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Category Archives: Creativity

Embrace the Mess: The Upside of Disorder

“We often succumb to the temptation of a tidy-minded approach
when we would be better served by embracing a degree of mess.”
— Tim Harford


The breadth and depth of products and services that promise to help us stay organized is almost overwhelming. Indeed, it would seem that to be messy is almost universally shunned, considered a sign of not being “put together,” while being tidy and neat is venerated to the nth degree.

Tim Harford has a different take. In his book Messy: The Power of Disorder to Transform Our Lives, he flips this notion around, showing us that there are situations in which disorder is beneficial, or at the very least that order has been oversold. (Tim previously introduced us to another counterintuitive thought with Adapt.)


One of the reasons why we put so much time and effort into being organized and tidy is because we make assumptions about what this will do for our productivity. If all our papers are neatly filed and email is neatly sorted, it will be easier to retrieve anything that’s important, right? Maybe not.

Harford cites a paper by Steve Whittaker and researchers at IBM called “Am I Wasting My Time Organizing Email?” to illustrate the fallacy.

Whittaker and his colleagues got permission to install logging software on the computers of several hundred office workers, and tracked around 85,000 attempts to find e-mail by clicking through folders, or by using ad hoc methods—scrolling through the inbox, clicking on a header to sort by (for example) the sender, or using the search function. Whittaker found that clicking through a folder tree took almost a minute, while simply searching took just 17 seconds. People who relied on folders took longer to find what they were looking for, but their hunts for the right e-mail were no more or less successful. In other words, if you just dump all your e-mail into a folder called “archive,” you will find your e-mails more quickly than if you hide them in a tidy structure of folders.

Okay, so taking the time to organize your email may not be as useful as we thought. Computers, after all, are designed as tools to help us work better and faster, so it makes sense that the simple search function would outperform us. But physical filing and keeping our work space neat makes us more productive right?

Once again, maybe not.

Quite a bit of research has been done on people’s working environments and it would seem that those with big piles of paper and/or clutter on their desks may be just as effective (and sometimes more so) than those pedantic ‘fillers.’

This is not to argue that a big pile of paper is the best possible filing system. But despite appearances, it’s very far from being a random assortment. A messy desk isn’t nearly as chaotic as it at first seems. There’s a natural tendency toward a very pragmatic system of organization based simply on the fact that the useful stuff keeps on getting picked up and left on the top of the pile.

David Kirsh, a cognitive scientist at the University of California, San Diego studies the differences between the working habits of the tidy types (he calls them ‘neats’) and the messy types (he calls them ‘scruffies’). Let’s look at what he found.

…how do people orient themselves after arriving at the office or finishing a phone call? Kirsh finds that “neats” orient themselves with to-do lists and calendars, while “scruffies” orient themselves using physical cues—the report that they were working on is lying on the desk, as is a letter that needs a reply, and receipts that must be submitted for expenses. A messy desk is full of such cues. A tidy desk conveys no information at all, and it must be bolstered with the prompt of a to-do list. Both systems can work, so we should hesitate before judging other people based on their messy desks.

So if both systems work, are there times when it’s actually more advantageous to embrace messiness?

Here Harford hits upon an interesting hypothesis: Messiness may enhance certain types of creativity. In fact, creativity itself may systematically benefit from a certain amount of disorder.

When things are too neat and tidy, it’s easy for boredom to set in and creativity to suffer. We feel stifled.

A messy environment offers disruptions that seem to act as a catalyst for new ideas and creations. If you think about it, we try to avoid these same disruptions when we focus on being more “organized.” But, if you sometimes embrace a little mess, you may be opening yourself up to more creative serendipity:

Messy disruptions will be most powerful when combined with creative skill. The disruption puts an artist, scientist, or engineer in unpromising territory—a deep valley rather than a familiar hilltop. But then expertise kicks in and finds ways to move upward again: the climb finishes at a new peak, perhaps lower than the old one, but perhaps unexpectedly higher.

Think about an “inefficiently” designed office plan that looks wasteful on the surface: What’s lost in efficiency (say, putting two departments that need to talk to each other in separated areas) can be more than made up for in serendipitous encounters.

