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What I Learnt from Antifragile (I)

There seems never to be the right time to write or the right amount that I could learn from Antifragile, so I’m just going to take a long, rambling stab at it this morning.

It will be a living document that I’ll keep adding to on the blog, sooner or later, but for now, this is just for you, my dear newsletter1 family.

Here goes …

While I love the way he writes, I don’t have that much a familiarity with English that, I can easily process stuff like this, every time I just want to grab a principle quickly.

“what physicists call the phenomenology of the process is the empirical manifestation, without looking at how it glues to existing general theories.”


“In Peri mystikes theologias, Pseudo-Dionysos did not use these exact words, nor did he discuss disconfirmation, nor did he get the idea with clarity, but in my view he figured out this subtractive epistemology and asymmetries in knowledge.”

Drives me bonkers every time.
Hence this little screed for me to look at, whenever I want to.


I got lucky when I stumbled on Antifragile in early 2013.

I was slogging at the end of nearly a decade long effort of digging my sorry ass out of debt.

And while I was doing that, I was trying to learn how to handle money better.

How to invest it well or at least the general principles, of how not to lose money, forget about growing it.

And more importantly, how be resilient enough, to handle stuff that life threw at me.

How not to stress.

I had it upto here, stressing about every bad thing that came along.

I was thinking about the same thing that Taleb espoused in this book.

It was not the title, Antifragile, that grabbed me, but the subtitle:

How to Live in a World We Don’t Understand

And the Prologue sucked me in totally,

Wind extinguishes a candle and energizes fire.

Likewise with randomness, uncertainty, chaos: you want to use them, not hide from them. You want to be the fire and wish for the wind. This summarizes this author’s nonmeek attitude to randomness and uncertainty.

We just don’t want to just survive uncertainty, to just about make it. We want to survive uncertainty and, in addition—like a certain class of aggressive Roman Stoics—have the last word. The mission is how to domesticate, even dominate, even conquer, the unseen, the opaque, and the inexplicable.


He then takes nearly 500 pages of dense prose like the two quotes up above to explain the how.

Make no mistake, I loved it. I enjoyed it.

I re-read this book every 8–12 months.

But I am definitely not smart enough to extract the principles I need, at a moments notice.

Hence this post(s).

Everything below, is now what I understand, (or think I understand) from Antifragile.

And why am I doing this?

Because the book changed my life for the better.

It gave me what Zig Ziglar called a new pair of glasses, to look at life with.

Or what Charles T Munger and Shane Parrish would call, a latticework of mental models.

Reading Order

If you get into Taleb zealotry like I have, and want to read the entire Incerto, then this is the order I suggest you do it.

  1. Antifragile
  2. Antifragile
  3. Antifragile
  4. The Bed of Procrustes
  5. Skin in the Game
  6. Fooled by Randomness / The Black Swan

Antifragile is the main work.

Even though it is the fourth chronologically. Every other book can be looked at as offshoots of some chapter in Antifragile.


It is always good to have options. It is always good to check alternatives.

You gain a lot of freedom that way.

Options might be free, or you might have to pay for them.

But unless they are really expensive (which it really is not in most of life), it is always good to have options.

Case in point, after one case too many of being burnt over non refundable tickets, I started buying my air tickets, directly from the airline with the option to get a full refund.

Twice now, paying a bit more for this option has saved my hind quarters. Once I had to reschedule an entire multi city trip and the other was full refund, just as Covid hit.

Lesson learnt.

Now I look for options and alternatives even more in other areas of my life.

Domain Blindness

Some principle you use / do / see in one area of your life, can just as easily exist in others.

You can either diet and go to the gym and lift weights or become a manual labourer who hasn’t enough to eat and carries loaded bags.

The principle is the same. And the end result is the same. You drop fat and gain a six pack.

If you we can’t see the principle at work, we have a case of domain blindness.

I knew I could do a little bit every day on a certain task at work and get it done.

It never struck me to do the same to develop my skills.

Now that I see and am no longer domain blind, I use the same principle (steady, slow iteration) to lose weight, to complete my 12th standard and learn programming.

This is all I remember for now.
I’ll write more, as I realise more.

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  1. This was sent to my newsletter subscribers on Oct 4th, 2020. If you are reading this on the blog, you really should subscribe, if you want to read my stuff as soon as I put it out. 

You are Awesome

I want to keep reading books and stories about how folks pick themselves up.
It helps me deal with the storms in my life better.
It assures me I am not alone.
And people often have it worse.

