Modern Wisdom #1008: Angelo Sommers – Why Life Feels So Pointless (and What to Do)
Release Date: October 18, 2025
Host: Chris Williamson
Guest: Angelo Sommers
Overview
In this thoughtful, wide-ranging conversation, Chris Williamson sits down with rising thinker and creator Angelo Sommers to address the fundamental sense of pointlessness and malaise that haunts many people, especially young men, in the modern world. Using their own personal stories and lessons from philosophy, psychology, and contemporary culture, they unravel why life can feel so empty, why striving and self-improvement don’t always bring fulfillment, and what practical steps can actually help. The exchange moves seamlessly from deep personal honesty to sharp cultural critique, making it not just a discussion of “what’s wrong?” but a roadmap for what to do next.
Key Discussion Points & Insights
1. The Trap of “Trying for 20” & Comparing Yourself to Others
[00:38–02:52]
- The Concept: Pushing yourself “twice as hard” as those around you can yield big external achievements, but it often comes from comparison, competition, or fear, leaving you feeling reactive and robbed of freedom.
- Angelo: “You might not be the happiest while you’re doing it, but you never know.”
- Chris: “The position is always lacking… you’re always going to be chasing an unrealistic opportunity.”
Memorable Quote
“You can end up just getting really good at shit you don't actually care about or making a lot of progress along a dimension that you wouldn't have otherwise.”
– Angelo Sommers [02:24]
2. Self-Belief, Success, and the Delicate Line Between Vision and Delusion
[04:37–08:06]
- Self-belief: Not something passively proven; you must act before proof emerges, creating a reciprocal upward or downward spiral.
- Retrospective Rationalizing: Societal tendency to interpret outcomes as “duh, obviously,” regardless of reality.
- Taleb Example: Most of the time, extreme strategies look foolish—until that big, rare payoff.
Memorable Quote
“The belief that the juice is worth the squeeze is not a product of the juice. The juice is actually a product of the belief that it's worth the squeeze.”
– Angelo Sommers [05:12]
3. Directionless Potential, Modern Malaise, and the Region Beta Paradox
[10:14–16:42]
- A Generational Yearning: Many young people feel “built for more,” but unfulfilled, stuck between agency and analysis paralysis.
- Region Beta Paradox: Life that’s not good enough to be fulfilling, but not bad enough to spark radical change, produces lingering dissatisfaction.
- Cultural Sedation: The ready availability of distractions allows for sedation instead of adventure or confrontation.
Memorable Quote
“There's plenty of fodder in your soul... but oftentimes we're actually avoiding the sparks because the sparks are stressors.”
– Angelo Sommers [13:40]
4. Hitting Rock Bottom and Revisiting the Sense of Self
[15:16–18:40]
- Rock Bottom Myths: Many people wait for a big crash to spark change but instead live in gradual “capable complacency.”
- Fragmented Self: Inspired by Nietzsche, the “self” is a story told by whichever internal drive wins—the rest is retrofitted narrative.
Notable Example:
Chris shares how trauma can cause us to rewrite our own past:
“If someone was to say... well, you used to love driving. No, no, no, I've never liked driving.”
– Chris Williamson [21:05]
5. Online Advice Culture: Coping, Coaching, and the Dangers of Certainty
[25:46–34:52]
- The False Promise of Advice: Talking or venting about the thing often replaces actually doing the thing—words rarely catalyze real transformation.
- Internet Self-help: Much of it is “retrofit cope,” offering vague platitudes that anesthetize but don’t change.
- Certainty as Performance: The illusion that confidence equals expertise misleads many confused searchers.
- Learning in Public: Chris’s approach is to build in public, remain aware of his ignorance, and encourage self-inquiry, not fixed answers.
Memorable Quote
“Certainty is not a proxy for expertise... Fluency is not a proxy for truthfulness.”
– Chris Williamson [36:52]
6. The Double-Edged Sword of Intelligence and the Limits of Introspection
[41:49–44:24]
- Intelligence as Self-Deception: Smart people are better at rationalizing what they already believe, not necessarily at seeing all sides.
- Character Matters More: Success is more about character traits (resilience, commitment) than raw intelligence.
7. Angelo’s Personal Story: School, Crisis, Drugs, and Recovery
[44:24–56:30]
- Early Alienation: Angelo’s anxiety about mortality and the meaninglessness of school pushed him to leave formal education at age 12.
- Nihilism and Descent: Free to direct his learning, he soon plunged into existential crisis, substance abuse, and a self-destructive spiral in his teens.
- Turning Point: Recognizing slow self-destruction and seeking a radical life change at age 18.
Notable Exchange
“I started to develop this sort of adversarial relationship with reality... and yeah, I think that sort of became the fuel for me to spin up various narratives that justified that sort of nihilistic, hedonistic obsession with pleasure and pain.”
– Angelo Sommers [50:12]
8. The Universal Sense of Brokenness and the Power of Relatability
[58:45–61:52]
- Many people feel uniquely cursed or broken, but hearing others (even famous ones) admit to the same feelings dissolves shame and brings comfort.
- Chris reflects on feeling like he had a “personal curse” of deficiency, and how throwaway confessions from role models are what actually matter to listeners.
Memorable Quote
“At least you're less alone than you thought you were, is a big source of comfort... as soon as you say at least there's two of us, you immediately infer there's probably millions.”
