Derek Sivers and his unusual take on life
saying No, your identity, journaling, money, directives on life
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Derek Sivers is a legend. He has been a musician for 15 years, ran a company called “CD Baby” for 10 years which he sold for $22 million and gave away all the money to charity. He says after that, for 12 years he has been exploring and adventuring and enjoying having no responsibility and feeling nomadic.
He has an amazing blog. It’s a rabbit hole where you can spend days. I highly recommend starting with his “about” page.
I don’t subscribe to that “blood is thicker than water” metaphor. I feel pretty equally connected to everyone. (We’re all cousins, anyway.) I don’t feel more bound or obligated to my immediate family than I do to strangers. In fact, because of my ambitious exploring nature, I’d rather focus on the unknown, and push further out into the world
I admire Derek for his unusual take on life. He does not follow the norms of the world. He is someone who has followed first principles all his life without even knowing the concept of first principles. For example, when he wanted to quit his first job, he found a replacement for himself. Who does that? There is a lot to learn from him. One e-mail will not do any justice. You must read his blog.
Derek is Unusual
Cares deeply about very little. He is attached to just a few people and a few interests.
He is very long-term oriented and future focused. Always like to ask himself “Will I want that when I am 80? If not, why do it?
Measures his time in money. Values his activities to figure if it’s worth doing or not.
He is writing his autobiography. He has already written the chapter “Now I am dead”. He is filling up the pages in between.
He is not into family. He does not hate his family but does not love them.
He is a minimalist. He only owns a pair of pants, and has a 7 year old laptop.
Prefers talking on the phone than hanging in person.
Derek’s Thoughts on Money
He has not made any money except for some that he made through his books. He enjoys doing things for free. He lives very cheaply so he doesn’t need much money. Recently, he made $250,000 through the sale of two of his books. He gave away all the money to charity. Very few of us would do that.
Ever since I was a teenager, I found a way to live so cheaply that I never really had to do anything I didn’t want to do. Instead, I would lower my expenses so that making a few hundred dollars a month would pay my cost of living. There’s always something you can enjoy while living off a few hundred dollars a month. That’s always been my approach to life.
According to him, wealth is having more than you need and the easiest way to become wealthy is to not need much in the first place.
Money is like sex. When you have NONE, you can hardly think of anything else. When you have PLENTY, you think of other things.
Derek is Famous for Saying NO
Derek loves to say NO to almost everything. He wants to leave space in his life. I highly recommend reading “Hell Yeah Or No”. By creating space, you’ll have the ability to do great things that takes many hours to create.
The hours don’t suddenly appear. You have to steal them from comfort.
He has crafted a life where he has lots of free time. He spends hours and hours a day just thinking and writing. He rarely watches movies or shows.
Derek has A Good Perspective on Identity
Derek does not like to talk about things he did in the past. He does not like to keep repeating the story about something he did in high school.
You have to keep earning your title or it expires.
If you did something 20 years ago which was a success, you cannot keep calling yourself successful today. It’s past tense. You were a success. You have to keep earning it. Old titles only give you the satisfaction without action. If you do not like losing your title, then you have to keep doing something to keep it. I personally think it’s a great mental model to keep earning your title.
Derek loves Journaling
Derek has a folder called “Thoughts On”. This is the folder where he has a couple of hundred files with names like accounting, language learning, airports, or interviews. Whenever he has a thought on any topic, he just goes and documents that in these files.
If you care about your thoughts, keep them.
They can be tiny. Like you see I have one on airports. I don’t have many thoughts on airports. I don’t fly that much. But I found that once or twice a year, when waiting at the gate, I had thoughts on the subject, so I’d open that file and start writing.
He also keeps a daily diary. Every day, he writes about what he did, how he is feeling and move on. It helps to clear his mind. This is important to him because he is doing this for his future self. It helps him make better decisions.
This is important because years from now you might be looking back, wondering if you were as happy or as sad as you remember during this time. So don’t only write the drama or dilemmas. Include the daily facts of life.
Derek likes to ponder on questions that are important to him. He will regularly ask himself -
What would I do if I had 100 million dollars?
What’s ultimately more important to you? Learning or creating? Money or time? Expanding or focusing?
Which were the top three best times in my life so far?
What are my biggest regrets?
What would I write a screenplay about?
If I had the magic lamp, what would be my three wishes?
What does the most ambitious version of myself look like?
What about the least ambitious version of myself?
How can I be a better dad?
At what would I most love to become an expert?
Is there anything I can’t do without?
How would my life be different if I was blind? Deaf? Paralyzed?
Derek Loves to Write Directives for Himself
Derek is someone who loves to make things as succinct and as actionable as possible. He calls it “the do this directives”. He has written about how to get rich, how to be useful to others, how to like people, how to thrive in an unknowable future.
How To Thrive In An Unknowable Future
Prepare for the worst
Expect disaster
Own as little as possible
Choose opportunity, not loyalty
Choose the plan with most options
Avoid planning
I highly recommend reading all.
Quotes from Derek
How you do anything is how you do everything. it all matters.
I like to think everything is a co incidence. Life feels more amazing to me if it has no meaning. No secret agenda. Beautifully random.
The standard pace is for chumps. If you are more driven than most people, you can do way more than anyone expects.
Whenever you feel dependent on something, you need to challenge the dependency and prove your independence.
The big idea is like, there’s no such thing as failure until you give up.
I don’t do something if it’s not fun and that’s a wonderful luxury to have.
Success comes from doing, not declaring.
Every month, pick something you hate or know nothing about, and get to know it.
Last week’s newsletter - The Simple Life of Murakami
On The Contrarian Living blog -
Framework for spending money and avoiding decision fatigue
What matters more, Identity or the message?
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Take care and stay safe.