The 7 Skills to Master Deep Reading
Deep reading is a supply-chain of skills.
If one step fails, the struggles pile up and everything goes to shit, I mean seriously why am I spending hours on this retarded prattle, what is he even saying? This doesn't mean anything? Hello? I hate you Hegel your comprehension suffers.
Or at least it creates hours of wasted effort that COULD have brought you closer to the real goal: transformation.
A new way to understand the world.
This is why I started the channel in the first place.
I was tired—and still am—of investing weeks of life and thousands of words into a book just for it to feel like a performative dance.
"yeah bro I've read Neecher. Or Niezche? Nietzsche. yeah him."
The opportunity cost is great.
Deep reading should make your effort pay.
These are the seven skills that make ideas stick, plus the practical advice to make it count.
1 - Discretion
How do you beat a master swordsman in a duel to the death?
You give him a cardboard sword.
Books won't slice us apart, but the principle is the same: if your choice of literature is poor, no amount of technical mastery can save you—there is nothing to use it on.
Say you live 60 adult years—the US average—and you read two books a month.
That's 1440 books.
Only 1440.
When you consider the hundreds of thousands of great books out there, this isn't all that many...
Two per month is also generous; the true figure is probably far lower, especially if the book is dense in wisdom and you slow down to reflect it.
Therefore, every choice is a precious investment, and if the book is empty of insight, you're wasting the most finite resource of all: time.
We can't let the algorithm shove our next read down our throat.
We can't let Barnes and Nobles trick us with their storeroom tables.
Only you know what resonates.
I aim for every new book I start to have three key features:
- Relevant - personal curiosity has to be sparked.
- Novel - it should offer new ideas, new angles, new theories.
- Challenging - learning is growth, growth takes friction.
Read the best, and only the best.
There isn't time for anything else.
Step one is a vague platitude by itself, so step two offers a way to apply it:
2 - Inspection
The most underrated reading skill.
Master inspection, and not only will you never DNF a book again, but you'll set yourself up for a smoother read.
I don't even remember the last time I quit a book. . . and that's all because inspection acts as insurance against bad choices.
Inspection is when you interrogate a book before a full reading to answer two questions:
- Is this relevant, novel, and challenging?
- What can I expect?
Inspection is like a first date at a café: it goes beyond mere appearances, but remains casual enough to walk away from without the guilt of sunk cost.
This is obviously easier in person, but you can also find free PDFs or previews if you dig around online.
(buy the book if it's a match for you. don't be a bum.)
I break it down into a few clear steps:
- Read the title - what does it cover?
- Read the blurb - does it show the entire scope?
- Read the contents page - how is it divided?
- Look for headers - what key topics or events show up?
- Skim key paragraphs - does the meat of the book sound relevant? Is it at your target level of discourse?
You'll be surprised at how many books are not what they appear.
Titles can be misleading, and online hype is near meaningless.
In most cases, they'll cover what you expect, but even then it's no waste of time; inspection builds a scaffold for future analysis, a kind of foresight or 'briefing' for the insights ahead.
Ten minutes of inspection can save you ten hours of disjointed reading.
3 - Dialogue
Around 399 BC, Plato introduced the Socratic dialogue to the world.
Aside from being our primary window into the mind of Socrates, his mentor, it also became an new style of prose and debate.
Rather than a confrontational argument, the Socratic dialogue is a cooperative cross-examination between two or more people, a kind of investigative crawl towards a higher truth . . .
. . . or more likely, an acceptance that we are so very far from it.
Books can only speak once, so it is up you to create the dialogue.
An author's ideas are not the end of your reading, but the start; they should ignite new thoughts and branch off to places only you could go, distinct from millions of other readers and full of personal meaning.
To inspire this bloom of knowledge, you 'talk' to the book through writing.
Or by literally speaking to Immanuel Kant's majestic forehead.
I won't judge.
A $1 pen is your tool of dissection, and the page margins become a canvas for reflection, debate, and personal inquiry.
This is your entry into analysis.
I can't tell you how to talk to a book—it's a deeply personal method—but I can offer my favourite techniques:
- Rephrase ideas in your own words. A quick way to cement ideas and confirm you truly understand them.
- Diagrams. To translate abstract ideas into images is tricky; it forces a deeper intimacy with concepts and their relations to one another.
