Derek Sivers podcast – Details, episodes & analysis

This is a real question. I don’t know the answer and I’m curious.

I lived in New York City for ten years and Los Angeles for seven years, and there are a lot of Jewish people in those two cities, so it could be coincidence.

But I honestly didn’t realize it until one day I was thinking about the difference between shallow versus deep friendships, and made a list of my closest friends. After I looked at the short list, smiling and appreciating, I looked again. Wow. All of them are Jewish. Is it coincidence, or a cultural attraction?

I meet a lot of people and like most of them, but it’s rare I feel that extra-extra click with someone. In Buenos Aires this year, I met with a musician named Alejandro Staro, and we instantly felt like old friends. Then two hours into the conversation, he said something about his Jewish culture, and I was shocked. I had no idea. If that was part of the reason I felt an instant click with him, how could that be?

When I got home to New Zealand, I called one of my best non-Jewish friends, to ask her about this. She’s from Iran, Bahá’í faith, and spent twenty years fighting terrorism on the front-lines of Afghanistan, Somalia, and Kenya, before taking a nice peaceful post in 2019, in Kyiv Ukraine. Oops. (Yes she’s a magnet for disaster, and has also been attacked by a dolphin and silverback gorilla.) But anyway. She’s also one of those rare people that I super-clicked with the minute we met, years ago. So I explained the situation and asked her why I’m so drawn to Jewish people.

She said, “Maybe that’s why you and I clicked so well.”

I said, “Ha. Wait. What? No. You’re Bahá’í.”

She said, “Yeah but my mom’s mom is Jewish, so it was always part of my family’s culture.”

Again! I had no idea, so it was another blind taste test.

So if this is a cultural attraction, then what is that really? My friends are vastly different, some religious, some not at all, from different countries and backgrounds, so any cultural similarity must be subtle.

Could the Talmudic tradition of questioning pass down through non-religious families? Is it a shared love of discussion?

I could relate to the worldview presented in “The Complete Idiot’s Guide to Understanding Judaism” — a surprisingly great book, written by a rabbi. My friend Maya inducted me as an honorary “member of the tribe”.

Am I recognizing a shared worldview in strangers, even though they seem to have nothing in common? Or is it something else entirely? I don’t know, so I’m asking the world for ideas. Please leave a reply here if you have any thoughts.

I was 36, and had been living in Portland for two years. I saw an amazing house for sale — really amazing — stunning design, ideal location on the edge of the city, and its backyard was the start of a huge state park. I had a visceral reaction.

For a minute, I daydreamed about living the rest of my life in that house. Find a wife, and raise a family in that house. A bunch of grandkids, and that house would be a multi-generational axis.

Then I snapped out of it. What was I thinking? That’s not the life I want!

In 50 years, what would I rather be saying?

“I bought this house 50 years ago, and I’ve been here ever since!”

… or …

“Hey honey, what year did we move to Berlin?”
“2030, after Buenos Aires. Because in 2040 we moved to Bangalore.”
“Oh right. Our bungalow in Bali was the year before Beijing.”

Now that’s the life I want! Nothing against the settled life for others, but it’s not for me. I want to live in every corner of the world.

We make a big choice, like a house, job, spouse, or dog. We think about the thing itself: the look of the house, what the job pays, what a sweet dog. But a choice has so many cascading consequences. One big choice shapes a hundred little others. I try to imagine the ripple effects — the later details that make the day-to-day difference.

Then I think in reverse. Knowing the consequences I want, what choice would create them? What big choice would nudge a hundred others that way?

Within an hour of seeing that house, picturing the two different paths, it was clear I wanted to leave America forever, so I booked a flight to London. I didn’t know the details, but I knew this big first choice would send me in the right direction. (And it has.)

Atomic habits? Decision fatigue? One big choice decides a hundred others. So it helps to think of implications, and daydream backwards.