– Chris Williamson [61:46]
9. Identity, Authenticity, and the Moving Goalposts
[66:51–73:40]
- Constructed Selves: We build up personas to be accepted—often losing touch with who we truly are beneath layers of performance.
- Inauthenticity: Even if you “succeed,” you’re applauded for the persona, not the person.
- Upward vs. Downward Spirals: Identifying as a ‘failure’ can itself be the necessary inflection point for change.
- The Curse of High Standards: People with high standards constantly move the goalposts, often never arriving at satisfaction.
Memorable Quote
“If you have wrapped your identity up in being the person who has high standards and is able to meet them... when you fall short a lot, it just feels like total loss of your sense of self.”
– Chris Williamson [72:02]
10. The Perpetual Battle Between Achievement, Gratitude, and Meaning
[83:03–94:57]
- Ever-Slippery Fulfillment: Achievers start to “change the game,” always seeking new, more complicated challenges, never arriving at rest.
- “Hard Gainers” of Gratitude: Some are dispositionally less able to feel grateful; for them, appreciation itself is a form of hard, deliberate practice.
- Meaning vs. Happiness: Many pursue meaning as a substitute for happiness; life’s core struggle is often a “thinly veiled attempt at quelling boredom.”
Memorable Quotes
“You prioritize meaning over happiness because happiness doesn't come easily to you.”
– Chris Williamson [94:57]
“It's the desire, not the desired, that we truly love.”
– Angelo Sommers [91:50]
11. Masculinity, the “Adventure Deficit,” and the Online Masculinity Grift
[105:49–114:05]
- Young men crave adventure and meaning but are instead offered sedatives and status games.
- Online masculinity and red pill figures offer easy (but deceptive) explanations, often appealing to insecurity and a hunger for direction.
- Real solutions are more nuanced and require facing uncomfortable truths about oneself.
Angelo on Masculinity Culture:
“It's a weird blend of modicums of truth mixed with like opportunism on the part of people who recognize the insecurity in others...”
12. The Modern Condition: Seeking Wisdom in a Mismatched World
[122:55–131:25]
- Contextual Meaning: Life isn’t about fitting into a neat narrative or finding definitive answers—meaning is contextual, messy, and often lost in translation.
- Procrustean Beds: We cut ourselves to fit abstract categories and explanations, which always miss the truth of our unique situation.
- Wisdom for Now: Modern Wisdom’s mission is to offer tools and reflections that acknowledge the inherent uncertainty, ambiguity, and messiness of life today.
Angelo on Meaning:
“Whenever you go about trying to answer what am I doing this for in a way that you could explain to somebody else, you are like trying to lift up water with a net.” [128:59]
Notable Quotes & Timestamps
- “You can end up just getting really good at shit you don’t actually care about...” – Angelo [02:24]
- “Self-belief... it's not like it goes proof and then belief or it goes belief and then proof. They're kind of like in a dynamic relationship with each other.” – Angelo [05:34]
- “You have to have some level of like, you just decide that you actually can. And that's the only way that you ever get any evidence that will actually come to serve as proof in the future.” – Angelo [05:21]
- “Of the high performers that I’m around, nine out of ten of them are running away from something they fear as opposed to the just pure alchemy of something that you want.” – Chris [95:52]
- “If it's not now, when is it? When will you start giving yourself credit?” – Chris [87:44]
- “The reason to win the game is so that you no longer need to play it.” – Chris [83:37]
- “It's not a nice case, it's not pleasant, but it is the case... at the end of the day, like, the floor feels like the fucking floor.” – Angelo [120:02]
Segment Timestamps (Approximate)
- “Trying for 20” & Competition: [00:38–02:52]
- Self-Belief & Proof: [04:37–08:06]
- Region Beta, Aimlessness: [10:14–16:42]
- Trauma and Identity Rewriting: [18:40–21:23]
- Online Advice & Certainty: [25:46–36:52]
- Personal Stories of Crisis: [44:24–56:30]
- The Curse of High Standards: [66:51–73:40]
- Gratitude, Achievement, and Meaning: [83:03–94:57]
- Masculinity & Online Culture: [105:49–114:05]
- The Challenge of Modern Meaning: [122:55–131:25]
Tone and Style
- Candid, self-aware, and steeped in personal experience
- Combines philosophical depth and psychological insight with relatable anecdotes
- Encourages listeners to adopt a nuanced, compassionate, and realistic view of self-improvement and modern struggles
Takeaways for Listeners
- The sense that "life is pointless" is deeply human and often rooted in societal, psychological, and personal feedback loops.
- Chasing external benchmarks, perfection, or internet advice often makes things worse—meaning and wisdom are far messier, contextual, and inside-driven.
- Everyone, even those who seem successful or put together, battles internal doubts and periods of despair.
- Genuine growth begins with self-honesty, accepting discomfort, and attending to real connections and day-to-day experience.
- Life is mostly made up of ordinary Tuesdays; fulfillment comes not from monumental achievements, but from navigating the daily mess with a sense of perspective and self-compassion.
Find Angelo Sommers at:
- YouTube: Angelo Somers
- Substack: Nav Notes
- Online tool: thecompassdiy
- angelasommers.com
Explore more with Chris Williamson:
“Your life is made up of ordinary Tuesdays. Your goal should be that your average Tuesday is just pretty good.”
– Chris Williamson [124:05]