Should be after:

• Cringy still/Don’t Cross the River if it’s 1 Meter Deep - on Average
• READY/WA/The man who changed my life.

I’ve written before on READY/WA/The man who changed my life.

The answer was yes.

This post is a personal reflection on how his philosophy shaped my thinking, my learning, and my way of living.

Over the past 15 years, nothing comes close to the impact that Nassim Nicholas Taleb had on me. His ideas on risk, antifragility, and skin in the game became foundational to how I approach life, work, and decision-making.

Here, I lay out what I learned from him—my lived experience. I still work on understanding, testing, and refining each one to this day.

The Barbell Strategy

The barbell strategy is simple: adopt the extremes and avoid the middle.

For my life, this means I should invest heavily in physical health. At the other end, I should give myself uncompromising periods of rest and low stress.

In investing, this means holding a mix of ultra-safe assets (cash, bonds) and high-risk ventures (startups) — avoiding the comfortable middle (e.g. index funds).

In tech engineering, this means working either on deeply complex problems (AI, security, foundational systems) or on minimalistic, sharp, efficient software—but never wasting my time in mediocre companies solving mediocre problems.

Stubbornness as a Virtue

Taleb taught me the difference between being stubborn and being brittle.

I must be uncompromising on principles, honesty, and work ethic.

But I must be flexible in what deserves flexibility—family, friendships, and people who built themselves with skin in the game.

I allow myself to be stubborn when someone bluffs about things they don’t understand.

But I try to be humble with anyone who built themselves from scratch—taʿallam min kēso. تعلم من كيسو in Arabic.

In investing, stubbornness means sticking to principles and avoiding fads. Meaning not panicking when everyone is, and panicking when everyone is not.

In tech, it means insisting on evolutionary architecture (containers, components, swappable modules, BFF) over big-bang “God Services.”

The Non-Negotiable Value of Hard Skills

Competence is not optional. There is no substitute for knowing my craft.

For me, this means I should have:

• deep technical expertise
• clarity in writing
• the ability to understand high-level and low-level systems — and know which level I should go into each time. I should have the ability to understand any core systems, depth-first, when it matters
• when I don’t know something, I must at least understand the consequences of being wrong. I need to remind myself of the difference between payoff, expectation E(x), and probability P(x). This governs business, engineering, and daily life.

I wrote about this in “Don’t Cross The River If It’s 1 Meter Deep—On Average.”

No BS, No Patience for Pretenders

I should have zero tolerance for nonsense.

I respect anyone who admits they don’t know. I dismiss those who pretend.

Clear thinking demands clear language—Einstein said it: if I can’t articulate an idea precisely, I don’t understand it.

This should affect how I choose people around me: intellectually honest individuals and avoid empty chatter.

In investing, I should ignore hype and only invest in what I truly understand.

In tech, I should call out over-engineering and buzzwords—common in big companies. And especially abundant with consultants.

In startups, I avoid founders who speak in jargon and focus on people who carry real risk and real skin in the game.

Learning the Right Things

Reading—deeply and widely—became a non-negotiable.

Popper, Hayek, and Russell shaped how I think about knowledge and freedom.

Montaigne taught me how to self-reflect.

NNT forced me to embrace skepticism and the limits of what I can know.

This should push me to be more precise, more critical of myself, and more grounded.

In investing, I should lean on foundational works instead of trendy newsletters and reels.

In tech, I study algorithms, data structures, design patterns, anti-patterns, Fred Brooks, Fowler, and the core texts, the bibles — chasing every new framework gets me nowhere. The new can have an edge, but not every new equals the edge.

Risk Awareness: Beyond Finance, Into Life

Taleb changed the way I perceive risk. It’s not only about markets—it’s about how I structure my life.

Fragility is the enemy.

My decisions—fitness, business, architecture, investing—should minimize catastrophic downside while maximizing upside.

Black swans exist; I should never assume I’m immune.

In investing, that means:

• limiting downside
• maximizing upside

And that, in practice, means:

• holding 80–90% in ultra-secure assets (bonds, prime-location real estate)
• placing 10–20% in high-upside opportunities (startups, new technologies, energy transitions)

In tech, it means building resilient evolutionary-based and extendable architectures—fault tolerance, recovery-first design, storage-first systems, replicas, fallbacks.

