Greg McKeown
host: Greg McKeown
We started talking Useful Not True beliefs, but ended up talking all about the superpower of journaling!
listen: (download)
watch: (download)
Transcript:
Greg McKeown
Welcome back everybody. I’m your host Greg McKeown. And today we have the one and only Derek Sivers. It’s so tricky to even frame Derek. He’s sort of one of a kind. I mean, he’s an American entrepreneur, an author, a musician, programmer. He’s unconventional and that’s part of what I think his appeal has been to so many people around so many things. Born 1969, Berkeley, California. Multifaceted life, music, technology, creative pursuits. Resides now in New Zealand, but also likes to have passports for all sorts of places in the world because that’s how he thinks, that’s how he rolls. Perhaps best known for CD Baby, an online platform for independent musicians to sell their music. Then, after having amassed a hundred million dollars in sales, sold it and then put the proceeds into a charitable trust because... Derek Sivers. Also well known for those that recall it, the TED talk in 2010, “How to Start a Movement”. It’s short, it’s incisive, it’s memorable, it’s its own sort of movement About the importance of the second person in being able to actually get a movement going and of course a little more than that But again, this is who we’re talking about but also as an author We’re thinking now 2011 the book anything you want on your music and people or hell yeah or no from 2020, but also I Should say how to live in 2021, but also a new book useful not true. I could say many more things, but it really is a pleasure to have you with the podcast today Derek welcome.
Derek Sivers
Thanks Greg. That was very theatrical. I imagined you walking on a stage saying, “But also! And one more thing! And you might have thought that was it, but no! There’s one more thing.”
Greg McKeown
Well, that’s funny you should say that because there was one more thing I was going to say and it’s this: Remember when Steve Jobs gave his quite famous now speech at Stanford, it was the convocation in which he was saying, “Look, okay, this is what I’ve learned about life,” and he just told these three stories. But he ended with those fabulous words. He didn’t come up with them, coin them, but sort of made them famous, and it’s “Stay hungry, stay foolish.” And that’s what I want to say about your approach. That’s my one take on thinking about how you approach your life, but also I think part of the theme of this book, and you’re going to tell me how I’m wrong.
Derek Sivers
No, not wrong. I am hungry and foolish.
Greg McKeown
But particularly the approach, I mean this idea of Useful Not True. I mean, I haven’t even expressed what it is and the meaning of it to people, but there’s something about this, the power of perspective and the power of not taking what people say is literally accurate and that you have to absorb it as true, and you know, that this idea of stay hungry, stay foolish, keep learning, keep challenging, keep questioning, wondering, you know, what really is most useful. Maybe you can share in your own words how you think about this new book.
Derek Sivers
Sure. Well, it’s not the book, per se. The book was my own little mini-exploration of an idea that kept coming up, when I would share some perspective I hold, some rule of thumb or philosophy that drives me, and every somebody in the comments would push back and say, “But that’s not true.” And I’d say, “I never said it was true. I said it’s useful. It’s useful for me to think this way. Thinking this way helps me take the right actions. Or thinking this way puts me into a mindset that helps me see opportunities.” And I had to explain this so many times that I thought, “Well, let me focus on this idea.” And it goes like this:
Derek Sivers
Around us there are people that we all know that are stuck. They’re stuck in a rut because they’re stuck in stories of the past. “Somebody wronged me.” “I’m no good at this.” “I live in a bad place.” “I’m not one of the lucky ones.” Etc. They have no ability to see opportunities. They look around and declare that they are in a jail cell. “This is it.” “I’m stuck.” “Dead end job.” “No opportunities.” “No chance of advancement.” They can’t even see it. In their mind, both of those things I just said are realities. It’s an absolute reality to them that they are in a jail cell, metaphorically.
Greg McKeown
Yeah, they are a prisoner.
Derek Sivers
Yeah, they are stuck. “There is no way out.” “I am a living tragedy.” “I’m not one of the lucky ones.” “I’m not one of those people who succeed.” Alright, I’m picking too-obvious examples, but you get the idea. Those feel like a reality because they’ve declared it as true. That’s a major, major, major problem. When we declare something as true, we stop questioning it. It’s a fact and that’s that. It’s a closed matter. It’s done. But as soon as you say something is not necessarily true — I’m not saying it’s false, just not necessarily objectively, absolutely, observably, empirically true for everyone, everywhere, always — as soon as you introduce a little doubt, you open it up and you say, “Well, how else could I see the situation?” “I’m not one of the lucky ones? How else could I see that situation? Nobody’s born lucky. Everyone has circumstances and they make things of them.” “I’m trapped? How else could I see that situation? Maybe I’m not trapped. Maybe if I’m in a metaphorical jail cell there’s actually a hole underneath the bed. There’s a trap door in here somewhere that I haven’t explored.”
Derek Sivers
The most successful people and the happiest people I’ve ever met are the ones who have the ability to reconsider a situation and not declare it true, closed and done.
