Curated Questions
host: Ken Woodward
power of questions, reframing, identity, influence of culture on questioning, journaling for self-reflection
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Transcript:
Ken
Today’s conversation is with Derek Sivers. That’s S-i-v-e-r-s. Derek is a unique human who consistently pushes the edges of convention, tests his assumptions, and embraces the new realities he finds on the other side. His identities have included musician, circus ringmaster, traveler, entrepreneur, father, programmer, speaker and author. Derek gave three TEDx talks in 2010 which have amassed 23 million views. His latest book, Useful Not True, will be released in 2024. Although American, he is a world citizen living in New Zealand and is true to his word regarding answering emails. Derek, welcome to Curated Questions.
Derek Sivers
Sweet intro, Ken. Thank you.
Ken
Absolutely. So a question that I always ask everyone and that is when did you first learn the power of questions?
Derek Sivers
Age 19. My boss at the circus was this gorgeous, wonderful woman that I adored. And she said, “You have to read this book called Awaken the Giant Within by Tony Robbins.” And because the referral was coming from her, I took it seriously and really ingested and internalized that book when I was 19 years old. And again when I was 21 and again when I was 23. I just kind of kept rereading it, and it just shaped the way I see the world. And its core message is about the importance of questions. Have you read it?
Ken
I have, I have. And I need to actually go revisit it and just actually signed up for a Tony Robbins thing here in a couple of weeks too, you know, virtual type thing anyway. But yes, I’ve appreciated Tony’s focus on questions and hopefully someday, you know, get him on the podcast here. But his focus on questions and I think that that’s one of the things involved with why I’m even doing what I’m doing because of the power of the questions.
Derek Sivers
That book, I just reread it last year for the first time in, I don’t know, 20 years, and it’s very dated. Just warning to anybody. It’s essential reading, but it’s not a great book. There is a good book inside that book, with a lot of dated references. You know, OJ Simpson, the hero, Michael Jackson et cetera. It’s really interesting how kind of 80s the book is. So don’t go expecting a great book. Go expecting a really a good book inside a bigger book. But it’s focus on questions is amazing, especially for any listener of this podcast. You already get it, but I loved the message that your brain will answer anything you ask it. So be careful when you say something like, “Oh, why am I such an idiot?” You know your brain will answer that. But I also loved the point that you can deliberately make a habit of asking a useful question, like when something goes wrong, you say, “What’s great about this?” Because in the moment you’re in this terrible state where you’re thinking like, “Oh my God, everything’s screwed. I’m devastated. I’m stuck. This is a disaster.”
Derek Sivers
And if you force yourself to say what’s great about this, I love the point that your first answer will probably be nothing. This sucks. It’s terrible. And then you just keep asking. You’re like, “All right, come on. Okay. Good job. Okay. That was your first response. Keep going. What’s great about this?” Nothing. It’s just bad. No, there’s really--- you know, for once, there’s truly nothing great about this. Okay. All right. But what’s great about this, and I love this idea of you keep going past your first answer. Let’s not glorify our impulses. Let’s not say that only your first answer to something is authentic. Now, I think your first answer to something is emotional response. It’s a dumb impulse. Or it’s a habit that you learned when you were a kid. You know, to throw a tantrum at first when something goes wrong or whatever it may be. You get past it. Your first thought is an obstacle to get past. And so you keep asking yourself healthy questions like, “How can I make this a great thing?” And then eventually you get to a better answer.
Ken
Is there an example that you can think of where you’ve done that recently, where something sucked and you’re like, okay. Hold on. Let me keep at this.
Derek Sivers
Almost every day. Definitely every week. You know, past relationships, breakups, locations, situations with my kid, situations with my health, whatever. It comes up almost weekly.
Ken
Gotcha. Yeah. All right. And we’ll get to journaling and that kind of thing. So I think that’ll probably come back up there. But just your practice of being so intentional. And from the bits and pieces that I’ve heard, I think are just an amazing example of really engaging with the questions in a deep way.
Derek Sivers
And it doesn’t have to be life size. It can be moment to moment like a big traffic jam. You’re like a traffic jam. You’re like, “You know what? I got some good music on this phone here. Hold on. Let me pull up something I haven’t heard in a long time. Let me crank some old nostalgia music from when I was 15. Oh, my God, what this does to my soul.” Yeah. There’s just a way to ask yourself that, how can I make the most of this kind of question, even just in the small moments. To me, that’s all reframing. I love the subject of reframing. In fact, as I’m finishing my new book called “Useful Not True”, which is all about reframing, an early reader said, “Hey, can you give more examples of some beliefs you find useful?” I said, “Well, basically everything I’ve written is that. I wrote a book about business called “Anything You Want”, and it’s just a bunch of useful, not true beliefs that I use to think about business. And then, “Hell Yeah or No” is a book about making decisions, and it’s just a whole book of me sharing my beliefs that I know they’re not true. But I find these beliefs useful to help think about how to make decisions.” It’s like that’s what I’ve been doing this whole time is sharing a bunch of beliefs I find useful, but not true. But on these are all reframing. You know, that’s what questions do, don’t they? They help you look at something in a different way.
Ken
Indeed. Now, you mentioned the woman that gave you the book or encouraged you to read the book. So what was the situation there? Because, I mean, was she the boss or?
Derek Sivers
Yeah. She’s one of my favorite people in life. She was my boss at the circus. I was 18, she was 36 or something like that. And she was not a mentor, but I met her at a very insecure time. You know, it’s tough to be 18. I just moved across the country to Boston from Chicago. Didn’t know anybody suddenly got a gig with the circus. And she was so nice to me. And yeah, that’s about it. She was really nice to me. She was really sweet to me. And yeah, I cared about her and she cared about me. That’s what I needed when I was 18. For somebody to feel like they saw me or me to feel like they saw me and got me, and yeah. Maybe so the fact that she was the one saying, “Hey, you need to read this.”
Ken
This scared a lot of weight then.
Derek Sivers
Yeah.
Ken
Yeah. It’s beautiful. Just those things of the importance of relationships, right?
Derek Sivers
Yeah.
Ken
The people that come across our path.
Derek Sivers
Some years later somebody said, “You’re very confident, aren’t you?” And I said, “Yeah, I guess I am.” And they said, “Why?” And I thought, “Oh, why, why am I so confident?” And I had kind of like rewound my life and I was like, it was her, wasn’t it? I was not a confident person but she gave me my confidence. I was in the circus for ten years. So just for years, just every week, over and over. She just kept being so nice to me and telling me nice things about myself. And eventually, I think after about two years, I started to believe them. I was like, “Yeah, yes I’m a pretty cool person.” That was thanks to her.
Ken
Important lesson in that too. Yeah. Just that consistent water drop of encouragement.
Derek Sivers
Yeah.
Ken
Yeah. Gotcha. Let’s see. Well let’s talk about your writing and journaling. So I’ve read that you write often, or, you know, a couple hours a day or 2 or 3 hours a day in your journal.
Derek Sivers
Yeah.
Ken
And so how do questions inform that. So let’s kind of in this little ecosystem of journaling because there’s a lot of questions involved in that process. What does that look like?
Derek Sivers
The main purpose of journaling for me was to question myself and what am I thinking. When I look at my old journals. That’s all they are, is I would only turn to my journal when I was confused and I wanted to straighten out my thoughts. I’d say, “Why am I upset? Or what am I confused about? How am I going to make this decision? What’s the real point? What are my options here? What am I really after? How else could I think about this? What’s the real point of that? Well, why am I doing that? Is that just leading to something else?” And so if I look at my past journals, that’s all you’d find in it. It would be, you know, a week of silence and then an entry like that, and then 20 days of silence and another entry about, you know, feeling confused about a situation. It wasn’t until I was 42 years old, and I was looking back at my diaries from ten years earlier, wishing that I would have kept a daily diary during that extremely exciting time in my life when I had so much going on. I was in this tornado whirlwind of the music industry. The whole like indie music revolution was going on and I was in the middle of it, but I was too busy to journal.
