The Book in 3 Sentences

1. The Prince is a wonderful improvisation on the use of power across time and space (at the time anyway). The translation is very conversational and modern, which I liked quite a bit. Some parts were rather dated, but by no means all.

Impressions

The book was much less cynical and much more descriptive than I would have thought.

How I Discovered It

Book club

Who Should Read It?

People interested in the classics, or anyone who really appreciates a good translation.

Summary + Notes

The Prince was written by a forty-four-year-old diplomat facing ruin.

For most of the fifteenth century there had been five major players in the peninsula: the Kingdom of Naples, the Papal States, Florence, Venice and Milan.

However, if the situation was rarely static, it is also true that there were few major changes. As soon as one power achieved some significant military victory, the others immediately formed an alliance against it to halt its progress. Florence, in particular, owed its continuing independence largely to the fact that if Venice, Milan or Rome tried to take it, the other two would at once intervene to prevent this happening.

Girolamo Savonarola ruled Florence from 1494 to 1498, during which time the city passed from being one of the centres of Renaissance Humanism to a book-burning, fundamentalist theocracy.

Had Machiavelli insisted on deploring this unhappy state of affairs, had he dwelt on other criteria for judging a leader, aside from his mere ability to stay in power and build a strong state, had he told us with appropriate piety that power was hardly worth having if you had to sell your soul to get it, he could have headed off a great deal of criticism while still delivering the same information. But aside from one or two token regrets that the world is not a nicer place, Machiavelli does not do this. It wasn’t his project. Rather he takes it for granted that we already know that life, particularly political life, is routinely, and sometimes unspeakably, cruel, and that once established in a position of power a ruler may have no choice but to kill or be killed.

In short, Machiavelli’s attention has shifted from a methodical analysis of different political systems to a gripping and personally engaged account of the psychology of the leader who has placed himself beyond the constrictions of Christian ethics and lives in a delirium of pure power.

For a diplomat like Machiavelli, who had spent his life among the powerful but never really held the knife by the handle, a state employee so scrupulously honest that when investigated for embezzlement he ended up being reimbursed monies that were due to him, it was all too easy to fall into a state of envy and almost longing when contemplating the awesome Borgia who had no qualms about taking anything that came his way and never dreamed of being honest to anyone.

The Prince was largely responsible for Henry VIII’s decision to take the English Church away from Rome.

It was in so far as Machiavelli allowed these dangerous implications to surface in his writing that he both unmasked, and himself became identified with, what we might call the unacceptable face of Renaissance Humanism.

there is also an undercurrent of excitement at the thought that it might be possible to take life entirely into one’s hands, manipulate people and circumstances at will and generally pursue one’s selfish goals without a thought for moral codes or eternal damnation: in this sense the Machiavellian villain looks ahead to the worst of modern individualism.

Cromwell frequently governed without parliament or elections for fear the people might not see things God’s way.

Members of court, Napoleon ordered, shortly after usurping power, must attend soirées with their wives, to appear respectable and avoid gossip. ‘The death of conversation’, Talleyrand opined. Certainly, when a leader has to rely on appearing respectable to claim legitimacy, he is on thin ice indeed.

As Rousseau saw it, the whole of The Prince was itself a Machiavellian ruse: the author had only pretended to give lessons to kings whereas in fact his real aim was to teach people to be free by showing them that royal power was no more than subterfuge.

Machiavelli after all declared himself a republican and a libertarian.

Others took a more traditional view: Bertrand Russell described The Prince as ‘a handbook for gangsters’,

one reaction that Machiavelli never seems to provoke is indifference.

The English have Prince Charles. And the thing about Prince Charles is that he is not King Charles and probably never will be.

Machiavelli’s word ‘prince’ does not mean ‘the son of the king’, and even less ‘an attractive young suitor’. Machiavelli’s ‘principe’ refers generically to men of power, men who rule a state. The prince is the first, or principal, man.

For Machiavelli ‘virtù’ was any quality of character that enabled you to take political power or to hold on to it; in short, a winning trait. It could be courage in battle, or strength of personality, or political cunning, or it might even be the kind of ruthless cruelty that lets your subjects know you mean business.

A ruler who inherits power has less reason or need to upset his subjects than a new one and as a result is better loved.

this for the simple reason that you can’t give them as much as they expected. And you can’t get tough with them either, since you still need them; because however strong your armies, you’ll always need local support to occupy a new territory.

Even where there is some difference in language, the customs of these territories are similar and people can get along with each other. So a ruler who has taken territories in these circumstances must have two priorities: first, to eliminate the family of the previous rulers; second, to leave all laws and taxes as they were. In this way the acquired territory and the king’s original possessions will soon form a single entity.

So, if you go and live in the new territory you’ve taken, you’re very unlikely to lose it.

