Among my favourite non-fiction books this year. Tim gives an interesting account of how messiness helps through variety, improvisation, flexibility, speed, and more. He covers a variety of areas and discusses the impact and understanding of messiness in them—from the current trend towards AI and automation to the humanity-old question of children and their play areas.

Combined with Range by David Epstein, this book has provided to me one set of perspectives and inputs. Another set is from Make Time by Jake and Jack, and Deep Work & Digital Minimalism by Cal Newport. Combining these—focus in the moment, and variety, improv and range in the themes—are a great direction for improvement.

The challenge though, as ever, is in the doing :)


… the ADHD sufferers were more creative in the laboratory than non-sufferers and were more likely to have major creative accomplishments outside the lab.

Clearly these people were not so completely incapable of focus that they couldn’t finish the album, the poem or the script. There needs to be at least some hill-climbing between the random leaps. But looking at these achievements, the word ‘hyperactivity’ takes on more positive connotations. One is reminded of the sardonic headline in The Onion: ‘Ritalin Cures Next Picasso’.

Brian Eno’s shuffle cards

And it is the effect that the cards can have on a creative project. They force us into a random leap to an unfamiliar location, and we need to be alert to figure out where we are and where to go from here. Says Eno, ‘The thrill of them is that they put us in a messier situation’

Ugly fonts

Half their classes, chosen at random, got the original materials. The other half got the same documents reformatted into one of three challenging fonts: the dense Hattenschweiler, the florid Monotype Corsiva or the zesty Comic Sans Italicised. These are, on the face of it, absurd and distracting fonts.
But the fonts didn’t derail the students. They prompted them to pay attention, to slow down and to think about what they were reading. Students who had been taught using the ugly fonts ended up scoring higher on their end-of-term exams.

Photo of the above passage from the book with the fonts illustrated

Switching topics

The top scientists switched topics frequently. Over the course of their first hundred published papers, the long-lived high-impact researchers switched topics an average of 43 times.
…the top scientists keep changing the subject if they wish to stay productive.

As Brian Eno says, the friend of creative work is alertness, and nothing focuses your attention like stepping on to unfamiliar ground.

3M’s flexible attention policy

In most companies, flexible attention means goofing off on the company dime. In 3M it means playing a game, taking a nap or going for a walk across an extensive campus to admire the deer.
3M knows that creative ideas don’t always surrender to a frontal assault. Sometimes they sneak up on us while we are paying attention to something else.

3M also rotates its engineers from one department to another every few years. This policy is one that many companies resist—not to mention some employees.
Why take someone with years of expertise in soundproofing or flat screen displays and make her work on a vaccine or an air conditioner? For the company it seems wasteful and for the employee it can be stressful. But for a company that makes masking materials out of sandpaper and sticky tape out of wrapping paper, the real waste would be to let ideas sit in their tidy silos, never to be released.

Multiple projects

Gruber and Davis observe that a dead end in one project can actually feel liberating. If one business model founders, an entrepreneur can pivot to something fresh. The writer can pull out some old jottings, the scientist acn turn to an anamoly she had long wanted to investigate. What would have been a depressing waste of time for a single-minded person can become a creative lease of life for someone with several projects on the go.

Twyla Tharp’s boxes

…but in practice, having many projects on the go is a stressful experience that can quickly degenerate into wheelspinning.

… assigning a box to every project. Into the box she tosses notes, videos, theatre programmes, books, magazine cuttings, physical objects and anything else that has been a source of inspiration. If she runs out of space, she gets a second box. And if she gets stuck, the answer is simple: begin an archeological dig into one of her boxes.

‘The box makes me feel connected to a project. It is my soil. I feel this even when I’ve back-burnered a poject: I may have put the box away on a shelf, but I know it’s there. The project name on the box in bold black lettering is a constant reminder that I had an idea once and may come back to it very soon.
Most important, though the box means I never have to worry about forgetting. One of the biggest fears for a creative person is that some brilliant idea will get lost because you didn’t write it down and put it in a safe place. I don’t worry about that because I know where to find it. It’s all in the box…’


Most tasks require a combination of bonding and bridging: flashes of inspiration to identify the right approach and hard graft characterised by selfless teamwork to put it into practice.