Derek Sivers
Damn, I wish I would have kept a daily journal then. I so wish I would have had a daily journal. Just what I was doing, what I was thinking. It would have taken 15 minutes a day. And what a cool thing to be able to look back on. And so at the age of 42, I started keeping a daily journal, not just of my big questions, wanting to reframe something or figure out something or sort out things. But also just here’s what I did today, and here’s how I’m feeling, and here’s what’s on my mind. So there’s that as a daily habit that I always do. But yes, now back to the core of it. Whenever I’m feeling, let’s say, less than absolutely amazing about something, anytime I’m feeling kind of mixed feelings or not quite happy or extremely frustrated or lost or confused, I go to the journal and I just open up an empty text document, and I start by saying like, “All right, what’s going on? I feel this, and this and that. But I’m not really sure what I want to do this or I’m upset because of that. Well, why is it upsetting? Because I have an expectation. Okay, so this person should have acted according to my expectations. What’s another way to think about this?”
Derek Sivers
But then I don’t just stop at the first one. It’s not like I’m looking to quickly get this sorted. And by the way, let’s come back in a second to the subject of Sherlock Holmes.
Ken
Okay.
Derek Sivers
So I’ll just keep asking myself questions that are basically intended to keep reframing the situation until I find a frame that feels good or useful. It’s not always good. Sometimes, you know, the most useful reframe is to realize I’ve been an idiot and made a horrible mistake.
Ken
Right. Yeah.
Derek Sivers
And I need to change everything. But sometimes it’s making peace with the past. There’s something that’s happened in my past, and it’s upsetting me still. And I need to ask myself some questions about it and reframe it until I find something that helps me feel at peace or gives me a useful takeaway that I can use in the future. So yeah, in short, it’s all about asking myself questions and then questioning my answers.
Ken
And so, assuming that it’s with all the same rigor and everything that you just did, to get to that initial position in your questioning back on whatever that resolution is. Is that is that a fair assumption that if you did five rounds of why, why, why, why type of thing anyway, then once you get done, you’re like, okay, this is where I end up on this thing. And then you do kind of another round of is that true? And diving back into that.
Derek Sivers
Yeah. Because we often even privately answer ourselves in a way that we think we should be answering. You know, you might have just read a book about habits and it’s still echoing through your head. And so now you answer all your questions in terms of that, because that author’s thoughts are still in your head, or who knows, you’ve just watched a superhero movie and you’re feeling heroic, you might be giving heroic answers to questions. But it might be bullshit. And so I think it’s really healthy to also doubt yourself and your own answers and say, “Really? Maybe that’s not true. What else could it be?” You get to even try on different personas, because who you are and your persona now is just a circumstance of your parents and where you grew up. And if you were born on the other side of the earth or adopted at birth, you would have had extremely different values and might not be so generous or might not be so selfish. And so it’s interesting to imagine yourself as a very different person with different values that are different but not wrong, and think how a different person would handle this. And you could just look at it like a menu. You could look at it like a menu of options that you can choose from. There’s not just one answer. And don’t stop at the second answer, but keep growing and keep going. Yeah, that was a nice slip.
Ken
Yeah, both of them. Yes.
Derek Sivers
Keep going, keep growing past the first, past the second one. It’s like the rule of brainstorming, right? Don’t just try to quickly end the process. You keep going.
Ken
Do you come back or to the journals? I mean, do you do any kind of review process where you’re like---
Derek Sivers
Yeah.
Ken
Oh, wow.
Derek Sivers
Big time. It helps that I type fast and I like my computer. For what it’s worth, my computer is usually offline. I’m not an internet addict. I keep it offline by default and then I turn on the internet for limited times to go do something I need to do. I keep it offline by default. I don’t use cloud services, I just keep everything local on the computer so that I can stay offline like that. And that’s where I do my best thinking, is just letting my fingers fly into text documents that are intended to be searched again in the future. So I’ll give you two examples. The first one is I realized that there were some thoughts that I kept coming back to. Say, 12 years ago, I was living in Singapore. My kid was born in Singapore. We moved to New Zealand, but I spent years kind of waffling on whether we should move back to Singapore or not. The pros and cons of that. So like in my daily diary, I kept bringing up Singapore again. Eventually I thought, you know, it would help me if I had all of my thoughts about Singapore in one place so I can review them. Well, what’s that called time wise? Chronologically?
Ken
Yeah.
Derek Sivers
And see how my thoughts on this have stayed consistent or changed. And so I started with what I call the “Thoughts on” journal. So in the folder called thoughts on I have maybe 100 subfolders. Thoughts on home, thoughts on getting a dog. Thoughts on Singapore. Thoughts on relationships. Thoughts on friends. And so whenever I’m having ongoing thoughts on a subject, I create a new thoughts on folder and I categorize them in there and it’s come in really handy. Say, for just something simple like the big decision about whether to get a dog or not, that’s a massive decision. It’s going to be like 15 years of your life that’s going to affect another sentient being. And so I thought really long and hard for years about whether to get a dog or not. And I dabbled with it. I took care of other people’s dogs and whatnot. And I kept all my thoughts on it in there, and it was really useful when I’d find myself, say, I’d see a video of an extremely well-trained dog that looked really sweet and affectionate and wonderful. And I thought, “God never did get a dog. I still really want a dog.” And then I go back to my thoughts on dog journal and I’m like, “Ah, no, thank you.”
Derek Sivers
I’ve just been reminded of all the reasons I decided not to get a dog. I had forgotten, okay, so that comes in handy. So I said two examples. So that’s number one. Number two is really personal, but I think it’s okay to say here. I was in a romantic relationship for two years and most of it was great. But then things were really hard. Like every day was really hard. It was like this everyday struggle. Just every time I’d come home, I’d kind of, like, stand outside the door for a minute and try to gather my strength, my emotional strength to go inside to deal with this relationship. And I thought, “Ah, but it’s been so great in the past. It’s just hard right now.” And then it got really hard to the point where I said, I need to go away for a few days. And I went away for a few days because we were living together. Went away for a few days and I went and reread every single diary entry since the day we had met. And remember my diaries are now like every day at the end of the day, I just share everything I did and thought today in one place.
Derek Sivers
And when I reread two years of diary entries. I found that I had almost never been happy that most days with her had been hard.
Ken
Wow.
Derek Sivers
And I had been selectively remembering the good ones, which were few, and thinking that this is a great relationship that’s just currently hard. But when I went back and looked at the everyday journals, it had always been hard. And so that helped me make the major decision to break up. And it was the right decision that was aided by that journal. Yeah, we were about to, like, have kids. We were about to let go, like, you know, planned pregnancy thing. And I’m so thankful for my daily journal that helped prevent me from getting into a situation where I would have been with somebody for decades that was just a bad fit. You know, we just wanted such different things out of life that it was just a constant clash. But I hadn’t seen it because I’m an optimist. And so I had been seeing the past through rose colored glasses and, “No, no, no, it’s great. She’s great. We’re great. It’s just something’s hard right now.” But yeah. Thank you journal for that.
Ken
Wow. Well thank you for sharing it. And sorry that the relationship turned out that it did.
Derek Sivers
Yeah. No I’m so thankful.
Ken
You’re right. That was a saving grace to have that journal to go back and find out what was true. Wow.
Derek Sivers
I’m extremely thankful that, like, almost every day, like, “Man, I’m glad I broke up.” Wow. You know, and instantly, I could just see, like, right after I did, it just felt so much better. Just elated that the difference between how hard it was every single day to be in that relationship, and how amazing it’s been to not be in that relationship. So yeah, that was just thanks to the Journal. If it weren’t for me keeping past journal entries, I would not have known that.
Ken
Well, yeah, at this point, I’m assuming that you’re now, if that inkling ever comes up to say I’m going to pass writing on the journal, you’re like, “No, no, no, no, no, no, I must right. Absolutely.”
Derek Sivers
I don’t miss a day. If I do miss a day, then the next day I write what I remember of the previous day. I figure it’s the next best thing.
