The Visual Display of Quantitative Information (1983)

What is to be sought in designs for the display of information is the clear portrayal of complexity. Not the complication of the simple; rather the task of the designer is to give visual access to the subtle and the difficult—that is, revelation of the complex.

The Design of Everyday Things (1988)

Good design is actually a lot harder to notice than poor design, in part because good designs fit our needs so well that the design is invisible...

The Seven Storey Mountain (1948)

The more you try to avoid suffering, the more you suffer, because smaller and more insignificant things begin to torture you, in proportion to your fear of being hurt. The one who does most to avoid suffering is, in the end, the one who suffers most.

interview by Scandinavian Mind

I believe design is just good engineering. That's why I tell my designers to always think like an engineer. So I set up really strict rules on how they are allowed to work. So for example, we're only allowed to use six or eight colours in total, same with the typeface, we only write in lowercase with one font in a set of sizes that is in a system connected to a grid.

On the Road (1957)

The only people for me are the mad ones, the ones who are mad to live, mad to talk, mad to be saved, desirous of everything at the same time, the ones who never yawn or say a commonplace thing, but burn, burn, burn like fabulous yellow roman candles exploding like spiders across the stars.

I am a creative (2024)

I am a creative. What I do is alchemy. It is a mystery. I do not so much do it, as let it be done through me.

Unknown

To find yourself think for yourself.

Twitter

The world operates on this weird law where the best things happen to you when you're not trying super hard to do anything other than just expressing yourself truthfully.

Disputed Origin

Yesterday I was clever, so I wanted to change the world. Today I am wise, so I am changing myself.

This Is Water (2009)

Because here's something else that's weird but true: in the day-to day trenches of adult life, there is actually no such thing as atheism. There is no such thing as not worshipping. Everybody worships. The only choice we get is what to worship. And the compelling reason for maybe choosing some sort of god or spiritual-type thing to worship—be it JC or Allah, be it YHWH or the Wiccan Mother Goddess, or the Four Noble Truths, or some inviolable set of ethical principles—is that pretty much anything else you worship will eat you alive. If you worship money and things, if they are where you tap real meaning in life, then you will never have enough, never feel you have enough. It's the truth. Worship your body and beauty and sexual allure and you will always feel ugly. And when time and age start showing, you will die a million deaths before they finally grieve you. On one level, we all know this stuff already. It's been codified as myths, proverbs, clichés, epigrams, parables; the skeleton of every great story. The whole trick is keeping the truth up front in daily consciousness.

A Great Wagon

Out beyond ideas of wrongdoing and right doing there is a field. I'll meet you there. When the soul lies down in that grass, the world is too full to talk about.

Walden (1854)

If one advances confidently in the direction of his dreams, and endeavors to live the life which he has imagined, he will meet with a success unexpected in common hours.

Living, Loving & Learning (1982)

The person who risks nothing, does nothing, has nothing, is nothing, and becomes nothing. He may avoid suffering and sorrow, but he simply cannot learn, feel, change, grow, or love. Chained by his certitude, he is a slave; he has forfeited his freedom. Only the person who risks is truly free.

Twitter

The foundational challenge in design is that it's easy to make things hard and hard to make things simple.

Twitter

I asked my hotness consultant if she could make people desire me and she said yes but once i became hot i realized everyone around me was suffering so i went and asked her why and she said desire and suffering are the same.

Twitter

Plans are worthless, planning is priceless. Spend a day making elaborate plans and then disregard them completely to make whatever you think is most compelling.

Collapsing the Talent Stack

Collapse the talent stack every chance you get. As I reflect on the teams I've led and hundreds of start-ups I've worked with, there is a consistent unfair competitive advantage i've witnessed when the talent stack was collapsed - when the lead designer was also the product leader, when the front-end engineer was also a designer, when the designer is also a great copywriter, when the product leader was also the founder/ceo, etc. Tighter conduits for decision making and synthesizing information are an incredible advantage when it comes to crafting products. Many start-ups enjoy the benefits of collapsed talent stacks and then undo them as they grow (and most big companies just don't understand this). In your hiring (and your consolidating)

Twitter

There are huge, huge swathes of expertise where six weeks of obsession makes you indistinguishable from someone who knows the field.

Unknown

Don't hurry, don't stop.

Twitter

You obsess over your identity in relation to others while your soul rots inside of you.

Unknown

Simplicity is the ultimate sophistication.

Twitter

You mock those who drown in pleasure because they can't find meaning. Yet you drown in meaning because you never learned how to feel pleasure. You became addicted to being the one who always delays the reward. You're under the illusion that you're noble, but the reality is that joy just feels foreign. Because ease feels undeserved. Because when you actually sit still, there's nothing there. So you built a fortress out of effort. You worship the work. You call it purpose but it's a coping mechanism. You sold your present for a future that never arrives. And still, you double down. Because it's easier to suffer with a reason than to admit you don't know how to be satisfied. Duties became your drug. Labor became your lord. In the end, you might realize you didn't beat the game. You just got really good at never cashing in on the life you're building. Forever delaying gratification is no gratification.

Twitter

Doomed are societies in which people, after hearing about Pythagoras' theorem, want to know Pythagoras' political party affiliation in order to decide whether the theorem is correct.

Pensées 139 (1670)

All of humanity's problems stem from man's inability to sit quietly in a room alone.

Unknown

Shared joy is a double joy; shared sorrow is half a sorrow.

Unknown

Talk to everyone you find attractive. Spend time with the ones you have good chemistry with. Date ones that you connect with intellectually and morally. Marry the one whose place in life and goals match up pretty well to yours.

Twitter

If you want respect, take on responsibility.