Brian Eno, considered one of the most influential and innovative figures in music over the last five decades describes it like this:

The enemy of creative work is boredom, actually,” he says. “And the friend is alertness. Now I think what makes you alert is to be faced with a situation that is beyond your control so you have to be watching it very carefully to see how it unfolds, to be able to stay on top of it. That kind of alertness is exciting.”

Eno created an amazing system for pushing people into ‘alertness.’ He came up with something he called “Oblique Strategies” cards. He would show up at the recording studio with a handful of cards and bring them out whenever it seemed that the group needed a nudge.

Each had a different instruction, often a gnomic one. Whenever the studio sessions were running aground, Eno would draw a card at random and relay its strange orders.

Be the first not to do what has never not been done before
Emphasize the flaws
Only a part, not the whole
Twist the spine
Look at the order in which you do things
Change instrument roles

Can you imagine asking the guitarist of a group to sit behind the drums on a track? These were the type of suggestions that Eno is famous for and it seems to be serving him well; at age sixty-eight he has a new album coming out in January of 2017 and some variation of his cards have been available for purchase since first appearing for public consumption in 1975.

We all won’t be able to embrace a card from Eno’s deck. Some people do well in tidy environments/situations and some do well in messy ones — it’s probably contingent on what you’re trying to achieve. (We wouldn’t go so far as recommending a CEO be disorganized.)

Reading through the book it would seem that the key is, like most things, to give it a try. A little “intentional messiness” could go a long way towards helping you climb out of a rut. And, if you are the tidy type through and through, it’s important not to try and force that on others — you just might be taking away a good thing.

If you like the ideas in Messy, check out Harford’s other book Adapt: Why Success Always Starts With Failure, or check out another important book on things that gain from disorder, Antifragile.

Warren Berger’s Three-Part Method for More Creativity

“A problem well stated is a problem half-solved.”
— Charles “Boss” Kettering


The whole scientific method is built on a very simple structure: If I do this, then what will happen? That’s the basic question on which more complicated, intricate, and targeted lines of inquiry are built, across a wide variety of subjects. This simple form helps us push deeper and deeper into knowledge of the world. (On a sidenote, science has become such a loaded, political word that this basic truth of how it works frequently seems to be lost!)

Individuals learn this way too. From the time you were a child, you were asking why (maybe even too much), trying to figure out all the right questions to ask to get better information about how the world works and what to do about it.

Because question-asking is such an integral part of how we know things about the world, both institutionally and individually, it seems worthy to understand how creative inquiry works, no? If we want to do things that haven’t been done or learn things that have never been learned — in short, be more creative — we must learn to ask the right questions, ones so good that they’re half-answered in the asking. And to do that, it might help to understand the process, no?

Warren Berger proposes a simple method in his book A More Beautiful Questionan interesting three-part system to help (partially) solve the problem of inquiry. He calls it The Why, What If, and How of Innovative Questioning, and reminds us why it’s worth learning about.

Each stage of the problem solving process has distinct challenges and issues–requiring a different mind-set, along with different types of questions. Expertise is helpful at certain points, not so helpful at others; wide-open, unfettered divergent thinking is critical at one stage, discipline and focus is called for at another. By thinking of questioning and problem solving in a more structured way, we can remind ourselves to shift approaches, change tools, and adjust our questions according to which stage we’re entering.

Three-Part Method for More Creativity


It starts with the Why?

A good Why? seeks true understanding. Why are things the way they are currently? Why do we do it that way? Why do we believe what we believe?

This start is essential because it gives us permission to continue down a line of inquiry fully equipped. Although we may think we have a brilliant idea in our heads for a new product, or a new answer to an old question, or a new way of doing an old thing, unless we understand why things are the way they are, we’re not yet on solid ground. We never want to operate from a position of ignorance, wasting our time on an idea that hasn’t been pushed and fleshed out. Before we say “I already know” the answer, maybe we need to step back and look for the truth.

