12 life principles I learned from Derek Sivers

While others chase K-pop stars and Elon Musk, I’m a fanboy of an eccentric writer living in New Zealand.

A while ago, I saw wiwi share Derek Sivers’ quotes, and I decided it was time to finally write this fan post.

I’m afraid I won’t capture Derek Sivers’ magic well enough, but how can my blog not have a post about Derek Sivers?

Derek Sivers is the person I admire most right now. No contest. Though I’ve only known about him for two years, I’ve never resonated with anyone this much. I’ve learned more from his articles, books, and podcast appearances than from any business or self-help book. We all know these truths, but when I read them in his words, they just make sense.

I started blogging because of him. I wrote “Player Mindset” because of him. I want to persist in writing like him, make complex ideas simple, and write things only I can write.

So I can say without hesitation: knowing Derek Sivers has made me become a better person.

Because his books are independently published, there aren’t many Chinese translations. But I hope more people in the Chinese-speaking world can get to know him and read his many unique and interesting ideas.

The first shock

My first exposure to Derek Sivers was listening to Tim Ferriss’ podcast episode 668, where Tim flew halfway around the world to New Zealand just to record with him. My first impression was how captivating his speaking was—the control of pace, tone, and pauses. I couldn’t help but want to keep listening (later I learned he was a circus ringmaster!).

In the show, he urged everyone to be tech independent—don’t rely on platforms, have your own website, use Linux. He even wrote an entire blog post teaching people how to do it step by step. Hard to imagine that a former musician is more of a true tech nerd than many actual tech people.

The most shocking part was at the end of the show when he said listeners could email him and he’d reply to everyone, because people who listen to Tim’s podcast are his kind of people. My reaction: Isn’t everyone on Tim Ferriss’ show super famous? He still has time to reply to emails?

Spoiler: He really does.

Who is Derek Sivers

And so I fell down the Derek Sivers rabbit hole.

Derek Sivers has an absurd number of identities:

• Musician: Berklee College of Music graduate, band frontman, toured with Ryuichi Sakamoto as guitarist
• Programmer: Self-taught coder, runs his own email server, started nownownow
• Entrepreneur: Founded CD Baby (service helping musicians sell CDs online), sold for $22 million in 2008
• Writer: Wrote five books, all self-published except the first (which he later reclaimed rights to and republished independently)
• Circus Ringmaster: Performed in circus (this explains his stage presence)

He’s written five books:

1. Anything You Want (2011) - 40 lessons on entrepreneurship
2. Your Music and People (2020) - Marketing wisdom for creative workers
3. Hell Yeah or No (2020) - What’s worth doing
4. How to Live (2021) - 27 philosophies of life
5. Useful Not True (2024) - Useful beats true

Each can be read in 90 minutes, but you’ll want to reread them. All deserve five stars.

His website has over 200 articles. The articles are short, but each goes straight to the point, no fluff, very useful.

What he’s done is even more absurd:

• Put all $22 million in a trust, only taking 5% annually, donating everything to music education after death
• Gave up his US passport and moved to Singapore, then New Zealand, house has only 3 cups and one plate
• Runs his own email server because he doesn’t want to depend on Google
• Runs his own bookstore because he doesn’t want to depend on Amazon
• Website design is as simple as a 90s site, but every article is worth reading three times
• Donates all book revenue to charity
• Recently he bought a small plot of land and plans to build a shed and move in. At first, just a bed. Whether he needs a toilet can be decided later. Building a house in a modular way like writing code.

His attitude toward money

This is what I admire most about him. Because I still care too much about money myself. His attitude toward money completely defies convention.

After selling CD Baby, he didn’t buy yachts or mansions. Instead, he put all $22 million in a trust fund, restricting himself to 5% annually, with everything going to music education after his death.

He doesn’t use publishers for his books—sells them all on his website, then donates the money. Why? Because he doesn’t need more money, but these charities do.

He says: “I already have enough money.”

In this age where everyone wants more of everything, people say “don’t value money too much,” but how many can actually do what he does?

12 life principles I learned from Derek Sivers

Below are 12 principles I’ve distilled from Derek Sivers, along with 60 curated blog posts. Worth rereading whenever life gets off track.