In this regard it’s worth noting that in general you must either pamper people or destroy them; harm them just a little and they’ll hit back; harm them seriously and they won’t be able to. So if you’re going to do people harm, make sure you needn’t worry about their reaction.

Seen in advance, trouble is easily dealt with; wait until it’s on top of you and your reaction will come too late, the malaise is already irreversible.

Remember what the doctors tell us about tuberculosis: in its early stages it’s easy to cure and hard to diagnose, but if you don’t spot it and treat it, as time goes by it gets easy to diagnose and hard to cure. So it is with affairs of state. See trouble in advance (but you have to be shrewd) and you can clear it up quickly. Miss it, and by the time it’s big enough for everyone to see it will be too late to do anything about it.

Time hurries everything on and can just as easily make things worse as better.

The desire to conquer more territory really is a very natural, ordinary thing and whenever men have the resources to do so they’ll always be praised, or at least not blamed. But when they don’t have the resources, yet carry on regardless, then they’re at fault and deserve what blame they get.

So Louis made five mistakes: he eliminated the weaker states; he enhanced the power of one of Italy’s stronger states; he brought in an extremely powerful foreign king; he didn’t go to live in the territory he’d acquired and he didn’t establish colonies there.

you must never fail to respond to trouble just to avoid war, because in the end you won’t avoid it, you’ll just be putting it off to your enemy’s advantage.

and when the cardinal told me that the Italians knew nothing about war, I told him that the French knew nothing about politics, because if they did they wouldn’t be letting the pope grow so powerful.

From which we can infer a general rule that always holds, or almost always: that to help another ruler to grow powerful is to prepare your own ruin; because it takes flair or military strength to build up a new power, and both will seem threatening to the person who has benefited from them.

To explain this situation let’s start by remembering that all monarchies on record have been governed in one of two ways: either by a king and the servants he appoints as ministers to run his kingdom; or by a king and a number of barons, who are not appointed by the king but hold their positions thanks to hereditary privilege. These barons have their own lands and their own subjects who recognize the barons as their masters and are naturally loyal to them. Where a state is governed by a king and his ministers the king is more powerful since he is the only person in the state whom people recognize as superior. When they obey someone else it is only because he is a minister or official and they have no special loyalty to him.

Looking at these two kinds of states, it’s clear that Turkey is hard to conquer but once conquered very easy to hold. France on the other hand will be somewhat easier to conquer but very hard to hold.

you’ll lose the territory you took as soon as your enemies get an opportunity to rebel.

Note:Similar to Afghanistan

It wasn’t a question of the abilities of each particular conqueror, but of the different kinds of state they had invaded.

When the states you invade have been accustomed to governing themselves without a monarch and living in freedom under their own laws, then there are three ways of holding on to them: the first is to reduce them to rubble; the second is to go and live there yourself; the third is to let them go on living under their own laws, make them pay you a tax and install a government of just a few local people to keep the state as a whole friendly. Since this government has been set up by the invading ruler, its members know they can’t survive without his support and will do everything they can to defend his authority.

If you conquer a city accustomed to self-government and opt not to destroy it you can expect it to destroy you.

And though we can hardly say much about Moses, since he merely carried out God’s orders, all the same we have to admire him for the grace that made him worthy of God’s attention.

Analysing their lives and achievements, we notice that the only part luck played was in giving them an initial opportunity: they were granted the raw material and had the chance to mould it into whatever shape they wanted. Without this opportunity their talent would have gone unused, and without their talent the opportunity would have gone begging.

Here we have to bear in mind that nothing is harder to organize, more likely to fail, or more dangerous to see through, than the introduction of a new system of government. The

no one really believes in change until they’ve had solid experience of it.

It’s easy to convince people of something, but hard to keep them convinced. So when they stop believing in you, you must be in a position to force them to believe.

Anyone who thinks that an important man will forget past grievances just because he’s received some new promotion must think again. Borgia miscalculated in this election, and the mistake was fatal.

Looking at Agathocles’ life and achievements, you won’t find much that can be attributed to luck.

On the other hand, we can hardly describe killing fellow citizens, betraying friends and living without loyalty, mercy or creed as signs of talent. Methods like that may bring you power, but not glory.

Cruelty well used (if we can ever speak well of something bad) is short-lived and decisive, no more than is necessary to secure your position and then stop; you don’t go on being cruel but use the power it has given you to deliver maximum benefits to your subjects. Cruelty is badly used when you’re not drastic enough at the beginning but grow increasingly cruel later on, rather than easing off. A leader who takes the first approach has a chance, like Agathocles, of improving his position with his subjects and with God too; go the other way and you have no chance at all.

So get the violence over with as soon as possible; that way there’ll be less time for people to taste its bitterness and they’ll be less hostile. Favours, on the other hand, should be given out slowly, one by one, so that they can be properly savoured.