Ken
Yeah. Wow. Wow. And so the tactical on that is you just open up a text document, you said, and just start going at it.
Derek Sivers
That’s what works for me. Paper could work. I understand some people prefer paper journals. I got to say, the huge benefits of having it in a computer means I can search for words.
Ken
Absolutely.
Derek Sivers
In the past, I mean--. Okay, sorry. We’re way off the subject of asking questions right now.
Ken
All good.
Derek Sivers
But years ago, I got my kid a chemistry set, and he loved that chemistry set. And then we moved. It was during Covid. We moved from England back to New Zealand. And so we did not pack the chemistry set. And he asked about it. He said, “I really missed that chemistry set.” And I thought, “Wow, I wonder where I even got that?” So I was like, “Hmm, let me just search my diary for the word chemistry.” It was somewhere in the years 2019, 2020 and searched chemistry. And there it was. It said, “Bought my kid a chemistry set today.” And I looked it’s July 29th, so I just went to my bank and like, found my transaction receipts and went just July 29th. And there it was, the name of the shop where I got the chemistry set. And I was like, “All right, that was useful.” That took like 30 seconds. And I found the exact same chemistry set because it was in my diary, you know. So handy, I love this, I highly recommend it to anybody. And it only takes a few minutes and I find it really therapeutic. It’s like an end of the day kind of cleansing out. Maybe if something was troubling you today, it’s really useful to take the 20 minutes or longer at the end of the day to work through, you know, “Why is this bothering me? What’s another way I could think about this? Is that what’s really bothering me about this? Well, how could I have reacted? How would I like it to be in a perfect world? What would be my ideal scenario? What would be the most generous way to look at this? Am I being too generous? Have I been not selfish enough? Have I not been doing enough self value, self care?” It really just helps at the end of the day, to just put aside a little time before bed to ask yourself these things.
Ken
So it sounds like you’re not necessarily going through the standard five questions. You’re just kind of-- because you’ve been doing this for a while at this point, that you’re just like, okay, noodling through it as as the path leads. Is that right?
Derek Sivers
Absolutely. I’ve never had standard questions, in fact, that one that I said of what’s great about this might be my only recurring question for decades. I mean, it’s a way of thinking to say, how can I make the best of this? Or how can I see this in a positive light where I can get some benefit out of something that seems like it has no benefit. That’s probably been my only consistent question over the years. I don’t do any set of five questions for the day that’s silly. Well, silly for me. If you find it useful. Good for you.
Ken
Yeah, absolutely. All right, so you mentioned Sherlock Holmes.
Derek Sivers
Ah. Thank you. The difference between a good detective and a bad detective. If you’ve ever read any Sherlock Holmes stories or watched any of the various versions, TV or film, the idea is that some crime or mystery happens. The local policemen send out somebody to say, “Well, there’s there’s the body, there’s the gun. We’re done.”
Ken
Yeah.
Derek Sivers
But then somebody says, “I don’t know, something feels wrong about this. Sherlock Holmes, can you come take a look?” And Sherlock Holmes doesn’t come to a conclusion so easily. He’s like, “All right, well, there’s the body, there’s the gun. But what else could it be?” And he looks harder and he goes past the obvious. And I think we should all be a little more Sherlock Holmes in our own questioning of our own psyches, to not say, “Why am I upset? Because that person’s evil.” There, it’s done. No, hold on. Keep going. You push past things like a great detective. It’s a nice image to remember. Be more like Sherlock Holmes. Push past the first answer. Go beyond the obvious.
Ken
Yes. Yeah. I was reading this book by Amy Herman and she’s got three questions. One is, what do I know? What don’t I know? And the other one is, what am I missing? Or something like that? I don’t have it right in front of me. But that idea of just coming into a circumstance and always, you know, acknowledging what you know, okay, what don’t I know? And then what am I missing? Then just go, okay, I’m not going to just go with my first answer. And you know, it’s been stated that like in emergency situations, it’s like all of your first assumptions are wrong. So you walk in and you’re like, been through some scenarios and it’s been like, “Okay, so we know that this is the case.” And it’s like, “No, you don’t. You only have little bits and pieces of the whole circumstance.” Just give it time and keep digging. Yeah. So yes, I’ll be a little bit more like Sherlock Holmes. Love it. Cool. All right. Let’s see. So what questions do you think should be asked more or ignored in general?
Derek Sivers
Ooh. I guess I kind of said it earlier that asking yourself constantly, what’s another way of looking at this? Or what’s a better way of looking at this? Maybe asking another way skips the whole judgment thing. Let’s put off judgment until later. What’s another way of looking at this? And try to reverse it. Try to do a deliberate creativity exercise so that if you’re, say, feeling that somebody wronged you, let’s reverse it. Let me assume that I wronged them, that, in fact, they’ve been extremely wronged by me. And that’s why they did what they did. Or Why am I stuck? Well, let me reverse that. Why am I not stuck? Let me list all the ways that I am not stuck. Why is this not working out for me? Instead of saying, how can I make it work out more? How can I make it work out less? What would be a worse way of doing this? What would be the stupidest thing I could do right now? It really helps your perspective to force yourself into these reversing kind of answers. I actually think of it, I don’t know if you ever played with a Spirograph.
Derek Sivers
Do you remember a Spirograph?
Ken
Yeah, yeah.
Derek Sivers
A Spirograph. The reason it’s interesting is it doesn’t do an exact 180. It keeps doing kind of like these 170 degree turns. It goes all the way around. So I like doing that, keep asking myself, what’s the opposite of this or what’s almost the opposite. Okay. Now it’s almost the opposite of that. And you go all the way around something and look at it from so many different points of view. So that’s something I feel safe to say we all should do that more. I think that’s useful for anyone, for any situation, always. What we should ask less are those harmful questions that have an assumption in them. Like, “Why am I such an idiot? Why do things never work out for me? Why do I keep sabotaging myself? Why am I stuck in this awful place?” You got to watch out for those assumptions that your brain will answer. Your brain will confabulate and come up with answers to anything you ask it.
Ken
So I think that there’s a connection here. But you had mentioned previously and based on your willingness to move and to change, so what goes into your thinking or your process here for when you decide to just up and change? Because you’ve done it multiple times. And what does that look like for you? Because I would submit most folks say, “This is comfortable. I don’t like this inconvenience or this pain point or whatever, so I will let it be or muddle through it.” But it seems like you’ve got lots of different things, and I’m assuming curiosity and love of life and all these other things that you’re like, “No, I’m going to make a change and I’m going to go make it happen.” Is it that magical and then the courage associated with, “Yes, I’m going to do it.” Whether it’s to a different country or...
Derek Sivers
Or leaving my company. That was all my security or whatever.
Ken
Yes.
Derek Sivers
I value living a full life. Like at the end of my life, when I can tell that I don’t have long to live, I want to be able to look back and go like, “Wow, I saw the world from many points of view. I did many different things.” That is such a top value for me. That when I’ve been doing one thing or staying in one place for a while, it actively feels harmful to keep doing the same thing I’ve been doing. It feels like that’s going to diminish my chances of a full life by continuing to do what I’ve already done. I need to take a different approach, see the world from a different point of view. It could be a physical location. It could just be a mental approach to say, “Okay, well, I’ve been a minimalist for many years. I think it’s time I try being a maximalist.” Whatever. Is that the word? It’s removing judgment. So instead of saying I am this way because this is the best way to be to say, well, I have been this way, so I should try another way of being. And that’s so important to me that I get past any initial discomfort from the switch. So that’s what really went into my decision to sell my company. So sorry audience if you don’t know.
Ken
Let’s dive into give a little bit of the backstory.
