Elevate with Tyler Chesser
host: Tyler Chesser
philosophy vs self-help, framing life experiences, starting with no money, saying yes vs no, journaling and reflection
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Transcript:
Tyler
Derek Sivers. Welcome to Elevate, my friend. How are you doing?
Derek Sivers
Thanks Tyler, good.
Tyler
Well, thank you so much for being here. I know you and I, we were actually just talking about this before we started recording here. This has been in the works for a couple of years now. So I just want to thank you again for being on the podcast and sharing your brilliance with Elevate Nation. If anybody is not familiar with Derek’s work, you’ve got to check out a lot of his books and his writings, and his readings, and his thoughts, because I would describe you as a modern day somewhat philosopher. What do you think about that Derek?
Derek Sivers
It’s funny. I like pop philosophy. I think academic philosophy often ends up just benefiting other philosophers. Whereas pop philosophy, a.k.a. on the verge of self help, ends up actually benefiting real people with situations they’re currently wrestling with. And to me, that’s the difference between philosophy and self help or pop philosophy. So the actual academic philosophy, I have no interest in determining whether reality is real or whatever. But things that are applicable to our daily life I’m endlessly interested in.
Tyler
It’s almost like what Dan Sullivan describes as a thinking tool. He talks about thinking tools, and a lot on this podcast we talk about mindset, perspective. I think a lot of what you present to the world in your wisdom that you’ve been able to glean through your own experiences, through studying others as well, is just really helping other people frame the world in a more appropriate way to take more appropriate action to go where they want to go. Does that resonate with you?
Derek Sivers
Yes, absolutely. That’s a beautiful description. The framing is everything, isn’t it? That the whole way we experience life is just our reaction to things. The events in life are very neutral. In the field you’re in, you’re presented with somebody who has said no. Okay, well, what does that mean that they’ve said no? It means nothing. It means nothing at all except the meaning that you project onto it. And the entire course that your life takes is based on how you’re going to frame and represent in your own mind what is happening in front of you. It just means everything. It changes everything. I love that.
Tyler
It is really interesting when you think about it. Everything that we interact with, it’s not the event, but it’s the meaning that we project upon that event. Once we start to separate that, the possibilities then open up. Because we can look at everything and say, No matter what happens, there’s an opportunity for me to learn to grow. Or there is a path that life is giving me that I now get to take a step forward to maybe something that is unexpected. Does that make sense?
Derek Sivers
Yeah. Even you saying life is giving me, that’s also not true. That’s just your representation. Life is not giving anything. That’s a neutral event that happened. If you choose to interpret--to say, I choose to think of it as life is giving me an opportunity, well then, hell yeah. You’ve just made that into an opportunity for yourself because you chose to think of it that way.So fulfilling.
Tyler
Absolutely. And the other side of it is, well, life is doing this to me, right? This tiny little shift.
Tyler
I’m the victim or everything that happens to me--it’s the perspective of the meaning that I’ve projected upon these circumstances. I’ve recently talked about problems and how problems can be gifts. I think it is a matter of your perception. It is a matter of the meaning that you project. And the meaning that you project, and I’d love to hear your thoughts on this, then turns into the actions that you take. The behaviour or the emotions that you experience, which is infectious in good ways or bad.
Derek Sivers
Right.
Derek Sivers
I guess maybe in the intro you’ll tell people who I am. Years ago I started, and grew, and sold a company. I had a music distribution company called CD Baby, that I ran for ten years and had 85 employees. In the final year things got really bad. It was financially great. It was successful, but just inside the culture of the company had turned so nasty and so awful that it was actually the reason I left. Its because I just hated what the company had become in its internal culture. That’s the reason I sold the company. I just wanted to either shut it down or walk away.
Derek Sivers
So in the years afterwards, I thought of all of the problems as their fault. Those damn employees, those entitled figures, those brats, those people that were staging a mutiny and making me walk the plank of my own company. I had all of these things where I was the object of the verb, and they were the subject. Suddenly one day I decided, what if everything is my fault? What if the entire company culture and the way that those 85 people came into work and how they saw their job each day, what if that was all my fault? Oh, I like this.