Greg McKeown
Yeah, I mean you’re combining the word “true” with the sense of “complete,” “fixed,” “ended,” “done.” And I think that’s an important distinction. What you’re sharing reminds me of a conversation I just had that’s slightly nuanced compared to what you just said, because there’s sort There are two ways one can be a prisoner to one’s thoughts. One is, like you’re saying, declaring a statement that is fixed and limited and so on. But then there’s another kind where you don’t actually know what the frame is that has you trapped. You just feel trapped. And you don’t know why. And in fact, you might have been trapped for a long time and tried to get out, but you You don’t know it’s because of the meaning frame that you have attributed to something. So if you’ll allow, let me just share a little more because it’s just, to me, an incredible story. This is a professor at Cambridge and a friend of mine who, several years ago, I went for this long walk with him and he was so excited about a new book that he wanted to write and was talking to me about, “Well, how do I do that?” We just talked for two or three hours on this walk, and he was just ready to go, and he started making progress on it. And then, you know, three years go by, and we’re going on a walk again, and he says, he says, “Things in my life are so good,” he said, “but now, every time I try to write that book, I’m frozen. I can’t make any progress, and I don’t know why.” So it’s interesting, because here you have this high performer, you know, high performance in let’s say there’s ten areas of life, and like nine of them he’s high performing in. And he used to be making progress on the book, but suddenly he’s not. This is of course fascinating to me and interesting to me. And I’m doing research specifically about this kind of trap that we get into. So I can’t help but go there as you’re describing this. And so I spent like a couple of hours in a, in a very particular listening process that we’ve been working on for years. And within that two hours, we identified what the trap was and unlocked it and he’s now on his way. So it was a really amazing experience. And he gave me permission to be able to share this. So this is literally like last week. So here’s how it worked. As he started work on the book, Russia invaded Ukraine. And he’s from Ukraine. And his mother was killed in that invasion. And it’s just enormously disruptive, as you would imagine. But it’s also really ambiguous, because they don’t know how she died. And they don’t know where she’s buried. It’s a horrific trauma to try and navigate. So what he didn’t know is that his mind had formed a code and the code was this So he didn’t know this When I work on this book the worst things in my life happen So, of course if that were true Then he shouldn’t work on the book. I mean everything in that code is Protecting him from the worst things that could possibly happen in his life. So, of course, he shouldn’t write the book of course something will You know overpower his desire to write it because and so literally seeing the belief was I Believe would as it was enough for him to change Now that isn’t where we stopped, but I think going from being a prisoner to an observer is So significantly different that you can start to make changes about things But then we changed one word which was when I was working on the book the worst thing in my life happened So suddenly you make it a shift from then and now so that was a big break But then before we were done before that two hours was over We came up with this phrase together, which is when I complete this book I Will have completed the most meaningful thing I will have healed from the most challenging thing in my life because he wants to dedicate the book to his mother and so on this was the process and two hours complete shift and I just couldn’t help but share that given what you’ve just described because It’s I think the very distinct Nature of trapped thinking Isn’t just true versus something false or whatever. It’s that a truth and Something false get fused together so now we’re really stuck because we’re holding on to the true part and And the false part’s like just spliced there into it.
Greg McKeown
And that’s why we’re trapped. So we keep holding on to the truth. The truth, this part is true. This is correct. This is right. And we can’t seem to dislodge it. And I think it’s because like two magnets, they hold together. So we have to discover them, find that code, recode it, and so on. Anyway, I thought that might be a good place for us to hear your thoughts and your sense of that example and story.
Derek Sivers
I love this. It’s like political commentary where they say, “This is what happened today, and this is what it means.” Well, the trouble is, one of those things is true when one of them is not. It’s hard to unbundle them. True, this political leader signed this paper today. That actually happened. What it means? That’s just one perspective. There are many, many, many perspectives you can look at on this. We do that in our own lives. “I tried to tell my husband I didn’t want to go with him to the ballgame, he didn’t speak to me for a week. So therefore, I can never tell him what I want.” One of those things is true and one is a perspective. And it’s not the only perspective. It helps so much to separate the observable physical reality of a situation, especially when you’re feeling really low, you’re feeling overwhelmed.
Derek Sivers
I think a lot of people come to your work because they feel overwhelmed, right? You have such a clear voice that helps them get out of this feeling of overwhelm. So when you’re feeling overwhelmed, it feels like reality, you know, “I am buried under so much stuff. I am overwhelmed. There’s too much. I’m freaking out. Life is horrible. I can’t handle this.” And it’s so useful in those moments to say, “Hold on. Look around me. I’m just sitting on a chair in a room. Am I in any physical danger? No. Okay, so I’m safe. If I turn off my screen, are these things a physical problem around me? Am I actually burdened under carrying heavy weights right now? No. So these are interpretations in my head. It’s not the only way to look at it.”
Derek Sivers
There was a moment at the end of my 10 years of running my company where I was feeling so overwhelmed that I called a friend and I said, “I have to do this and I have to do that and I have to do this.” And he said, “Derek, you don’t have to do anything!” I said, “Yes, I do. I have to pay my employees. I have to pay my taxes. I have to ship the orders that people have bought today.” He goes, “No, you don’t.” I said, “Yes, I do. I have to pay my employees.” And he said, “Derek, I’m not just being metaphysical here. You need to understand this point. You don’t have to do anything. Right now, you could just go to a park, lay down on a park bench like Eckhart Tolle, who just laid down on a park bench at one point in his life and just let the whole world pass in front of his eyes for a couple years. You could do that. You could lay down on a park bench and just ignore everything.”