At the same time, starting with a strong Why also opens up the idea that the current way (whether it’s our way or someone else’s) might be wrong, or at least inefficient. Let’s say a friend proposes you go to the same restaurant you’ve been to a thousand times. It might be a little agitating, but a simple “Why do we always go there?” allows two things to happen:

A. Your friend can explain why, and this gives him/her a legitimate chance at persuasion. (If you’re open minded.)

B. The two of you may agree you only go there out of habit, and might like to go somewhere else.

This whole Why? business is the realm of contrarian thinking, which not everyone enjoys doing. But Berger cites the case of George Lois:

George Lois, the renowned designer of iconic magazine covers and celebrated advertising campaigns, was also known for being a disruptive force in business meetings. It wasn’t just that he was passionate in arguing for his ideas; the real issue, Lois recalls, was that often he was the only person in the meeting willing to ask why. The gathered business executives would be anxious to proceed on a course of action assumed to be sensible. While everyone else nodded in agreement, “I would be the only guy raising his hand to say, ‘Wait a minute, this thing you want to do doesn’t make any sense. Why the hell are you doing it this way?”

Others in the room saw Lois to be slowing the meeting and stopping the group from moving forward. But Lois understood that the group was apt to be operating on habit–trotting out an idea or approach similar to what had been done in similar situations before, without questioning whether it was the best idea or the right approach in this instance. The group needed to be challenged to “step back” by someone like Lois–who had a healthy enough ego to withstand being the lone questioner in the room.

The truth is that a really good Why? type question tends to be threatening. That’s also what makes it useful. It challenges us to step back and stop thinking on autopilot. It also requires what Berger calls a step back from knowing — that recognizable feeling of knowing something but not knowing how you know it. This forced perspective is, of course, as valuable a thing as you can do.

Berger describes a valuable exercise that’s sometimes used to force perspective on people who think they already have a complete answer. After showing a drawing of a large square (seemingly) divided into 16 smaller squares, the questioner asks the audience “How many squares do you see?”

The easy answer is sixteen. But the more observant people in the group are apt to notice–especially after Srinivas allows them to have a second, longer, look–that you can find additional squares by configuring them differently. In addition to the sixteen single squares, there are nine two-by-two squares, four three-by-three squares, and one large four-by-four square, which brings the total to thirty squares.

“The squares were always there, but you didn’t find them until you looked for them.”

Point being, until you step back, re-examine, and look a little harder, you might not have seen all the damn squares yet!

What If?

The second part is where a good questioner, after using Why? to understand as deeply as possible and open a new line of inquiry, proposes a new type of solution, usually an audacious one — all great ideas tend to be, almost by definition — by asking What If…?

Berger illustrates this one well with the story of Pandora Music. The founder Tim Westergren wanted to know why good music wasn’t making it out to the masses. His search didn’t lead to a satisfactory answer, so he eventually asked himself, What if we could map the DNA of music? The result has been pretty darn good, with something close to 80 million listeners at present:

The Pandora story, like many stories of inquiry-driven startups, started with someone’s wondering about an unmet need. It concluded with the questioner, Westergren, figuring out how to bring a fully realized version of the answer into the world.

But what happened in between? That’s when the lightning struck. In Westergren’s case, ideas and influences began to come together; he combined what he knew about music with what he was learning about technology. Inspiration was drawn from a magazine article, and from a seemingly unrelated world (biology). A vision of the new possibility began to form in the mind. It all resulted in an audacious hypothetical question that might or might not have been feasible–but was exciting enough to rally people to the challenge of trying to make it work.

The What If stage is the blue-sky moment of questioning, when anything is possible. Those possibilities may not survive the more practical How stage; but it’s critical to innovation that there be time for wild, improbable ideas to surface and to inspire.

If the word Why has penetrative power, enabling the questioner to get past assumptions and dig deep into problems, the words What if have a more expansive effect–allowing us to think without limits or constraints, firing the imagination.

Clearly, Westergren had engaged in serious combinatorial creativity pulling from multiple disciplines, which led him to ask the right kind of questions. This seems to be a pretty common feature at this stage of the game, and an extremely common feature of all new ideas:

Smart recombinations are all around us. Pandora, for example, is a combination of a radio station and search engine; it also takes the biological method of genetic coding and transfers it to the domain of music […] In today’s tech world, many of the most successful products–Apple’s iPhone being just one notable example–are hybrids, melding functions and features in new ways.