Derek Sivers
It’ll just take a second. Yeah. When I was 29 years old, I started a music distribution company because I was just a full time musician selling my music, and people asked if I could sell their music too. And so, oops, I accidentally started a music distribution company that because nobody else was doing it. This is like 1998, 1997/98. Nobody else was doing anything like that. It instantly became the largest seller of independent music online. For ten years, I had 85 employees and millions of dollars and hundreds of thousands of musicians using my service. And after ten years of doing it I felt this thing that we’re talking about, which is like, I’ve been doing this too long. Yes I could make way more money by continuing to do it. But I want a full life. I don’t want to keep just doing the same thing in the same place. And so I made myself leave. And at first, I was just going to quit. I was like, just going to walk away. And then I was just going to shut it down. And then a friend of mine said, “You idiot, you know, you can sell a company, right? You don’t have to shut it down.” I went, “Oh, right.” So then I was like, but I don’t want to sell it.
Derek Sivers
So my second idea was, I’m going to do it like Willy Wonka. I’m going to hide five golden tickets into five CDs and announce to the whole world that, you know, the new owner of CD Baby will be whoever finds one of these golden tickets. And then, you know, I just have to push them into rivers of chocolate or whatever. And then again a friend said, “No, seriously, you’re being an idiot. You can sell it.” And I went, “Really?” So then I looked into selling the company. I went, oh, “Okay. Yeah, that’d be nice.” So I sold the company. But it was yanking out my whole identity. I was Derek@cdbaby.com. That’s who I am. And it felt like this is the learning, growing experience to remove the thing that I’m leaning on so that I can venture off a new direction. Maybe because of this value system I got from reading Abraham Maslow as a teenager, you know, the pyramid of self-actualization and trying to be all that you can be. Abraham Maslow had a little quote that said something like, “Every day you’re presented with a choice between safety and risk.” He said, “Make the growth choice a hundred times a day.” And I like that. Just like even like day to day little moments.
Derek Sivers
What’s the thing I usually do? What would be the uncomfortable thing while doing the uncomfortable thing is the growing experience. And so every day I try to choose that choice. And then even on the big scale, I looked at my options when I was feeling done with my company. I said, “Well, I could just remain the owner and I would be the owner. I just don’t work there. I’ll just own it.” It’s like, all right, that would make me a lot of money, but I wouldn’t be growing. I’d just be doing the same shit I’ve been doing for ten years.
Ken
Yeah.
Derek Sivers
The growing experience would be to walk away and into the void and have nothing waiting for me. That’s scary as hell. So therefore that’s what I should do. So same thing with moving countries. If it were just up to me, I think I would be living in Saudi Arabia or India right now or something like that. But I have a kid that I adore and his mother does not like traveling, so I want to be with him every week and so does she. Therefore, I live in New Zealand, which is a safe, comfortable, beautiful place. But I am yearning to go live somewhere less comfortable right now.
Ken
Do you have any idea why you are so willing to just challenge? I mean, because that is outside the norm. And we as a species are normally about comfort. I’ve got a cousin that he in a similar way. He’s made decisions every couple of years to move. Now he stayed in local cities. I mean, he’s moved to a little bit around the country, but he’s like, “Nope, I got to move every couple of years I need to move.” And he’s changed like which name he goes by at his company. When he changes a company, he’s like, “Okay, this is my first name. Now I’m going by this other name.” And such, and it’s in a similar vein of no, I got to have change and I’m going to do this intentional. There’s going to be some uncomfort and the rest, but this is what it looks like. Where does that come from? And then certainly you’ve nurtured it. And so while there’s still the uncomfortableness on the spectrum and uncertainty and such, I think that there’s for you because you’ve done it so much. There’s at least a little bit of, “I’ve done something like this before and I’m not going to die. The odds are pretty good. I’m not going to die.” But even that initial thing to the first two or 3 or 4, it’s a greater risk I guess, because of the unknown. But kind of where does that come from?
Derek Sivers
Oh, your cousin sounds like my kind of guy. I think just valuing the long term view and consequences. So if you choose comfort, you get acclimated to comfort, which then makes you weaker. Because as you get more acclimated to comfort, you become less and less capable of handling discomfort. And so if I’m thinking long term, I do not want life to be easier. I want to be stronger. And so I deliberately keep choosing situations that are uncomfortable, to keep strengthening myself so that I can be happy in a wider variety of situations. I was going to say any situation, but, you know, come on a wider variety of situations. That to me is just obvious and rational. Get stronger instead of weaker. Court ongoing blips of discomfort and acclimation over and over again to strengthen yourself instead of just sticking with one that, you know. But yeah, you’re right. Thanks for reminding me. I have been doing this since I was a teenager. I had a little rule of thumb that says, whatever scares you, go do it. And I live my life by that, whether on a tiny moment to moment level, like, “Oh, wow, that woman is gorgeous. She’s intimidating. I’m scared to talk to her.” And I go, “Oh, I’m scared. Okay, I’m going to go do it.”
Ken
Here we go. Off I go.
Derek Sivers
You know, that was me at 18, getting the courage to talk to the hot girl. And then at age 20, I graduated college early, and I was like, “Well, the scary thing for me to do would be to move to New York City right now. I don’t know anybody in New York City. It’s the big, scary place. So here I go.”
Derek Sivers
And living in New York City every day, it’s like, well, the scary thing would be to go up to that band on stage and ask if they need a new guitarist, or walk up to that music industry executive that I recognize and give him my demo tape or whatever. You know, that was me in New York City in the 1990s. I just kept doing this and yeah, kind of like your cousin. Every two years, I feel like, “All right, that’s enough living this place, I want to live in a different place.” Even if it’s in the same town. Like, I’ve been living in an apartment in Union Square for a while now. I want to try living in a house in the country for a while. I’ve been in a house in the country for too long, now I want to try living in Union Square again or whatever, you know, just to change it up. Just to keep seeing the world from different perspectives, like we’re talking about with questioning. What’s another way to see this? What’s another way to see this? You can do that with your life choices. Yeah. And you could keep pushing into discomfort, which then gives you the ultimate security of feeling strong and capable. That, to me, is a greater reward than the short term reward of comfort.
Ken
That’s beautiful. Now, you also mentioned identities. So this is kind of staying in the same area of conversation. So I’ve gone through some identity shakeups here in the last few years. And it’s been really hard because you’ve got about six months on me in this human experience. So we’re right about the same age. And so now it was late 40s. I’ve had this consistent set of identities. And then I started to learn and identities shifted and it is brutal in doing this shift and becoming someone that, oh, historically, I would never have talked to or I would have had very critical judgments about necessarily who I’ve become or some of the identities that I’ve kind of taken on versus who I had been. And there just continues to be this ongoing thing where, like one is very big in our family. The Woodward name and the rest. And I’ve mentioned this a couple other times, but I found out 18 months ago that I have a sister that’s five years older than me. Yeah. That look. Yeah. Yeah, that’s pretty much. It’s like, “Whoa whoa whoa whoa. Hold on just a second.” My dad is a lovely guy, you know? And he’s got all the identities of the morally right thing and everything. And he passed away in 2010. And so now I’m like, “Well, what do I do with this?” Because there’s this whole identity of who we are as our family and the values and all the rest. And now I’m looking at this wonderful woman in front of me who is my sister, who I lost half a century with, of you know, having an older sister and such. And she’s a remarkable woman, lovely family and all the rest. But it’s like having to contend with this crumbling identity and it’s like, “Oh, no, no, no, this is what it now looks like.”
Derek Sivers
Yeah.
Ken
So there’s been a bunch of these. And so with you shifting identities, choosing to set some aside, take on new ones. And the rest, are you doing kind of a similar thing of... I guess, what might cause you to set aside an identity, if you will, we talked about location, perhaps, or that how has it been for you? And like, I know that you gave up your guitars a few years ago. And you’re like, okay, clearly this is setting aside an identity where now they’re not sitting there. What does that look like for you?
