Derek Sivers
Author of How to Live and Anything You Want, founder of CD Baby
Where to hear and read about Derek Sivers1 episode or test
Derek Sivers is the author of Anything You Want and How to Live and the founder of CD Baby, who writes by cutting every idea down to its essence. The thing most worth learning from him is to publish one simple idea at a time, test it on people, and only then gather the survivors into a book.
is this really worth killing a tree over
Derek Sivers: No Wasted Words
Derek Sivers: the story and the lessons
1Why Derek Sivers writes his ideas down
Sivers writes so his thinking outlasts him. His friend Milt Olin never wrote anything down and was killed on his bicycle, so his wisdom stayed with the few people he talked to.
After every long restaurant talk with Milt, Sivers went home and took notes, so some of it was kept. He still asks himself what Milt would say in hard situations.
He asks what a mentor would say before contacting them. His article at sive.rs/ment describes imagining a mentor's answer before sending the message.
Often he never sends it, because imagining the answer was enough.
He shares even unremarkable views because sharing a view shares you. He sees personality as everything you have learned, filtered through the traits you adopted. Publishing a point of view passes that filter on.
He writes hoping to change one reader's view of the world. Books that blew his mind motivate him to share his own insights. He pictures a reader anywhere from Nepal to Nebraska saying this helps them live.
He emails the author of every book he loves. After each book he loves, he finds the author's address, digging if he has to, and says why he loved it. They almost always reply.
He thinks far fewer readers do this than people assume, and that one sincere note means more to a writer than seven figures of page views.
2How Sivers built his books
Sivers posts ideas one at a time before they become a book. His first advice on writing a book is not to think of it as a book. He posts each idea as its own article, sees where he was thinking wrong, then collects the ones that held up.
A great idea on page 280 rarely gets read, because few people buy books and fewer finish them.
The Hell yeah or no idea took shape in a phone call. Sivers was dreading a conference in Australia and wanted to say no to almost everything. The musician Amber Rubarth reframed it as a choice between 'fuck yeah' or no, and he wrote the article that night.
His first version was longer and credited her, and he changed the word to 'hell' later. Penguin cut it to about 10 sentences for a Seth Godin book, and he was fine with that.
Anything You Want took about 20 hours because the stories were already told. Seth Godin phoned him out of the blue asking for a manifesto of 10,000 to 11,000 words. About half was how Sivers started, grew and left CD Baby, a story he had told friends and conference audiences.
He had heard where listeners laughed, so he knew what to keep. He sent it to Godin, who liked it, and it came out a week later.
How to Live took almost four years and shrank from 1,300 pages to 112. It was his attempt to put everything important he had learned into one book. He cut a 1,300-page draft down so each original page became about a sentence.
Editors kept asking how to make it more persuasive, and each chapter felt like the answer until the next argued the opposite. He drew the line somewhere and called it good enough. He also stopped reading new books while writing so no new wisdom would disturb the draft.
He sells his books directly and gives all the money to charity. His own site offers four books at one price that covers paper, ebook and audiobook. Bought directly, the full $15 goes to charity, and buyers get an email from him whose replies come straight to him.
He had built a store before with CD Baby. Former 80s and 90s rock stars told him that seeing the name and comment of each direct buyer felt better than a million sales through Warner Brothers or EMI.
He writes daily but publishes only once or twice a week. He tried posting an article every day for 30 days, copying Seth Godin, and felt it lowered his standard. He now publishes only ideas that feel like 'damn, that is so worth sharing'.
A reader who knows his work well judged the 30 daily posts no worse than the rest. Sivers allows he may be wrong to pre-filter, and admits he has shared too little in the past couple of years.
3Sivers's method for cutting writing down
Sivers dumps every thought, then argues against it. He writes everything he thinks into a document unfiltered, then questions each point, answers the questions, and questions the answers until the dump is exhaustive.
He keeps the process as a short list at sive.rs/seven.
He outlines only the gist, so articles stay short. After the dump he asks what the gist of his conclusion is and writes a bullet outline of a few words per point. He adds a sentence of context only where a point would not make sense without it.
The average article on his site comes to about 22 sentences.
He writes like he talks, minus the unnecessary words. His writing is a simplified version of how he speaks. He puts little conscious thought into craft and focuses on the core idea.
He says young writers who imitate novels come out trying too hard.
He treats filler phrases as pollution. He singles out phrases like 'going forward', 'on the other hand' and 'come to think of it' as adding nothing. A sentence that does not need to be there should not be put into the world.
He tests every sentence against the cost of a tree. When he decided to print hardcovers, thinking about the paper made him cut harder than he would for online-only writing.
Each sentence had to be 'worth killing a tree over'.
