Derek Sivers

Interviews → What You Will Learn / Adam Ashton

Fun conversation. Reading, what makes a great book, the definition of a philosopher, how to get rich, being meta-considerate.

Date: 2020-05

Download: mp3



Welcome back to What You Will Learn. My name is Adam Ashton, and today I am interviewing Derek Sivers.

Derek Sivers is the author of the book, Anything You Want, which was the first ever episode of the What You Will Learn podcast all the way back in June of 2016. Almost four years later, I had the pleasure of speaking to the guy that started it all. He’s got three brand new books coming out later this year – Your Music and People, Hell Yeah or No, and the one I’m probably most excited for, How to Live.

In this episode, we talk about pop philosophy, what it means to be a philosopher, whether that’s a definition or a description that one wants to take on or not. We talked about considering all the different angles, giving an answer and questioning your answers, considering a different possible answer to the same question.

We then spoke about books. We spoke a hell of a lot about books. We discussed what makes a good book, what books you should read next, Derek’s recommendations, and of course, finished off by talking about some of Derek’s favorite books.

I hope you enjoy this interview with Derek Sivers.

Derek Sivers, thank you so much for joining me for this conversation. First, I have to say a very big thank you. Anything You Want was an important read for me. It shook me out of a bunch of beliefs I had around entrepreneurship. Out of all the different books I had read up to that point, Anything You Want gave a very opposite, but also true way of looking at the same problems.

Second, thank you because Anything You Want was our first ever episode back on this podcast back in June 2016, almost four years ago now. Your book kickstarted it all.


I had no idea I was your first. Thank you!


Thank you. It was the very first one and admittedly it was not the best one. Of course, the show is very different now. Back then, we hit record, talked for 20 minutes and hit publish. We’ve evolved a lot. But it was a it was a perfect one to start with.


That’s so cool though.

I wish more people would do that to get over the creative hurdle of the first release. My favorite example of this is from a couple decades ago. I read in an interview with Sean Lennon, John Lennon’s younger son, that people had been asking him ever since he could remember, “Well little Sean, when are you going to record your music? When can I hear your music?” And he said he felt such pressure his whole life thinking, “Oh, my God my record has to be a masterpiece when I finally make my first album.”

Then one day, he said, “I’m sick of this pressure. I’m going to go make a record this week,” and he just did it. He didn’t love it, but he just put it out. He said, “Now I’ve gotten past the first release. I can only improve from here.”


That’s so good. We had slightly less pressure on us, not carrying the name Lennon [laughter].

I was recently on another podcast, and the host asked who my favorite philosopher was. I love Meditations by Marcus Aurelius and I love the Tao Te Ching by Lao Tzu, but I felt a bit pretentious to pick one of those guys or any of the famous names since I haven’t read a lot of their stuff. I don’t know what they’re all about.

So, I said Derek Sivers, and I would say that you are my favorite philosopher. Would you call yourself a philosopher?


First, holy shit. Thank you. That’s a great compliment. As for calling myself a philosopher, I have mixed feelings on this. Technically, I guess I am. But I would never say so, if a stranger asked, “What do you do?” I would find it so pompous to say, “I’m a philosopher.”

My mixed feelings come from the fact that the word philosopher has two definitions. The Wikipedia page on Philosopher says, in the classical sense, a philosopher is someone who lives according to a certain way of life, someone who challenges what is thought to be common sense, doesn’t stop asking questions, and reexamines the old ways of thought. But then it says, in a modern sense, a philosopher is an intellectual who has contributed in one or more branches of philosophy.

In the classical sense, that sounds like me. But in the modern sense, I haven’t contributed to the field of philosophy at all. Maybe that’s something to aspire to.


But philosophies are already set in stone. You can’t create a new one. So, you’re only a philosopher if you contradict the old ones, right?


[Laughter] Exactly. That’s why if somebody were to say, “I’m a philosopher,” I’d say, “No you aren’t. Because I’ve never heard of you. If you were a philosopher, you would be in the books. You’re not a philosopher until you’re in the books.”

Also, shouldn’t there be a target to that definition? We don’t say someone is a lover. We say they’re a lover of something. We don’t say somebody is an aficionado.

Instead, we could say a philosopher OF something.