In every city one finds these two conflicting political positions: there are the common people who are eager not to be ordered around and oppressed by the noble families, and there are the nobles who are eager to oppress the common people and order them around. These opposing impulses will lead to one of three different situations: a monarchy, a republic, or anarchy. A

A king who comes to power with the help of the rich nobles will have more trouble keeping it than the king who gets there with the support of the people, because he will be surrounded by men who consider themselves his equals, and that will make it hard for him to give them orders or to manage affairs as he wants. But a man coming to power with the support of the common people holds it alone and has no one, or hardly anyone, around him who’s unwilling to obey. What’s more, you can’t in good faith give the nobles what they want without doing harm to others; but you can with the people. Because the people’s aspirations are more honourable than those of the nobles: the nobles want to oppress the people, while the people want to be free from oppression. What’s more, a king can never be safe if the common people are hostile to him, because there are so many of them; but he can protect himself against the nobles, since there are not so many.

A man who becomes king with the support of the people, then, must keep those people on his side. This is easy enough since all they want is to be free from oppression. But the man who becomes king against the will of the majority and with the support of the wealthy nobles must make it an absolute priority to win over the affection of the common people.

what’s more, to keep people well fed without draining the public purse, they stock materials for a year’s worth of work in whatever trades are the lifeblood of the city and whatever jobs the common folk earn their keep with.

Mercenaries and auxiliaries are useless and dangerous. If you are counting on mercenaries to defend your state you will never be stable or secure, because mercenaries are ambitious, undisciplined, disloyal and they quarrel among themselves. Courageous with friends and cowardly with enemies, they have no fear of God and keep no promises. With mercenaries the only way to delay disaster is to delay the battle; in peacetime they plunder you and in wartime they let the enemy plunder you.

they’re happy to be your soldiers while you’re not at war, but when war comes, they run for it, or just disappear.

And a republic with a citizen army is less likely to fall victim to a coup than a republic paying for mercenary armies.

Rome and Sparta stood for many centuries armed and free. The Swiss are extremely well armed and completely free.

fight his neighbours, the emperor of Constantinople brought 10,000 Turks into Greece and when the war was over they wouldn’t leave, which was how the infidels began to get control of Greece.

To summarize, the big danger with mercenaries is their indecision, with auxiliaries their determination.

having your own army means having a force made up of subjects, or citizens, or men dependent on you. All other forces are mercenaries or auxiliaries.

A ruler, then, must have no other aim or consideration, nor seek to develop any other vocation outside war, the organization of the army and military discipline.

if you always want to play the good man in a world where most people are not good, you’ll end up badly. Hence, if a ruler wants to survive, he’ll have to learn to stop being good, at least when the occasion demands.

With time, when people see that his penny-pinching means he doesn’t need to raise taxes and can defend the country against attack and embark on campaigns without putting a burden on his people, he’ll increasingly be seen as generous – generous to those he takes nothing from, which is to say almost everybody, and mean to those who get nothing from him, which is to say very few. In our own times the only leaders we’ve seen doing great things were all reckoned mean. The others were failures.

Note:Republicans

A ruler in power and a man seeking power are two different things. For the ruler already in power generosity is dangerous; for the man seeking power it is essential. Caesar

Spending other people’s money doesn’t lower your standing – it raises it. It’s only spending your own money that puts you at risk.

if you have to choose, it’s much safer to be feared than loved.

Men are less worried about letting down someone who has made himself loved than someone who makes himself feared. Love binds when someone recognizes he should be grateful to you, but, since men are a sad lot, gratitude is forgotten the moment it’s inconvenient. Fear means fear of punishment, and that’s something people never forget.

And a ruler won’t be hated if he keeps his hands off his subjects’ property and their women.

Above all, he mustn’t seize other people’s property. A man will sooner forget the death of his father than the loss of his inheritance.

The positive qualities without the cruelty wouldn’t have produced the same effect. Historians are just not thinking when they praise him for this achievement and then condemn him for the cruelty that made it possible.

Since a ruler has to be able to act the beast, he should take on the traits of the fox and the lion; the lion can’t defend itself against snares and the fox can’t defend itself from wolves. So you have to play the fox to see the snares and the lion to scare off the wolves. A ruler who just plays the lion and forgets the fox doesn’t know what he’s doing. Hence a sensible leader cannot and must not keep his word if by doing so he puts himself at risk, and if the reasons that made him give his word in the first place are no longer valid.

There is nothing more important than appearing to be religious. In general people judge more by appearances than first-hand experience, because everyone gets to see you but hardly anyone deals with you directly. Everyone sees what you seem to be, few have experience of who you really are, and those few won’t have the courage to stand up to majority opinion underwritten by the authority of state.

You’ll be held in contempt, on the other hand, if you’re seen as changeable, superficial, effeminate, fearful or indecisive. So a ruler must avoid those qualities like so many stumbling blocks and act in such a way that everything he does gives an impression of greatness, spirit, seriousness and strength; when presiding over disputes between citizens he should insist that his decision is final and make sure no one imagines they can trick or outwit him.