Companies, too, can be smart recombinations. Netflix was started as a video-rental business that operated like a monthly membership health club (and how it has added “TV production studio” to the mix). Airbnb is a combination of an online travel agency, a social media platform, and a good old-fashioned bed-and-breakfast (the B&B itself is a smart combination from way back.)

It may be that the Why? –> What if? line of inquiry is common to all types of innovative thinking because it engages the part of our brain that starts turning over old ideas in new ways by combining them with other unrelated ideas, much of them previously sitting idle in our subconscious. That churning is where new ideas really arise.

The idea then has to be “reality-tested”, and that’s where the last major question comes in.


Once we think we’ve hit on a brilliant new idea, it’s time to see if the thing actually works. Usually and most frequently, the answer is no. But enough times to make it worth our while, we discover that the new idea has legs.

The most common problem here is that we try to perfect a new idea all at once, leading to stagnation and paralysis. That’s usually the wrong approach.

Another, often better, way is to try the idea quickly and start getting feedback. As much as possible. In the book, Berger describes a fun little experiment that drives home the point, and serves as a fairly useful business metaphor besides:

A software designer shared a story about an interesting experiment in which the organizers brought together a group of kindergarten children who were divided into small teams and given a challenge: Using uncooked spaghetti sticks, string, tape, and a marshmallow, they had to assemble the tallest structure they could, within a time limit (the marshmallow was supposed to be placed on top of the completed structure.)

Then, in a second phase of the experiment, the organizers added a new wrinkle. They brought in teams of Harvard MBA grad students to compete in the challenge against the kindergartners. The grad students, I’m told, took it seriously. They brought a highly analytical approach to the challenge, debating among themselves about how best to combine the sticks, the string, and the tape to achieve maximum altitude.

Perhaps you’ll have guessed this already, but the MBA students were no match for the kindergartners. For all their planning and discussion, the structures they carefully conceived invariably fell apart–and then they were out of time before they could get in more attempts.

The kids used their time much more efficiently by constructing right away. They tried one way of building, and if it didn’t work, they quickly tried another. They got in a lot more tries. They learned from their mistakes as they went along, instead of attempting to figure out everything in advance.

This little experiment gets run in the real world all the time by startups looking to outcompete ponderous old bureaucracies. They simply substitute velocity for scale and see what happens — it often works well.

The point is to move along the axis of Why?–>What If–>How? without too much self-censoring in the last phase. Being afraid to fail can often mean a great What If? proposition gets stuck there forever. Analysis paralysis, as it’s sometimes called. But if you can instead enter the testing of the How? stage quickly, even by showing that an idea won’t work, then you can start the loop over again, either asking a new Why? or proposing a new What If? to an existing Why?

Thus moving your creative engine forward.


Berger’s point is that there is an intense practical end to understanding productive inquiry. Just like “If I do this, then what will happen?” is a basic structure on which all manner of complex scientific questioning and testing is built, so can a simple Why, What If, and How structure catalyze a litany of new ideas.

Still Interested? Check out the book, or check out some related posts: Steve Jobs on CreativitySeneca on Gathering Ideas And Combinatorial Creativity, or for some fun with question-asking, What If? Serious Scientific Answers to Absurd Hypothetical Questions.

Paula Scher on Process versus Outcome

Paula Scher
Iconic typography designer Paula Scher discusses her creative process, including the famous Citi logo. Interestingly, the idea came to her in seconds and that presented a problem for the client. They wanted to buy a process not an outcome. Scher’s process is very much one of combinatory creativity, whereby she combines existing things in new ways.

A lot of clients like to buy process. It’s like they think they are not getting their money’s worth because I solved it too fast.


How can it be that you talk to someone and it’s done in a second? But it IS done in a second — it’s done in a second and 34 years. It’s done in a second and every experience, and every movie, and every thing in my life that’s in my head.

This reminds me of an old story with many variations. Here is one version.

A giant ship engine failed. The ship’s owners tried one expert after another, but none of them could figure but how to fix the engine.

Then they brought in an old man who had been fixing ships since he was a young [boy]. He carried a large bag of tools with him, and when he arrived, he immediately went to work. He inspected the engine very carefully, top to bottom.