Derek Sivers
I said, “No, but I have to pay my employees.” He said, “No, you don’t have to pay them. They would eventually stop showing up to work. Maybe somebody would try to file in small claims court to recoup the money that you were supposed to pay them last week, but maybe not. Maybe they just say, ‘Oh, well, that guy’s crazy. He’s lost it,’ and move on with their lives. The people whose orders you don’t ship, maybe they’ll contact their credit card company and get a refund saying the company never shipped the order. And maybe a few years later the IRS will contact you saying you owe them some more money. But you don’t have to do anything. You could just... You’re choosing to do all of this. But you could walk away from all of it at any moment and you need to know that. That this is all optional. All of this you’ve chosen.”
Derek Sivers
I think of this so much with my friends in India and China that have a strong sense of family obligation. “My parents need me to do this. My parents are expecting this. My parents are insisting I get married. My parents are insisting I live at home.” And I say, “Well, you don’t have to.” And they say, “Derek, you don’t know what it’s like to grow up in this family.” I say, “I’m just saying it’s physical reality!” You can do this from any culture, look around you, you don’t have to do anything. You’re choosing to do it. You’ve always got to remember that this is a choice you’ve made that you can walk away from.
Greg McKeown
One of the things I love in the things you’ve said so far is connecting for me in a recent thought, which is that the meaning frame you want is the one that maximizes agency. And seems to run like a kind of a gold thread through this recent unbook that you’ve written. That, you know, it’s instead of, okay, just holding an idea as if it’s the truth the end, it’s like, well, which way of looking at this will maximize my sense of choice here instead of minimizing it, literally almost to zero based upon whichever frame you have. And anyway, I’m curious about your reaction to that.
Derek Sivers
Yeah. It’s brainstorming. The rule number one of brainstorming is you keep going past your first, past your second, past your third or fourth idea. You keep coming up with more ideas. Don’t stop because one seems pretty good. You keep asking yourself, “What are other ways to look at this?” Once you have a whole collage or rainbow or collection of ideas, then you might notice that there was one in particular that excited you the most, or one in particular that gave you the most peace of mind. Say if you’re feeling traumatized by something in the past, or overwhelmed, like we just said, there might be one perspective that makes you go, “Wow, actually, that’s a wonderful way to look at it.” Or, if it’s about motivation and taking action, you helped your friend from Ukraine see a particular point of view that was one of many. There are hundreds of ways he could have looked at it, but you helped him find one that’s making him take action. And therefore, that’s the way we should judge a good perspective or a bad perspective is does it help you be who you want to be or do what you need to do or just to feel at peace. If it helps you in this goal, then it’s the right perspective for you. You’re not saying it’s right for everyone. You don’t need to judge it as objectively right or wrong. Who’s to say? If it helps you do what you need to do or be who you want to be or feel at peace, then it’s the right one for you for now. It doesn’t even need to be the right one for always, it’s just for now.
Greg McKeown
Yeah, it’s a perpetual flexibility in thinking. A kind of willingness to constantly upgrade one’s thinking. I like what you’re saying, it’s like, you know, what does it need, how do we need to look at it right now? You know, I mean, I like that too. It’s like not necessarily just always upgraded, just, okay, what’s a useful perspective now to have on this so that I can operate in the right way, you know, the best way that I can in this moment. Something you said earlier sparked a thought for me which is what your friend seemed to do with you when you were running the business and feeling so tightly constrained by the responsibilities that you had. It is, you know, the quote is from Stephen Covey, it’s that between stimulus and response there is a space and in that space lies all of our freedom for growth and so on and it’s it’s completely almost universally misattributed to Viktor Frankl Almost everywhere. In fact, it is named as by Viktor Frankl and I absolutely guarantee everybody listening. It is not I think to Frankl there’s nowhere that he said that the only reason people think it is by the way is because actually, it’s kind of a meta moment because in seven habits the ideas appear next to each other and So somebody’s connected them just like we’ve been describing like a truth with a with it with a fake idea Combined it and then like you can’t undo it but What is interesting is I went back at least for me. I went back to speak to one of the Ghost writers of seven habits one of the collaborators on that to find out what book did inspire it because that’s not stated anywhere publicly and And they came back to me and they said it was as a result of Stephen reading Gift of the Sea by Murrow and I just went back to to reread that book and Every part of the book is breathing This idea is never stated precisely that way, but it’s illustrated everywhere We have all of this noise, all of these responsibilities, all of these burdens, all of these have-dos, and how do you create some space inside of yourself so that you can choose and operate and I’m not going to get into the details of the process, but there’s a lot of information that’s out there.
Greg McKeown
That’s kind of a theme through this treatise that you’ve written. You have to react to your own thoughts, to what other people say is the way of the world. You can step aside, become the observer of yourself, of everything, and then from that point of view start to explore ways of looking and ways of thinking.
Greg McKeown
It just seems like to me there’s two kinds of life, and the one is before you realize you have You know you have that ability and the one that’s after it You know that you are not your thoughts, and you’re not other people’s thoughts You are the observer. That’s the real you and you get some space to make some choices How do you how do you respond?
Derek Sivers
I love this subject. What was the name of that book that was filled with this idea?
Greg McKeown
Gift of the Sea is written by Anne Murrow Lindbergh and Murrow Lindbergh and it is beautiful. I know you have like hundreds of books on your list. So it’s a it’s terrible to be a book pusher when somebody is so So burdened already by the number of books that they have written but also have read but also the ones that they haven’t yet But this is this is worth pushing up on the list.