He unlearned page counts and keeps asking how to say less. He calls the school habit of writing 10 pages or a 300-page book the hardest to unlearn, because padding makes it sound like you say something when you say nothing.
He cites Jason Fried's exercise: write two pages, then one page, then a paragraph, then a sentence, keeping the same information.
He keeps craft from overshadowing the idea. Deep skill makes him notice details like an echo in a song, but craft is pointless without a good idea underneath. Lovely word combinations can hide a banal point.
He watched Natural Born Killers repeatedly just for its editing, and has to switch off his editor's ear to hear the point.
He applies the same simplicity to tools and objects. He calls himself not hyper disciplined but hyper simplified, and asks of every idea, task and object how it could be simpler. He works full screen in a Unix terminal on OpenBSD with the ratpoison window manager.
Twelve designers produced 36 cover designs for How to Live, and he chose just title and author, like an old library book. His wife objected when he tried to make her house that minimalist, so he drew the line there.
4How Derek Sivers gets ideas and keeps learning
Sivers tests ideas in conversation like a comedian. His favorite ideas came from two-way banter, in person or by phone. He watches whether the other person shrugs, pushes back or says 'that's so true', and turns what lands into articles.
In two years in Singapore he had 490 one-on-one coffees, then moved to New Zealand for his son and for focus. Living far from people costs him ideas, but he still has calls with friends around the world.
He types up notes on every nonfiction book he reads. In 2007 he found he remembered nothing from a book he had read five years earlier. He now underlines while reading, then types favorite ideas, often paraphrased, into a text file.
He posts notes for about 330 books at sive.rs/book, scans old notes weekly, and rereads the relevant ones when wrestling with a problem. He can give away the book and reread two pages of notes instead of 300.
He practices writing the way musicians practice. Musicians repeat the awful-sounding bits they cannot yet play, and Sivers suggests writers find what they cannot yet do and drill it.
He studied songs to find exactly which note, chord or word worked. At Berkeley School of Music, teachers assigned three songs by Thursday using one technique, such as splitting an eight-bar phrase into five and three. Some of his best songs came from those challenges.
He says to keep looking when you think you have nothing to write. He links comedy, drawing and writing through attention to detail. In the fish story, a teacher put a fish on the table, students said there was nothing to write, and he told them to keep looking.
By semester's end they were to write about 3,000 words on its scales, color and history.
He tests his assumptions by living in very different cultures. He wanted to open a silent co-working space in Singapore called solitude.sg, and his Singaporean friends pushed back. In Chinese culture, they said, noise is life and silence is death.
He argues that cultures are philosophies in action, so you should go beyond visiting and try to see the world that way.
Derek Sivers: No Wasted Words
Derek Sivers explains how he writes short, simplified pieces by dumping every thought, arguing with himself, then cutting to the gist, and why he publishes ideas one at a time before they become a book. The habits worth hearing are his arguing-with-yourself brain dump, his 22-sentence outline method, and his book-note routine.
Sivers writes so his thinking outlasts him. His friend Milt Olin never wrote anything down and was killed on his bicycle, so his wisdom stayed with the few people he talked to.
After every long restaurant talk with Milt, Sivers went home and took notes, so some of it was kept. He still asks himself what Milt would say in hard situations.
He asks what a mentor would say before contacting them. His article at sive.rs/ment describes imagining a mentor's answer before sending the message.
Often he never sends it, because imagining the answer was enough.
He shares even unremarkable views because sharing a view shares you. He sees personality as everything you have learned, filtered through the traits you adopted. Publishing a point of view passes that filter on.
He writes hoping to change one reader's view of the world. Books that blew his mind motivate him to share his own insights. He pictures a reader anywhere from Nepal to Nebraska saying this helps them live.
He emails the author of every book he loves. After each book he loves, he finds the author's address, digging if he has to, and says why he loved it. They almost always reply.
He thinks far fewer readers do this than people assume, and that one sincere note means more to a writer than seven figures of page views.
Sivers posts ideas one at a time before they become a book. His first advice on writing a book is not to think of it as a book. He posts each idea as its own article, sees where he was thinking wrong, then collects the ones that held up.
A great idea on page 280 rarely gets read, because few people buy books and fewer finish them.
The Hell yeah or no idea took shape in a phone call. Sivers was dreading a conference in Australia and wanted to say no to almost everything. The musician Amber Rubarth reframed it as a choice between 'fuck yeah' or no, and he wrote the article that night.
His first version was longer and credited her, and he changed the word to 'hell' later. Penguin cut it to about 10 sentences for a Seth Godin book, and he was fine with that.
Anything You Want took about 20 hours because the stories were already told. Seth Godin phoned him out of the blue asking for a manifesto of 10,000 to 11,000 words. About half was how Sivers started, grew and left CD Baby, a story he had told friends and conference audiences.
