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Derek Sivers reads like an engineer looking for ideas he can install. The founder of CD Baby — which he sold for about $22 million and handed to a charitable trust for music education — has spent two decades publishing rated, first-person notes on every book he finishes, now more than 480 of them, at sive.rs/book. His ratings are refreshingly literal: a number from one to ten for how strongly he would recommend a book to anyone — out of ten random people, how many should read it — not how much he personally liked it. He keeps only the surprising or useful ideas, and re-reads the few that matter — Alison Gopnik's The Gardener and the Carpenter "often," some notes almost weekly.
What he takes from books is filtered through a small, consistent set of rules. He prizes usefulness over truth — adopt an idea because it helps, not because it is provably correct. He is proudly skeptical ("the opposite may also be true") and will argue against his own beliefs for a fresh angle. He says yes only to a "hell yeah," and no to almost everything else. And he hates waste. The result is a reading list that leans hard toward the actionable: psychology, Stoic philosophy, entrepreneurship and clear writing, chosen less for prestige than for what they change in how he lives and works.
Read together, Derek Sivers's recommendations look like a self-assembled operating manual for thinking and doing — practical philosophy over pure information. The origin point is Tony Robbins's Awaken the Giant Within, which he calls his "Bible" and the source of most of his beliefs: the idea that your feelings and beliefs are chosen, not given. Almost everything else is a refinement of that premise.
From there the list branches along steady lines. An entrepreneurial thread — Michael Gerber's The E-Myth Revisited ("absolutely everyone who is an entrepreneur needs to read this") and Seth Godin's This Is Marketing — treats business as a designed system and an act of generous connection rather than hustle. A Stoic-and-psychology thread runs through William Irvine's A Guide to the Good Life (Stoicism, which he says matches the philosophy he'd lived by since seventeen), Ryan Holiday's Ego Is the Enemy, and the Adlerian The Courage to Be Disliked — all about doing the work and caring less what others think. A human-nature thread — Stumbling on Happiness, Cialdini's Influence, and Sapiens — keeps him honest about how badly minds misjudge themselves. And a craft thread — On Writing Well and Pressfield's The War of Art — insists that clear expression and beating resistance are skills, not gifts.
The through-line is method as much as taste. Every book is rated by how strongly he would recommend it, kept as notes, re-read, and acted upon; the point is behaviour change, not shelf decoration. It mirrors his own arc — musician and circus performer, then the accidental entrepreneur of CD Baby, then a writer and philosopher — a reader steadily converting other people's ideas into a usable way to live.
Once you accept that beliefs are chosen, the next question is practical — how to build something that runs as a system, not on willpower.
A business that works still has to reach people, which Godin reframes as generous, human connection rather than hustle.
Success exposes the deeper question Stoicism answers: what is actually worth wanting, and how to keep an even keel.
And knowing how to live still leaves the daily fight — sitting down and beating the resistance that stops the work.
His single most life-changing book — the source of his conviction that beliefs and feelings are chosen.
“This 1992 book changed everything about my life. It's my Bible. Most of my beliefs come from it.”WebsiteSource: Derek Sivers — book notes (sive.rs)
His most-recommended book for entrepreneurs — building a business as a system rather than a job.
“Absolutely everyone who is an entrepreneur or wants to be one needs to read this book.”WebsiteSource: Derek Sivers — book notes (sive.rs)
Marketing reframed as generous, human connection — a natural companion to his own business writing.
“A must-read for every entrepreneur. A holistic, generous, human, emotional, long-term, story-driven approach.”WebsiteSource: Derek Sivers — book notes (sive.rs)
The book that gave a name to the Stoicism he had been living by instinctively for years.
“The quirky philosophy I've been living by since 17 matches up exactly with a 2000-year-old philosophy: Stoicism.”WebsiteSource: Derek Sivers — book notes (sive.rs)
The Stoic-practical case for discipline over self-regard — do the work, drop the ego.
“Forget yourself and focus on the work. Be humble and persistent.”WebsiteSource: Derek Sivers — book notes (sive.rs)
A 10/10 for him — Adlerian psychology on choosing your own life regardless of others’ approval.
“A profound little philosophy book from Japan, communicating the psychology of Alfred Adler.”WebsiteSource: Derek Sivers — book notes (sive.rs)
A 10/10 on beating creative resistance — the daily discipline of simply sitting down to do the work.
WebsiteSource: Derek Sivers — book notes (sive.rs)
The craft book behind his famously plain, generous prose — clear writing as clear thinking.
“Great blunt advice about writing better non-fiction. So inspiring.”WebsiteSource: Derek Sivers — book notes (sive.rs)
A 10/10 of hard psychology, not self-help — how badly we predict what will make us happy.
“I read and loved Stumbling on Happiness. Loved that book!”WebsiteSource: Derek Sivers — book notes (sive.rs)
The persuasion classic he has carried for decades — how decisions are really made.
“I read it 15 years ago, thought about it ever since, and re-read it now.”WebsiteSource: Derek Sivers — book notes (sive.rs)
He likes it most where Harari shows how shared "truths" are useful fictions — a theme close to his own.
WebsiteSource: Derek Sivers — book notes (sive.rs)A 10/10 that reframes almost everything in life as negotiable once you see your own power.
“A must-read classic from a master negotiator, filled with so many memorable stories.”WebsiteSource: Derek Sivers — book notes (sive.rs)
His pick for the definitive habits book — and Clear, in turn, credits Derek as an influence.
“Holy crap! It's GREAT! Feels like the definitive masterpiece on how to make good habits and break bad ones.”WebsiteSource: Derek Sivers — book notes (sive.rs)
A 10/10 he re-reads often — parenting (and much else) as gardening, not carpentry.
“Such a beautiful mindset and outlook. Required reading for every parent.”WebsiteSource: Derek Sivers — book notes (sive.rs)
A 10/10 of pure imagination — the one piece of fiction that shows his taste for perspective-shifting ideas.
“Awesomely creative think-piece: 40 very short fictional stories about what happens when you die.”WebsiteSource: Derek Sivers — book notes (sive.rs)
Derek names Tony Robbins’s Awaken the Giant Within as the most life-changing — he calls it his "Bible" and says most of his beliefs come from it, chiefly the idea that your beliefs and feelings are chosen rather than given.
For entrepreneurs he most often recommends Michael Gerber’s The E-Myth Revisited and Seth Godin’s This Is Marketing. Across everything, his highest-rated picks include The War of Art, The Courage to Be Disliked, Stumbling on Happiness, On Writing Well and A Guide to the Good Life.
He rates every book he reads from 1 to 10 by how strongly he'd recommend it — out of ten random people, how many should read it — rather than how much he personally liked it or how good it objectively is. He publishes notes on more than 480 books at sive.rs/book, and the list updates as he re-reads.
His practical-philosophy shelf centres on Stoicism and psychology: A Guide to the Good Life (William Irvine), Ego Is the Enemy (Ryan Holiday), and the Adlerian The Courage to Be Disliked. They share one message he lives by — do the work and care less what others think.
Yes. The E-Myth Revisited is his top pick for anyone starting a company, This Is Marketing reframes marketing as generous connection, and Cialdini’s Influence explains how people actually decide — all rated 9–10/10 in his notes.
On his own site at sive.rs/book, where he keeps rated, first-person notes on every book he reads. He also names favourites in interviews, especially across his many appearances on The Tim Ferriss Show. Each entry above links to its source.