Derek Sivers
One of my favorite moments of writing is in the exploration of an idea, you come across a new epiphany that didn’t necessarily come from anywhere but your own connecting of ideas inside of you. As I was writing Useful Not True, I came across a sentence that I just adore, partially for the inner rhyme, which is, “Your first thought is an obstacle.” I love that idea. Your first thought is an obstacle. We should not honor our instincts. We should not glorify our first reaction as some kind of authenticity that is our true self. It’s from your past. It’s an old habit that you picked up unintentionally, unthoughtfully. We should think of our first thought as an obstacle that we need to get past.
Derek Sivers
Something happens, somebody yells at you, your first reaction is not the one you should be acting on. You should stop and think, “Alright, well, that was my first reaction. What’s another reaction I could be having right now? Hmm, that’s another one. What’s another one? And what’s another one? Of all of those, I’m going with number four. I’m choosing that reaction.” What a better world. What a better way to live. We would all benefit from getting past our first reaction to anything and thinking of other ones.
Greg McKeown
Yeah, one of the phrases I love for this idea is just “third thoughts”. We don’t really normally say first thoughts, but you say “oh, and second thoughts”, you know, so that, you know, you sort of represent that there’s a first thought, but it’s like just beyond that. What’s your third thought? You know, like, just push beyond, notice your first thought, notice the second thought, keep going, because there’s so many limits we don’t recognize because the code is just... well, if you don’t notice the thoughts, the code, the system, it’s already running you. So trying to see it seems to me to be, Well, what have you found, you know, what have you found to be the most useful tool or habit or mechanism for shifting from being a prisoner to thoughts to being an observer of those thoughts?
Derek Sivers
Journaling, hands down. I have a very personal-to-each-his-own approach to life, but one of the only things that I think absolutely everybody should do is journaling. Whether you handwrite or type into text files or speak into a voice recorder or whatever it may be, journaling helps you process today’s thoughts, consider other options, consider other ways of looking at things. It also historically helps you go back and accurately see your past self in the moment without the fog of memory, which then helps you make better decisions for the future. It’s so useful in so many ways. I could go on and on and on about journaling.
Greg McKeown
Please do! We share a great love for this.
Derek Sivers
I didn’t start doing this until I was 42 years old because I found myself considering starting another company. And I thought, “Yeah, I miss having a company. I want to do that again.” And then I thought, “Wait... Do I? Do I really miss having a company? Hold on, I’m not sure I’m remembering it well. I’m remembering it fondly, but is that just the pleasant purple fog of memory and nostalgia? Has my remembrance of this gone blurry through time?”
Greg McKeown
Better get clear about this before ten years are invested in something that!
Derek Sivers
I wished that I had a journal from age 28 to 38 that I could have read exactly what I was doing every single day and how I was feeling and whether I was actually happy or not. That would have helped so much to help me decide whether I actually wanted to start another company or not based on how I actually enjoyed it in the day. So, at the age of 42, I wished that I would have been keeping a journal this whole time. Especially going way back to when I was 22 years old and I was touring Japan with a Japanese pop star and like so many things in my life. I wish I had a journal from that time. It’s just gone. It’s just a few faint little memories. One of my biggest regrets in life is that I didn’t keep a daily journal ever since then.
Derek Sivers
I don’t just mean a diary that you only turn to when you’re upset to vent to if your friends don’t want to listen to you. I used to do that too. I did have in my 30s some diary entries that I would only open up the diary if I really had muddled thoughts that I wanted to sort out. But then if you look back through the past of those, you only see an entry every 12 days when I have muddled thoughts. And that’s not useful to future self.
Derek Sivers
So my prescription for anyone listening, if you haven’t already started, start now. Best time to plant a tree was 20 years ago. Second best time is now. Start a daily habit, it could just be five minutes of ideally at the end of the day, just writing down what you did today and how you felt and if anything’s unresolved before you go to sleep, try to just work it out a little bit. Just try to accurately describe how you’re thinking and feeling about this and then, as we were saying in the moment, consider another point of view or maybe you don’t consider it till tomorrow. Maybe just the act of describing to your future self how you’re feeling today will help you think more clearly about it overnight and you’ll have more insights tomorrow. And then you can go back to see what you said yesterday or a year ago.
Derek Sivers
What I love about text files is it’s easy to search for a certain word. So I can just search for a word like “overwhelmed” or search for a word like “Singapore.” If I remember that something happened when I was in Singapore and I want to find that, I don’t remember what day it is, but just search the word “Singapore.” There it is. I like text files for this. But whatever works best for you that gets you actually doing it every night. So, so useful to help you make better decisions about your future to get more clarity about your past and your decisions and how you’re feeling today and help you process today’s thoughts and mixed emotions.