Two of the ship’s owners were there, watching this man, hoping he would know what to do. After looking things over, the old man reached into his bag and pulled out a small hammer. He gently tapped something. Instantly, the engine lurched into life. He carefully put his hammer away. The engine was fixed!

A week later, the owners received a bill from the old man for ten thousand dollars.

“What?!” the owners exclaimed. “He hardly did anything!” So they wrote the old man a note saying, “Please send us an itemized bill.”

The man sent a bill that read:
Tapping with a hammer………………….. $ 2.00
Knowing where to tap…………………….. $ 9,998.00

*Effort is important, but knowing where to make an effort makes all the difference!*

This mini interview prompted me to order a copy of Scher’s Make It Bigger, which looks at graphic design from the vantage point of business.

(image source)

Free Radicals: Don’t Follow your Passion, Cultivate it

“Luck is what happens when preparation meets opportunity.”
— Seneca


maximize your potential

We’ve entered a new phase of self-invention.

Thanks in large part to technology and the pace of the modern world, finding your way through the labyrinth is more difficult than ever.

Maximize Your Potential: Grow Your Expertise, Take Bold Risks & Build an Incredible Career (Kindle), edited by Behance’s 99U editor-in-chief Jocelyn Glei, and featuring contributions from over twenty of today’s creative minds, explores the timeless skills—generating opportunities, building relationships, and taking risks—that can help you navigate today’s changing landscape.

In the foreword to the book, Behance founder Scott Belsky, author Making Ideas Happen, explains the concept of free radicals.

Chalk it up to new technology, social media, or the once out-of-reach business tools now at your fingertips. The fact is, we’re empowered to work on our own terms and do more with less. As a result, we expect more from those that employ us and we expect more from ourselves. When we get the resources and opportunities we deserve, we create the future.

Here’s a name for us: Free Radicals.

Free Radicals want to take their careers into their own hands and put the world to work for them. Free Radicals are resilient, self-reliant, and extremely potent. You’ll find them working solo, in small teams, or within large companies. As the world changes, Free Radicals have re-imagined “work” as we know it. No doubt, we have lofty expectations:

We do work that is, first and foremost, intrinsically rewarding. But, we don’t create solely for ourselves, we want to make a real and lasting impact in the world around us.

We thrive on flexibility and are most productive when we feel fully engaged. We demand freedom, whether we work within companies or on our own, to run experiments, participate in multiple projects at once, and move our ideas forward.

We make stuff often, and therefore, we fail often. Ultimately, we strive for little failures that help us course-correct along the way, and we view every failure as a learning opportunity, part of our experiential education.

We have little tolerance for the friction of bureaucracy, old-boy networks, and antiquated business practices. As often as possible, we question “standard operating procedure” and assert ourselves. But even when we can’t, we don’t surrender to the friction of the status quo. Instead, we find clever ways (and hacks) around it.

We expect to be fully utilized and constantly optimized, regardless of whether we’re working in a start-up or a large organization. When our contributions and learning plateau, we leave. But when we’re leveraging a large company’s resources to make an impact in something we care about, we are thrilled! We want to always be doing our best work and making the greatest impact we can.

We believe that “networking” is sharing. People listen to (and follow) us because of our discernment and curatorial instinct. As we share our creations as well as what fascinates us, we authentically build a community of supporters who give us feedback, encouragement, and lead us to new opportunities. For this reason and more, we often (though, not always) opt for transparency over privacy.

We believe in meritocracy and the power of online networks and peer communities to advance our ability to do what we love, and do well by doing it. We view competition as a positive motivator rather than a threat, because we want the best idea—and the best execution—to triumph.

We make a great living doing what we love. We consider ourselves to be both artisans and businesses. In many cases, we are our own accounting department, Madison Avenue marketing agency, business development manager, negotiator, and salesperson. We spend the necessary energy to invest in ourselves as businesses—leveraging the best tools and knowledge (most of which are free and online) to run ourselves as a modern-day enterprise.

Maximize Your Potential

One of the best insights in the book revolves around cultivating passion. We’re told from a very young age to follow our passion. Cal Newport, author of How to Become a Straight-A Student: The Unconventional Strategies Real College Students Use to Score High While Studying Less, points out the flaw in this wisdom.