Neil Pasricha shares his story in You are Awesome.
Most of which are relates with everything we face in our lives.
And I was meh.
But he also shares his parents stories.
And those are really, really inspiring.

I stumbled on the book, after I stumbled across his 3 Books project.
And I stumbled upon that after Shane [retweeeted] about his episode on said project.
A week of binging and I now have so many books to read.
You don’t have to go listen to all the episodes if you just want the book list. They are readily available here.

So where was I? Oh Neil’s book.
I heard about it on the podcast and went and got it.
He is a gifted storyteller with an awesome voice.
So listening to the podcast or reading the book, never feels boring.
He takes us from beginning to the end in a lovely, engaging, flowing manner.

The book is not about the stories though.
It’s about how you can pick yourself up, dust your self and get back on the horse after life’s kicked you in the gut.

Some quotes, alongside the nine steps to become more resilient.

Add a Dot-Dot-Dot

Sometimes the hardest thing to do is simply making the decision to keep going.
I use my mom’s story to show how easy it would have been for her to just stop and give up, to shut off the taps. It’s much harder to keep the taps on. It’s harder to add a “yet” to the end of a self-judgment.
How does the magic word look in practice?
“I can’t meet new people… yet.”
“I don’t have any better options… yet.”
“I’m not good at anything else… yet.”
“I don’t waltz… yet.”

Shift the Spotlight

When we fail …

We have to be aware and remember that we are quick to internalize. To self-flagellate. To point the dagger straight at our stomachs. To let the spotlight shine brightly into our own set of eyes. But a big part of resilience, of remembering we really are awesome, is performing this crucial mental separation.
“Oh, wait. I’m thinking this failure is all about me. I’m pointing the spotlight at myself. I’m taking all the blame here.” Stop. Separate. Remember:
It’s actually egotistical to think it’s all about you.
So what do you do?
Dance with it. Work with it.
Set it beside you, not inside you.
It’s not about you. It’s not about you. It’s not about you.
You have to shift that spotlight.
Because there’s a lot more work to do.
And you can’t start till after you shift that light.

See It as a Step

See the failure you’re going through as a step up an invisible staircase toward a Future You in a Future Life you can’t even imagine yet.
We all think that the way things are now is the way things will continue to be.
But inevitably, everything we go through in life really is a step to help us get to a better place.
We confuse the challenge of picturing change with the improbability of change itself.
But there are more steps.
And change will come.
It always does.

Tell Yourself a Different Story

Your problem is not the outside world. Your problem is the story you’re telling yourself about the outside world. And that story is a choice. If you’re not happy with the story, tell yourself another story. Period. That simple. And most people will hear what I just said and not change anything.

Do you hate your stretch marks? Can you try to see them differently? Can they be timeless tattoos commemorating how you brought your beautiful children into the world?
Are you ashamed of your dozens of one-night stands? What if they helped you understand your own sexual chemistry enough that you knew what you needed in a partner?
Do you curse yourself over the extra ten pounds on your gut? Can you instead love the fact that you have a weekly pizza and wings night with your friends?
We have to remember that we retain the choice, we hold on to the choice, we get to make the choice to tell ourselves a different story.
We can rewrite our shame stories, we can be gentler on ourselves, we can take the kindness we preach… and treat ourselves more kindly first.
Tell yourself a different story.
Three big questions to help achieve this secret
1. Will this matter on my deathbed?
2. Can I do something about this?
3. Is this a story I’m telling myself?

The truth is that most of what we think is a story we’re telling ourselves.
Only you can decide what story you tell yourself. So tell yourself a better one.

Lose More to Win More

We don’t want to hear that some things just take time.
They just take time.
They take lots of failure, lots of loss, lots of experience.
So ask yourself:

Am I gaining experience?
Will these experiences help?
Can I stay on this path for a while?

Sometimes the answer will be no. Sometimes the answer will be yes. But the answers will help point out the fact that you are learning, you are doing, you may be failing, but you’re moving…
Moving through failures is the real success.
Do you love it so much you can take the pain and punishment, too?
1. Go to parties (where you don’t know anyone) (aka, put yourself in a position to fail. where the downsides are low. – mjb)
2. Have a failure budget
3. Count your losses
The truth is when we look at our flops we’re really giving ourselves credit for all the learning and stamina and resilience baked into those moments when we made ourselves a little stronger.
We don’t trust people who haven’t failed and we really don’t trust people who don’t even know they haven’t failed or like to pretend they haven’t failed.
We need to talk about failures. Flops. The more we have, the more we grow. So put them out there. The jobs you sucked at, failed at, got fired from. The relationships you failed at. The goals you didn’t accomplish. We know they moved you forward. Share that. Share how. Not only will owning your failures humanize you, but being honest about your trip-ups and slip-ups means honoring how you got to where you are today. Acknowledging that growth helps you recognize and appreciate it.