Greg McKeown
There’s a lot to unpack in what you just said, but it makes me think of a conversation I had with my wife Anna earlier today about change and how to make a long-term change in your life, and we could just apply it to journaling for a second. She was trying to articulate to me, sort of summarized in this idea, like a commitment that in the future you will never again not do something. Okay, there’s a bit more. Meaning, with journaling for example, I just heard it in the subtext of what you were saying, is there’s a difference between what I think a lot of people do with change, including specifically with journal keeping. I’m going to write a great journal every day of my life from now on. That’s one way to frame it. And it’s really predictable. Day one you write an essay, day two you’ve got no time to write that essay again so that you skip day two and then day three you feel bad, but now you’ve got two days to catch up and so it’s over before you begin. But it’s different, it’s different when you get to a point like you did with journaling where you go, “Ah, I wish I had had that. I’m never going to not have it.” And here’s why I think it matters so much the distinction because what we really want is a high commitment to a low standard. So that you say, it’s not I’m going to write a journal every day of my life forever and ever and amazing, it’s I’m never not going to. It’s different. If I miss a day, my intent is still there. I’m going to still write a tiny amount. I’m going to come back to it because I never want to be in that position where I look back and go, “Where is it? It’s not there. I don’t have it.” And that was absolutely key to my own journaling, which I mean, I think I’m at, I think 14 years without missing a day.
Greg McKeown
And it was: I’m never not going to have a sentence. It wasn’t, “I’m going to write masses.” In fact, I had an upper limit, so it was like five sentences was the maximum, So that I could just keep going for a long time for a few months until I never would miss a day one sentence at least Five sentences the most so that you just keep it going until it becomes a part of your system now I’ll write more, but if I ever miss it so to speak It’s fine because if I have to make up three days you can do a sentence three three sentences And then you course up for three days so that that difference of like I’m never not going to have any for a long period of time.
Greg McKeown
That seems similar to me in what you’re describing and what changed for you. Did I get it wrong?
Derek Sivers
That’s right. I think it’s beautiful. I love the idea of just five sentences or setting a maximum. That’s brilliant. I do often miss a day, say once a week. It’ll happen that I fall asleep at night while tucking my kid into bed. We’ll be sitting there reading a story and I’ll fall asleep too. And then I’ll go straight to bed and the next day I’ll think, “Oh, I didn’t write anything yesterday.” That’s fine. I just open up yesterday’s day and I just type, “Had a great day with my kid. Fell asleep in bed. Happy day.” That’s it. But man, there are some days, and we all know these days where you have a big decision in front of you. You’ve got some options to work through, you’ve got a lot to sort out, and man, it really helps to just have this place where you can just free flow your thoughts into this and just write and write and write, or speak and speak and speak. My kid actually, I got him, generally he really prefers the voice recorder. He keeps a little voice recorder with him at all times, like in his school backpack, and sometimes on the way to school or on the way home from school, he’s voice recording into his little journal. I never hear it, but he’s got a daily thing he tells me. And so handy. Yeah, if you need to go back and make up your updates.
Greg McKeown
I was studying this just within the last week, doing a deep dive on language, and the degree to which we can think if we don’t have language. This was my fun deep dive. And there is some evidence that if you lose, for example, and some people do completely lose their speech, they can still think, they can still solve. So they can’t speak anymore, but they can solve mathematical problems and so on. So there’s obviously something, you know, I don’t want to overstate the point that I’m about to make because there is evidence of this. But there’s such an enormous loss in your thinking quality if you don’t have language. So first that spoken language, right? So there’s a fascinating case study of an infant who grows up with almost no human interaction at all. And so by the time they are discovered by people, you know, they have no spoken language and their cognitive ability is massively depreciated because of that. So having spoken language is key to your ability to think clearly. Okay, so that’s one thing, right? So we have to be able to communicate, talk with each other as we’re talking, we start learning and seeing our thinking and this is one of the reasons free speech matters so much as a fundamental way of living because you, if you can’t, to some extent, if you can’t speak you I can’t think, but then, let’s go one step further.
Greg McKeown
What does writing give you that speaking doesn’t? Among the things it gives you is it allows you to store for the future. So there’s a huge difference. If this conversation, if we’re having it and nothing’s recorded, we could still have something that really triggers a thought or an insight or a change. But the difference of recording it, the difference of having a transcript, the difference of being able to, means the whole, for the rest of forever, we can access it.
Greg McKeown
Journaling matters so much because it transfers thinking as units, like a library from which you can, you can continue to grow and continue to access and continue to evolve your understanding, which compounds! The compounding benefit of writing thoughts versus just speaking thoughts versus just having those thoughts is really distinctive and different. That’s what I hear you describing here, that the writing has been a game changer for you.
Derek Sivers
I started to see the huge upside of having that daily journal going back for years. That’s the thing that keeps me going more than some proclamation that I’m never not going to miss a day or anything like that. Everybody’s got their own motivations. Mine is seeing the massively huge benefit that would have for my future self to be able to look back at every single day in my past going back many years. So as of now it’s been 13 years that I haven’t missed a day. And I can tell you, it has helped so much, so, so much. In even just tiny concrete ways.
Derek Sivers
I’m going to give you a huge example, but I’m going to be succinct about this story. I was in a romantic relationship, a very serious one where we were on the verge of having kids and getting married and all of that. It had been great, but it was currently really rough. And one friend nudged me to go back and look at my diary because she said, “I think you’re remembering the past a little differently.” And so, as we were about to make this massive leap into like, “Let’s have a baby, let’s get married,” and I was feeling so, oh man, how do we get through this current trauma or this current dilemma. I went back and re-read every diary entry since the day I had met her and only then I realized it had always been hard. Or I say like 80% of the time on a day-to-day level had been really hard. And that helped me make the huge difficult decision to break up. And it was the right thing to do. But damn it was hard. And it was only possible because of that journal history. If not for that I would be in a bad relationship right now. I am so thankful for that.