Derek Sivers
I was probably influenced by musical role models like Miles Davis, David Bowie and maybe even artists like Picasso that did a certain style for a while and then said, “Okay, now in the name of artistic growth, I need to push myself to do a new style.” Miles Davis is a great example of that. He was the man for bebop trumpet. He was right there alongside Charlie Parker in the heart of bebop, and then he pushed himself out of that to do the cool jazz thing, and then he pushed himself out of that to work with more orchestral things with Gil Evans. And he pushed himself out of that to do this, like rock band. Even losing fans the whole time and even knowing that he might be bad at this, like, even though he was an amazing bebop trumpet player. He might not be a very good rock band trumpet player. But it’s important for personal growth to explore different sides to yourself or just keep not resting on your laurels. So maybe just growing up as a musician, hearing these stories, I was going to say parables. Fables, because we we extract lessons out of them. I think that probably shaped the way I see the world, too. But yeah, anyone can just do it as a choice and identity wise, it doesn’t even have to mean leaving all your friends and family behind and moving to Mongolia. A friend of mine in Los Angeles that absolutely identified as a musician through and through. She moved to L.A. to become a famous musician, and in her struggle to be a professional musician, she got a job at a music magazine just because she met somebody from the magazine.
Derek Sivers
They hired her to do something, and eventually they put her into doing sales, and she was pretty good at sales. And after years of pursuing a music career and feeling like through and through, “I am a musician. This is who I am. I’ve got this little day job doing sales for a music magazine, but really, at my core, I’m a musician and I’m only working here to get more connections in the music industry.” Eventually, she said, “You know what? I think I’m feeling done trying to be a musician. I also play in this cover band in Long Beach on weekends, or I just get up and sing the 80s hits and people love it. I’m just going to keep doing that.” And she ended up getting like a big ass sales job at Time Warner for, like big money, because she was really good at selling for this little music magazine. And that was this huge identity shift for her to say, like, I’m going to take my sales job seriously now. And suddenly she was in corporate sales. And then after doing that for a few years, she shifted into the new world of 3D printing at that time, and she left her safe, cozy job at Time Warner for a sales job in a 3D printing company and just crash coursed on this subject she knew nothing about last week. Suddenly, she’s just reading all the books and going to all the events and watching all the YouTube videos about 3D printing and becoming an expert in 3D printing, and just made this shift again. But all of that was while living in Los Angeles with her family.
Derek Sivers
Just making these career shifts, which of course, create identity shifts. So it doesn’t always have to mean, you know, throw it all away and move every two years. Go to Timbuktu. It can just be different approaches. Here’s another one. A friend of mine who is an alcoholic and finally admitted that to herself and went to AA and became sober. And now that’s like a core definition of her is, you know, “I am sober.” But then also had been out of shape her whole life and started exercising a lot. And now she actually includes the word athlete in her self-definition, not just fit, athlete. That’s a different level. So she just realized, like, I’m an athlete and I train like an athlete. I am an athlete. I was like, “Damn, that was a big shift.” You know, I’ve known her for 15 years. And she did that shift about ten years ago, and it’s stuck. And she’s been a very urban central Manhattan person this whole time, and she’s just about ready to move out to the Colorado countryside and make another big identity shift, location wise. I think she’ll still, of course, be the sober athlete. But yeah, these identity shifts are, I think, a wonderful part of living a full life, you know? I mean, that’s just my definition, you know, no need to take my values on. But for me, I love these things. At the end of your life, feeling more empathy and compassion and connection with different people and different walks of life because you’ve walked a bunch of different ways yourself, it helps you be less judgmental.
Ken
Beautiful. And as you’ve moved around to different places how have you encountered questions in these different places? Right. So there’s a couple different ways of looking at this if we can explore. One is, this country over here thinks a lot about this kind of question, and this one over here doesn’t care. So they completely ignore it. So that’s kind of one thing. But then also there’s are different countries, cities, whatever, that really just answer questions completely different. The same question but they just see it completely different. Like I know many Asian countries right, the respect and honor, you know, if you slight someone in the respect and honor that is almost unforgivable is my understanding. But over here. You know, in America we may just shoot your whatever if we don’t like it. But, you know, honor, you know, it’ll look different. What does that look like with all the different places that you’ve lived? Any particular things come to mind?
Derek Sivers
Yeah. Moving from California to Singapore. For the first six months or so, I felt that they were wrong and I was right. And it didn’t help that I had just sold my company for a ton of money and people were kissing my ass, telling me I was right. And so suddenly I’m in Singapore and I meet all these people that would say things like, “Oh, I always wanted to be a musician. But, my parents told me no, that I had to go to law school. So I stopped making music and I’m a lawyer now.” And I’d say, “No, you’re wrong. What are you doing? That’s stupid. No. If you want to make music, you got to make music. You got to do what you want to do. It doesn’t matter what other people say.” Blah, blah, blah. And for months I went on like this. But living in Singapore for two and a half years, I was extremely social. I sat down one on one and had conversations like this. Except, you know, not interview, but real two way conversations with about 500 people in two years. So I got to know a lot of Singaporeans, and it took a few months for it to sink in. As they explained to me, why the selfish whim is not always the right thing to do, that it’s the greater good.
Derek Sivers
You do what’s best for your family, and you do what’s best for your community or even your country. Even if your personal mood might say, “Oh, I want to make music.” Different cultures value and devalue different traits like your current mood might be at its peak valuation on the coasts of America, let’s say your current mood is everything. It needs to be honored, “I don’t feel like serving a good coffee today. I’m being authentic to my true self.” And in other places, your personal feelings right now are just passing whims. It’s like learning a lesson from meditation where you sit still and you feel emotions come into your head and you let them go, and you feel thoughts come into your head and you let them go. You don’t need to act on every thought and every emotion you have. And I saw the wisdom in this. Well, okay, I get it now. Thank you. So I now no longer think that following your current whim and emotion is the imperative, necessary thing to do. I see it as an option. I’m not now saying that it’s bad, and that doing what’s best for your family is always the right thing to do, but it’s cool to see that you have a choice of different ways of looking at this.
Derek Sivers
So back to questions. I guess you could say in Singapore, a common question is, what’s best for your family? What’s best for others? In Chinese cultures, status is very highly ranked or valued. So big decisions are often made by what would give me more status. Would buying this thing give me more status? Would this job give me more status? Status is very, very important in Chinese culture, whereas maybe it means nothing in California culture. In New Zealand, it’s all about taking it easy and New Zealand and England are very, very similar. It’s this kind of very domestic--- I mean, most people here are from England, Scotland, the British Isles. So have this kind of British mentality of taking it easy. But then you mix in a little kind of South Pacific surfer living for the moment culture, and then you have New Zealand culture. Okay sorry, but back to questions. It’s really interesting to me that some countries cultures have a culture of questioning things and not questioning things. Have you heard about--- Malcolm Gladwell wrote a story about the Korean airliner that crashed. Does this sound familiar?
Ken
Yes. Go ahead and walk through it. But yes, it’s on the periphery of the memory.
Derek Sivers
This big 747 commercial Korean Airlines or something like that crashed. And when they listened to the black box, the senior pilot was making a big mistake. But in Korean culture, the junior pilots do not question the senior pilot. He is the senior. So what he says goes. And it was somehow apparent that the junior pilots knew that the senior pilot was making a big mistake. There was some indication that they were aware, but culturally they just couldn’t question his decision. And so the plane crashed and everybody died. But then there are cultures like Germany and even Israel I found. That some of the most interesting conversationalists you’ll ever meet, because it’s this constant questioning of everything. Even in a friendly conversation, you’ll say something and the other person will say, “Well, no, that’s wrong. That’s not right. Well, I think you’re being full of shit right now. Think about what you just said. That’s not right.” And it’s friendly, but pushing back and, damn, it makes for a more interesting conversation than say, if you’re talking with somebody that might be smart and interesting in Korea, but if you’re seen as having higher status, they’ll just say like, “Oh yes, yes.” They’ll just agree and not question what you’re saying.