He had heard where listeners laughed, so he knew what to keep. He sent it to Godin, who liked it, and it came out a week later.
How to Live took almost four years and shrank from 1,300 pages to 112. It was his attempt to put everything important he had learned into one book. He cut a 1,300-page draft down so each original page became about a sentence.
Editors kept asking how to make it more persuasive, and each chapter felt like the answer until the next argued the opposite. He drew the line somewhere and called it good enough. He also stopped reading new books while writing so no new wisdom would disturb the draft.
He sells his books directly and gives all the money to charity. His own site offers four books at one price that covers paper, ebook and audiobook. Bought directly, the full $15 goes to charity, and buyers get an email from him whose replies come straight to him.
He had built a store before with CD Baby. Former 80s and 90s rock stars told him that seeing the name and comment of each direct buyer felt better than a million sales through Warner Brothers or EMI.
He writes daily but publishes only once or twice a week. He tried posting an article every day for 30 days, copying Seth Godin, and felt it lowered his standard. He now publishes only ideas that feel like 'damn, that is so worth sharing'.
A reader who knows his work well judged the 30 daily posts no worse than the rest. Sivers allows he may be wrong to pre-filter, and admits he has shared too little in the past couple of years.
Sivers dumps every thought, then argues against it. He writes everything he thinks into a document unfiltered, then questions each point, answers the questions, and questions the answers until the dump is exhaustive.
He keeps the process as a short list at sive.rs/seven.
He outlines only the gist, so articles stay short. After the dump he asks what the gist of his conclusion is and writes a bullet outline of a few words per point. He adds a sentence of context only where a point would not make sense without it.
The average article on his site comes to about 22 sentences.
He writes like he talks, minus the unnecessary words. His writing is a simplified version of how he speaks. He puts little conscious thought into craft and focuses on the core idea.
He says young writers who imitate novels come out trying too hard.
He treats filler phrases as pollution. He singles out phrases like 'going forward', 'on the other hand' and 'come to think of it' as adding nothing. A sentence that does not need to be there should not be put into the world.
He tests every sentence against the cost of a tree. When he decided to print hardcovers, thinking about the paper made him cut harder than he would for online-only writing.
Each sentence had to be 'worth killing a tree over'.
He unlearned page counts and keeps asking how to say less. He calls the school habit of writing 10 pages or a 300-page book the hardest to unlearn, because padding makes it sound like you say something when you say nothing.
He cites Jason Fried's exercise: write two pages, then one page, then a paragraph, then a sentence, keeping the same information.
He keeps craft from overshadowing the idea. Deep skill makes him notice details like an echo in a song, but craft is pointless without a good idea underneath. Lovely word combinations can hide a banal point.
He watched Natural Born Killers repeatedly just for its editing, and has to switch off his editor's ear to hear the point.
He applies the same simplicity to tools and objects. He calls himself not hyper disciplined but hyper simplified, and asks of every idea, task and object how it could be simpler. He works full screen in a Unix terminal on OpenBSD with the ratpoison window manager.
Twelve designers produced 36 cover designs for How to Live, and he chose just title and author, like an old library book. His wife objected when he tried to make her house that minimalist, so he drew the line there.
Sivers tests ideas in conversation like a comedian. His favorite ideas came from two-way banter, in person or by phone. He watches whether the other person shrugs, pushes back or says 'that's so true', and turns what lands into articles.
In two years in Singapore he had 490 one-on-one coffees, then moved to New Zealand for his son and for focus. Living far from people costs him ideas, but he still has calls with friends around the world.
He types up notes on every nonfiction book he reads. In 2007 he found he remembered nothing from a book he had read five years earlier. He now underlines while reading, then types favorite ideas, often paraphrased, into a text file.
He posts notes for about 330 books at sive.rs/book, scans old notes weekly, and rereads the relevant ones when wrestling with a problem. He can give away the book and reread two pages of notes instead of 300.
He practices writing the way musicians practice. Musicians repeat the awful-sounding bits they cannot yet play, and Sivers suggests writers find what they cannot yet do and drill it.
He studied songs to find exactly which note, chord or word worked. At Berkeley School of Music, teachers assigned three songs by Thursday using one technique, such as splitting an eight-bar phrase into five and three. Some of his best songs came from those challenges.
He says to keep looking when you think you have nothing to write. He links comedy, drawing and writing through attention to detail. In the fish story, a teacher put a fish on the table, students said there was nothing to write, and he told them to keep looking.
By semester's end they were to write about 3,000 words on its scales, color and history.
He tests his assumptions by living in very different cultures. He wanted to open a silent co-working space in Singapore called solitude.sg, and his Singaporean friends pushed back. In Chinese culture, they said, noise is life and silence is death.
He argues that cultures are philosophies in action, so you should go beyond visiting and try to see the world that way.