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Artful Learning

Fragments from imaginary dialogues

“What is Artful Learning?”

“The phrase The Art of Learning has become so ubiquitous that people tune it out – it has become (or maybe it has always been) a what I call verbal empty [<link; short read], a string of words that sound good but don’t change behavior in any way.

The Art of Learning means thinking of learning as an art.
Artful Learning means doing learning as an art.

The Deliberate-Practice System

Fragments from imaginary dialogues

How can I optimize deliberate practice?

There are two aspects to deliberate practice:

Skill-Specific Practice
The Deliberate-Practice System

The former varies with every skill; the latter stays the same regardless of skill.

Gain clarity on and endlessly optimize the deliberate-practice system.” 

What are the components of the deliberate practice system?

I’ve identified the following:

Deconstructing Skills

Every skills is a bundle of sub-skills. To deliberately and efficiently practice a skill, you need to identify its highest-leverage sub-skills – the fundamentals. Practice the fundamentals until they become second nature.

Identifying Principles

Principles are essentially mental models. They are meaningful, abstract patterns that are transferable across disciplines.

The Practice Loop (Scott H. Young)

Repeatedly performing a skill with the intention of improving it. Deliberate practice is a feedback loop. The purpose of the loop is two-fold:

– identifying and fixing weaknesses
– identifying and internalizing quality


The most efficient way to practice is by having access to a coach. In the absence of a coach, you need to become your own coach. In this process, writing is invaluable. It helps you gain clarity on your practice, it allows you to track progress, and it helps you gain self-knowledge.

Self-knowledge? Are you still talking about deliberate practice?

All practices, regardless of form, converge on the same Path: The Path of Wisdom and Mastery.”

Project Linguistics

The creation of language was the first singularity for humans. It changed everything. Life after language was unimaginable to those on the far side before it. (Kevin Kelly)

Fragments from imaginary dialogues

I’ve spent most of my life taking language for granted. As for most of us, it was invisible.

What changed that?

The catalyst was Viktor Frankl’s beautiful book Man’s Search for Meaning. That book had a profound impact on my life. It led to me to ask one of the big questions of my life:

What is meaning?

On a winding path, the question led me to language. In a moment of insight, I realized that we use language to shape our subjective reality. Jason Silva puts it beautifully:

The words you use to map reality affect your experience of reality. Words do not just describe; words are generative.

Language is for us like water to the fish, and just like water to the fish, invisible. At that moment, for the first time in my life, I saw the water.

Language and meaning are tools. We can metaphorically think of them as an instrument. Much like a cellist uses the cello to create music, people play the instrument of language to create worlds and experiences. 

People play the instrument of language. I also play with the instrument itself. I play a meta-game [<link; short read].

I’ve been playing the meta-game on my own for several years now. But recently, while reading the Wikipedia article about affixes, I discovered… linguistics.

There’s a whole field of study about language!

It wasn’t on my mental map until then. Well, I did know what linguistics was, but I hadn’t connected it with my interests. 

I started reading an introduction to linguistics and… I fell in love. Learning about the nuances and intricacies of language made me appreciate this beautiful instrument of ours more and more. Linguistics has also given me a new set of conceptual tools to play with and, more importantly, a new lens through which to look at language. Once you learn about morphemes, the structural components of words (the object of study for the branch of linguistics called morphology), the world of words will never be the same.

In the linguistics book I’m reading, there’s a fun example about the morphemes that make up the longest word in English:


– establish
dis-establish – to reverse the action of establishing
– disestablish-ment – result of disestablishing
– disestablishment-arian – supporter of disestablishment
– disestablishmentarian-ism – practice of disestablishmentarians
anti-disestablishmentarianism – opposition to disestablishmentarianism
– antidisestablishmentarianism-ist – someone who opposes disestablishmentarianism

What’s next?

Linguistics marks the next stage of my exploration of meaning, and the next level of my meta-game. I call it Project Linguistics.”

Funny Examples

Fragments from imaginary dialogues

“How can I make learning more fun?”

“What are you studying?”

“I want to get better at editing, so I’m studying punctuation. As part of my learning process, I’m writing a handbook [<link; short read] on the subject.”

“You’re giving a lot of examples to explain the rules, I imagine.”


One way you can make it more fun is by using funny examples.

Make it a habit to make all your examples funny from now on. You can thus practice humor at the same time.”

The Art of Asking Questions 4

Fragments from imaginary dialogues

“How do you deliberately practice questioning?”

“I have a system for it. I’ve even created my own terminology.

The system has several components:

  • QuestionCollecting (QCollecting)
  • QuestionGeneration (QGeneration)
  • QuestionEvaluation (QEvaluation)
  • QuestionOptimization [<link; very short read] (QOptimization)
  • QuestionTemplating [<link; medium read] (QTemplating)

QCollecting is exactly what it sounds like. I collect questions to use as tools and to learn from them. Key to this process is collecting not only good questions but also bad ones – they help you identify error patterns.