Derek Sivers
They won’t push back because that would be incredibly rude. So I like having conversations with people from cultures where questioning what you’re saying is not rude, because I feel I learn more from those conversations. I like when people push back and challenge me. In fact, even my email inbox, some of the most interesting emails I’ve ever received have been from Germany. From people like a stranger out of the blue. When I had defined myself as an introvert somewhere on the about page of my website. A stranger out of the blue emails me from Germany saying, “Yeah, I don’t think that’s true. I think you might want to look at that.” He said, “You might feel like an introvert, but you shouldn’t pigeonhole yourself like that. You contain multitudes.” Okay thanks Hans, whoever you are. And I actually did think about it later that night and I went, “Wow. Hans has a good point. Why am I limiting myself to saying I’m an introvert and that’s that?” And I really appreciated that this stranger emailed me out of the blue to challenge me. Challenge, that’s a good word. Questions are a challenge.
Ken
Right. Lovely. All right. So let’s see, how do questions inform slow thinking?
Derek Sivers
Ooh, that’s back to Sherlock Holmes. The local detective just wants to make a quick, open and shut case. Sherlock Holmes can take his time. In fact, I think that’s my definition of stupidity, is jumping to a conclusion. When someone’s being stupid, it’s because they want to jump to a conclusion. They don’t want to think it through. Somebody is acting rude they say, “That person’s an idiot.” There, it’s all wrapped up. It’s done. That person’s an idiot. Taking another minute or two to think it through, saying, “Well, why do I think that person is being rude? They’re violating my values. Could it be that they have different values? Are they acting in a way that they’re proud of right now? Do they want to be this way, or are they at their wit’s end and short circuiting and acting in a way that they don’t actually want to be acting either?” If you think it through for another minute, you’re no longer being stupid. Yeah. Sorry. What was the question?
Ken
Just how do questions influence slow thinking?
Derek Sivers
Oh, yeah. So slow thinking is taking a little longer.
Ken
Taking the time.
Derek Sivers
To think it through. And that’s being smarter to me is taking a little longer to think something through. I do not value quick answers.
Ken
And I had heard author Ta-Nehisi Coates once say from stage, I couldn’t believe that somebody would say this. Somebody asked him a question. He said, “I don’t think I’m informed enough to speak on that.” And I’m aghast. I’m like, “Whoa, no, hold on. If you’re on stage, you’re supposed to have an opinion about everything.” And so it’s just that I don’t think I have any value to add here. So I’d rather not offer, like, wow.
Derek Sivers
I think that can be such a smart thing to say, is to say I don’t know. It shows that you’re thinking and it shows that the other times when you didn’t say, I don’t know that they should be valued a bit. Because if you don’t know, you’ll say, I don’t know instead of just moving your mouth anyway. You asked me some questions before our interview today. You sent me an email with some questions, and I sent you some quick answers, mostly to say like these 2 or 3 questions. I’m going to tell you in advance. My answer for that is I don’t know. So we don’t need to go there. There’s nothing interesting there. And I’m glad that I got to do that in advance, because you might have asked me a big, serious, loaded question like, tell me how questions have influenced your parenting, and you might have even framed it wonderfully and set it up for me. And I might have said, “Well, it hasn’t.” That would have been the end of that. That’d be embarrassing.
Ken
But I have no problem launching out questions. And if they’re a dud, okay, so be it. I have no problem with that. So regarding all these countries that you’ve been to and how many languages do you speak?
Derek Sivers
Oh, none.
Ken
Really?
Derek Sivers
Just English. Yeah. In a perfect world, I’d love to be fluent in a few languages. My top three would be Chinese, Swahili, and Indonesian, but it’s always been like fourth priority to me underneath other things. So it hasn’t happened yet.
Ken
And so as you’ve been in the different countries that you’ve lived, English, I guess, has served you well enough where you’ve been able to get the things accomplished that you need to with English, I guess.
Derek Sivers
Yeah. I’ve only really lived for real in US, England, Singapore and New Zealand.
Ken
Okay.
Derek Sivers
And all of those are English speaking. Again, this is a compromise with my boy’s mother, who does not want to live in a place that doesn’t speak English. If it were just up to me, I would only be living in places that don’t speak English. I would only be doing that to push myself out of my comfort zone and make myself learn my target language by living there and refusing to speak English. But that’s me. And being a good dad is more important to me than learning another language. So I choose being here with my boy in an English speaking country, which means learning Chinese is fourth or fifth priority. And so it doesn’t happen.
Ken
And so in the days ahead when you have wider options, do you assume that yes, as you move to one of these other countries that yes, you’ll dive into the language learning and---
Derek Sivers
Yeah. That’s the plan. That’s what I enjoy daydreaming now. That in six years, when my boy is 18 and off to university somewhere and doesn’t need me around anymore, that I will go straight to, I don’t know, Kenya, China, who knows where and just make myself live in the new language and live according to a different set of values. Kind of like your cousin. I don’t think I’ll change my name, but I like the idea of living in a different way for a while.
Ken
Gotcha. And on your page. Question for you how has having a pet or what has having a pet rat taught you?
Derek Sivers
Okay, we only got pet rats a few weeks ago.
Ken
Yes. All this is new, so love it.
Derek Sivers
I was against it at first. We we had a pet mouse. We had pet mice. And even that I was against at first. The local pet store owner convinced me that they never bite. They make great pets. And we did. They were wonderful pets. We had pet mice for 3 or 4 years and all the mice died. And as soon as the last mouse died, my boy said, “I want pet rats.” I went, “What? Are you serious or kidding?” He said, “Serious. I want pet rats.” And then he showed me some YouTube videos of how sweet and cuddly they are. I went, “Wow. Okay.” I lived in New York City where, you know, rats were something to be killed. I have killed many rats in my life. I have set many rat traps and dumped many rat bodies in the garbage and thought of them as just pests. And if you go to YouTube and search like cute, cuddly pet rats, you’ll see a lot of people scratching under their chins and little rats. They’re like little kittens. And my boy really wanted this. And I went, “All right, I also want him to have a full life.”
Derek Sivers
And rats only live about two years, so let’s try it. So I found a local breeder, got two boys, and I got to admit, for the first two weeks I was thinking, “Oh, what have we done? Oh, my God, now I’ve got rats.” But after about two weeks, I got to tell you, they really grew on me, as I sit here writing all day. I’d say like five times a day, eight times a day. I go over and and open their cage and I take them out and they, like, run up to my shoulders or like into my arms, and I cuddle them. And one of them is more cuddly than the other and just loves just like snuggling into my arms. And just like when I scratch under his chin, he closes his eyes and they’re so warm and cuddly and affectionate. They lick my fingers all the time and they’re really sweet. Just in the past ten days, really just something switched and I really kind of fell in love with these two little pet rats. Yeah. They’re affectionate and cuddly and sweet. They’re really like little quarter sized kittens.
Ken
I do have my own rat story, so.
Derek Sivers
Oh, cool.
Ken
Yes. So I can only validate. Now, I’m sure that folks who have only. The experience of the city rats or whatever are probably cringing. You can skip ahead a couple minutes or whatever. But yeah, the plan was I want a dog. My dad was like, “No, we’re not going to do a dog that’s too big of a commitment.” So we went with a rat. So I had Squeaker the Rat for a couple years. Very much the case.
Ken
Would have been about ten.
Derek Sivers
How old were you?
Derek Sivers
Okay. Yeah, same as my kid. Cool.
Ken
And I would tuck my shirt in and let him ride on my shoulder as I would ride up and down the street on my bike. And then he would go down the shirt and run around inside, you know, because it’s tucked in, you know. Yeah, very affectionate. And when I’d make pancakes. Right. You got the dribbles, right? And so you get these little tiny pancakes. So you put, butter and syrup on there, take them in on the fork and then pull off this big old mass of pizza for him. And yeah. So when I saw that I was like, “Aha. Yes.” Not a lot of folks actually embrace the whole rat adventure, I guess so. Lovely to see that’s been your experience so far.