Table of Applications Across Domains

Below is a summary of the above in a table format for easy referencing.

Taleb’s philosophy is not just a way of thinking—It’s a way of living. And I feel blessed that he changed my mind. I feel grounded when everyone around me was following trends.

Resources

We detest the abstract and are moved by the concrete. Meaning, we love narratives and stories (the concrete.) And we hate and avoid what we don’t understand (the abstract.)

The Barbell Life: A Guide to Thinking, Learning, and Living with Purpose

In life, as in everything else, I follow a barbell strategy: extreme balance. On one side, I work on hard skills—deep, technical, and practical knowledge that makes me valuable. On the other, I keep my mind open, absorbing philosophy, history, and economics, understanding the grand narratives that shape the world. Everything in between is noise.

Stubbornness as a Virtue

I am stubborn where it counts. When it comes to principles, intellectual honesty, and work ethic, there’s no room for compromise. This doesn’t mean being inflexible—it means knowing what to be flexible about. The trick is knowing the difference.

Mastery of Hard Skills

Being skilled matters. There’s no substitute for competence. I invest in learning things that compound: deep technical expertise, writing with precision, and understanding systems at a granular level. If I don’t know something, I learn it. If I can’t learn it, I shut up about it.

No BS, No Tolerance for BS

I have zero patience for nonsense. I respect people who admit what they don’t know. I can’t stand people who pretend. If you’re going to talk, know what you’re talking about. Otherwise, silence is the better option. Orwell understood this—language matters. It shapes how we think, and if our language is muddy, so is our thinking.

Learning the Right Things

I read widely and deeply. Philosophy, history, economics—these aren’t just intellectual pursuits; they shape how I think about risk, decision-making, and the world. Popper and Hayek are foundational to how I view knowledge and society. They remind me to stay skeptical, to demand evidence, and to value freedom.

Risk Awareness in Everyday Life

Understanding risk isn’t just for finance—it’s for life. I incorporate it into every decision I make. From my work to my workouts to how I structure my time. Black swans exist. Avoiding fragility is key.

All or Nothing: Work, Play, Health

When I work, I work intensely. When I take time off, I rest completely. No half-measures. Same with food, training, and running. Either I’m fully in Zone 2, building endurance, or in Zone 3, pushing limits—but never wasting effort in between. Everything should have a purpose.

Language and Thought

The limit of my knowledge is the limit of my language. If I can’t articulate something precisely, I don’t fully understand it. Orwell’s clarity principle applies here—simplify, remove unnecessary complexity, get to the essence.

Learning from Those Who Came Before

I admire great thinkers, but I don’t idolize them. I recognize their limits. I recognize that they, too, had blind spots. Even those who feel familiar—who look and sound like people I knew growing up—are not infallible. I can acknowledge their wisdom while remaining critical of their mistakes.

The Never-Ending Journey

Every time I reread their works, I realize how much I still don’t understand. That’s the point. If I ever think I’ve ‘got it all,’ I’ve failed. I need to stay humble. There’s always more to learn.

Gratitude and Skepticism

I’m deeply grateful for the thinkers who have shaped my intellectual life. But gratitude doesn’t mean blind obedience. I question them. I challenge them. And I expect others to challenge me the same way.

This isn’t just a way of thinking—it’s a way of living. Be serious when it matters, be light when it doesn’t, and never stop learning.

Resources

Barbel Strategy

Stubborn

Work on hard skills

Know what I am talking about or Shutup

Same as GEorge Orwell

Debunk BSer

Dont be a BSer

Learn about economics history and philosophu

Understand Risk and incorporate it in my every day life

Love Popper and Hayek

Read as much as I can, breadth and depth

Take off days seriously and take on days seriously. Play hard work hard and nothing in between. Same for food work gym running

Do huge amount of zone 2

Do medium amount of zone 3

Understand the limit of my knowledge is the limit of my language

Understand that he looks and talks like my grandfather (also from Lebanese origions) yet, he’s not my grandfather.