…did brilliantly and had a miserable time.

It makes sense that for most teams there mst be a trade-off between the cohesion of a rowing team and the radical openness of an Erdos network. The trouble is that we systematically get the trade-off wrong.
Faced with a choice of more cohesion versus more openness, our temptation to be tidy-minded means we’ll go for cohesion every time. Cohesion makes us feel more comfortable. We mistakenly think that diversity is getting in the way even when it’s helping.


Building 20 at MIT

When people praise Building 20, they often point to something the Steve Jobs himself would have admired: the building’s propensity to throw people together at random. This was as much by accident as anything—for instance, Building 20 had a baffling system of office numbering.
For example, if you wanted to find the Office of Naval Research—a descendant of RadLab—it was in Room 20E-226. But where exactly was that. The 20 of 20E-226 was clear enough: it referred to Building 20. The ‘E’ referred to E wing, which was parallel to and sandwiched between A wing on one side and D wing on the other. C wing was further along. B wing was the spine that linked all other wings together. (In a more logical world, B should have been A, A should have been B, E should have been C and C should have been E.) The 226 meant room 26 not on the (American) second story but on the third, Building 20 being one of the only buildings in America to have unilaterally adopted the British system for labelling floors.

This absurdly inefficient way of organising a building meant that people were constantly getting lost and wandering into places they didn’t intend to go. Better still, because Building 20 was low rise and sprawling, when chance meetings occurred, they didn’t happen in elevators, the eternal home of the glib, tidy monologue we call the ‘elevator pitch’. They began in long corridors, where a genuine conversation could develop.

More important, the combination of people who could have those conversations was strange and wonderful. In the early 1950s, Building 20 contained departments that were wartime holdovers—nuclear science, flight control, the ‘Guided Missiles Program Office’—but also plastics research, the adhesives lab, the acoustics lab, the electronics lab and even an outpost of the architecture department: a lighting design shop. Over the next ten years, MIT’s data processing group was added, along with the ice research lab, MIT Press and the student hackers at the Model Railroad Club. Into the mix were stirred machine shops for the nuclear scientists and for the electronics research lab, the photography labs, a materials lab for the anthropologists, and solar car researchers who wold use the building’s corridors as driveways f and car parks. Building 20 even hosted a piano repair shop and the Reserve Officers’ Training Corps offices, right next to the office of anti-establishment linguist Noam Chomsky.


Speed, economy and flexibility: three advantages of the messy process of improvising.

We rarely have complete control, just a comforting illusion of control instead. The speaker without a script may bungle his lines, but he is also free to change course in response to a question or to cut things short if the event is running late. Having a script makes that harder. The improviser has given up full control on her own terms; the person who relies on the script risks having control wrenched away on someone else’s terms.

Miles Davis once explained his approach to jazz improv as creating ‘freedom and space to hear things’. The phrase is fascinating: not freedom and space to play things, but to hear things—what the other instruments are doing, even the sound of your own playing, and to respond.

The habit of yes

The idea is to keep opening up new conversational possibilities rather than shutting them down. Always add to what has been said so far. Never say ‘no’; always say ‘yes, and…’
…another way this is sometimes phrased is ‘enter their world’.

Conversing, Listening and Improv

Listening is easy, in principle. In practice it can be terribly hard—especially when you have so much to lose. A really good conversation is mentally demanding. Listening and responding is messy, exhausting—and exhilarating. A great conversation is a rare joy because it is full of surprises and thus requires constant improvisation.
As the philosopher Gilbert Ryle wrote, ÆTo a partly novel situation the response is necessarily partly novel, else it is not a response.


Sometimes it is wise not to improvise. If you never speak in public but must say something at a wedding, and your highest ambition is not to embarrass yoursel, then the risk-reward calculation is likely to point to writing a script.


So what does it take to improvise successfully?

The first element, paradoxically, is practice. … practice the craft until much of what you do is entirely unconscious. The most common form of improvisation is human conversation, and that is something that all of us have been practising all our lives.

The second element is a willingness to cope with messy situations.