Peter Thiel is a philosopher of business. Brian Eno is my favorite philosopher of music. Pema Chödrön is a philosopher of acceptance. And Seth Godin? I’m curious to hear what you think he’d be a philosopher of.


The obvious answer is a philosopher of marketing. That’s what he’s most well known for. But these days, he’s definitely pushing more towards a philosopher of modern culture.


I would think so, too. But if you talk to him, he says his main focus in life is making change. He wanted to keep being a summer camp counselor, and it was his wife who wanted to live in New York City. Summer camp was too far away, so he started writing books. He says that the common thread in his life is making change. So, he might be a philosopher of change. That’s the common thread in his work.

Nassim Taleb is a philosopher of probability, and Andy Warhol was a great philosopher of art. I don’t think it’s really his art that we like, it’s his philosophy of art that we like. I like thinking of these people as like philosophers of things.

I’m recently realizing how much Brian Eno influenced my thought on many things.


Interesting. I like that you mentioned Nassim Taleb. Jonesy will like that because that was his answer to his favorite philosopher. I get the feeling that Nassim would classify himself as a philosopher [laughter].


[Laughter] He has that arrogance, doesn’t he?


Most certainly. In the original definition of what an ancient philosopher was, you discussed questioning assumptions and challenging the way society does things.

That’s definitely you to a T. If someone asks you a question, you’ll reply and say, “But that’s just one answer to one specific situation. There aren’t ‘one size fits all’ solutions to anybody’s problems.”

You’re always looking to question your answers or looking for different answers.


That’s my favorite pastime.

It’s a thinking game. I’m never trying to be accurate. I’m never trying to figure out the right answer to the problem of life. Instead, I find it more fun to keep thinking of other perspectives.

It’s play. It’s fun. It’s not about being accurate. It’s about being creative to deliberately find another point of view.

Do you know what a spirograph is? It’s a little plastic cog wheel and you put a pen inside. Then you put different sized cogs inside and there’s a hole where you put your pen. As you spin it around the cog, it ideally doesn’t go exactly opposite. Instead, it goes almost opposite on each rotation. It’s a 170-degree turn instead of a 180-degree turn. If you keep moving your pen around and around and around with each flip, you’re seeing it a little differently.

I’m fascinated with the idea of opposite, but not a 180-degree opposite. I like the idea of a 170-degree opposite, so that you can keep going. Keep flipping, and it’ll be different each time. I play this little creative game with friends and with my kid. We’ll say, “What is the opposite of this?”

I asked my musician friends, “What’s the opposite of music?” We had a fun time coming up with an answer, which is not silence and not noise. The opposite of music is business.

Then, what’s the opposite of business? Charity.

What’s the opposite of charity? Greed.

What’s the opposite of greed? Generosity.

What’s the opposite of generosity? Fear.

What’s the opposite of fear? Love.

What’s the opposite of love? Seduction.

I like this because it’s opinionated. If you say the opposite of love is seduction, there’s an implied philosophy and strong opinion there. If you say that seduction is the opposite of love, someone else could argue in a wonderful, poetic way that seduction is love and both people could be right.

It’s not about trying to be accurate. What’s interesting about opposites is that the creative part is choosing what aspect to make opposite. If you’re saying the opposite of love is seduction, it makes you question, how so? What aspect of seduction are you saying is the opposite of love?

My kid and I will play this, too. What’s the opposite of a mountain? Is it a meadow? Because it’s not jagged, it’s flat. How about a crater or a sinkhole? But our favorite answer is quicksand.

We thought about the fictional quicksand that we see in cartoons. You’re walking and all of a sudden, you’re stuck and get pulled all the way underground. This answer focuses on the challenge aspect of a mountain – the effort to get up a mountain. It takes continuous effort and if you were to give up, you’d tumble down.

Quicksand pulls you in, even against your will. But a mountain takes great will to climb. I think, “Why would I choose quicksand as the opposite of a mountain?” Because it’s more fun. It’s a more amusing and interesting thought.

I do the same in all subjects every day. Like if I hear somebody talk about how it’s important to be kind. I think, “Hm. Is it? When is it not? Let’s explore. What’s the opposite of kind?”

These are fun mind games.


I like it a lot.


I think it’s a good exercise.