In fact, one of the most powerful preventive measures against conspiracies is simply not being hated by a majority of the people. People planning a conspiracy must believe that killing the ruler will be popular; when they realize that, on the contrary, it would be unpopular they lose heart, because conspiracies are always beset with endless difficulties. Experience

My conclusion, then, is that so long as he has the people on his side a ruler needn’t worry about conspiracies, but when they are against him and hate him he’ll have to watch everyone’s every move.

This prompts the following reflection: that a ruler must get others to carry out policies that will provoke protest, keeping those that inspire gratitude to himself. In conclusion, let me repeat that a ruler should respect the nobles but must make sure he is not hated by the people.

No one new to power has ever disarmed his subjects; on the contrary, finding them disarmed new rulers have always armed them. When you’re the one giving people arms, those arms become yours; men who were potentially hostile become loyal, while those already loyal become your supporters rather than just your subjects. It’s true you can’t arm everyone, but in favouring some you can feel safer about the others too.

Looking carefully at the reasons for this and drawing on the examples available from ancient and modern history, we find that it is much easier to win over those who were content with the previous government, and hence your enemies, than the men who were not content and so made an alliance with you and helped you take the country.

A ruler will also be respected when he is a genuine friend and a genuine enemy, that is, when he declares himself unambiguously for one side and against the other. This policy will always bring better results than neutrality.

For example, if you have two powerful neighbours who go to war, you may or may not have reason to fear the winner afterwards. Either way it will always be better to take sides and fight hard. If you do have cause to fear but stay neutral, you’ll still be gobbled up by the winner to the amusement and satisfaction of the loser; you’ll have no excuses, no defence and nowhere to hide. Because a winner doesn’t want half-hearted friends who don’t help him in a crisis; and the loser will have nothing to do with you since you didn’t choose to fight alongside him and share his fate.

A ruler must also show that he admires achievement in others, giving work to men of ability and rewarding people who excel in this or that craft. What’s more, he should reassure his subjects that they can go calmly about their business as merchants or farmers, or whatever other trade they practise, without worrying that if they increase their wealth they’ll be in danger of having it taken away from them, or that if they start up a business they’ll be punitively taxed.

Note:Supply side Machiavelli

In responding to these advisers, as a group or separately, he should make it clear that the more openly they speak, the more welcome their advice will be. After which, he shouldn’t take advice from anyone else, but get on with whatever has been decided and be firm in his decisions.

So a ruler must always take advice, but only when he wants it, not when others want to give it to him. In fact he should discourage people from giving him advice unasked.

I realize that many people have believed and still do believe that the world is run by God and by fortune and that however shrewd men may be they can’t do anything about it and have no way of protecting themselves.

My opinion on the matter is this: it’s better to be impulsive than cautious; fortune is female and if you want to stay on top of her you have to slap and thrust. You’ll see she’s more likely to yield that way than to men who go about her coldly. And being a woman she likes her men young, because they’re not so cagey, they’re wilder and more daring when they master her.

Justice is definitely on our side because ‘war is just when there’s no alternative and arms are sacred when they are your only hope.’ The

God doesn’t like doing everything himself, he doesn’t want to deprive us of our free will and our share of glory.

It’s true that the Swiss and Spanish infantries are thought to be formidable, but both have weak points that would allow a third force not only to face them but to feel confident of beating them. The Spanish can’t stand up to cavalry and the Swiss are in trouble when they run into infantry as determined as themselves.

ACUTO, GIOVANNI Italianization of John Hawkwood (1320-94). Having served in the English army in France, in 1360 Hawkwood joined mercenary soldiers in Burgundy and later commanded the so-called White Company fighting for different states and factions in Italy. Constantly playing off his employers against their enemies, he built up considerable wealth. From 1390 on he commanded Florentine armies in their war against the Viscontis of Milan.

Illegitimate son of Cardinal Rodrigo Borgia, later Pope Alexander VI, Cesare Borgia was made Bishop of Pamplona at fifteen and a cardinal at eighteen.

Cesare then became the first person in history to resign his position as cardinal, upon which Louis made him Duke of Valentinois, hence the nickname, Duke Valentino.

COMMODUS Lucius Aurelius Commodus Antoninus (161–193), Roman emperor (180–93). The son of Marcus Aurelius, Commodus rejected his father’s stoic asceticism, giving himself over to pleasure and amusement while allowing a series of favourites to run the empire. Boastful about his physique, he regularly took part in naked gladiatorial combat. Eventually a conspiracy against him led to his being strangled by the wrestler Narcissus.