For many years, I was a touring musician, performing live on stage every week. But I didn’t like attending concerts. I liked making music more than listening to music. I felt I must be in the wrong line of work, creating something that I don’t consume. I never reconciled this feeling.

Since then, I’ve met a:

• vegetarian cattle farmer
• masseuse that doesn’t enjoy receiving massage
• elevator builder that lives in a single-story house
• heart surgeon that has never needed heart surgery

We sweat salt water. We cry salt water. But we don’t drink salt water.

The comparisons are a nice reminder that we don’t have to take in what we put out.

I now feel reconciled that this is not a problem or a sign that we’re in the wrong line of work.

Not a new idea, but just another visualization and reminder.

Wealth, feeling like you have plenty, is an equation.

Wealth = Have ÷ Want

If you have nothing, then focus on having some.

Once you have some, the easiest way to increase your wealth is to decrease your needs.

Have 10 but want 100? You are poor.

Have 10 but only want 5? You are wealthy.

Have 10 but are happy with 1? You are very wealthy.

Making money depends on other people, so it’s harder. It’s not entirely under your control. It’s an outer game.

Reducing what you “need” to be happy is easier. It’s entirely under your control. It’s an inner game.

I used to look for ways to make money, but I haven’t done that in years. Now I keep looking for ways to want less.

You know that frustration of reading a book that should have been an article? Me too. So I try to do the opposite — to write so succinctly that you wish I would have said a little more. You complete it with your own thoughts.

That’s why I edit the hell out of my writing. I delete every unnecessary sentence and word, then craft the few that remain. It takes more time for me, but saves time for everyone else. Hopefully this approach, where you fill my gaps with your own examples, is more powerful and effective. Maybe, as a side-effect, even more beautiful.

But then how should I approach its translation? I’m willing to spend time and money to help make the best possible translations into Chinese, Spanish, Portuguese, and French. Maybe other languages, too, based on the potential audience. My books have been the primary creations of my life, and will be what’s left of me after I’m dead, so I’d like to help make great translations of them while I’m here.

They’re not poetry, but I put the same care into rhythm, structure, and even sound of the words. I can’t just crap out a computer-generated translation, or under-pay an over-worked translator. I could hire one expensive translator, and that person could do one interpretation, but then what if it’s too uniquely biased?

You’ve heard of The Wisdom of Crowds? The collected ideas of many people can be better than any one person’s ideas. It doesn’t apply to everything, but might apply to translations.

I built a tool for translators, reviewers, and editors, called Inchword. It lets anyone suggest translation improvements, even if they have just a few minutes or hours to improve a few words or chapters. Editors review and approve those suggestions. Reviewers read the finished chapters. All of these people can ask me questions for clarification. And at some point, multiple people agree that it’s as good as can be, and I mark the translation as finished. It’s the “official author-approved translation.” (What to do with it after that is a different issue.)

I’m not sure this is the best plan, so I’m open to suggestions. Please leave a reply, below, with any ideas. Or if you can help as a translator, reviewer, or editor, please email me.

P.S. For the past few years I’ve licensed to foreign publishers who do their own translations, and nothing wrong with that, but I’d rather collaborate more closely with the translators to make sure each translation is the best it can be.

I’ve asked my favorite musicians if, when they’re done writing a new song, they feel it’s the best song ever. All of them said yes.

I’ve asked my favorite authors if, when they’re done writing a new book, they feel it was the best book ever. All of them said no.

I don’t know why the two groups are so different. Do you? (Please post your thoughts, below, if so.)

As for me? I think the best book ever written is “How to Live”.

If I did nothing else with my life but write that book, it would have been a worthy life. It’s not ego. It’s not that I think I’m so special. But that book is definitely something very special.

I spent thousands of hours writing everything I ever learned, from the 400+ books I’ve read, and the 50+ years I’ve lived. Rough draft: over 1300 pages.

Then I spent thousands of hours editing it down to 112 poetic pages. Not a single unnecessary word.