Like I said earlier, I recently realized what an influence these music thinkers like Brian Eno and John Cage have had on my approach to life. I’m not looking for the right answer in life. I’m looking for another interesting way of looking at it. Because that’s what musicians are all about.

Brian Eno is in the studio constantly recording album after album, either for himself or for other artists. He’s constantly thinking, “How can we make this different? How can we make this surprising? How can we take what you came in here with and come out with something else?” I take that approach to life, too.


One of my favorite articles you wrote is called How I Got Rich, On the Other Hand. Can you tell us about it?


Sure. What did you like about it?


When you read the title, it seems surface level, but there’s a much deeper answer – the real way to get rich. I also like the element of magic. Magicians are always doing something with one hand, but with their other hand, the real work is happening.


Cool. I don’t usually talk about money with my friends, but that was sparked by a friend who said, “Hey, can I ask you a weird question?”

I said, “Of course.”

He said, “What was it like to get rich?” He really wanted the specifics. He wanted the whole story. So, I told my whole story.

I was 22 years old and I had a day job in midtown Manhattan. I was making $20,000 a year – basically minimum wage. I was also performing at the circus on weekends and earned about $300 per weekend. My rent in New York City at the time was $333 a month because I shared a flat with three roommates. I made peanut butter sandwiches three times a day and that’s all I ate. Maybe some eggs, but I never ate out. I never took a taxi. I was able to keep my cost of living to under $1,000 a month. Since I was earning about $1,800 a month and did this for two years, I saved up $12,000 by the time I was 22 years old. That’s when I quit my job. I’ve been free ever since. That was last time I had a job.

My friend said, “Dude, what about when you sold your company? You made millions.”

I said, “Yeah, but those were just details. That wasn’t when I became rich. I became rich when I was 22 because that’s when I had $12,000 saved up, which was more than I needed. I’ve never touched that $12,000 since.”

Being rich is not about how much you bring in, it’s the difference between what you spend and what you have. If you have more than you spend, then you’re rich. If you never touched that $12,000, you’re rich. On the other hand, no matter how much you bring in, if you spend more than that, you’re not rich. If you live cheaply, it’s easy to be free.

I don’t know a damn thing about magic, but from what I hear, magicians are often doing something very distracting and flamboyant with one hand while the humble hand is down by their side actually doing the real work. They wave one hand around to get your attention, but it’s the other hand that’s actually doing the trick.

To be smart, watch the other hand. We’re all focused on how we can make money and bring in more of it, but the real trick is in the spending.


I like that a lot.

I was reading through the comments of that post, and you also gave the opposite opinion. You countered your own answer in the comments of that post.

You said that maybe for some people, the need and desire to get rich and buy lots of luxurious things actually drives them. It fuels them to achieve more. If they work really hard, they can make lots of money and give back or create an awesome business that helps the whole world.

That blog post is so important, and the meta lesson that you wrote in the comments is also important.


Yeah. Motivation matters a lot. It’s funny, I once met the pop star, Regina Spektor. She was one of my clients for years, but we had never met until the TED conference in 2010.

We sat around talking for hours.

I said, “Now that you’re famous, do you ever miss how much you would hustle to make $100 at a gig?”

She said, “Yeah!”

Once you have plenty of money, there’s this weird thing – the joy of making a hundred bucks goes away a bit. During my early years as a musician, I worked so hard to find a way to make $200 instead of $150 at a gig. I’d get such a joy if I found a way to talk up my rates or sell a $20 CD at the gig instead of merely $5.

Sometimes, when you have too much money, you can lose that joy. It was funny that we were commiserating in that together.

So, motivation matters a lot. And yet, despite what I may say about watching the other hand – cut your spending, live frugally, don’t worry about what comes in, and focus on what goes out – if that doesn’t motivate you, then maybe you need to be motivated by the dream of having a Ferrari. If that makes you go add more value to the world, then alright.


I revisited another article of yours recently. When I first read it, I wasn’t sure about it. But weeks after, I was still thinking about it and coming up with ideas. This was the idea of meta-considerate.

Would you tell us a bit about that blog post?


Sure. The meta-considerate idea is easiest to see with dating and romance.

A friend of mine told me a story about this woman he had a crush on. I was friends with both of them and he was putting her up on a such a pedestal. He said, “Oh my God. If only she would talk to me. She is the most amazing woman that ever lived. Blah, blah, blah. . .”