FORLÌ, COUNTESS OF Caterina Sforza (1463–1509), an illegitimate daughter of Galeazzo Sforza, Duke of Milan. She married Girolamo Riario, officially the nephew but possibly the son of Pope Sixtus IV. Riario was Count of Forlì and after his murder in 1488 Caterina took control of the town until it was captured by Cesare Borgia in 1500. She is famous for having refused to hand over the citadel of Forlì to rebels despite their threatening to kill her children, whom they held hostage. Exposing her genitals from the castle walls, she told them she was perfectly capable of producing more children.

Despite impressive victories he was forced to return home when the Romans attacked Carthage, and was defeated at the Battle of Zama (201 BC) by Scipio Africanus.

Eventually, to avoid falling into Roman hands, he killed himself by poisoning.

He died of natural causes and was immediately deified.

Note:Worth noting cause of death

While his domestic reforms enjoyed a certain amount of success, his foreign policies were confused and ineffective and led to the loss of Switzerland, which became an independent confederation in 1499.

his preaching appeared to be vindicated and he became head of the Florentine government, leading the city as a theocracy from 1494 to 1498 and encouraging people to burn anything profane (books, paintings) on his so-called Bonfire of the Vanities.

THESEUS Legendary Greek hero, son of Aegeus, King of Athens. He slew the Minotaur in the Cretan labyrinth and was the first lover of the adolescent Helen of Troy. He united the region of Attica under the administration of Athens.

The Book in 3 Sentences

1. A somewhat padded but useful book about what to record and how to record any bit of information you come across in your life. It started out as a course but was distilled down into several guiding principles and put into book form. I found it worth reading if you plan to actually put the lessons of the book into action. It could have been shorter without missing anything of value but such is the nature of the beast.

How I Discovered It

From the Thomas Frank Youtube/Nebula Channels

Who Should Read It?

People who intend to be more organized

How the Book Changed Me

How my life / behaviour / thoughts / ideas have changed as a result of reading the book.

• A better notion setup
• More focused note taking
• Better overall information organization.
• A focus on the reusable “intermediate packets” – which is a valuable concept

Summary + Notes

We spend countless hours reading, listening to, and watching other people’s opinions about what we should do, how we should think, and how we should live, but make comparatively little effort applying that knowledge and making it our own. So much of the time we are “information hoarders,” stockpiling endless amounts of well-intentioned content that only ends up increasing our anxiety.

To be able to make use of information we value, we need a way to package it up and send it through time to our future self.

The Building a Second Brain system will teach you how to: Find anything you’ve learned, touched, or thought about in the past within seconds. Organize your knowledge and use it to move your projects and goals forward more consistently. Save your best thinking so you don’t have to do it again. Connect ideas and notice patterns across different areas of your life so you know how to live better. Adopt a reliable system that helps you share your work more confidently and with more ease. Turn work “off” and relax, knowing you have a trusted system keeping track of all the details. Spend less time looking for things, and more time doing the best, most creative work you are capable of. When

I became the project manager of my own condition, taking detailed notes on everything my doctors told me, trying out every suggestion they made, and generating questions to review during my next appointment. With

Research from Microsoft shows that the average US employee spends 76 hours per year looking for misplaced notes, items, or files.

This digital commonplace book is what I call a Second Brain. Think of it as the combination of a study notebook, a personal journal, and a sketchbook for new ideas. It is a multipurpose tool that can adapt to your changing needs over time.

You’re allowed to reference your notes at any time, provided you took them in the first place.

For modern, professional notetaking, a note is a “knowledge building block”—a discrete unit of information interpreted through your unique perspective and stored outside your head.

Their stories convey a pervasive feeling of discontent and dissatisfaction—the experience of facing an endless onslaught of demands on their time, their innate curiosity and imagination withering away under the suffocating weight of obligation.

There are four essential capabilities that we can rely on a Second Brain to perform for us: Making our ideas concrete. Revealing new associations between ideas. Incubating our ideas over time. Sharpening our unique perspectives.

Before we do anything with our ideas, we have to “off-load” them from our minds and put them into concrete form. Only when we declutter our brain of complex ideas can we think clearly and start to work with those ideas effectively.

In its most practical form, creativity is about connecting ideas together, especially ideas that don’t seem to be connected.

Having a Second Brain where lots of ideas can be permanently saved for the long term turns the passage of time into your friend, instead of your enemy.

American journalist, author, and filmmaker Sebastian Junger once wrote on the subject of “writer’s block”: “It’s not that I’m blocked. It’s that I don’t have enough research to write with power and knowledge about that topic. It always means, not that I can’t find the right words, [but rather] that I don’t have the ammunition.”

The second way that people use their Second Brain is to connect ideas together. Their Second Brain evolves from being primarily a memory tool to becoming a thinking tool. A piece of advice from a mentor comes in handy as they encounter a similar situation on a different team.

To guide you in the process of creating your own Second Brain, I’ve developed a simple, intuitive four-part method called “CODE”—Capture; Organize; Distill; Express. These are the steps not only to build your Second Brain in the first place, but also to work with it going forward.

The solution is to keep only what resonates in a trusted place that you control, and to leave the rest aside.