Greg McKeown
What I heard you just describe there was the difference between the dots of life and then connecting the dots. You know, it’s what’s happening and so what, what does it mean? And I do think it’s profound because it’s so relatable that you couldn’t tell. You know, like how could you not tell? I mean, all of us. How can we not tell what’s happening? We’re there! There, you’re in the relationship, it’s years, how can we not know? It’s such a strange thing about life that you can be living it and doing it and in a relationship and not, and miss the news of your own life. You know, really though, and I think unless you have a mechanism for actually capturing the dots. And then it took a prompt to be able to go back and look at all the-- you can’t connect them. I just-- I think it’s very hard, given the limits of our memory.
Greg McKeown
I mean, I think it’s extraordinary. When I challenge myself like this-- everyone listening can do the same thing-- What did you do last Thursday? Okay, like can you remember? Maybe people can okay. Well, I know on a Thursday I do this. What about the Thursday before that? What about the Tuesday before that? Okay, that’s it. It’s gone. There’s no I think there’s like nobody listening Who can immediately unless there was some particular thing that they have, you know, like randomly, you know They don’t know what they did two Thursdays ago Tuesday before that And yet they were there And if they had the right prompt, it’s all stored, it’s in the hard drive of our mind, but it’s not there, it’s accessible. And that’s like three weeks ago, that’s nothing. So there’s such a limit in our ability to remember and connect the dots. And so, I mean, to me, that’s a profound part of your story. To miss the news of a relationship you are in, experiencing all the time, unless you have a mechanism for observing it over a period of time.
Derek Sivers
Your daily recollection of today and your sharing of how you’re feeling today, right now, is so much more accurate than even tomorrow’s look back at today. That’s why it’s ideal to try to capture at the end of today, capture how you’re feeling today, Because sometimes just after a good sleep you’re saying, “You know what? I was complaining yesterday but it’s not so bad.” But you really need to capture that complaint because your future self will be in the complaint, not in the day after the complaint. You’re always in the now, living that.
Greg McKeown
Yeah, the degradation, the depreciation. That speed of falling off. When I’m doing a catch-up day, I’m amazed at the difference. Just... today I can just write, fill a page. So many things have happened and so many thoughts. And if I’m rewriting, it’s like, okay, I guess I can, I think I did this, and let’s look at the calendar, and let’s remember, and you’re kind of capturing it, but it’s, that day was just as rich as today, did my memories not? So, and then you were saying that there were specific small things, though, that you gained from doing it, too?
Derek Sivers
Yeah. Oh, okay. I’ll just pick some real core ones. Often when a dear friend calls, I’ll jot it in my diary somewhere. Maya called today and we talked about this and this and this. And there have been times when I have wondered, like if I started to lose touch with a friend that I’m able to see, “Wow, it seems like Maya and I used to talk more often.” I’ll say, “Well, let me go look at the facts. Look at this. We used to talk every two or three days. Now we’re talking every two or three weeks. When did this change happen?” So it’s interesting to, again, find the facts instead of just your fuzzy recollection.
Derek Sivers
Including when I haven’t talked with an old friend in a few years, I’m able to pull up the last time we talked. Look at this, it was five years ago and here’s what we talked about. “How have you been, Andrew? It’s been a long time.” That’s handy.
Derek Sivers
There was one time entering the US or filing my taxes or something where they said, “Please list your entry and exit dates of all of your visits to the US over the last 10 years.” Actually I have those! I just searched for the word “flight” or “plane” or “airport” or something like that. And there it was, even though I didn’t know I was logging that. But just by the fact that I mention long flight, at the airport, something like that. There it is, every entry and exit date.
Derek Sivers
Here’s my last one to end on. It’s interesting to see what ideas and desires have stuck around for the longest. So I just last week posted an article on my blog called “How to Listen to Ulysses” and it was a recipe for an idea I had. Usually the kind of thing that I just keep in my journal and let it pass, but Seth Godin told me I should post it. So I posted it. And after posting it, I thought, “You know, I really should go download the audiobook for Ulysses. Like, just buy the mp3 or buy the CDs and rip them or whatever I need to do. And I’m gonna do this. I’m gonna listen to Ulysses all the way through.” And I started in the process and there in my hard drive was Ulysses already downloaded and encoded something like twelve years ago when I had the same idea. And I went, “Oh my god!” I searched my diary for the word Ulysses and I’ve had this thought a few times over twelve years! So to me that bumps something up in my to-do list. Like, alright, this isn’t just today’s whim. I’ve wanted this for twelve years. It’s time to do something about it.
Derek Sivers
So I’ve started collecting thoughts on a certain subject that I keep coming back to, instead of just mixing them in my daily diary, I have a separate “Thoughts On” journal, which is a topic-based journal because it’s just on a computer anyway, it’s easy to just make a new folder. I thought for years about whether to get a dog or not. I thought for years about whether to move back to Singapore again or not. I thought for years about what does home mean to me. What’s my definition of home? When do I feel most at home? I keep coming back to this thought on what home means to me. So there’s a folder called thoughts on home. There’s a folder called thoughts on Singapore. A folder called thoughts on dog. And every time I have a new thought about a dog, getting a dog, or Singapore, or home, I just put it in that diary and then I’m able to look back through 15 years of thoughts on whether to get a dog or what home means to me. It’s so fun.