I said, “Dude, don’t do that.”

He said, “Don’t do what?”

I said, “You’re lowering your own value by raising her up so high. In the physical metaphor, if you lift somebody up on a pedestal, you make them look down on you. She doesn’t want to be with somebody that she’s looking down on. She doesn’t want to be with somebody that says, ‘If only I was worthy to be with you.’

No, she also aspires to be with somebody that’s above her. And you’re making it clear that you don’t think of yourself as on her level in any way, let alone above her. You think you’re being considerate, when you’re really being meta-inconsiderate.

It’s actually meta-considerate to let somebody chase you a bit, let somebody long to be with you, or let somebody aspire to be with you.”

That’s where the idea came from. But I think of it a lot in parenting. You may think it’s considerate to always give your kid what they want, but it’s meta-inconsiderate. It’s meta-considerate to help them learn that they don’t need a reward to do work.

It’s always a social interaction thing. Considerate and inconsiderate are targeted on somebody else. They’re social words. You can’t be considerate and inconsiderate when you’re sitting alone with yourself. That’s a different word.


For some reason, this article really stuck with me, even though at first, I only saw the surface level of how it applied to dating or relationships or parenting. But then I thought of a few examples.

One example is buying a gift for someone special like a close partner or a family member. Maybe you’ve been buying this person gifts for years. You think it might be considerate to tell them, “This is what I want this year. This is where you can get it.” It’s very considerate. It makes things easy. You get what you want. They’re off the hook from having to think of something.

But it’s meta-considerate to not make it so easy on the gift giver. They have to think a bit harder, consider your wants and needs, and think of something a bit more from the heart. I think the recipient would prefer a gift that the other person thought of, rather than the gift they just told them to get.


I like that. It reminds me of the slang phrase two cents. Don’t add your two cents. For those listeners who might not know the phrase, if you say, “Let me add my two-cents,” it means OK, I agree with everything you just said, but let me add a little bit more to that idea.

Marshall Goldsmith wrote this brilliant book called What Got You Here Won’t Get You There.

It’s a book about leadership, written towards somebody who’s already a successful leader of people. His best bit of advice in there and the bit that struck me the hardest is where he said, “Don’t add your two cents. If one of your employees comes to you with a project that they’ve worked on and presented for your consideration, it’s tempting to think you need to add a little something to it and leave your comment, but when you do, they now feel that you’ve given them an order.

Now this project that was 100 percent theirs this morning, is now less theirs and more yours. They’re not going to have the same enthusiasm to follow through with it as they would if you would have just kept your mouth shut and let them own it completely. Even if you felt that your two cents would be an improvement. Keep your mouth shut and let them own it completely.

You’d think it would be considerate to add your two cents, but it’s meta-considerate to keep your mouth shut and not add your two cents.


Another example of this deals with feedback. Considerate feedback is soft and gentle. It cushions the blow a little bit. But meta-considerate feedback is very direct and honest. It lets the person feel a little bit of pain, but then gives them a clear way to improve.


Cool. I heard that Walt Disney in the early days had a cork board in the hallway with their current projects. Posted above it would always ask, “How can we improve this?”


“How can anybody add their two cents to this idea?” [Laughter].


I think it’s different if you’re asking for it. It could be a power thing. If the boss is saying, “Please, everyone, tell us how we can improve this.” Now, you’ve been given leeway for everybody to contribute.


I like it. My final example deals with the What You Will Learn podcast episodes. At the beginning of our podcast journey, we said, “Hey this is a 300-page book. There are three or four core ideas. There are many stories, anecdotes, and studies that all back this up. Let’s edit those out and just get straight to the point.”

It was considerate because people didn’t have to read the books. We gave them the best stuff. Now, we’ve moved towards meta-considerate. We’re actually leaving in the exact right amount of that stuff. We leave in some of the story, a short glimpse of the study, and it gives people tension. It allows them to learn and discover it for themselves. Instead of whacking them over the head with the lesson, they’re surprised by the lesson when it comes.


I often think of book notes as the punchline of the joke, but you don’t actually know the joke.

Somebody can say, “. . .and then the duck says, ‘Who is this guy?’”

And you laugh and say, “Ohhh yeah, I remember that one.” But you don’t.