The best way to organize your notes is to organize for action, according to the active projects you are working on right now. Consider new information in terms of its utility, asking, “How is this going to help me move forward one of my current projects?”

Every time you take a note, ask yourself, “How can I make this as useful as possible for my future self?” That question will lead you to annotate the words and phrases that explain why you saved a note, what you were thinking, and what exactly caught your attention. Your notes will be useless if you can’t decipher them in the future, or if they’re so long that you don’t even try. Think of yourself not just as a taker of notes, but as a giver of notes—you are giving your future self the gift of knowledge that is easy to find and understand.

Information is always in flux, and it is always a work in progress. Since nothing is ever truly final, there is no need to wait to get started.

Information is food for the brain. It’s no accident that we call new ideas “food for thought.”

A knowledge asset is anything that can be used in the future to solve a problem, save time, illuminate a concept, or learn from past experience.

Knowledge assets can come from either the external world or your inner thoughts. External knowledge could include: Highlights: Insightful passages from books or articles you read. Quotes: Memorable passages from podcasts or audiobooks you listen to. Bookmarks and favorites: Links to interesting content you find on the web or favorited social media posts. Voice memos: Clips recorded on your mobile device as “notes to self.” Meeting notes: Notes you take about what was discussed during meetings or phone calls. Images: Photos or other images that you find inspiring or interesting. Takeaways: Lessons from courses, conferences, or presentations you’ve attended.

If you try to save every piece of material you come across, you run the risk of inundating your future self with tons of irrelevant information. At that point, your Second Brain will be no better than scrolling through social media.

The renowned information theorist Claude Shannon, whose discoveries paved the way for modern technology, had a simple definition for “information”: that which surprises you.7 If you’re not surprised, then you already knew it at some level, so why take note of it? Surprise is an excellent barometer for information that doesn’t fit neatly into our existing understanding, which means it has the potential to change how we think.

If what you’re capturing doesn’t change your mind, then what’s the point?

but if you take away one thing from this chapter, it should be to keep what resonates.

First, you are much more likely to remember information you’ve written down in your own words. Known as the “Generation Effect,”10 researchers have found that when people actively generate a series of words, such as by speaking or writing, more parts of their brain are activated when compared to simply reading the same words. Writing things down is a way of “rehearsing” those ideas, like practicing a dance routine or shooting hoops, which makes them far more likely to stick.

I eventually named this organizing system PARA,I which stands for the four main categories of information in our lives: Projects, Areas, Resources, and Archives. These four categories are universal, encompassing any kind of information, from any source, in any format, for any purpose.

PARA can handle it all, regardless of your profession or field, for one reason: it organizes information based on how actionable it is, not what kind of information it is. The project becomes the main unit of organization for your digital files.

There’s another way. I will show you how to take the notes you’ve captured and save them according to a practical use case. By taking that small extra step of putting a note into a folder (or tagging itIII) for a specific project, such as a psychology paper you’re writing or a presentation you’re preparing, you’ll encounter that idea right at the moment it’s most relevant. Not a moment before, and not a moment after.

With the PARA system, every piece of information you want to save can be placed into one of just four categories: Projects: Short-term efforts in your work or life that you’re working on now. Areas: Long-term responsibilities you want to manage over time. Resources: Topics or interests that may be useful in the future. Archives: Inactive items from the other three categories.

Projects have a couple of features that make them an ideal way to organize modern work. First, they have a beginning and an end; they take place during a specific period of time and then they finish. Second, they have a specific, clear outcome that needs to happen in order for them to be checked off as complete, such as “finalize,” “green-light,” “launch,” or “publish.”

Each of these is an example of an area of responsibility, and together they make up the second main category of PARA. All these areas, both personal and professional, require certain information to be handled effectively, but they’re not the same as projects.

The third category of information that we want to keep is resources. This is basically a catchall for anything that doesn’t belong to a project or an area and could include any topic you’re interested in gathering information about.

Any note or file that isn’t relevant or actionable for a current project or area can be placed into resources for future reference.

Finally, we have our archives. This includes any item from the previous three categories that is no longer active.

The archives are an important part of PARA because they allow you to place a folder in “cold storage” so that it doesn’t clutter your workspace, while safekeeping it forever just in case you need it.

Projects are most actionable because you’re working on them right now and with a concrete deadline in mind. Areas have a longer time horizon and are less immediately actionable. Resources may become actionable depending on the situation. Archives remain inactive unless they are needed.