QGeneration and QEvaluation are complementary practices.

QGeneration is the practice of generating multiple alternative questions. One component of it is a practice I call QStorming [<link; short read], which is essentially BrainStorming with questions. You start with a central point of focus (QFocus), which can be a theme or a problem you’re trying to solve, and you generate questions based on that focus.

QEvaluation is the practice of narrowing down the generated questions to discover the best ones. Another aspect of it is a practice I call QAnalysis: deconstructing questions with the purpose of learning from them.

QOptimization is the practice of optimizing questions. Taking a bad question and turning it into a good question. Taking a good question and turning it into an optimal question – or set of questions.

QTemplating is the practice of turning repeated question patterns (QPatterns) into question templates (QTemplates). This means, whenever you notice multiple questions with the same structure, keeping the fixed part of the questions and replacing the changing part with variables:

How can you optimize Learning?
How can you optimize Writing?
How can you optimize x? (QTemplate)

What ties everything together is a practice I call Meta-Questioning: the process of asking questions about asking questions – I call this type of questions Meta-Questions [<link; short read] (MQ).

Can you ask a better question? (MQ)
Can you ask a bigger question? (MQ)
Can you ask a x question? (MQTemplate)
Can you ask this question better? (MQ)

On practicing Self-Awareness

Fragments from imaginary dialogues

“How can I practice Self-Awareness?”

“Take a moment to think of a color and look around you. Notice how all instances of the color start popping into view, many of which were invisible in plain sight a few moments ago. This is an instance of directing attention – a fundamental operation of the human mind. In this case, I intentionally used the color as an attention-directing tool. I call such perceptual tools, lenses [<link; short read].

In the same way, Self-Awareness requires directing attention to certain aspects of yourself. Part of the practice is gaining clarity on what the most important things to notice are.”

“What are the most important things to notice about yourself?”

“These are the most important lenses I’ve identified so far:

Lens of Expansiveness

When you’re focusing your attention on something and when lost in thought, your field of awareness collapses and you lose touch with your sensory awareness. 

Use the lens of expensiveness to do awareness checks throughout the day.

Question: Are you expanded or contracted?

Practice: Meta-Awareness, Expanding Awareness, Peripheral Vision

Lens of Posture

There’s an optimal position of the head on top of the spine – one of the core insights of the Alexander Technique. When you find this sweet spot, the result is lightness; it feels as if the head is floating over your shoulders. Some people describe this feeling as ‘antigravity’, or ‘freeing the neck’. This is the key to posture.

To discover the sweet spot, imagine a thread that runs from the top of your head all the way down through your spine, and gently pull the thread up. Relax your shoulders. Feel your spine lengthen. Chest up, chin down.

Use the lens of posture to do posture checks and free your neck throughout the day.

Question: How is your posture?

Practice: Alignment, Body Awareness

Lens of Breathing

Emotional states influence our natural breathing patterns. By changing your breathing pattern, you can change your state. Slowing down your breathing has a calming effect.

Use the lens of breathing to do a breath check every time something disturbs your inner balance.

Question: How is your breathing?

Practice: Breath Awareness, Conscious Breathing, Body Awareness

Lens of Feelings

Emotions are nothing more than physical sensations that have been named and have had a story woven around them. To deal with any unpleasant emotional sensation, always choose awareness over avoidance.

Another important physical sensation is muscular tension. Releasing muscular (and mental) tension helps you relax. Tension is often located in the shoulders, neck, and face.

Use the lens of feelings to fully experience your emotional sensations and to notice muscular tension.

Where are you feeling this emotional sensation in your body? What was the trigger?
Where are you holding tension?

Practice: Body Awareness, Body Scan, Non-Judgmental Awareness, Non-Doing [<link; medium read], Relaxation, Letting Go

Lens of Thoughts

Everything we experience is influenced by our thoughts. Our thoughts create our reality.

We view reality through a filter of meaning. Everything we experience is an interpretation. Change your interpretation of something, and your experience of it changes.

Use the lens of thoughts to notice your thought patterns. Notice judgment [<link; short read], assumptions, ruminations, desires and expectations.

Question: What kind of thought pattern is this? Is it resourceful or unresourceful?

Practice: Metacognition, Non-Judgment, Letting Go”

Antifragility as skill

Antifragility is beyond resilience or robustness. The resilient resists shocks and stays the same; the antifragile gets better. (Nassim Taleb)

Fragments from imaginary dialogues

“If we think of antifragility as a skill, what are its subskills?”

“A tentative list looks like this:

Recovery – the capacity to recover balance in the moment and gain access to your inner resources. Recovery is the most important subskill. It’s an enabler – it allows the other skills to function. 

Perception – the capacity to optimally direct attention and to find the empowering meaning in anything.

