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Iterative Learning

Fragments from imaginary dialogues

“What is iterative learning?”

“Not long ago, at my brother’s suggestion, I watched a video on YouTube called Iterative Drawing, by a guy called Sycra Yasin, describing a beautiful learning method. I realized the method can be applied to learning anything, not just drawing – and so the idea of iterative learning was born.”

“What’s the essence of the method?”

“If you want to improve at anything, repetition is key. The metaphor Sycra uses is mileage

To improve, you need to get a lot of rep(etition)s in. (Quantity) There’s no way around it.

To improve faster, you need to maximize the learning from each rep. (Quality) In other words, it requires deliberate practice.

A quality-rep is a learning cycle [<link; short read]. 

Quality-rep = Learning Cycle = Feedback + Reflection

The method is brilliant in that it addresses both quantity and quality at the same time (thus increasing practice-density [<link; short read]), which allows you to gain mileage quickly.

You pick something you want to focus on (clear goals).

You fill a page (or more) with variations on that thing. Each iteration is essentially an experiment.

With each iteration, you analyze and reflect on it, extracting key lessons and principles.”

“Can you give an example of how you’re applying it to something other than drawing?”


One of the things I’m learning about is humor. I want to get better at it. 

I’m currently reading a book about humor called You Can Be Funny and Make People Laugh by Gregory Peart.

One actionable insight from the book is that direct questions are an opportunity to practice humor.

Direct questions, like, “Where are you going?” or “What are you doing?” are perfect opportunities for experimenting with unanticipated humorous responses. The question-asker is likely expecting a literal answer, so a lighthearted and funny response could result in easy humor simply because it’s unexpected.

This is an opportunity to practice iterative learning.

I write a question at the top of a page, and I start generating possible answers (thus practicing creativity at the same time). The focus is on quantity, not quality. Whenever I stumble upon a funny response, I give it a rating (1 – mildly funny, 2 – funny, 3 – very funny), and reflect on what makes it funny.

For instance:

What are you doing?


– breathing autumn. (1)
– breathtaking.
– digging for treasure. (2)
– growing hair. (3)
– hiking around the sun. (3)
– knitting. (1)
– living danjerously. (2)
– playing at adulting. (3)
– pacticing average. (1)
– practicing awkwardness.
– questing. (1)
– ruminating ruminations. (1)

The goal is to do as many as possible. Dozens. This is an open process [<link; short read]. Whenever I come up with another idea, I add it to the page.”

The Parkour Walk

Be your unapologetically weird self. (Chris Sacca)

Fragments from imaginary dialogues

“I go for a walk every single day. It’s not your typical walk. It’s a game.”

“What’s the game about?”

“It’s one of those endlessly evolving games. 

Structurally, it’s a collection of rules and themes. The rules serve as creative limitations [<link; short read]; the themes serve as guidelines. 

The game is modular. Adding and removing rules and themes is itself a part of the game.

The main theme of the game is Parkour.”

“So you’re training Parkour every day?”

“Yes. And I plan to never stop.

The game is a playful exploration of my neighborhood – or whatever location I’m in. 

The main rule of the game is to always take a different route.

We have a tendency to take the same route and do the same things every time, to get stuck in habitual patterns. The rule ties in with one of the game’s themes, which is pattern-breaking – breaking out of familiar patterns.

In taking a different route I’m also scouting the neighborhood to discover potential training spots and challenges, and I’m creating a mental training-map.

Another theme of the game is what I call creative training. Going beyond the obvious, and looking for creative training possibilities within the environment.

One aspect of it is an idea I adore, which I know from Max Henry [<link], one of my favorite Parkour practitioners and coaches. It’s called Something Out of Nothing. Looking at a seemingly uninteresting spot in the environment and coming up with creative ways of playing with it.

Another theme is Quantity. By that I mean maximizing training-density [<link; short read]. Getting as much training done as possible within that time span. One aspect of it is maximizing the use of what I call transitional-space [<link; medium read] – the space between training spots or rep(etition)s.”

“Can you give an example?”

“Let’s say I want to get from training spot A to training spot B. The space between the spots is a transitional-space. I could walk the distance, or I could QM the distance – traverse it using Quadruperdal Movement, so on all fours. In the second case, I’m increasing training-density, I get more training done.