Do it for free for ten years.
Take more losses.
Take more pictures.
And talk about it.

Lose more to win more.

Reveal to Heal

We all need contemporary confession.
Research also shows that holding on to regrets causes us to take more aggressive and risky actions in the future. So the healthiest and happiest people are aware of regrets they harbor and then choose to let them go.
Every morning I grab an index card or a journal and write these three prompts:

I wil let go of …
I am grateful for …
I will focus on …

It takes only two minutes to do, and the difference in my life has been both immediate and incredible. Completing three simple sentences helps me “win the morning,” which helps me start to “win the day.”

Find Small Ponds

There are far more problems and opportunities in the world than there are talented and hard-working people to solve them.
Different is better than better.
Find the small ponds so you can be the big fish.

Regardless of age, socioeconomic background, nationality, or cultural upbringing, when you’re in a smaller pond, your opinion of yourself—what’s called “academic self-concept”—goes up. And importantly, *it stays up even after you leave the pond.
There’s no shame putting yourself in situations where you feel really good about yourself. Should you downgrade yourself? No! Definitely no. But there’s nothing wrong with entering the marathon in the slowest category. Playing in the house league instead of the rep league. Teeing off from the tee closest to the pin.
You know what you’re doing?
Setting yourself up for success.
You’ll move up because you believe in yourself.

Go Untouchable

Before you jump, ask yourself:

The Regret Question: What will I regret not doing more when I look at it from the future?
The Plan B Question: What will I do if it fails?

As our world gets busier and our phones get beepier, the scarcest resource of all is quickly becoming attention. How are we supposed to focus?
I finally found a solution that I feel has saved my career, my time, and my sanity.
I bet you need this solution, too.
I call it “Untouchable Days.”
These are days when I am literally 100% unreachable in any way… by anyone.
(read Cal Newport’s Deep Work or check his blog for a really deep dive into this point – mjb)

Never, Never Stop

There is magic in doing things simply.
It’s the final step to remember on the path to awesome.
The fact is we can only ever really go forward.
So the point is to just start going that way.
And never, never stop.

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The Undoing Project

It’s a Michael Lewis book.
That alone, is enough for me to tell you to go read it.

Kahneman and Tversky’s work has probably been the biggest influence on my life in recent years, since Taleb.1
We cannot think in probabilities in our daily lives.
We keep fooling ourselves, with various biases.
And the intuition we have, is because we are really amazing biological machines. And even that is subject to error. Unless the intuition is backed by extensive experience. And even then we can easily be fooled.
That basically is the gist of their work (to me, so far).
I flunked nearly every experiment in Danny Kahneman’s Thinking, Fast and Slow.2
We need to think slowly, through every implication, when it comes to the few big decisions in life.

So how did this work come about?
The Undoing Project tells us the story.
Of Kahneman and Tversky’s friendship and years of collaboration.
Of how a MacArthur Fellow and and Nobel Laureate are in the end, only human, and even they could not undo the events in their lives and their relationship.
Of how the world is patently unfair and never treats people equally.

It’s a lovely read.

  1. Taleb was the one, who introduced me to Kahneman’s work, in the first place 

  2. A Lindy book, if there ever was one 

Change is the Only Constant

If Taleb convinced me that Mathematics was beautiful philosophy, Ben Orlin is the one made me fall in love with it.
Change is the Only Constant is beautiful and funny at the same time.

It’s the story of Calculus over the ages and through domains.
It weaves through life and time, through people, interesting and otherwise.
And the way Ben tells it, it bears no resemblance to the dry crap that is taught in schools and colleges.
It’s beautiful and wonderful, but not paramount and still subject to the vagaries and complexities of life and nature.

In their more insufferable moods, the “hard” sciences like to boast and crow, as if “hard” means complicated and “soft” means simple. This is, of course, exactly backward. The softer the science, the more complex its phenomena.
Physicists can predict what atoms will do. But gather enought atoms, and the calculations grow unwieldy. We need new, emergent laws—chemical laws. Then, gather enought chemicals, and complexity overwhelms us again. We need biology to step in with new theories and rules. And so on down the line. At each tipping point, the role of math evolves: from certain to tentative, from deterministic to statistical, from consensus to controversy. Simple phenomena (like quarks) follow mathematical rules with slavish fidelity. Complex phenomena (like toddlers) less so.

Loved it!