This pattern is common in the lives of people who end up loving their work. As described in Lesson 1, careers become compelling once they feature the general traits you seek. These traits, however, are rare and valuable—no one will hand you a lot of autonomy or impact just because you really want it, for example. Basic economics tells us that if you want something rare and valuable, you need to offer something rare and valuable in return—and in the working world, what you have to offer are your skills. This is why the systematic development of skill almost always precedes passion.

In other words Newport argues that what you do for a living matters less than you think.

“[T]he right question is not “What job am I passionate about doing?” but instead “What way of working and living will nurture my passion.”

Stepping back, he writes:

The goal of feeling passionate about your work is sound. But following your passion—choosing a career path solely because you are already passionate about the nature of the work—is a poor strategy for accomplishing this goal. It assumes that you have a pre-existing passion to follow that matches up to a viable career, and that matching your work to a strong interest is sufficient to build long-term career satisfaction. Both of these assumptions are flawed.

Newport argues a more sophisticated strategy for finding passion means “we should begin by developing rare and valuable skills.” Once we’ve done that, we can use these skills to navigate our career towards the general lifestyle that resonates with us.

milton erickson

In a section on reprogramming your daily habits, Scott Young speaks to how automatic many of our decisions become and how routines drive our lives.

If you think hard about it, you’ll notice just how many “automatic” decisions you make each day. But these habits aren’t always as trivial as what you eat for breakfast. Your health, your productivity, and the growth of your career are all shaped by the things you do each day — most by habit, not by choice.

Even the choices you do make consciously are heavily influenced by automatic patterns. Researchers have found that our conscious mind is better understood as an explainer of our actions, not the cause of them. Instead of triggering the action itself, our consciousness tries to explain why we took the action after the fact, with varying degrees of success. This means that even the choices we do appear to make intentionally are at least somewhat influenced by unconscious patterns.

Given this, what you do every day is best seen as an iceberg, with a small fraction of conscious decision sitting atop a much larger foundation of habits and behaviors.

We are What we do

Maximize Your Potential: Grow Your Expertise, Take Bold Risks & Build an Incredible Career explores how creating opportunities, building expertise, cultivating relationships, and taking risks can propel you forward. With contributions from Tony Schwartz to Ben Casnocha, you’ll be left thinking about the next opportunity and how to get there. (Best served with a side of its prequel: Manage Your Day-to-Day.)

Are Cities More Innovative?

Jane Jacobs in The Death and Life of Great American Cities: “The larger a city, the greater the variety of its manufacturing, and also the greater both the number and the proportion of its small manufacturers.”

The benefits that cities offer to smallness are just as marked in retail trade, cultural facilities and entertainment. This is because city populations are large enough to support wide ranges of variety and choices in these things. And again we find that bigness has all the advantage in smaller settlements. Towns and suburbs for instance are natural homes for huge supermarkets, and for little else in the way of groceries, for standard movie houses or drive ins for little else in the way of theatre.

There are simply not enough people to support further variety, although there may be people(too few of them) who would draw upon it were it there. Cities, however, are the natural homes of supermarkets, and standard movie houses, plus delicatessens, Viennese bakeries, foreign groceries, art movies, and so on, all of which can be found co-existing, the standard with the strange, the large with the small. Wherever lively and popular parts of the cities are found, the small much outnumber the large.

“Cities, then,” writes Steven Johnson in Where Good Ideas Come From: The Natural History of Innovation, “Cities, then, are environments that are ripe for exaptation, because they cultivate specialized skills and interests, and they create a liquid network where information can leak out of those subcultures, and influence their neighbors in surprising ways. This is one explanation for superlinear scaling in urban creativity. The cultural diversity those subcultures create is valuable not just because it makes urban life less boring. The value also lies in the unlikely migrations that happen between the different clusters.”

And Samuel Arbesman, in The Half-life of Facts, adds: “Larger groups of interacting people can maintain skills and innovations, and in turn develop new ones. A small group doesn’t have the benefit of specialization and idea exchange necessary for any of this to happen.”

Still curious? If you want a deeper understanding, read Growth in Cities.