Derek Sivers
Cool. Yeah, the shorthand, you know, same thing with having pet mice is I would tell people that seemed creeped out by it. I’d say, look, it’s understandable. Imagine if you lived in, I don’t know, Sudan. And the only dogs you saw were wild dogs. And then try to imagine getting somebody to be comfortable with a poodle. And the difference between a wild dog and a poodle is the difference between a wild rat and a domesticated rat. They’re the poodles of rats and the pet mice, which are actually called fancy mice. They’re actually called that, domesticated mice are called fancy mice. They just come from a long breed, a long line of being affectionate and sweet and cuddly and yeah, very different from wild mice and wild rats. Highly recommended. Especially anyone with a kid, because it can be a drag if you know your eight year old kid says, “I want a dog.” And you say, okay, and you get a dog, and then you have the dog until they’re 24 and they’re off at college and they’re long gone. And it becomes---
Ken
We’re living it right now. Yep.
Derek Sivers
Okay. There you go.
Ken
Yeah.
Derek Sivers
So I’m glad that they have this two year lifespan. I feel that probably matches his attention span of wanting pet rats.
Ken
Yep. That’s fair. That’s fair. Well, I know you are a voracious reader, so and on your website you’ve listed a bunch of books and you take extensive notes and I want to thank you because I’ve read “The Courage to Be Disliked and “Sum 40 Tales From The Afterlife”. I did that one on audiobook. So those were two thank yous, appreciated those. Yeah, they were lovely in their own right. So through all of those books, as you scroll through the catalog, any particular books that kind of handle questions in new or creative ways or that come to mind?
Derek Sivers
Well, yeah. You mentioned the book Sum by David Eagleman. I love that format of having 40 different answers to one question, because the question of the book is: What happens when you die? And I just love that format of one chapter saying, “Here’s what happens when you die. You awaken in a room and later you find out that there’s nobody there.” And then the next chapter says, “Here’s what happens when you die. You find out that you are an artificial intelligence program.” The next chapter says, “Here’s what happens when you die, all your atoms split apart.” Or whatever. I love this format of making yourself come up with many different answers to one question, for obvious reasons. The whole subject of this podcast. Forcing yourself past your first answer, past your second answer, and to keep going and to make yourself see things from different points of view. I love how the book “Sum” did that, and I loved it so much that that’s the format for my book called “How to Live”, is a direct homage to Sum by David Eagleman, because after reading his book twice and loving it. One day I was driving down the road and I went, “Oh, oh my God, I want to write a book called How to Live in the same format as Sum, where each chapter says, here’s how to live. And it has a strong opinion.”
Derek Sivers
It says, “This is the way.” And then the very next chapter says, “No, no, no, no. Here’s how to live.” And has a very different answer because that’s what it’s like reading the self-help books of the world, right? They all have a very different answer, and they’re convinced that their way is the way. “Just follow this methodology and you will be successful and happy.” And then another book that says, “No, no, no, no, no, the complete opposite. Follow this way and you’ll be successful and happy.” And they’re all right and they’re all wrong and they’re all just an option. And I thought, “God, wouldn’t that be fun to have that all in one book where every chapter is disagreeing with every other chapter, just like Sum by David Eagleman.” So yeah, that book not only changed me, but led me on to a four year project of writing “How to Live”.
Ken
Wow. Okay. I didn’t realize that it had that deep of a connection on those. Well that’s beautiful.
Derek Sivers
Oh, yeah. The first page of the book, How to Live, says, “This book is an homage to the book, Sum by David Eagleman.” Most people miss that, but it’s in the page before the table of contents, where people are usually just thanking their wife.
Ken
Skipping over and. Yeah. Gotcha. Well, I know that you are or for those--- and I highly encourage folks signing up for your newsletter or just on your mailing list because you had sent out an early look at “Useful Not True” and appreciated that where there were a couple or there was definitely one in particular, there was an immediate application for me for something that I was having a terrible drive into work, commute wise or whatever it was, and just a lot of voices in my head. And that particular chapter on aliens, the concept of the aliens, one of them can hear what’s going on in your head, and the other one sees what’s going on in the outside, and the aliens go back very confused because the two different worlds were looking at these humans. I hopefully summarize that okay. That was super helpful. And so immediately did some application on that. And I’ve referenced it or thought about it often when I start to go down this path of, “Oh no, woe is me, the world is coming after me.” And the rest. So it’s been helpful.
Derek Sivers
Well, thanks for telling me that. Actually, that’s really helpful because I had just axed that chapter and because I thought like, “Oh, I don’t know, is this weak.” So hearing you say that, I’m going to go take another look at that. I’m still making last minute changes to the book. So yeah, that helped a lot to hear you say that. Thank you.
Ken
Yeah, that one certainly resonated. I don’t know, maybe it’s just the aliens, and maybe we’re finding out that they’re real or whatever we’re learning in today’s world.
Derek Sivers
Right? Yeah. Thank you. The “Useful Not True”. Well, like I said, in the very, very beginning. It’s been underlying everything I’ve written about for over ten years now, that I’m deliberately choosing beliefs that are useful not because they’re true, but because they’re useful to guide my thinking or my actions in the way that I want it to go. So I’ll choose beliefs for the actions they create. And people kept challenging me on this, saying, “Wait, why are you saying you believe this? That’s not true.” And I’d say, “I know it’s not true. I believe things because they’re useful to me, not because they’re true. What the hell is true anyway? Anybody that believes anything, there’s somebody else that believes something else. So what? They’re wrong and you’re right. Or vice versa. Come on. Everything’s just a perspective anyway.”
Ken
Even the name. Well, all right, so there’s two things. One, I appreciate the name because it is so concise. And that’s something that I’ve also often thought about, is just that concept of, okay, whether, yeah, somebody else on the other side of the world or whatever believes something different than me. But in this case, if I was to believe that it would drive a particular behavior on my part. And that would actually be helpful right now to get me through whatever. So very much appreciate it. And where all this is going is. I guess I marvel at the assumption at how much time you put into probably writing and rewriting and trying to eliminate every single word or phrase in your writing because I receive it as so very crisp with like all the fat taken out. Kill the baby, right? It’s like, “Nope, I like this one. Nope. It’s got to go. It doesn’t matter because it doesn’t fit.” So appreciate that. Just for the succinct nature of your work, because it is very concise. So thank you.
Derek Sivers
Thanks. It makes me happier. It makes me prouder of a book. But mostly I think it’s more considerate because we’ve all probably read a book that should have been an article and you think, “Ah, damn it. Like, come on, I got the point ten pages. Why did you need to go on for 300 pages? You didn’t. So why did you? That was inconsiderate.” How many millions of hours of human time have been spent reading your page? Just because your publisher told you to make it longer, or you just wanted to talk longer, or you just wanted to say that you’ve published a 300 page book, not an 80 page book. It was inconsiderate to everybody that read that you did not need to make it that long. So my books are basically just the good bits. Everything else, every sentence that doesn’t need to be there has been axed. Every sentence needs to be there. I make it as short as it can be. In fact, I’m very excited that this next book, “Useful Not True”, might be my shortest one yet. My books are usually about 100 pages, and I’m hoping that this one is going to come in at about 85 pages. We’ll see.
Ken
Gotcha. Gotcha. So and kind of tying that maybe to minimalism. Because I know that that’s at this point, as you had mentioned earlier, that’s somewhat of an identity or that’s how you’re living at this point. So what questions do you ask of an item that’s going to be added to your collection of stuff around your house, whatever that is? What is that rubric that anything has to go through in order to become one of your things?
Derek Sivers
Good question. Good subject. Yeah. Nobody’s asked me that. Anytime I think about getting something, I think really long term, like, am I really going to want to take care of that for the rest of its life, for the rest of my life? Do I really want that in my space? Will that complicate my life? Will that take up room? Will that make it harder for me to leave on a moment’s notice? If I want to move somewhere new, if I get some opportunity to, I don’t know, start a new business in India, would that hold me back? And there’s a whole bunch of hurdles that an item has to pass before I’ll say. Okay, I’m going to let this item into my life. I take it very seriously because it clutters up my space, and now it’s something I have to fucking take care of forever, or is going to sit there untaken care of.