Every now and then, I hear someone quote it. When they do, I think it’s the most beautiful quote I’ve ever heard. Then I remember I wrote it.

I feel I’m not supposed to admit all of this. But it’s honest.

Why don’t more writers feel this way?

I just got the call from the super-connected Alex Steininger that our mutual friend Ben Kihnel died in his sleep. He was only 48.

Ben was employee #2 of CD Baby. (#1 was the great John Steup.) John hired Ben the day we moved the company to Portland, Oregon. I don’t even know how we met Ben. Then all of the early employees at CD Baby were Ben’s friends, so Ben was really the start and the heart of everything for us in Portland.

Ben was one of my favorite people. Such a warm, open, empathetic guy. Such a great conversationalist. People often talk insincerely — echoing cliché phrases, or saying one thing but meaning another. But even Ben’s shortest communications were really sincere and engaged — fully listening, understanding, and sharing. He was always great at getting to the heart of things.

I hope I remember to tell people how I appreciate them when they’re alive.

So sad he died so young. We last talked a year or two ago, and he was wonderful as ever. I’ll always remember him fondly. He was a really special person — an exceptional soul. The world was a better place with him in it.

Ben was the one who told me to post the “232 sand dollars” story on my website, because he thought it defined me. That’s why many of the comments on that page from 2011 are thanking Ben.

I don’t take many photos, so the only two I have of him are from 2002: on the phone at work, and at a New Year’s Eve party. But I can hear his voice clearly in my head.

This is a lukewarm little story with a few connected bits, but it might be interesting or even helpful. Follow the links in it, for full effect.

For decades, I’ve wanted the experience of carrying on a conversation in another language.

My language-teaching polyglot friend Benny Lewis said that if you’ve never really spoken another language, then the best strategy is to start with the easiest possible language to learn, which is Esperanto. His advice is to spend just a few weeks learning and having conversations in Esperanto, so that you can feel the experience of detaching from your mother tongue. Then you’ll be better-prepared to go learn the language you really want to learn.

A few years ago, during Christmas holidays, when the world expects less of us, and I actually had spare time, I procrastinated something by thinking, “I should look into Esperanto.” I sat down mid-afternoon and checked out lernu.net, which seemed to be the most popular Esperanto-learning site. And oh my god! It’s fascinating! The language is so well designed! Everything made sense and with each new thing I learned, I thought “That’s brilliant!”, and wanted to learn more. I was so riveted that I didn’t realize it had gotten dark, and by the time I got out of that chair it was 10pm.

So I decided to learn Esperanto to a conversational level. It was December, and there was an annual Esperanto conference in Seoul Korea in July, so I signed up to attend the conference and made that my deadline for fluency. I found an Esperanto teacher, signed up for live conversation practice, and started learning for one to three hours a day. I was a keen and diligent student, and had Esperanto books shipped from overseas, which I read slowly, learning new vocabulary. I watched videos in Esperanto made by a funny Australian dude. I used Anki flashcards, and wrote my own command-line dictionary for quick reference of every word I’d learned. I was so into it that my friend Elina got annoyed and asked if I could please stop talking about it so much.

After six months of study, I was able to have conversations in Esperanto. I was able to say almost anything I wanted to say, and understand almost anything someone said.

I was on my way to Seoul Korea for that Esperanto conference, but stopped for a few days in Singapore. There’s an app (made by the funny Australian dude) that helps you find other Esperanto speakers in your area that are willing to meet up and talk in Esperanto. So I turned it on in Singapore. It said that just a mile away from me was an Esperanto speaker named Sonja Lang. Wait a minute… I know that name… Oh my god it’s her!

You’ve heard of the Sapir-Whorf hypothesis? It suggests that the structure of the language you speak affects the way you think.