Greg McKeown
You’re describing, I think, the creation of a second mind.
Derek Sivers
I think that’s a trademarked phrase. I’m not sure we’re allowed to use it.
Greg McKeown
Who trademarked it? I don’t know.
Derek Sivers
No, no, no, no, no, no, I’m kidding, kidding. That’s Tiago Forte’s thing, the second brain.
Greg McKeown
Oh, yeah, okay. Good, good. Well, we’ll use it anyway.
Greg McKeown
Well, I have a friend who has kept a mind web for the last 20 years, of everything. Everything. If he’s met you, you’re in it. So it’s literally like the most complete mind map, probably, that anyone’s ever done. I mean, he is just, you know, it’s a different kind of journaling, but he is literally constantly connecting the dots as he’s doing it. And I don’t exactly know what he gets from it precisely, but it’s a pretty fascinating approach to be able to constantly be adding experiences within certain buckets and connecting those with other things so that he’s looking at this vast kind of a kind of mind palace that he’s created so that he’s just so much more aware than the sort of the reactive way of going through life.
Greg McKeown
Tell me this, What do you think is the number one thing you would miss if you couldn’t write your journal anymore, couldn’t write thoughts down? Like what’s the loss like for you in such a proposition?
Derek Sivers
It would be like somebody who lives in a driving place not having a car anymore and what used to be a 10-minute drive would now be a 5-hour walk on the highway to get somewhere. It would feel like I had lost 90% of my power. My journal has become my augmented memory. To lose that power would feel like I don’t know how to walk anymore. I can only crawl from now on. Like, okay, life is still worth living, but oof, it’s so much harder now. It’s just, everything’s disappeared.
Derek Sivers
I really love reviewing my past thoughts so much. That’s the second most important. But number one is processing today’s thoughts.
Derek Sivers
If I couldn’t write, well then, damn, I better have a very patient best friend who’s going to listen to me talking and talking and talking about today and processing. And yes, I do have best friends and we do have our daily sharing of ideas and perspectives and events and processing and echoing. So important. But man, without also being able to write it down, that would be hard.
Greg McKeown
Well, it’s such an interesting description that it would be like crawling or it would be so slow I mean, I think that idea of the I think that’s one of the hesitancies people have about Journaling is that it takes so much time in their minds They think because it has to be this complex version of it and so on But but also just it’s a clear an actual time commitment that you know, you’re spending time doing this So you must be making a trade-off but the idea that it is accelerates your thinking Accelerates your processing accelerates the quality of that thinking That that’s an interesting and I think in a way a little surprising answer The speed it’s like the speed of journaling or I don’t know something like that.
Derek Sivers
Feels like a power boost.
Greg McKeown
You know the movie Limitless (2011)? I’m not tempted by drugs. The premise of the movie is if you there’s this one pill and if you take it it unlocks your full capacity - your every thought you’ve ever had you have access to it Immediately you can bring anything back to any moment You can memorize a language in a weekend write a best-selling book in an afternoon. It’s just this enormous accelerating experience and so yeah if that existed per se that would be tempting because there’s so much to learn and life is so Short and you know, this is the upload speed is extremely frustrating to me So it just it just feels aligned somehow to that That if you want to accelerate your thinking access more of your potential speed up the that you’re you’re you’re You’re learning capacity you know. Journaling I mean so many people wouldn’t make that connection. I think but that’s what you’re saying.
Derek Sivers
I hadn’t heard of that movie but once you started describing what it feels like, yeah, journaling feels like a superpower. So I don’t usually do predictions. All predictions are wrong. But it was a fun daydream to think recently, what if the best AI engines we have now get five times better? And you’re able to have it locally and private so you’re not uploading anything to OpenAI or Anthropic or DeepSeek, but it’s completely local on a private computer in your home that’s not connected to the internet. There’s no chance of it ever going to anyone else ever. It’s on a private Linux computer that you set up and you control it. And it’s got an AI on that’s five times better than anything we’ve got now. Now imagine this: passing it every single thing you’ve ever written in your private diary that you would not let another human see. Imagine if you started recording every conversation you’ve had with everyone, microphones in your house that are ensured to be private, not uploading to Apple or Google. And you let it have access to all of this. Weirdly enough then that AI would know you better than anyone, almost. It could really aid in consultation when considering decisions. You could say, “Based on every other time I’ve considered going out on a Saturday night with Jeffrey, do you think I should do this?” And it might be able to, in a snap, say, “Your happiness level over the last seven meetings has diminished by 50%. I would not recommend doing it. I’ve noticed that your happiness level on these Alternative actions has been increasing and based on what you said six weeks ago, I think your current values are shifting as such and you should instead choose to do this.” You don’t have to obey it blindly, but damn that would be helpful, wouldn’t it?
Greg McKeown
I love the thought experiment and I love that it’s not connected to uploading your life to somebody else, which is extremely frustrating with the current situation. Makes a huge difference.
Derek Sivers
It was when somebody said that we could run the current DeepSeek R1 on a home PC that costs $6,000 and they gave specifics. They said here this is what it costs. I priced it out. This will run the current best full-powered DeepSeek R1 model on your home computer not connected to the Internet. $6,000 and I thought, “Whoa, that does change everything.”