Learning – the capacity to optimally learn from shocks. It’s a matter of mindset and method.

Creativity – the capacity to spot creative possibilities and turn shocks into creative inspiration.

Preparedness – the capacity to always be prepared for shocks so that they never take you by surprise.

Adaptability – the capacity to use obstacles as stepping-stones, to improvise and constantly readjust to your surroundings.”

Compressing Wisdom

Since writing is very hard and rewriting is comparatively easy and rather fun, I always write my scripts all the way through as fast as I can, the first day, if possible, putting in crap jokes and pattern dialogue—“Homer, I don’t want you to do that.” “Then I won’t do it.” Then the next day, when I get up, the script’s been written. It’s lousy, but it’s a script. The hard part is done. It’s like a crappy little elf has snuck into my office and badly done all my work for me, and then left with a tip of his crappy hat. All I have to do from that point on is fix it. So I’ve taken a very hard job, writing, and turned it into an easy one, rewriting, overnight. I advise all writers to do their scripts and other writing this way. (John Swartzwelder [<link; Wikipedia])

Fragments from imaginary dialogues

“The idea in this quote has a beautiful actionable kernel.

What is your process for extracting it?”

“I follow a two-stage process.

The first stage is Paraphrasing/Editing. I seek to express the idea as a directive [<link; article by Derek Sivers] in as few words as possible.

Writing is hard; rewriting comparatively easy and fun.

Finish writing as fast as you can. It will be lousy, but the hard part is done. All you have to do from that point on is fix it.

You thus take a hard job, writing, and turn it into an easy one, rewriting.

The second stage is Tweet Writing. I seek to capture the essence of the idea as a tweet/aphorism.

Write fast.
Rewrite slowly.

Input/Output Oscillation

The 50/50 Rule: Learn for 50% of the time and explain what you learn for 50% of the time. (Thomas Oppong)

Fragments from imaginary dialogues

“What is the optimal input/output ratio [<link; short read] for learning?”

“Which is more important, the input or the output?”

“The output – processing information, implementation/experimentation, explaining what you’ve learned, deliberate practice.”

“Our tendency is to lean towards the input because it’s easy. Spending a few hours absorbing information gives you the illusion of learning. But your efficiency is so low that you’d have been better off using that time elsewhere.

The main principle of Essentialism applies here as well:

Less, but better.

The input/output ratio is a useful metric to get a general sense of how well you’re doing. But it doesn’t tell the whole story. 

Efficiency emerges from the structure of the learning process.

Let’s compare two structures:

(1) Half the day input, half the day output.

(2) Alternating between a pomodoro (30m) of input and a pomodoro of output, for the same total duration.

Both amount to the same input/output ratio at the end of the day, but in terms of efficiency, (2) is vastly superior.”

“Why is it superior?”

“Because it integrates the input with the output into one structure. You no longer conceive of input without immediate output. The input and the output together form a learning cycle.

Learning Cycle = Input + Output

Also because you get faster feedback. Feedback on what you’ve just learned, but also on the efficiency of the learning process itself.” 

“So every learning cycle is also an optimization cycle.”


To increase efficiency, decrease the distance between input and output. Get more cycles in.

It can be 1 pomodoro of input / 1 pomodoro of output.
It can even be 1/2 pomodoro of input / 1/2 pomodoro of output.”

“Does it have to be 50/50?”

“That’s a useful guideline. But don’t take it as gospel. Experiment, see what input/output ratio works best for you.”

The most important aspect of note-taking

Fragments from imaginary dialogues

“What is the most important aspect of note-taking?”

Processing the information.

There are two types of note-taking:

Passive note-taking – saving information by copy/pasting it; effortless, and low value.

Active note-taking – processing information before saving it; effortful, and high value.”

“I noticed I have a tendency toward passive note-taking.”

“We all do. The path of least resistance is our default. An important aspect of the growth process is countering this tendency. The best way to counter it is by putting systems in place.

In the case of the note-taking process, you can insert an intermediary step, a mandatory processing stage.”

“So passive note-taking has two stages: A => B
Active note-taking has three stages: A => P => B”


Just like in passive note-taking, you copy/paste the information in the processing area. 
Unlike passive note-taking, the information leaves the area only after you’ve processed it.”

“What is the output of processing?”

Think of processing as an opportunity to practice multiple skills in a short time-framelife-stacking [<link; medium read] style. 

You can practice editing/proofreading. Copy the text as is, and look at it with the editing eye. Do a structural and stylistic analysis, and think of ways to improve it.

You can practice meta-thinking [<link; short read]. Do a meaning analysis, deconstruct the meaning and identify the units of meaning –  models, metaphors, mental operations, underlying assumptions.

You can practice writing. Express the information in your own words (paraphrasing) and in as few words as possible (brevity). Start developing and integrating the ideas by asking questions (questioning) and connecting them with your prior knowledge and experiences.”