Sonja Lang, a brilliant linguist and translator, was inspired by Taoist philosophy, and found she felt best when she simplfied her thoughts and concentrated on basic things. So she decided to apply the Sapir-Whorf hypothesis and created a new language that has only 137 words. With so few words to communicate everything, you have to simplify your thoughts and concentrate on the basic essence. She called it Toki Pona. I had heard of it for years, found the idea fascinating, and even read a little book about it.

So I texted Sonja Lang through the Esperanto app, and asked if she would meet up with me. She said yes, but only if we speak only Esperanto. We met up the next day at a restaurant in Singapore. She’s like a rock star to me, so I was nervous and excited, and I’d sometimes break into English to tell her something. But she patiently responded in Esperanto, and spoke only Esperanto for two hours with me that evening.

I wanted to stay friends with her, but we only connected through that app, and only that one time. Still, I was starstruck, and count it in my top ten celebrity encounters.

I’d always wanted to go to Korea, and this was my first time. So excited to be there, and excited for this Esperanto conference.

OK so this is why I said this story is “lukewarm”: because I have mixed feelings about what I’m going to say next, and I’m going to trash something (maybe myself) in a way I usually don’t.

I went into the conference, and was immediately disappointed. The average age of the attendees around me was probably 55. They were disheveled and unkempt. They had signs saying we could have world peace if everyone spoke Esperanto. They were singing sappy songs with acoustic guitars and hand-drums about Zamenhof, the linguist who invented Esperanto in 1888. I cringed. It’s hippie Klingon.

I talked with the funny Australian (in Esperanto, of course), after watching so many hours of his videos, that was cool to meet him. But everyone else? Eh. I realized I had no desire to talk with these people. And then I felt bad for my lack of interest. I’ve attended many conferences about the Ruby programming language, and really loved nerding out on those conversations with fellow enthusiasts. But I just didn’t like these Esperanto people. I felt like a bad person for not being more interested in them. So I forced myself to have a few more Esperanto conversations with strangers, but I still didn’t like it. And so I left and never spoke Esperanto again.

I feel bad saying that I liked the language but not its speakers. I feel like it’s my fault. They’re all probably really interesting people, and the problem is me, which makes me feel worse.

I realize that I lost the plot and didn’t do what Benny had suggested. I was supposed to spend just a few weeks on Esperanto, have a few conversations in it, then move on. But I was just so intrigued with the language itself that I dove all the way in. So I’m left with a feeling of regret.

Esperanto is interesting but almost useless. Almost nobody speaks it, and they all speak English and other languages too. So I can’t ever feel the joy of using it to communicate with someone who I couldn’t otherwise.

I spent over 400 hours practicing Esperanto, and I wish I had spent that time learning a more useful language. For an English speaker like me, Spanish, French or Portuguese would have been almost as easy. A year later, I moved to Portugal, and deeply felt that regret.

So now it’s just something I nerded-out on for six months, and have a lingering admiration for how well it’s designed.

Linguist John McWhorter has a lot to say about language. I’ve spent probably 50 hours listening to his great courses and podcast about languages.

He said that if he could have chosen a language, instead of English, to be the world’s shared second language, then it would be Swahili or colloquial Indonesian. He said both of these languages have been learned by millions of people as their second language, so all the weird edge-cases have worn away, and they are as smooth and beautiful as a river stone. No weird grammar. No weird tones. No exceptions. In all of his studies of hundreds of languages, he said Indonesian is the closest thing to an ideal language he has ever encountered.

I still want to learn to speak another language to a conversational level. I’m very tempted to learn Indonesian or Swahili, to experience what he loves about them. Like learning to play a song that an expert says is the most beautiful song ever written. And each one could connect me to millions of native speakers that don’t speak English.

I daydream about what it would have been like if, instead of Esperanto, I learned Swahili and went to Zanzibar (birth place of the language) to speak nothing but Swahili for a week. Or learned this ideal language of colloquial Indonesian, and instead of going to a hippie nerd conference I would have talked with people around the Indonesian islands. These scenarios are much more inspiring to bridge the communication gap.