This order gives us a convenient checklist for deciding where to put a note, starting at the top of the list and moving down: In which project will this be most useful? If none: In which area will this be most useful? If none: Which resource does this belong to? If none: Place in archives. In other words, you are always trying to place a note or file not only where it will be useful, but where it will be useful the soonest. By placing a note in a project folder, you ensure you’ll see it next time you work on that project. By placing it in an area folder, you’ll come across it next time you’re thinking about that area of your work or life. By placing it in a resource folder, you’ll notice it only if and when you decide to dive into that topic and do some reading or research. By placing it in archives, you never need to see it again unless you want

started. The goal of organizing our knowledge is to move our goals forward, not get a PhD in notetaking. Knowledge is best applied through execution, which means whatever doesn’t help you make progress on your projects is probably detracting from them.

There is a parallel between PARA and how kitchens are organized. Everything in a kitchen is designed and organized to support an outcome—preparing a meal as efficiently as possible. The archives are like the freezer—items are in cold storage until they are needed, which could be far into the future. Resources are like the pantry—available for use in any meal you make, but neatly tucked away out of sight in the meantime. Areas are like the fridge—items that you plan on using relatively soon, and that you want to check on more frequently. Projects are like the pots and pans cooking on the stove—the items you are actively preparing right now. Each kind of food is organized according to how accessible it needs to be for you to make the meals you want to eat. Imagine

PARA isn’t a filing system; it’s a production system. It’s no use trying to find the “perfect place” where a note or file belongs. There isn’t one. The whole system is constantly shifting and changing in sync with your constantly changing life.

Any piece of information (whether a text document, an image, a note, or an entire folder) can and should flow between categories.

They had repeatedly postponed their creative ambitions to some far-off, mythical time when somehow everything would be perfectly in order. Once we set that aside and just focused on what they actually wanted to do right now, they suddenly gained a tremendous sense of clarity and motivation.

You could also create folders for your areas and resources, but I recommend starting only with projects to avoid creating lots of empty containers. You can always add others later when you have something to put inside them. Although you can and should use PARA across all the platforms where you store information—the three most common ones besides a notetaking app are the documents folder on your computer, cloud storage drives like Dropbox, and online collaboration suites like Google Docs—I recommend starting with just your notes app for now.

Each time you finish a project, move its folder wholesale to the archives, and each time you start a new project, look through your archives to see if any past project might have assets you can reuse.

don’t worry about reorganizing or “cleaning up” any existing notes. You can’t afford to spend a lot of time on old content that you’re not sure you’re ever going to need. Start with a clean slate by putting your existing notes in the archives for safekeeping. If you ever need them, they’ll show up in searches and remain just as you left them.

They require a bit more refinement to turn them into truly valuable knowledge assets, like a chemist distilling only the purest compound. This is why we separate capturing and organizing from the subsequent steps: you need to be able to store something quickly and save any future refinement for later.

Your job as a notetaker is to preserve the notes you’re taking on the things you discover in such a way that they can survive the journey into the future.

Discoverability is an idea from information science that refers to “the degree to which a piece of content or information can be found in a search of a file, database, or other information system.”

Progressive Summarization is not a method for remembering as much as possible—it is a method for forgetting as much as possible. As you distill your ideas, they naturally improve, because when you drop the merely good parts, the great parts can shine more brightly.

A helpful rule of thumb is that each layer of highlighting should include no more than 10–20 percent of the previous layer.

When the opportunity arrives to do our best work, it’s not the time to start reading books and doing research. You need that research to already be done.

Our time and attention are scarce, and it’s time we treated the things we invest in—reports, deliverables, plans, pieces of writing, graphics, slides—as knowledge assets that can be reused instead of reproducing them from scratch. Reusing Intermediate Packets of work frees up our attention for higher-order, more creative thinking.

Fourth, and best of all, eventually you’ll have so many IPs at your disposal that you can execute entire projects just by assembling previously created IPs. This

While you can sit down to purposefully create an IP, it is far more powerful to simply notice the IPs that you have already produced and then to take an extra moment to save them in your Second Brain.

Ask yourself: How could you acquire or assemble each of these components, instead of having to make them yourself?

Note:This is a key insight . design for future discoverability and use

Our creativity thrives on examples. When we have a template to fill in, our ideas are channeled into useful forms instead of splattered around haphazardly. There are best practices and plentiful models for almost anything you might want to make.

Those four retrieval methods are: Search Browsing Tags Serendipity

Search should be the first retrieval method you turn to. It is most useful when you already know more or less what you’re looking for, when you don’t have notes saved in a preexisting folder, or when you’re looking for text,

If you’ve followed the PARA system outlined in Chapter 5 to organize your notes, you already have a series of dedicated folders for each of your active projects, areas of responsibility, resources, and archives.

You will begin to see yourself as the curator of the collective thinking of your network, rather than the sole originator of ideas.

This is a turning point in the life of any creative professional—when you begin to think of “your work” as something separate from yourself.

Translated to English, it means “We only know what we make.”

One of my favorite rules of thumb is to “Only start projects that are already 80 percent done.” That might seem like a paradox, but committing to finish projects only when I’ve already done most of the work to capture, organize, and distill the relevant material means I never run the risk of starting something I can’t finish.