1. Keep it simple

Derek’s writing is like programming: every line has a function, delete what’s useless. Every sentence in his books is carefully selected, edited down until nothing more can be removed. Even his domain sive.rs is ultra-short, though he also owns sivers.com. Life should be simple too—don’t be bound by materialism and rules. Simplicity comes from subtraction, not addition.

• Subtract - Change your life through subtraction; the world pushes addition, but the secret is subtraction
• Writing one sentence per line - Write each sentence on its own line to see which ones shouldn’t exist
• My writing process - Core of seven-step writing: after finishing, keep only the outline, delete everything else
• Write plain text files - Just use plain text files; simple tools can carry a lifetime of thoughts
• To hone your writing, hire a translator - How translation costs force you to delete every unnecessary word

2. Be clear

If you can’t explain it clearly, you don’t really understand it. His articles are all very simple and clear. Using “donkey starving between two haystacks” to teach about choices, using “learning to love China/Dubai again” to talk about change. Clarity comes from painful editing until it can’t be misunderstood.

• You should feel pain when unclear - One unclear sentence cost CD Baby five thousand dollars; lack of clarity is costly
• Here’s how to live: Learn - If you can’t explain it in your own words, you haven’t learned it yet
• Learning the lesson, not the example - Use metaphors to understand complex concepts, don’t get stuck on the examples themselves
• Obvious to you. Amazing to others - What’s clear and obvious to you is mind-blowing insight to others
• Just tell me what to do - Compress knowledge into executable instructions

3. Reduce choices

Efficiency isn’t doing more, it’s choosing less. Automate 80% of decisions, save attention for the truly important 20%. Fewer choices create greater impact.

• Don’t be a donkey - Fable of donkey starving between two haystacks teaches long-term thinking in choices
• Hell Yeah or No - If it’s not “hell yeah,” say NO; automate 80% of decisions
• Saying no to everything else - One decision can replace all decisions; say yes to one thing means saying no to everything else
• Here’s how to live: Commit - “Decide” in Latin means to “cut off” other options
• One big choice shapes a hundred more - How one big decision reduces future decision burden

4. Be useful

He takes “useful” very seriously. Every article must let readers learn or reflect. Don’t worry about what’s true or right—what’s useful to you matters most. Useful beats correct.

• How to be useful to others - Four ways to be useful to others
• Happy, Smart, and Useful - Major life decisions need to balance happiness, intelligence, and usefulness
• How do you grade yourself? - Measure yourself by how much useful stuff you create
• Here’s how to live: For others - No one helps those who don’t help others
• Useful Not True - Choose beliefs based on usefulness, not absolute truth

5. Embrace long-term thinking

When making decisions, ask: “Ten years from now, will this still matter?” Look at today from ten years in the future, automatically filter noise and meaningless actions. We often overestimate what we can accomplish in a year but underestimate what we can accomplish in 10 years. Long-term thinking solves short-sighted problems.

• Here’s how to live: Think super-long-term - We overestimate what we can do in a year, underestimate what we can do in ten years
• After fifteen years of practice - From age 14 determination to age 29 realization, the true story of fifteen years of practice
• Here’s how to live: Value only what has endured - Only value what has stood the test of time
• Are you present-focused or future-focused? - Deep dive into time orientation psychology
• Possible futures - One folder containing 72 possible futures

6. Be independent

Better to deal with hassle than hand your fate to big companies. Use Linux, self-host servers, sell your own books, because losing control is slow death. Independence is the foundation of all freedom.

• Here’s how to live: Be independent - All suffering comes from dependence; self-host servers, use open source, control your own data
• Tech Independence - Complete tutorial: how to build your own server and escape corporate cloud captivity
• Write plain text files - Use plain text to ensure your words outlive any company
• Anything You Want — third edition - Why he bought back rights from Penguin to self-publish
• Where we do and don’t want automation - Using a bad old Linux laptop, refusing uncontrolled automation

7. Take the different path

Mainstream markets are crowded, weird paths are still empty. Innovation happens at the edges, not the center. Give up US passport. Self-host an online store to independently publish books. He’s so famous yet still replies to hundreds of emails from strangers daily. But it’s precisely because he doesn’t take the normal path that he’s so cool. Edge paths have more opportunities than crowded mainstream.