Understand that he’s an arse sometimes but that’s OK

that everytime I reread his books, I do understand that I still don’t understand

… be humble that I still have long way to go.

… be thankful for him openning. The door for me to learn lots of things

.. keep an open mind and question him. He’s wrong sometimes.

Over the past 15 years, none come close to the profound impact of Nassim Nicholas Taleb on me. His ideas on risk, antifragility, and skin in the game have become foundational to how I approach life, work, and decision-making. This post is a reflection on how his philosophy has influenced my thinking, learning, and way of living.

I’ve written before on READY/WA/The man who changed my life.. The answer was yes.

Here, are the things I learned from him over the years.

The Barbell Strategy: A Framework for Life

Taleb’s concept of the barbell strategy is simple: balance extremes, avoid mediocrity. This applies to investments, knowledge, and even personal growth.

Example: In life, we should invest heavily in physical health through structured endurance training while also indulging in complete relaxation. In investment, we should balance between ultra-safe assets (cash, bonds) and high-risk ventures (startups, crypto) while avoiding the middle ground of index funds. In tech engineering, I either work on highly complex AI models or focus on minimalistic, efficient software—never mediocre abstractions. In startups, I either build fully bootstrapped businesses or go for high-risk VC-backed ventures, never getting stuck in between.

Stubbornness as a Virtue

One of Taleb’s key lessons is knowing when to be stubborn and when to be flexible. I have learned to be uncompromising when it comes to principles, intellectual honesty, and work ethic. This doesn’t mean rigidity—it means being precise about what deserves flexibility. The trick lies in recognizing the difference.

Example: In life, I refuse to compromise on integrity, even if it means losing opportunities. In investments, I stick to my principles of risk management, avoiding fads despite market pressures. In tech, I insist on clean, maintainable code even when deadlines loom. In startups, I hold firm to product-market fit rather than chasing trends.

The Non-Negotiable Value of Hard Skills

Competence is non-negotiable. There’s no substitute for knowing your craft. I invest in learning things that matter—deep technical expertise, writing with clarity, and understanding systems at a granular level. If I don’t know something, I learn it. If I can’t learn it, I stay silent. The world is already full of noise; there’s no need to add to it.

Example: In life, I continuously build my skills in writing and critical thinking. In investments, I study financial models deeply before making decisions. In tech, I ensure I have a deep understanding of distributed systems rather than relying on high-level abstractions. In startups, I prioritize mastering unit economics and business fundamentals before scaling.

No BS, No Patience for Pretenders

I have zero tolerance for nonsense. Taleb's philosophy reinforced this: respect people who acknowledge their ignorance, but dismiss those who pretend to know. Clear thinking requires clear language—something Orwell emphasized. If you can’t articulate an idea precisely, you don’t truly understand it.

Example: In life, I surround myself with intellectually honest people and avoid empty chatter. In investments, I ignore hype and only invest in what I deeply understand. In tech, I call out over-engineering and buzzword-driven development. In startups, I avoid founders who rely on jargon instead of real business insights.

Learning the Right Things

Reading widely and deeply has become a non-negotiable part of my life. I don’t just read for entertainment—I read to sharpen my thinking. Philosophy, history, and economics shape my worldview. Karl Popper and Friedrich Hayek remain foundational to my understanding of knowledge, decision-making, and freedom. Their emphasis on skepticism and the limits of human knowledge has made me more critical, more precise, and more pragmatic.

Example: In life, I balance classic literature with modern science. In investments, I read foundational works on risk instead of trendy financial blogs. In tech, I study fundamental computing theories rather than just following new frameworks. In startups, I learn from history’s great business minds instead of only modern Silicon Valley success stories.

Risk Awareness: Beyond Finance, Into Life

Taleb’s work has made me rethink how I approach risk. It’s not just about financial markets—it’s about life itself. Fragility is the enemy. Whether in business, fitness, or decision-making, I structure my life in a way that minimizes exposure to catastrophic risks while maximizing opportunities for growth. Black swans exist, and I don’t intend to be caught off guard.