Or let’s say I jump from point A to point B. This is one rep. I could choose to walk back to A and do another rep, or to jump back from B to A. In the second case, I’m increasing training-density. In the same time-span I’ve performed two reps instead of one.

Another theme is Quality [<link; short read]. The how is as important as the what. This means striving to be as present as possible at all times, and only counting quality-reps – or beautiful-reps, as I like to call them.

Another theme is Variety. I aim to move in as many different ways as possible. In the same session I might jump on the markings of a parking lot, balance on a fence, vault over a garbage can, climb a tree, roll on a patch of grass, do a wall-run followed by a climb-up, etc.

I live on the 8th floor, so every session ends with a little strength & conditioning session up the stairs – I always take the stairs.

And yet another theme is a focus on the fundamentals of Parkour. I don’t train only the fundamentals, but there’s no session in which I don’t train some of them.”

“Don’t you mind looking weird to the people around you?”

“That’s an essential aspect of the practice.”

The Juxtaposition Game

Fragments from imaginary dialogues

“How do you practice Creativity?”

“One way I like to practice is by playing a little game I call The Juxtaposition Game.”

“What’s it about?”

An important Creativity skill is the ability to generate random output.

There’s a practice I know from a TED talk called 3 random words – coming up with 3 random words in quick succession.

The Juxtaposition Game is a similar practice which I invented for myself, but with two random words instead of three.

The essence of Creativity is connecting things.

After I generate the words, I play with discovering connections between them – the goal is to discover as many connections as possible, both literal and metaphoric –, and to making up a little story including both. 

By viewing it through the lens of Humor, I practice Humor as well. The juxtapositions themselves can be funny, and/or the connections between them, and/or the story.”



This is a high-density practice. I practice randomness, making connections, storytelling, Imagination and Humor at the same time.”

Creative Limitations

Restrictions breed creativity. (Mark Rosewater)

Fragments from imaginary dialogues

“What do you think about the practice of expressing Gratitude for three things?”

“Our brain is not good at open-ended choices. Whenever it’s faced with such a choice, it retreats to known pathways.

If you set as the goal to think of three things you’re grateful for, it’s likely that you’ll always think of the same handful of things.

By adding constraints, you force your brain to explore new pathways. This is a fundamental principle of creativity. I call it the creative limitations principle.

In practical terms, that means making each of the three things you want to express Gratitude for thematic. Something like:
– ‘people who care about me’
– ‘resources’
– ‘experiences’

The theme can vary from more general to more specific. I like to think of it as the specificity spectrum. The more general the theme, so the lower the specificity, the wider the possibility-space.

If you do your Gratitude practice in writing, you can play with exploring different themes every session.”

Collector 3

The purpose of querying an oracle is not so much to foretell the future as to enable the questioner to delve more deeply into his own intuition when dealing with a problem.

Most oracles contain a series of messages from which the questioner randomly selects.

The oracle is intentionally ambiguous in order to force you to go beyond the first right answer.

Random insights can force you to look at your problems in a way you would not have otherwise.

(Roger von Oech, Expect the Unexpected (Or You Won’t Find It))

Fragments from imaginary dialogues

“Why are you collecting cryptic and ambiguous quotes? I thought you valued clarity.”

“Both clarity and ambiguity have value.

Clarity has value for communication and understanding.
Ambiguity has value for stimulating creativity.

I collect cryptic and ambiguous quotes for my Oracle [<link; short read]

The Oracle is a wonderful creativity tool, for generating ‘(Creative) Movement’ – to use Edward de Bono’s terminology.

Whenever I’m in the generative phase of the creative process, or I’m feeling stuck, I like to extract one at random and see where it takes me.”

Life-Artist 4

When people say: “You do so many things. You’re a musician, you’re a painter, you’re a composer, you’re a cinematographer, you’re the editor.” I go, “No, I only do one thing. I live a creative life.” When you put creativity in everything, everything becomes available to you. (Robert Rodriguez)

Fragments from imaginary dialogues

“How can I make my life a work of art?”

Live a creative life. Make your Creator identity a central aspect of your being, make Creativity a central value of your life.

