective than pursuing predefined outcomes.

00:00 The Myth of Yale's Goal-Setting Study
00:35 The Cult of Goal Setting
00:56 Innovators Who Avoid Goals
01:16 The Power of Constraints
01:48 Constraints in Creativity
02:09 The Illusion of Goal Setting
02:35 The Importance of Invisible Constraints
03:03 NASA's Constraints and Creative Solutions
03:36 Constraints vs. Goals in Decision Making
04:19 The Psychology of Antigoals
04:45 The Stoic Approach to Constraints
05:42 When Goals Make Sense
06:20 Closing Thoughts: Goals vs. Constraints

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 applause

This 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 Merton
00:25 The Birth of the Information Economy
00:49 The Creator Monk: A Middle Path
01:50 The Costs of Scale
03:04 The Value of Depth Over Reach
05:58 The Alternative Theory of Success

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 essays
• The work of Julia Wertz and Impossible People
• The difference between information consumption in 1933 vs. today
• Why more information doesn’t mean more understanding
• The signal-to-noise problem in modern media
• The illusion of being informed
• The 90% Solution: How I curate my information diet
• Strategies I use for reclaiming mental clarity and focus

Key Takeaways:

• Modern media operates like reality TV—designed for engagement, not understanding
• High-volume information consumption leads to shallow thinking
• There are only two types of information worth keeping: foundational knowledge and actionable intelligence
• A strategic information diet improves decision-making and cognitive depth

Mentions:

• Pizza Party Webcomic
• Julia Wertz’s Impossible People
• Nassim Taleb on the ‘Rational Flâneur’

Actionable Steps:

1. Audit your current information consumption habits.
2. Unfollow, unsubscribe, or block sources that don’t provide real value.
3. Prioritize deep, high-quality sources over fragmented, reactionary content.
4. Introduce regular ‘fasting’ days from news and social media.
5. Focus on understanding, not just knowing.

In this episode, I explore a fundamental truth that plays out across every field: simplicity is mastery.

We watch the ambitious MBA graduate design an elaborate business strategy while the seasoned entrepreneur focuses on one thing and does it exceptionally well. We see the aspiring chef juggle exotic ingredients while the master chef transforms simple elements—salt, heat, and time—into something extraordinary.

This pattern repeats everywhere:

• The elite athlete masters the fundamentals, while the beginner clings to complexity.
• The skilled negotiator wins with silence, not argument.
• The best investors choose focus, not chaos.

So why do we keep making things more complicated than they need to be?

I break down the psychology and mathematics behind why we label things "impossible" and how to overcome these false barriers. Through examples from aviation history to Amazon's evolution, I explore how taking that first step – even in the wrong direction – creates valuable information for success.

Key Points:

• Why experts often wrongly label things "impossible"
• The cognitive bias of viewing complex tasks as monolithic challenges
• How bad first steps can provide more valuable information than good ones
• Why the path to success never looks like we expect
• A framework for evaluating potential first steps

Quote: "Nothing is impossible (if you're willing to be wrong repeatedly and publicly while figuring out how to do it)."

I explore an unsettling discovery at McDonald's - men order dramatically more food when facing a screen instead of a person. This kicks off a deeper examination of how digital interfaces strip away the social guardrails that evolved to protect us from our worst impulses.

Key Points:

• What McDonald's learned about male ordering patterns through self-service kiosks
• How digital interfaces bypass thousands of years of evolved social wisdom
• Why that moment of hesitation before ordering a second burger matters
• The hidden costs in dating apps, social media, and digital shopping
• When friction might actually help us make better choices

Notable Quote: "The screen knows what we want in the moment because it doesn't ask us to consider the future."