Example: In life, I avoid unnecessary risks but take calculated ones for growth. In investments, I hedge against market crashes while betting on high-upside opportunities. In tech, I design resilient architectures that can handle failures. In startups, I structure companies to survive downturns rather than relying on continuous funding.

Table of Applications Across Domains

This isn’t just a way of thinking—it’s a way of living. Be serious when it matters, be light when it doesn’t, and never stop learning.

The Barbell Life: A Guide to Thinking, Learning, and Living with Purpose

In life, as in everything else, I follow a barbell strategy: extreme balance. On one side, I work on hard skills—deep, technical, and practical knowledge that makes me valuable. On the other, I keep my mind open, absorbing philosophy, history, and economics, understanding the grand narratives that shape the world. Everything in between is noise.

Stubbornness as a Virtue

I am stubborn where it counts. When it comes to principles, intellectual honesty, and work ethic, there’s no room for compromise. This doesn’t mean being inflexible—it means knowing what to be flexible about. The trick is knowing the difference.

Mastery of Hard Skills

Being skilled matters. There’s no substitute for competence. I invest in learning things that compound: deep technical expertise, writing with precision, and understanding systems at a granular level. If I don’t know something, I learn it. If I can’t learn it, I shut up about it.

No BS, No Tolerance for BS

I have zero patience for nonsense. I respect people who admit what they don’t know. I can’t stand people who pretend. If you’re going to talk, know what you’re talking about. Otherwise, silence is the better option. Orwell understood this—language matters. It shapes how we think, and if our language is muddy, so is our thinking.

Learning the Right Things

I read widely and deeply. Philosophy, history, economics—these aren’t just intellectual pursuits; they shape how I think about risk, decision-making, and the world. Popper and Hayek are foundational to how I view knowledge and society. They remind me to stay skeptical, to demand evidence, and to value freedom.

Risk Awareness in Everyday Life

Understanding risk isn’t just for finance—it’s for life. I incorporate it into every decision I make. From my work to my workouts to how I structure my time. Black swans exist. Avoiding fragility is key.

All or Nothing: Work, Play, Health

When I work, I work intensely. When I take time off, I rest completely. No half-measures. Same with food, training, and running. Either I’m fully in Zone 2, building endurance, or in Zone 3, pushing limits—but never wasting effort in between. Everything should have a purpose.

Language and Thought

The limit of my knowledge is the limit of my language. If I can’t articulate something precisely, I don’t fully understand it. Orwell’s clarity principle applies here—simplify, remove unnecessary complexity, get to the essence.

Learning from Those Who Came Before

I admire great thinkers, but I don’t idolize them. I recognize their limits. I recognize that they, too, had blind spots. Even those who feel familiar—who look and sound like people I knew growing up—are not infallible. I can acknowledge their wisdom while remaining critical of their mistakes.

The Never-Ending Journey

Every time I reread their works, I realize how much I still don’t understand. That’s the point. If I ever think I’ve ‘got it all,’ I’ve failed. I need to stay humble. There’s always more to learn.

Gratitude and Skepticism

I’m deeply grateful for the thinkers who have shaped my intellectual life. But gratitude doesn’t mean blind obedience. I question them. I challenge them. And I expect others to challenge me the same way.

This isn’t just a way of thinking—it’s a way of living. Be serious when it matters, be light when it doesn’t, and never stop learning.

Resources

Barbel Strategy

Stubborn

Work on hard skills

Know what I am talking about or Shutup

Same as GEorge Orwell

Debunk BSer

Dont be a BSer

Learn about economics history and philosophu

Understand Risk and incorporate it in my every day life

Love Popper and Hayek

Read as much as I can, breadth and depth

Take off days seriously and take on days seriously. Play hard work hard and nothing in between. Same for food work gym running

Do huge amount of zone 2

Do medium amount of zone 3

Understand the limit of my knowledge is the limit of my language

Understand that he looks and talks like my grandfather (also from Lebanese origions) yet, he’s not my grandfather.

Understand that he’s an arse sometimes but that’s OK

that everytime I reread his books, I do understand that I still don’t understand

… be humble that I still have long way to go.

… be thankful for him openning. The door for me to learn lots of things

.. keep an open mind and question him. He’s wrong sometimes.