And make today a work of art. Your life is but a precious string of todays.”

What if

Fragments from imaginary dialogues

“What’s the most powerful creative question-template [<link; medium length] you know?”

What if … ?

“What if you started every day with such a question?”

Beautiful Models: Focused/Diffuse Thinking

To turn it on, learn to turn it off. (Josh Waitzkin)

Fragments from imaginary dialogues

“What is Focused/Diffuse Thinking?”

“Focused/Diffuse Thinking is a beautiful idea I know from Barbara Oakley’s wonderful book A Mind for Numbers about learning how to learn.   

Focused Thinking is a state of concentration, of deep focused attention.
Diffuse Thinking is a state of relaxation.

When people think of problem-solving, they usually tend to think only of the former. However, counterintuitively, the optimal approach requires both: thinking deeply about the problem, and letting it go. 

Focused/Diffuse Thinking is an oscillation between the two.

Taking distance from the problem leaves room for the subconscious mind to work on it in the background and make intuitive leaps.”

“So it’s a kind of priming.”


Not taking distance from the problem prevents the subconscious mind from doing its magic.

Moreover, Focused Thinking is energy intensive and cannot be sustained for long periods of time. Breaking away from the problem, conserves energy.

I’d go so far as to say the Focused/Diffuse oscillation is essential. In optimizing it you’re optimizing creative-efficiency and energy-efficiency at the same time.”

The Essence of Implementation

Fragments from imaginary dialogues

“What is the essence of Implementation?”

“I like to express it as two directives:

Think something different.
Do something different.

“What does it mean?”

“The first directive expresses two ideas (so far):

Thought is the blueprint for action.

It all starts in the mind. First as an idea-seed, which grows into a plan, which blossoms into action.

Thought is the fundamental means by which we access our resources. It’s a tool-making tool – a meta-tool.

Implementation is a creative process.

You can get inspired by the ideas of others, but you must adapt them to your own circumstances. It’s a beautiful opportunity to express yourself creatively and innovate.

The second directive expresses three ideas (so far):

Implementation means changing your behavior.

If you do what you’ve always done you’ll get what you’ve always gotten. (Tony Robbins)

To change something about your life, you must change your behavior.

Eben Pagan took it one step further:

Learning is behavior change.

Implementation is a design process.

This is an extension of the point about implementation being a creative process. What this one emphasizes is that implementation is essentially problem-solving, hence focused on the practical.

Design is a structured creative process. It’s a beautiful opportunity to embrace your Designer identity.

Implementation is experimentation.

Implementation is an iterative process. You generate ideas, you evaluate and narrow them down, you test them, get feedback, then repeat the process, optimizing with each iteration.”

On dealing with negative thoughts

To give one small illustration, whenever somebody is unkind to me, I can immediately unroll the panorama of that person’s good qualities. Instantly the balance is set right. As with most skills, this is a matter of practice. When you are having trouble getting along with someone, a simple first step is to sit down quietly and recall how many times that person has given you support. You are using positive memories to drive out negative ones before they have a chance to crowd together and form a mob, which is all resentment really is.

The first strategy is literally ‘changing one thought for another’: a negative thought for a positive one, an unkind thought for a kind one. ‘Just as a carpenter uses a small peg to drive out a bigger one,’ the Buddha says, ‘you can use a right thought to drive out one that is wrong.’

(Eknath Eswaran, Conquest of Mind)

Fragments from imaginary dialogues

“What’s your practice for dealing with negative thoughts?”

“The essence of the practice is, in Eknath Eswaran’s words,

changing one thought for another: a negative thought for a positive one, an unkind thought for a kind one.

Whenever a negative thought arises, I think/feel ‘Loving Kindness‘, and say to myself: ‘I love you Dani‘.

“You can take it one step further.

Turn negative thoughts into creative inspiration.”


“Think of the negative thought as a seed, from which you branch out to create a beautiful tree.”

“Like a mind-map?”

“Precisely. A mental mind-map focused on positivity and beauty.

You can even have a word or phrase that initiates the process.

For me it’s Connections.

What if you’re dealing with recurring negative thoughts?”

“Think of each as one more rep(etition), one more beautiful opportunity for practice.”