My father planned for creativity. He strategized his creativity. When it was time to make progress on a painting, he gave it his full focus, but that wasn’t the only time he exercised his imagination. Much of the rest of the time he was collecting, sifting through, reflecting on, and recombining raw material from his daily life so that when it came time to create, he had more than enough raw material to work with.

What I learned from my father is that by the time you sit down to make progress on something, all the work to gather and organize the source material needs to already be done. We can’t expect ourselves to instantly come up with brilliant ideas on demand. I learned that innovation and problem-solving depend on a routine that systematically brings interesting ideas to the surface of our awareness.

One of the most important patterns that underlies the creative process is called “divergence and convergence.”

The first two steps of CODE, Capture and Organize, make up divergence. They are about gathering seeds of imagination carried on the wind and storing them in a secure place. This is where you research, explore, and add ideas. The final two steps, Distill and Express, are about convergence. They help us shut the door to new ideas and begin constructing something new out of the knowledge building blocks we’ve assembled.

Your Second Brain is a powerful ally in overcoming the universal challenge of creative work—sitting down to make progress and having no idea where to start.

When you distinguish between the two modes of divergence and convergence, you can decide each time you begin to work which mode you want to be in, which gives you the answers to the questions above. In divergence mode, you want to open up your horizons and explore every possible option. Open the windows and doors, click every link, jump from one source to another, and let your curiosity be your guide for what to do next. If you decide to enter convergence mode, do the opposite: close the door, put on noise-canceling headphones, ignore every new input, and ferociously chase the sweet reward of completion. Trust that you have enough ideas and enough sources, and it’s time to turn inward and sprint toward your goal.

I used to lose weeks stalling before each new chapter, because it was just a big empty sea of nothingness. Now each chapter starts life as a kind of archipelago of inspiring quotes, which makes it seem far less daunting. All I have to do is build bridges between the islands.

An Archipelago of Ideas separates the two activities your brain has the most difficulty performing at the same time: choosing ideas (known as selection) and arranging them into a logical flow (known as sequencing).

The goal of an archipelago is that instead of sitting down to a blank page or screen and stressing out about where to begin, you start with a series of small stepping-stones to guide your efforts. First you select the points and ideas you want to include in your outline, and then in a separate step, you rearrange and sequence them into an order that flows logically. This makes both of those steps far more efficient, less taxing, and less vulnerable to interruption. Instead of starting with scarcity, start with abundance—the abundance of interesting insights you’ve collected in your Second Brain.

How do you create a Hemingway Bridge? Instead of burning through every last ounce of energy at the end of a work session, reserve the last few minutes to write down some of the following kinds of things in your digital notes: Write down ideas for next steps: At the end of a work session, write down what you think the next steps could be for the next one. Write down the current status: This could include your current biggest challenge, most important open question, or future roadblocks you expect. Write down any details you have in mind that are likely to be forgotten once you step away: Such as details about the characters in your story, the pitfalls of the event you’re planning, or the subtle considerations of the product you’re designing. Write out your intention for the next work session: Set an intention for what you plan on tackling next, the problem you intend to solve, or a certain milestone you want to reach.

Note:Make this a notion thing

Knowing that nothing I write or create truly gets lost—only saved for later use—gives me the confidence to aggressively cut my creative works down to size without fearing that I’ve wasted effort or that I’ll lose the results of my thinking forever.

Set a timer for a fixed period of time, such as fifteen or twenty minutes, and in one sitting see if you can complete a first pass on your project using only the notes you’ve gathered in front of you. No searching online, no browsing social media, and no opening multiple browser tabs that you swear you’re going to get to eventually. Only work with what you already have.

The three habits most important to your Second Brain include: Project Checklists: Ensure you start and finish your projects in a consistent way, making use of past work. Weekly and Monthly Reviews: Periodically review your work and life and decide if you want to change anything. Noticing Habits: Notice small opportunities to edit, highlight, or move notes to make them more discoverable for your future self.

The practice of conducting a “Weekly Review” was pioneered by executive coach and author David Allen in his influential book Getting Things Done.III He described a Weekly Review as a regular check-in, performed once a week, in which you intentionally reset and review your work and life.

The truth is, any system that must be perfect to be reliable is deeply flawed. A perfect system you don’t use because it’s too complicated and error prone isn’t a perfect system—it’s a fragile system that will fall apart as soon as you turn your attention elsewhere.

orchestrating and managing the process of turning information into results.

We can try to describe how we do these things, but our explanations always fall far short. That’s because we are relying on tacit knowledge, which is impossible to describe in exact detail. We possess that knowledge, but it resides in our subconscious and muscle memory where language cannot reach.

you can always fall back on the four steps of CODE: Keep what resonates (Capture) Save for actionability (Organize) Find the essence (Distill) Show your work (Express)

Thank you to Venkatesh Rao for serving as my introduction to the online world of ideas.