The third crucial element is the ability to truly listen, whether you’re a jazz trumpeter, a corporate tweeter, on a date or working as a customer service rep at Zappos.

The most important element is being willing to take risks and to let go.
This is much easier when you have little to lose, but even when there is a lot on the line, improvising can be the best way forward.


A script can seem protective, like a bulletproof vest; sometimes it is more like a straitjacket. Improvising unleashes creativity, it feels fresh and honest and personal. Above all, it turns a monologue into a conversation.


OODA loop and ‘Patterns of Conflict’

‘Observe-Orient-Decide-Act’ or, in plain English, working out what’s happening then responding.

Getting inside the opponents’ OODA loop

…changing the situation faster than the adversaries could figure out what was going on.

If you could make quick decisions, that was good. If you had a strong sense of what was going on around you, that was good too.

But more profoundly, if you could disorient your opponent, forcing him to stop and figure out what was going on, you gained an advantage. And if you could do this relentlessly, your opponent would be almost paralysed with confusion. Just as he was about to act, something new would happen and he would have to stop and think again.


Donald Trump

Trump’s image took plenty of knocks over the course of the campaign, but he minimised the damage through an ability to change the conversation whenever he wanted. He chose his battlefields, even skipping a TV debate on the even of the vital Iowa caucuses and dominating the headlines as a result. Trump made sure both the media and his opponents reacted on his terms.
He wasn’t always perfectly prepared, but his preference for speed over perfection ensured that opponents were always scrambling to figure out a response.


Leadership qualities of the British Army as defined in conversation with Rommell in 1941. Means ‘ponderous’.

There was demonstrated, in British actions, rigidity of mind and reluctance to change positions as swiftly and readily as situations demanded…great fussiness and over-elaboration of details in orders.
rather than being quick, deft, heedless of details and happy to make things up on the fly, they were slow, clumsy, tidy-minded and unwilling to improvise.

If you’re trying to win by creating a mess and backing yourself to figure it out more quickly than your opponent, it helps if your opponent is schwerfallig.

Some principles of Messy tactics

First, get yourself into a position of opportunity.
Stirling didn’t know which officers he might meet if he broke into British headquarters, but he knew he’d meet somebody. Jeff Bezos felt much the same way about the early web: it was impossible to predict how it might evolve, but clearly something exciting was possible.

Second, improvise your way around obstacles.
The sentry didn’t buy his excuses, so Stirling sneaked past instead.

Third, speed counts for a great deal.
Both Stirling’s break-in and his successful briefing to General Ritchie were possible because he moved faster than the people who were trying to stop him.

An unexpected corollary of the third principle is that while the team should understand their broad goals, they shouldn’t waste time trying to coordinate with one another.
Stirling was happy to split his forces and let them operate independently. So was Rommel. Perhaps surprisingly, so too was Jeff Bezos, who once notoriously told his management team to spend less time communicating.

‘synchronisation is for watches, not for people’

…trying to synchronise activities wasted time and left everyone marching at the pace of the slowest.



What happens when a detailed statistical analysis slavishly follows historical data.
An overfitted line looks more like a dot-to-dot puzzle, trying to pick out a pattern that isn’t really there. When new data arrive—new dots—they are unlikely to be anywhere near the wriggling curve.

Making targets more complex can’t be the right answer. A complex measure is just as likely to be gamed, and a simple rule of thumb is often an accurate guide to what is happening.

Solution to gaming of measurement metrics

Think about how examinations work. You study for months, or years, knowing that only a tiny fraction of the knowledge you’re accumulating will come in handy when you sit your final exam.
…the deliberate ambiguity as to what might be asked had the effect of ‘impossibilizing the knowledge’ of how to game the examination. The only response to having one’s knowledge of the test ‘impossibilized’: work hard and try to be good at everything.


The answer is neither the weighty rulebook of Basel nor one simple rule of thumb. Instead, we should be defining many rules of thumb and deliverately leaving it ambiguous as to which will be used in any given situation.


Paradox of automation

The three strands

First, automatic systems accommodate incompetence by being easy to operate and by automatically correcting mistakes. Because of this an inexpert operator can function for a long time before his lack of skill becomes apparent.