Book notes are the punchline. But if you haven’t read the joke leading up to it, it doesn’t have an impact. The book notes on my site are absolutely not meant to be a summary of the book. They’re just the punch lines that hit me, so I save them for my own personal use to reflect on later. They’re not for anybody else’s sake but my own.

It’s weird when people say, “Thanks so much for posting those summaries, so I don’t have to read the book.”

I think, “Oh, you’ve missed the whole point.”

I’m just sharing my personal notes from that book. If you think the notes sound interesting, please go read the book.


What sparked your love of books, and why do you read?


I started reading as a teenager because I wanted so badly to be a successful musician, so I read books on how to do so. I read James Riordon’s book, Making it in the New Music Business from 1988. Before that, there was a guide book called The Platinum Rainbow released in the 70s. I devoured every word. I thought those books contained the key to becoming rock star.

But the first big punch-to-the-gut, blow-my-mind type of book was Tony Robbins’ Awaken the Giant Within.

When I read that, I thought, “Whoa, Oh my God!”

It opened my mind to a way of thinking bigger. I read about all of these philosophies around the idea that you can do something about your feelings. We often say, “I can’t help the way I feel,” and Tony Robbins’ whole thing is “yes, you can help the way you feel.”

If it’s not serving you, then stop doing it. Think about what beliefs you need to have to be the person you want to be. Then, make yourself have those beliefs. Think of supporting beliefs that would help you think that way.

I felt like that book was helping me achieve my dreams. Then, I started reading books on marketing because I wanted to be more successful. Only later did that branch out into other subjects that weren’t just direct problem solving. But the first 10 years of me reading books was all about problem solving.


How would you classify if a book if good or not?


A good book changes my mind. A great book changes my actions. But, it’s your job to change a good book into a great book. If you speed through a list of books and say, “There. I read all of those,” you’ve missed the point. You have to apply what you learned to your life and that takes deliberate reflection. You must go through what you learned and think about how you could apply it to different aspects of your life.

It also usually takes metaphorical thinking. For example, a book on tennis might have the best metaphorical insights that you could apply to parenting.

I like books that tell me what to do. But most authors don’t want to be so presumptuous. I loved the book, The Paradox of Choice, by Barry Schwartz. He spent the whole book describing the problem of choice and having too much selection.

This book had such an impact on me. It was only in the last chapter where he said, “Now we’ve come to the last chapter. My editor says that since I spent the whole book describing the problem, I should at least offer a little solution. And of course, that was my favorite chapter.”


And it was only about 10 pages.


Right. I might have been able to figure out the solutions for myself, but it was really nice to have them clearly spelled out.

I used to think that it was important to retain what I read. I thought I needed to memorize it, but now I realize that I don’t need to retain it. I need to review it. I need to reflect on it, and I need to apply it. That’s what turns a good book into a great book.


I like that a lot. At, you have many book recommendations and you rate all of them on a scale from 1-10 by how much you recommend them.

Is there a difference between how you rate it versus how much you recommend it?

For example, we both love The Laws of Human Nature by Robert Greene. We both rate that book 10/10, but it’s massive. It’s 600 pages. It contains some deep, dark human shit and maybe it’s not great for somebody to read straight up. If someone asked, “What’s the first book I should read?” I wouldn’t recommend it.

I know Adam Jones loves his Jared Diamond – Collapse and Guns, Germs, and Steel. He gives them great ratings. But they’re 700 pages. I don’t think I would recommend that for a beginner. If you contrast that with, say, The Compound Effect by Darren Hardy, which is 150 pages or so. Really great advice, especially at the very start of your reading journey.

But I think maybe if you’d read 200 books, it’s probably like I’ve read this before. It’s sort of obvious and boring. So, I think it’s different how much I would rate it for myself versus how much I’d recommend it for somebody else.


You nailed it. And also, if it seems like the book is going to be of general interest, then I’m more likely to recommend it to others. But I’ve read some wonderfully nerdy books like Au Contraire, Figuring Out the French, which is a great, fascinating book to help you understand French culture and philosophy, but that’s me nerding out on other cultures.

I wouldn’t say everybody needs to read that because I don’t think everybody needs to understand the French. But, hey, if somebody is asking me what’s the best book I’ve ever read on understanding and culture, then I’d definitely recommend Au Contraire, Figuring out the French. It’s the best.