• Aim for the edges - Mainstream center is hollowed out, aim for the edges for opportunities
• Proudly exclude most people - Loudly reject 99% of people to better clarify who you are
• When in doubt, try the difference - When in doubt, try the different approach
• Doing the opposite of everyone is valuable - The more people do something, the less valuable it is; play a completely different game
• Uncommon Sense - Success comes from being different enough that everyone you meet tells their friends

8. Create > Consume

Invest your time in your own creations. Consuming makes you like others, creating makes you yourself.

• Here’s how to live: Create - Most people die with their work still in their hearts; the way of creation is to die empty
• Obvious to you. Amazing to others - Don’t be a terrible judge of your own work; publish it and let the world decide
• Here’s how to live: Make change - The world doesn’t need more audience members; it needs change-makers
• Why wreck a blank canvas? - Ironic explanation: don’t let perfectionism stop you from creating
• Would you make your art if you were the last person on earth? - The motivation to create purely for creation’s sake

9. Action > Ideas

A work that’s 60% complete beats an idea that’s 100% perfect. Because ideas without action are worthless. Action gives ideas value.

• Ideas are just a multiplier of execution - An idea alone is worth $20; idea plus excellent execution is worth $20 million
• Goals shape the present, not the future - Good goals tell you immediately what to do next
• Start now. No funding needed - Start with 1% of the vision; CD Baby launched with $500
• Version 0.1 = Start lo-fi - Don’t wait for funding, start with a low-fidelity version
• Here’s how to live: Master something - People fail not because they choose wrong, but because they don’t choose

10. Adapt and accept change

Life is impermanent. Identity changes. Taste changes. Disliking something is just disliking it now, not forever. Change is the norm, not the exception.

• Here’s how to live: Reinvent yourself regularly - Your so-called personality is just past tendencies; new contexts need new responses
• Loving what I used to hate - From hating Tom Waits to loving him, from hating Indonesia to loving the people there
• The past is not true - Carried guilt for 18 years turned out to be a misunderstanding; the “truth” of the past can completely change
• Here’s how to live: Do whatever you want now - Past and future only exist in your mind
• My old clothes don’t fit - Metaphor of taking off old clothes to put on new ones

11. Be free

Don’t add unnecessary relationships, jobs, “shoulds,” or contracts. Go where you want. Do what you want. Freedom comes from reducing dependencies.

• Here’s how to live: Do whatever you want now - If you want to do it, do it now; if you don’t want to do it now, you don’t want to do it
• Is there such a thing as too much freedom? - When you’re so free you can do anything or nothing, what should you do?
• The security of no security - Being able to independently take care of yourself is true security; you’re a free person, you can do anything
• Why I don’t want stuff - Not wanting stuff lets him move anytime
• The joy and freedom of upsetting social norms - Joy and freedom from breaking social norms

12. Be content

Money is enough when it’s enough. We really don’t need that much money in life. Contentment comes from lowering needs, not increasing possessions.

• Wealth = Have ÷ Want - Wealth is having divided by wanting; the fastest way to increase wealth is to reduce needs
• You have enough - Quick way to double income is to halve expenses; you already have enough wealth
• Ah, to own nothing! - Writing on a seven-year-old computer, living out of a backpack; less ownership brings more freedom
• Here’s how to live: Get rich - After getting rich, feeling indifferent about money; nothing much to buy anymore
• What if you didn’t need money or attention? - If you were completely fulfilled, what would you do and stop doing

Closing thoughts

These principles are all topics I’ve been very interested in and value highly. I’ve studied them in minimalism, Buddhism, and Stoicism. But I’ve never seen someone embody all of them and practice what they preach. Though I’ve never met him in person, and my brain has probably romanticized a lot, for me he’s a living role model I can aspire to—more inspiring than philosopher emperor Marcus Aurelius.

I’m a Derek Sivers fanboy. His ideas are worth chewing on again and again for me.

In this age of chasing fame and fortune, he chooses seclusion and contentment.

In this age of chasing efficiency and scale, he chooses authenticity and simplicity.

This is the Derek Sivers I admire.

I hope you’ll like him too.

P.S. If you want to get to know him, start with Anything You Want, or check his /now page for recent updates. Or just email him—he really does reply.