Derek Sivers
There’s probably a better word for that. And then that’s going to make me feel icky inside to see something that I bought that’s sitting there unused. Just every day I see that it’s just going to like,” Oh, I bought that thing, and it’s just sitting there unused. And, God, maybe I should be spending more time with this thing that I just decided to buy, or now I’m going to have to sell it. I have to go to eBay and make a little ad and take pictures of it and get bids and then ship it. You know what? Never mind. I just won’t get it in the first place. I know I want it, but not bad enough to deal with all of that.” So yeah, that’s why I hardly ever buy anything is that everything has to pass through all those hurdles.
Ken
Is there anything in particular in recent in recent history that has been a oh, “I got to have that.” And it quickly jumped all those hurdles.
Derek Sivers
You know, a big one that has been worth it is right there. Like five feet to my left, is a big squat rack with the heavy weights and the barbell that I was going to the gym. But the nearest gym is in a shitty part of town. I don’t mean like a bad part of town. It’s actually like smack in the middle of the most commercial busy intersection. And parking always meant I had to, like, drive up seven floors of those circular parking lots and park up on the seventh floor because I’d go there at, you know, 11 a.m. and I just would get cranky every time I’d go there. Just like the traffic. And I thought, this isn’t worth it. I know I’m trying to avoid having a big thing at my house, but in this point, the benefits are outweighing the downside. So yeah, I have a big squat rack, which is huge and heavy and totally worth it. And the other one, actually, I am standing inside talking to you right now. I’m standing inside something that is the size of a phone booth that is completely soundproof.
Derek Sivers
Because I was trying to record my audiobooks and the neighbor was mowing his lawn, like, all day long, and then I was like, “Well, I can’t record my audiobook today. Hopefully tomorrow.” And then the next day, there was just some dog that wouldn’t stop barking. I was like, “Well, can’t record my audiobook today, maybe tomorrow.” And I kept trying. But, you know, the sounds of the neighbors were coming in over the microphone. So I said, “All right, I’m going to have to go into a recording studio.” So I looked at the price of going into a recording studio, and all in all, it was going to be more expensive than just buying this soundproof recording booth. And so this thing is big and heavy, and these two things are right next to each other. You know, my recording booth and rack. And again, totally worth it. Like, I know this is going to be a pain in the ass. And yes, I know this will hold me back from moving on a dime to somewhere new. And when I do move, it’s a pain in the ass to move. I’ve done it a few times already.
Ken
Yeah.
Derek Sivers
But still totally worth it.
Ken
Well, I would submit that your audio quality I love. Thank you for doing it because the audio quality is amazing.
Derek Sivers
Sound is important to me too. And it’s recording not just an interview like this, but yeah, the audiobook version of my books or whatever. It’s just nice to know that no matter what. Actually, right now it’s kind of hurricaney right here. I live in Wellington, New Zealand, which is officially the windiest city in the world. And this morning it’s been living up to its name. It’s like almost a hurricane out there. Things are thumping against the house. I’m going to find out later. You know what fell down this morning. But you can’t hear any of it because we’re in a recording booth. I love this.
Derek Sivers
It’s amazing.
Derek Sivers
Studiobricks.com. I mean, obviously they’re not paying me.
Ken
Shout out. All right, there we go.
Derek Sivers
It’s worth it. Anybody I highly recommend go to studiobricks.com they’re actually made in Spain and had it shipped from Spain to New Zealand because it was worth it.
Ken
Nice. Okay. Shout out and we’ll tag him in the show notes of course. So cool. Cool. All right. Well let’s see, in being respectful of your time and moving towards wrapping up. So do you have any thoughts or encouragements about how questions that we haven’t touched on might be used?
Derek Sivers
Conversations. We didn’t touch on this at all, and I didn’t realize it till just right now when you asked. That I think most of us, not all of us, most of us have a tendency in conversation to talk about ourself. And then you talk about yourself as somebody, and then that person tells you something about themselves. And I found it so useful and enriching to kind of bite my tongue, catch myself. And at the moment where I’m thinking of making a statement, instead, I stomp and I phrase it as a question. I’ll just pick a quick dumb example, but say I had a a terrible experience while driving since you were just talking about driving. Let’s just say that instead of just saying, I had a terrible experience driving today, I might, whoever I’m talking with say like, “How often do you have a terrible driving experience? Like, is driving usually terrible to you?” And now we’ve opened up the subject, and I’m not being coy or withholding. I’m not waiting for them to ask me so I can, you know, share my story. It might come up, but actually, even if it doesn’t, it’s fine.
Derek Sivers
It’s so useful to notice that I’m interested in this subject. So instead of just telling you my thoughts on this subject, to make it into a question with the person so we can have this two way conversation About it. I love this so much more. And actually it’s thanks to Alicia Souza, an illustrator in Bangalore, India, who in our conversations, she would do this to me. She would just make everything into a question, like something would annoy her and she’d say, does this ever happen to you? Or she would love a particular song and she would turn it into a question like, why do you think we love a particular song? And I noticed that I just loved having conversations with her because she would turn everything into a question. And I want to do this too. I want to be more like Alicia. So yeah, I thin that could be a whole different podcast topic. For another episode about the use of questions in conversation.
Ken
All right. Sounds like a plan. All right. We’ll have to do that, then. Yeah. I just had Brian Fretwell on, and he’s got a company called Finding Good. And he’s all about asking the questions as well. And one of the concepts that he has is that he calls “Finding the blueberries.” And the idea is, oh, well, you’ve been out doing something right. This is, you know, our ancestor days anyway, you found blueberries and you came back with them. So now let your curiosity be very much on whatever topic, it’s tell me about how you found the blueberries, because now the rest of the group can benefit from that. And it’s less about what hardships you had. We can talk about those, right? Or how you screwed up or you spilled some coming back or whatever. No, no. So I’m interested and in asking questions in your conversations with friends about that. So it becomes that kind of a self-centered curiosity. But now it’s like, “Hey, I’m fascinated because you’ve just lived through hell or you’ve just gone through hell. How did you do that?” And really pulling those strings. So I appreciated his work and like, one of the questions that he asked that he often starts off with is, “What do you want more of?” And I love that because while it’s a direct question, it’s also expansive because now it’s like, what are you seeking more of in your life or on this particular topic or. And I just I found that very helpful.
Derek Sivers
I like that. Which of course, then I’d be tempted to also make sure to ask the counter question of what do I need less of? Or why do I think I need more? Is more the solution? Is less the solution here?
Ken
So what’s beautiful in preparing for this? I was thinking about asking that question to you, but then I knew I was like, and then obviously we need to ask what would we be less? Because I can just imagine Derek saying, why do we assume that we need more?
Derek Sivers
Yeah. It’s fun to challenge the question itself, because people do often ask you these leading questions like, “When I say successful, who’s the first person that comes to mind?” And I’d say, “Well, I don’t think the first person is interesting. Shouldn’t we think past the first, you know?” And it’s fun to challenge questions themselves and especially your own. So yeah. Fun subject. Thanks, Ken.
Ken
Indeed, indeed. All right, so where’s the best place for folks to engage with you and learn more about what you’re excited about?
Derek Sivers
Only my website.
Ken
Excellent.
Derek Sivers
I don’t love social media. Does anybody? I just don’t do it. Sive.rs is my website. It’s all there. And as you know, because you emailed me out of the blue. I like it when people email me out of the blue. I actually really enjoy it. I am living on an island in the middle of the Pacific Ocean. New Zealand is wonderful, but I think it’s so fun to meet people from around the world that email me and say hello and tell me something about themselves, so please do.
Ken
That’s how I got here. So yes, he’s legit. He will answer those emails. Yep. Appreciate that. Well. Good deal. Well, Derek, thank you for the discussion. I appreciate you sharing how living with questions and seeking the edges of our conventions leads to a more inspiring life. And for those who have joined us through the gift of technology, thank you for being here. Questions changed my life for the better. Derek provided amazing examples of how to use questions and perhaps new ways that we hadn’t considered before. Please take all you have learned here and be a light to those around you. Gratitude.