The Elements of Typographic Style (1992)

With type as with philosophy, music and food, it is better to have a little of the best than to be swamped with the derivative, the careless, the routine.

interview on Invest Like The Best

If Stripe is a monstrously successful business but what we make isn't beautiful and Stripe doesn't embody a culture of incredibly exacting craftsmanship, I'll be much less happy. My intuition is that more of Stripe success than one would think is down to the fact that people like beautiful things and for rational reasons. Because, what does a beautiful thing tell you? It tells you the person who made it really cared, and you can observe some superficial details, but probably they didn't only care about those and did everything else in a slapdash way. So, if you care about the infrastructure being holistically good, indexing on the superficial characteristics is not an irrational thing to do.

having fun (2023)

You have to do the thing you actually enjoy doing, not the thing you find conceptually exciting. You have to date the person you actually like, not the ideal perfection you fetishise in your mind. And you have to have enough self-knowledge to know what you enjoy.

Unknown

When I am working on a problem I never think about beauty. I only think about how to solve the problem. But when I have finished, if the solution is not beautiful, I know it is wrong.

Unknown

Never complain, never explain.

Luke 14:28-30

For which of you, intending to build a tower, does not sit down first and count the cost, whether he has enough to finish it — lest, after he has laid the foundation, and is not able to finish, all who see it begin to mock him, saying, 'This man began to build and was not able to finish'?

Taste for Makers

When you're forced to be simple, you're forced to face the real problem. When you can't deliver ornament, you have to deliver substance.

The Prophet (1923)

And I say that life is indeed darkness save when there is urge, And all urge is blind save when there is knowledge, And all knowledge is vain save when there is work, And all work is empty save when there is love.

Discourses, Book I, Chapter 2 (1535)

What then? Because I have no natural gifts, shall I on that account give up my discipline? Far be it from me! Epictetus will not be better than Socrates; but if only I am not worse, that suffices me. For I shall not be a Milo, either, and yet I do not neglect my body; nor a Croesus, and yet I do not neglect my property; nor, in a word, is there any other field in which we give up the appropriate discipline merely from despair of attaining the highest.

Either/Or: A Fragment of Life (1843)

He cannot become old, for he has never been young; he cannot become young, for he has already become old; in a way he cannot die, for he has never lived; in a way he cannot live, for he is already dead.

interview on Jack Neel Podcast

Figure out what you want. Ignore the opinions of others. And do so much volume that it would be unreasonable that you would be unsuccessful.

Hamlet Act 1, Scene 3 (1601)

…This above all: to thine own self be true, And it must follow, as the night the day, Thou canst not then be false to any man…

Chapter 2, Verse 47

You have the right to work only but never to its fruits. Let not the fruits of action be your motive, nor should you become attached to inaction.

The Art of Fielding (2011)

You told me once that a soul isn't something a person is born with but something that must be built, by effort and error, study and love. And you did that with more dedication than most, that work of building a soul - not for your own benefit but for the benefit of those who knew you.

Unknown

Sometimes magic is just someone spending more time on something than anyone else might reasonably expect.

Unknown

The brave do not live forever, but the cautious do not live at all.

Psychology and Alchemy

People will do anything, no matter how absurd, to avoid facing their own souls. They will practice Indian yoga and all its exercises, observe a strict regimen or diet, learn theosophy by heart, or mechanically repeat mystic texts from the literature of the whole world – all because they cannot get on with themselves and have not the slightest faith that anything useful could ever come out of their souls. … It is rewarding to watch patiently the silent happenings in the soul, and the most and the best happens when it is not regulated from outside and from above. I readily admit that I have such a great respect for what happens in the human soul that I would be afraid of disturbing and distorting the silent operation of nature by clumsy interference.

Skin in the Game (2018)

Anything you do to optimize your work, cut some corners, or squeeze more "efficiency" out of it (and out of your life) will eventually make you dislike it. Artisans have their soul in the game. Primo, artisans do things for existential reasons first, financial and commercial ones later. Their decision making is never fully financial, but it remains financial. Secundo, they have some type of "art" in their profession; they stay away from most aspects of industrialization; they combine art and business. Tertio, they put some soul in their work: they would not sell something defective or even of compromised quality because it hurts their pride. Finally, they have sacred taboos, things they would not do even if it markedly increased profitability. Compendiaria res improbitas, virtusque tarda—the villainous takes the short road, virtue the longer one. In other words, cutting corners is dishonest.

Unknown

To the extent that all I've done is pick stocks that have gone up, and sat on my ass as my family got richer, I haven't left much contribution to society. I guess it's a lot like Wall Street. The difference is, I feel ashamed of it. I try to make up for it with philanthropy and meetings like this one today. This meeting is not out of kindness. This is atonement.

interview on mtv.com

I have a theory, which has not let me down so far, that there is an inverse relationship between imagination and money. Because the more money and technology that is available to [create] a work, the less imagination there will be in it.

Unknown

It is the mark of a charlatan to explain a simple concept in a complex way, and it's the mark of a genius to explain a complicated thing in a simple way

interview on Storytelling by WNYC

Nobody tells this to people who are beginners, I wish someone told me. All of us who do creative work, we get into it because we have good taste. But there is this gap. For the first couple years you make stuff, it's just not that good. It's trying to be good, it has potential, but it's not. But your taste, the thing that got you into the game, is still killer. And your taste is why your work disappoints you. A lot of people never get past this phase, they quit. Most people I know who do interesting, creative work went through years of this. We know our work doesn't have this special thing that we want it to have. We all go through this. And if you are just starting out or you are still in this phase, you gotta know its normal and the most important thing you can do is do a lot of work. Put yourself on a deadline so that every week you will finish one story. It is only by going through a volume of work that you will close that gap, and your work will be as good as your ambitions. And I took longer to figure out how to do this than anyone I've ever met. It's gonna take awhile. It's normal to take awhile. You've just gotta fight your way through.