- Numbering ideas. If you notice a sequence of related points or arguments, number them to make it easier to follow.
- Underline important bits. Even if you write nothing, these act as markers for a later analysis: you can flick through and see what stood out within seconds.
- Ask questions. These will prompt you to look for answers. They're like side-missions you set for yourself.
- Highlight connections. What other authors can add to this conversation? What ideas of your own did this spark?
3.5 - Immersion
This is a bonus point primarily for fiction.
I suspect most fiction-haters only avoid the medium because they never invite immersion into their reading.
Even the finest writer needs time to forge a world around us and warm us up to the characters; that's impossible if we jump ship mid-sentence and come back a week later, having forgotten everything.
Who are you again?
To let a story work on us, we ought to make room for it.
Be consistent in your reading, start only when you know you can finish, and try to read it in as few sittings as possible: the more immersed you are, the greater the snowball effect and the easier you can blast through it.
4 - Criticism
A reader's worst nightmare is to spend weeks with a book only to be dumbfounded when asked:
"Now explain it . . ."
Criticism is the antidote.
Criticism finishes what dialogue started.
It turns you from a passive spectator in the lecture hall to a panel member on stage, fighting tooth and nail for the truth—you have a stake in the literature.
Neutrality is the safe position: eh, it was alright.
Anyone can blurt out their superficial first impression.
Only the well-read can fortify that with reason and argument.
To criticise is to explore why you think the way you do; it's not easy to make an aesthetic or technical judgement, but that hard work and reflection is what imprints a book into your brain.
Every judgement asks for analysis, logic, and argumentation, and there are no shortcuts to fool yourself with.
Criticism is the ultimate proof of understanding.
5 - Application
Some readers forget this step and waste an entire book.
Ironically, the self-improvement bros I mock are dead accurate when it comes to this; it's the one point they stress over and over.
If a book is practical in nature—meaning it calls you to do something in the real world—you have to fulfil that.
Otherwise, the book remains unfinished and the potential lost.
Much of philosophy and non-fiction carry explicit lessons we can use to live more meaningful, moral lives.
Socrates teaches us how to dissect arguments to find truth.
Nietzsche says to examine the historical and psychological nature of our morality.
St Augustine tells us to 'order our loves' for a virtuous life.
Of course, the author's duty is to convince us of:
- The value of the end itself
- The effectiveness of the means to that end, if they propose any.
If we agree with both, it's our duty to 'complete' the book by taking action in the real world.
Theory is one thing, but it can never become escapism.
It should launch you into growth and fulfillment; you should grab it like a paintbrush and sweep it across the canvas of life, to affirm it as real and tangible.
Not all books will spell out this practical element.
Fiction, especially, will invite you between the lines—it speaks to a thousand readers in a thousand unique ways, and the characters that do the most to inspire us and steer our actions often don't exist at all.
Alexander the Great modelled himself after Achilles.
Julius Caesar measured his worth against Alexander.
Napoleon Bonaparte studied Caesar's tactical excellence.
One man of fiction changed the course of civilization.
Imagine what a thousand could do.
You just have to listen.
6 - Patience
The hardest step of all.
My reading used to be a misery because I'd load myself with impossible standards:
Everything had to be understood.
Everything had to brand itself in my memory.
Everything had to fall into place, right now.
If you set a goal you can never reach, you doom yourself to eternal failure and suck the life out of something you ought to love.
Instead, I opted for Justin Sung's suggestion:
Treat literature as N+1, not 0 to 100.
There is no finish line in the intellectual world.
You are born ignorant, you will die ignorant.
While uncomfortable to accept, it should also empower you: the only way is up, and no matter what position you are currently in—represented by N—your daily duty is to improve on it by +1.
One new insight.
One clearer image.
One more essay.
With some patience, the change will come: you will notice yourself thinking more sharply, pondering more deeply, and gaining ownership of your future.
With bloated standards, the sun melts your wings and you crash.
With N+1, you glide on and enjoy the breeze.
Much love and happy reading,
Odysseas
P.S.
Find value in these letters?
I just launched a premium tier that grants you two extra deep-dive letters per month.
For example, the most recent one was on "Digital Pharisees," how the internet rots critical thinking, and how you can fight back.
Check it out here.
Responses