Derek Sivers
I didn’t do it because next year it would be $3,000 or next year it would be five times better. But just the thought idea of it being fully private where I would be willing to give it all of my private diaries that literally no other human besides me has ever seen, that changes a lot.
Greg McKeown
It seems to me that one of the assumptions underlying all of this, including this AI thought experiment that you’ve just offered us, is that you can upgrade, you can upgrade the way you see things and think about things. And although this feels, perhaps to some it will be just one more conceptual thing, it’s been a very useful idea to me, which is a growth mindset squared.
Greg McKeown
So, okay, so I’m sure most people listening know about the growth mindset and fixed mindset from Carol Dweck, who was at Columbia for 20 odd years and then at Stanford and so on. And what she’s saying is, you know, if you have a fixed view of intelligence, then you will tend to avoid new challenges and experiences because it will Subconsciously show you that you are that your intelligence You know that you’re not as intelligent as you Thought you were and so you want to protect yourself from that and so that’s limiting But if you have a growth mindsets growth intelligence, which says okay, I can get smarter So if I take on a new challenge, and I don’t do well at it. It’s just fine because I can get smarter Okay, that’s her thing and it’s very powerful and I think it’s powerful mostly because she’s identified a perspective that happens to be fixed for almost everybody. Because we were taught it was fixed, because of the way that IQ was first framed and then the IQ test particularly around it, meant that it became a sort of hardwired concept in all of education and you know especially particularly in the West. So that’s the growth mindset versus fixed mindset. But the growth mindset squared is the same idea but you say this, you say, “I can upgrade my mindsets.” So she’s talking about one mindset versus another mindset, and that’s extremely powerful, but we have hundreds of mindsets, and the idea that you have those mindsets and that those mindsets can be upgraded, a whole mindset can be upgraded, is a completely different level of flexibility and intelligence possibility and just human potential. I mean, that’s the kind of, that’s the limitless idea, I think. You don’t have to be locked into whatever, all of those mindsets you had before. They can all be upgraded, not all at once, but over time they can all be upgraded.
Greg McKeown
I think this is the difference between being locked, limited or limitless. And I think that that’s the thread that I hear in what you’ve shared, what we’ve discussed today. Also, what you’ve been writing about is that we can upgrade the very mindsets that are currently governing our thinking, our feeling, our actions, our sense of the world. Your final thoughts?
Derek Sivers
Love it.It helps so much to be an outsider. You’re not living where you grew up. I’m not living where I grew up. Moving out of your hometown helps you detach from the perspective that you heard too much growing up. It really helps to go to another part of the world, to feel at home, to really make friends with people that have a completely different way of seeing this, with a different moral framework and a different set of right and wrong, ideally they grew up in a different religion with a different culture around them, and every idea you talk about, they can present to you a very different way of seeing it. After a while, you internalize this yourself, and you can look at anything that comes up in your life or in the news and you can hear your first reaction and then hear your friend’s reaction even if only in your own head. Maybe hear the reaction of a fictional character that you know from your favorite book or movie. And then think of, “What would Greg McKeown say about this? What would Derek Sivers say about this?” Name any person, because they’re all the mentors, they’re all mindset possibilities for you.
Derek Sivers
That’s why I read books, mostly, is to deeply understand another mindset and now that’s why I travel. I realized succinctly, recently, that the reason I travel is to inhabit philosophies. I can read about them, I can hear people from another place. But I go to that place and try to inhabit that philosophy, to feel it in my gut and on my skin. I can understand that mindset better and I can try it on, like wearing the local clothing and know how that feels and see the world from that point of view. That’s why I travel is to keep increasing my options of perspectives.
Greg McKeown
Derek Sivers, not just an optimist, an optionist!
Derek Sivers
Ooh, Optionist! Dude, did you just coin my new one-word title? I like this! Optionist!
Greg McKeown
That’s it. Yeah. If we see it in your bio, we know we’ve been successful here in our conversation.
Derek Sivers
Derek Sivers, Optionist. Not author, not entrepreneur, Optionist. Fuck yeah! Coined by Greg McKeown.
Greg McKeown
It’s an idea that I really genuinely love myself. Because, well you said this earlier on about the brainstorming. Like, we’ve all heard what brainstorming is and you sort of pick it out. “Okay, we have a meeting, let’s brainstorm something.” Okay, that’s not really at all what you were saying. That’s not what I mean when I think about it either. It’s a perpetual process, literally all the time, because you’re trying to break out of, well, once you realize how imprisoned you actually are, not by anybody, not by anything else, but just by all the frames you currently have, You want to constantly be upgrading them, challenging them, thinking, pushing the limits of them.
Greg McKeown
I’d added Johnny Ives about Steve Jobs, that he was the most curious person he ever met. But also he said that he got frustrated with the limits of his mind the same way that Johnny got frustrated with the limits of his body. You know, that is a very particular way of thinking about your thinking. And I feel so frustrated by the limits of my thinking. You know, the phrase that’s meaningful to me is this poetic way of saying it, “But thy mind, O man, must stretch.” And to live perpetually in that sense of, you know, “Optionist! What are the options? How could we think about this? How might we see it differently?” There’s not two ways to think about it. There really is a hundred ways. Keep thinking, keep exploring, keep learning, keep being less wrong.
Greg McKeown
Derek, what a pleasure to have you on here to riff, to stretch our minds together, and to learn. I’m edified, I’m happy. Thank you for being on the podcast.