Second, even if operators are expert, automatic systems erode their skills by removing the need for them to practice.

Third, automatic systems tend to fail either in unusual situations or in ways that produce unusual situations, requiring a particularly skillful human response.

For each of these three strands, a more capable and reliable automatic system makes the situation worse.

Weiner’s laws of aviation and human error

Digital devices tune out small errors while creating opportunities for large errors.

‘Automation will routinely tidy up ordinary messes, but occasionally create an extraordinary mess.’


A high error rate (in automatic recognition systems) is actually a source of comfort, because it means the method won’t be relied on.
The rarer the exception gets, the less gracefully we are likely to deal with it. We will assume that the computer is always right, and when someone says the computer made a mistake, we will assume they are wrong or lying.

Automation bias

once a computer has made a recommendation, it is all too easy to accept that recommendation unthinkingly.


When the algorithms are making decisions, people often stop working to get better. The algorithms can make it hard to diagnose for failures. As people become more dependent on algorithms, their judgement may erode, making them depend even more on the algorithms. That process sets up a vicious cycle. People get passive and less vigilant when algorithms make decisions.’—Gary Klein

Decision experts such as Klein complain that many software engineers make the problem worse by deliberately designing systems to supplant human expertise by default; if we wish instead to use them to support human expertise, we need to wrestle with the system.
GPS devices, for instance, could provide all sorts of decision support, allowing a human driver to explore options, view maps and alter a route. Bit these functions tend to be buried deeper in the app. They take effort, whereas it is very easy to hit ‘Start Navigation’ and trust the computer to do the rest.

Systems that supplant, not support, human decision-making are everywhere. We worry that the robots are taking our jobs, but just as common a problem is that the robots are taking our judgement.


It is possible to resist the siren call of the algorithms. Rebecca Pliske, a psychologist, found that veteran meteorologists would make weather forecasts first by look ing at the data and forming an expert judgement; only then would they look at the computerised forecast to see if the computer had spotted anything that they had missed.
By making their manual forecast first, these veterans kept their skills sharp.


‘The number of scenarios that are automatable will increase over time, and one fine day, the vehicle is able to control itself completely, but that last step will be a minor, incremental step and one will barely notice this actually happened’—Raj Rajkumar, autonomous driving expert at Carnegie Mellon University


An alternative solution is to reverse the role of computer and human. Rather than letting the computer fly the plane with the human poised to take over when the computer cannot cope, perhaps it would be better to have the human fly the place with the computer monitoring the situation, ready to intervene.
Computers, after all, are tireless, patient and do not need practice. Why, then, do we ask the people to monitor the machines and now the other way around?


Rather than attending to their task through sheer willpower, or dividing their attention, trying to do both their job and their email at the same time, they distracted themselves in brief bursts.
A few minutes with their back to the drone monitors, doing something completely different, would refresh them when they returned to the task.

(Moi: another advantage of the Pomodoro technique)

Such behaviour suggests that when humans are asked to babysit computers, the computers themselves should be programmed to serve up occasional brief diversions. Even better might be an automated system that demanded more input, more often, from the human—even when that input wasn’t strictly needed.
If you occasionally need human skill at short notice to navigate a hugely messy situation, it may make sense to artificially create smaller messes, just to keep people on their toes.

Oudehaske roads

First, the existing traffic signs were removed. The signs might ostensibly be asking drivers to slow down. However, argues Monderman, because signs are the universal language of roads everywhere, on a deeper level the effect of their presence is simply to reassure drivers that they were on a road—a road like any other road, where cars rule.
Next, he replaced the tarmac with red brick paving, and the raised kerb with a flush pavement and gently curving guttering.

(Also seen on the Exhibition road, aka Museums road, in London)

…now the drivers were faced with a messy situation and had to engage their brains. It was hard to know quite what to do or where to drive—or which space belonged to the cars and which to the village children.

‘Rather than clarity and segregation, he had created confusion and ambiguity.’


Hidalgo has discovered that there is a strong correlation between being a diversified economy, a complex economy and a rich economy.
It is unusual for a country that exports highly sophisticated products to do only tat; it will also tend to export a wide variety of much simpler things. It is also unusual for a country to make lots of different kinds of simple products yet no sophisticated products. And if a country exports only a small number of products, it’s a safe bet that they will be simple, not complex.
Variety and sophistication go hand in hand.