But for me, still, the language with the greatest unlocking power is clearly Mandarin Chinese. Over one billion speakers that don’t speak English, from a rich and admirable culture with its own thing going on.

Some day.

Kevin Kelly invited me to walk 100 kilometers (62 miles) through northern Thailand for seven days, ending in Chiang Mai. Walking with us were ten other smart interesting people, including five other authors whose work I’ve loved for years. It’s a “Walk and Talk”.

One of the walkers lives in Thailand, speaks Thai, and made all the local arrangements, scoping the track in advance. Two of the walkers had done this many times before, in Uzbekistan, Spain, Japan, and China. The rest of us were in good hands, going with the flow of the unknown.

A sweet wild dog joined our pack halfway through, walking and sleeping with us for four days and 70km, until we brought him to a vet at the end, and found him a good permanent home.

Read the write-ups by Dan Wang, Craig Mod, Jason Kottke, and Liz Danzico, who were also on this walk, and go into more depth than I do here.

I highly recommend this activity and format. You can start one yourself. It goes like this:

UPDATE: Kevin Kelly and Craig Mod released their “Walk and Talk: Everything We Know” PDF which is much more thorough and helpful than my brief overview, below. Download it here.

1. Choose where to walk — somewhere with lodging for 8 people every 15 km — where someone else can drive everyone’s bags from place to place.
2. Someone (local person or business) walks it all in advance to make sure it’s actually good. This person is the navigator.
3. Make a shared document of details of where to meet and what to bring, a group chat for questions, and a shared place to upload photos afterwards.
4. Invite a diverse group of conversationalists — ideally eight. Walkers send money to the local navigator to pre-pay for the lodging and meals.
5. Meet at the initial hotel for dinner and introductions.
6. Walk together for the next 6-7 days — ideally without phones — about 3-5 hours of walking per day, led by the navigator, with long breaks every two hours. Everyone naturally goes in and out of little 2-3 person conversations while walking.
7. Every night over a private dinner, the entire group has a single conversation around one subject, which the group chose the night before. Everyone stays involved in this one conversation, exploring one topic to exhaustion.

During this Thailand walk, our nightly conversation topics were:

• How do you stay motivated?
• What do you escape or resist?
• What does home mean to you?
• Shocking solutions to public problems.
• Tell us about a failure.
• Frameworks to make big decisions.
• What is your health regime?
• How do you use lists?
• What do you believe that your heroes do not?

Some people spout their thoughts as soon as they come to mind. Other people need to be persuaded to share. It helps to moderate the conversation to keep the contributions balanced.

More than half of the conversations were during the day, one-on-one, while walking or resting. It’s wonderful that you can come back to something someone said a day or two before, and share more thoughts or questions that came to you overnight.

It’s one of the best things I’ve ever done. Very healthy for your brain, body, and friendships. I highly recommend it for anyone.

I plan to host some in the future. If you know a good place to do a “walk and talk”, (see criteria #1 above), please leave a suggestion in the comments here.

People search for their passion or purpose. But “purpose” and “passion” are words we use when we’re not working.

When we’re actually engaged in the flow of fascinating work, we don’t think in these terms. The task at hand fills our mind. The task itself is what keeps us up all night, not some extracted story of purpose.

Imagine you put a GPS tracker on a dog, then you set him free to run in the countryside. He dashes. He digs. He stops to sniff. He romps with another dog.

Later, when you map his recorded GPS data, you see that he generally went north-east. But would you say that going north-east is his passion and purpose?

Just do whatever interests you now. Don’t seek a story of purpose to guide or label your interests.

When we announce something, we have a social need to be congruent. If you say that your purpose or passion is to go north-east, but then you get interested in something to the south-west, you might ignore that interest and limit your play to what fits the narrative. Don’t do this to yourself.

Focus on what fascinates you, even if it’s uncharacteristic. There is no purpose because there is no line connecting moments in time. There is no plot. You are not a story.