We deem things as “must-reads,” and that implies that someone needs it. But we don’t know everyone’s needs. Some people really need to make money. Some people don’t have money problems, but they really need to make peace with their past. Some people really need to be more considerate. Other people are considerate to a fault and really need to work on their self-worth. So that’s why we can’t say, “Everyone needs to read this.”

I like the idea of qualifiers for book recommendations. If you’re having trouble letting go of the outcome of a difficult situation that’s out of your control, then you should read this. If you want to start adventuring far away from home, then you should read this.

But we can’t say, “Everyone should read this.” That’s too broad.


Are there any books that you’d say are broadly applicable and great places to start if you don’t read? Or again, does it always come down to each individuals’ needs?


I don’t know. The timing of when you read a book makes a huge difference. The first time you encounter an idea, it blows your mind. But then if you go read two more books on that same subject, those books won’t impress you as much.

Book number one still feels like a masterpiece. By book number three, you think, “Yeah, it was OK. It was average.”

But if someone else read those same three books in reverse order, then they’d declare what you know as book number three to be a masterpiece and book number one to be average.

When I met Tim Ferriss back in 2007, we were comparing notes on books that totally changed our lives. The book that changed his life, I found it to be completely average and vice versa. We realized it’s because the books we read first, opened our minds up to these new ideas and ways of thinking. By the time I got to the next book, I got used to that idea.


Tim Ferris’s book was The Magic of Thinking Big and yours was Awaken the Giant Within?


Wow. You’re good.


Jonesy and I had the same thing with The Compound Effect and The Slight Edge. They’re both very similar. The idea is that the same small, tiny little decisions you make every single day, compound and add up during the course of your life.

We both absolutely loved both books. But The Compound Effect was around the tenth book I read. It was in my top 10 for ages. I think The Slight Edge is probably better. I’d probably recommend that to somebody more. If it had been the tenth book I read instead of the 270th book, it would have been awesome. But when I read it, it felt like I’ve read that that exact same book before.


I had a similar experience with Daniel Gilbert’s book, Stumbling on Happiness. It blew my mind. Then I read three more books on happiness which had diminishing returns. I gave the fourth one I read on the subject an average rating on my site.

Somebody said to me, “Oh my God, how could you call that book average man? That book totally changed my life.” And I guess it’s because it was the fourth one I read on that specific subject. All of the authors referenced Daniel Kahneman, and all of them mentioned the same research. I was over it.


We re-read Thinking Fast and Slow recently. We first read it maybe three years ago. We reread it maybe six or nine months ago. It was so funny that after we re-read it, of the next 15 books we read, like 12 of them referenced it.


Well, when I read Thinking Fast and Slow, I had read books that referenced him for around ten years. So finally, it was like The Master Speaks.

I tried to go back and read Awaken the Giant Within by Tony Robbins because the book completely changed my life. I read it at 19 and again when I was 21 and again when I was 23. Over and over again, this book completely changed my life. But in my late 40s, I tried to read it again and just couldn’t. So boring.


How do you pick what you read next?


It’s always to solve a current problem.

A current problem might be as concrete as wanting to be better at parenting, writing, or discipline. But a current problem might be as vague as yearning for adventure, wanting to understand Finland, or thinking more about silence.

Curiosity itself is a mini problem. Last month, I heard an interview with the linguist John McWhorter, and it instantly created a problem. Because now, I wanted to know much more about linguistics. I immediately stopped what I was reading and instead went and found one of John McWhorter’s books on linguistics and delved into it. This little tidbit of an interview made me so curious that my curiosity was a bigger problem than whatever I was reading before.


With every book you read, curiosity gives you three more to add to the pile. It never gets any shorter.

We always ask everybody this question – what are some of your favorite books? Do you have a book you would currently recommend?

Of course, everyone can go to and see the full list there.


This is a variation of what I said five minutes ago.

When I get an email from somebody asking for book recommendations, I say, “I don’t know what you’ve gone through. Depends what your current problem is.”

That’s why at, I write a few sentences about each book to offer the gist of what you’ll read. That’s the whole idea. You can scan this list and whatever problem you’re currently wrestling with or whatever idea seems to captivate your intrinsic interest the most, that’s the one you should be reading. Not the one that somebody’s most loudly or most emphatically says you should read.