Borges shows us why trying to categorise the world is not as straightforward as we like to believe.

Filing in triplicate reduces Borges’ fourteen categories to three.
Make three copies of correspondence and file once by date, once by topic and once by correspondent.

Yukio Noguchi system

place each incoming document in a large envelope. Write the envelope’s contents neatly on its edge and line them up on a bookshelf, their contents visible like the spines of books.
Now, every time you use an envelope, place it back on the left of the shelf. Over time, recently used documents will shuffle themselves towards the left and never-ued documents will accumulate on the right.
Archiving is easy: every now and again, you remove the documents on the right.
To find any document, simply ask yourself how recently you’ve seen it.

‘A Perfect Mess’ twist:

Turn the row of envelopes so that the envelopes are stacked vertically instead of horizontally, place the stack on your desktop, and get rid of the envelopes.

a.k.a. A pile of papers on a messy desk


nothing is ever quite so totally lost as when it has been tidied away according to an organisational system that is opaque.


…even if we cannot engage in a point-blank refusal to make appointments (Marc Andreessen and Arnold Schwarzenegger), we probably could benefit from nudging ourselves a little in that direction—making fewer firm commitments and leaving more flexibility to adapt to circumstances.
A plan that is too specific will soon lie in tatters. Daily plans are tidy, but life is messy.

Dan Ariely’s date chat experiment

Participants were given access to an instant-messaging system, which they used to chat online while discussing a possible first date. The system, however, forced them to pick from a choice of rather disruptive conversational moves—‘How many romantic partners did you have?’; ‘When was your last break-up?’; ‘Do you have any STDs?’; ‘How do you feel about abortion?’
People loved the conversations that resulted, because rather than tidily moving through a ritualistic exchange, these questions put the conversation somewhere new, dangerous and exciting.

Crazy as this may seem, there’s a long tradition of using courageous questions to get us out of our tidy conversational habits.
One list of questions was made famous by the novelist Marcel Proust, including ‘What is your most treasured posession?’; ‘What is the trait you most deplore in yourself?’; ‘What is your favourite journey?’; and ‘How would you like to die?’
All of these questions beat ‘What do you do for a living?’


‘First-take feelings, if they’re anywhere near right, they’re generally the best’—Miles Davis on improvisation

’It takes place in real time and you can’t control what you’re going to say’—High school senior on why the text generation finds face-to-face conversations difficult, even frightening.

Formal vs informal games

In an informal game, everyone must be kept happy: if enough players stop wanting to play, the game will end. That implies the need to compromise, to empathise and to accommodate younger, weaker and less skillful playmates; no such need arises in formal games where those who are having a miserable time on the losing team are obliged to keep going until the final whistle blows.
As different children arrive and leave, people must switch sides to keep things interesting, evening up the numbers and the skills levels: ‘them and us’ is alien to informal play.


hunter-gatherer societies in New Guinea, who ‘consider young children to be autonomous individuals whose desires should not be thwarted, and who are allowed to play with dangerous objects such as sharp knives, hot pots, and fires’.
Though plenty of these kids grow up with physical scars, they are the opposite of being emotionally scarred. Their ‘emotional security, self-confidence, curiosity and autonomy’ sets them apart from children brought up by cautious Westerners.

…it turns out that children adjust for risk: if the ground is harder, the play equipment sharp-edged, the spaces and structures uneven, they will be more careful.
…some play experts argue that standardising play grounds encourages children to become careless and may make them more likely to have accidents in other environments.

Standardisation is dangerous because play becomes simplified and the child does not have to worry about his movements. This lesson cannot be carried over to all the knobbly and asymmetrical forms with which one is confronted throughout life.
Learning to be alert to risk is a better preparation for self-preservation outside the playground than bouncing around like a pinball in a padded funhouse.

When we overprotect our children, denying them the opportunity to practice their own skills, learn to make wise and foolish choices, to experience pain and loss, and generally make an almighty mess, we believe we’re treating them with love—but we may also be limiting their scope to become fully human.