You should read whatever captures your current interest today – not your interest this year or last week – just today. Let’s say you choose a book on willpower because today it seems like a massive problem in your life. But by Friday, when you’re a third of the way through the book, if willpower doesn’t like a problem, you can stop reading it.


You’re reading a book on willpower, but you don’t have the willpower to get through the book [laughter].


There’s a joke in there, but it’s a good reminder that you don’t need to force yourself to finish something if you’re feeling satiated on that subject.

You might start reading a book about wanderlust, or travel, or vagabonding. But you might make it a few chapters in and say, “I thought this was an interest of mine, but that was a few days ago. Now it’s not anymore.”

You don’t need to make yourself finished reading Vagabonding just because somebody said you should. If it’s not your interest today, then you can stop and read something that’s more fascinating to you today.


On your site, your top recommended books are listed first. The one that pops up at the top is a book called Sum by David Eagleman. Some of these chapters are real eye openers.

Can you talk a little bit about Sum and how this book led you to your newest book project?


I love the format the most. The subtitle is 40 Tales from the Afterlives. The big idea is that there’s an invisible question asked over and over again, which is: What happens when you die? Each one of these little, tiny chapters, which are two to five pages long, answers that same question.

But the chapters deliberately answer this question differently and conflict with all the other chapters. One chapter will say, when you die, you’re greeted by a bunch of thuggish little cavemen looking creatures that keep saying, “What is answer? What is answer?” You find out that your whole life was an artificial intelligence program. Now that the program has stopped running, the people that wrote the program are trying to find out the meaning of life because that’s why they wrote your program.

No matter what you try to tell them, they don’t understand. They keep saying, “What is answer?”

You realize that if we were to write in an artificial intelligence program to figure out the meaning of life, we wouldn’t be smart enough to understand what it’s trying to tell us.

Then another chapter says, when you die, you find out that in your last life you chose to be a man. In every lifetime, you get to choose what creature you want to be. So, you remember a wonderful day in a beautiful field once where you admired a horse grazing in the grass and you thought, “What a nice, simple life a horse must have.”

So, you tell your greeter there that you’d like to be a horse now. No sooner said than done, you start to feel your body change. Your hands turn into hoofs. Your shoulders get more muscular. You start to feel your face getting longer. But then you start to feel your brain turning into a horse’s brain and you feel yourself starting to forget what a man is.

You realize you’ve made a horrible mistake. You enjoyed being a complex man admiring the simple life of a horse, and if you’re just a simple horse, you won’t be able to appreciate it because you have nothing to compare it against.

You yell out, but all that comes out is a neigh. Right before your brain completely turns into a horse’s brain, your last terrible thought is, “I wonder what kind of complex, beautiful creature I must have been before I chose the simple life of a man?”

Each chapter contains beautiful, amazing little short stories. But more than anything, I love the format of continually asking one question and then answering differently each time.

One day I was driving down the road and I gasped out loud. I said, “Oh, my God, I want to write a book called How to Live in that same format, where each chapter is convinced it has the answer on how to live. Every chapter will deliberately conflict with all the other chapters.”

So, that’s the book that I’ve been writing for the past year. It’s a blast. I’m having so much fun writing it. The whole time I’ve been writing this book, I thought, “How is this going to end? Do I list 40 different ways to live and then I’m done?”

One day an ending came to me that created not just a gasp, but a squeal. I can’t reveal the ending yet, but it’s been a blast to write and I can’t wait to finish and release it.


Fantastic. That’s an awesome cliffhanger. I’m really looking forward to the day that you finally announce it’s ready for people to buy. As we just wrap up now, I just want to again say a big thank you for the first book that kickstarted this whole podcast.

I also apologize for some of those early emails I sent you when I was a 22-year-old. Looking back, they were extremely cringeworthy [laughter]. But I appreciate your kind responses to those.

Is there anything you want to leave us with now?


For one, thanks for having me. It’s fun to nerd out and talk about books. Thanks for the philosopher’s compliment, too.

For anyone who’s listening, the reason I do all these interviews is to hear from people.

I really like meeting people, especially the kind of people who nerd out on Adam’s podcast. Go to and send me an email and introduce yourself.