Derek Sivers
This is powerful. This feels better. Then I look at the whole world going, “Wait, what if all of this is my fault? What if the reason that these bad politicians are in office is my fault? What if the reason that there’s pollution in India is my fault?” This is all up to me. I like this. I know this is not a true belief. I’m not judging this belief on its accuracy, but I’m thinking, first how does that make me feel? And I like it. Other people don’t like it. They think maybe--people grew up with a guilt complex and parents or partners that were always guilt tripping them.
Derek Sivers
For them, a belief of everything is my fault won’t work for them. They would not like that. But for me, I like this. I like taking responsibility. Then I thought, “Now this can change my actions.” Because instead of feeling helpless about pollution or hunger or politics, I can think, “But it’s all up to me. So I need to take actions to change this.” I like this, and I can change it because it’s my fault. I choose beliefs because they’re useful, not because they’re true.
Tyler
Man, that is a sound bite right there. But I think about what you just described, in particular in half the population would be just overwhelmed by that thought. To say that everything is their fault. The other half may be energized by that, as you were. I think it almost goes down to the thought of gamifying what empowers you with your beliefs, and choosing those thoughts. And creating this reality based on what is actually going to be in the best interest of your future self. Does that resonate with you Derek?
Derek Sivers
Yeah, everything except the word gamifying. Choosing your thoughts that empower you, absolutely. Gamifying, I’m just curious, how do you define that or how does that apply?
Tyler
I’m almost brainstorming while we’re having this discussion, so you’ll have to forgive me.
Derek Sivers
Yeah, me too. It’s fun.
Tyler
And I’m thinking of it as a game because you don’t know for sure whether or not this will truly empower your future self. You are almost exploring this thought of, “Well, what happens if I start to think that everything is my fault.” And you didn’t really necessarily know how that was going to play out. So maybe it’s almost like you’re playing a game with yourself and you’re almost betting on a probability of a certain future outcome. Does that make sense?
Derek Sivers
Yeah. You just made me realize that when we say gamifying, we usually mean this quantified scorekeeping, points keeping, how many karma points do I get on Reddit? How many likes did I get on my post? That’s usually what we mean by gamifying these days. But you’re right. A game--two kids playing make believe, pretending that there’s a monster in the hallway. That’s a game. Actually, no. Make believe and a game are slightly different. The difference between play and a game is that a game has rules for the purpose of cooperation. If it has rules for the purpose of cooperation, we call it a game. If it’s just a kid making mud pies or pretending to be an astronaut in their bedsheets, we call that play, not necessarily a game. So I think of what I’m doing, not as gamifying, but as play, experimentation, make believe.
Tyler
There you go. Which you could look at as play or you could look at that as a game, maybe with no object or no outcome in particular other than enjoyment or curiosity or adventure. As I study your work and I study your background and your perspective and really where you’re taking things now and your creativity, to me it’s just fascinating. Because you just describe some of the pain, the suffering that you went through as the business owner that then exited and so forth, and reflecting upon that. But now thinking about where you’re taking this and you’ve even just looked at businesses and life in general as play.
Tyler
And you said everyone needs a company because it can be your own art or your own music. And going back to just being a musician yourself. I do want to talk about that monomaniacal focus that you had for many years. And being a musician, and what you learned about yourself and how that shaped you. Also just moving forward because that almost seems like that was such a formative experience that you’ve applied that thought process to business, to life, to being an author, to being who you are today. Does that make sense?
Derek Sivers
Yeah, I guess that’s what you’re doing with real estate, right? You were fascinated with real estate and you take the lessons you’ve learned not just about the industry, but about the personal development and the emotional mastery that you’ve had to do for yourself. And you’re applying that in a more broad field outside of real estate as well. So, yes, I did that [crosstalk].
Tyler
That is exactly right. But I read that from you, I’m like, this is a game. And the game within the game is yourself, the internal dialogue. To me that is universal. That’s why I love having these conversations with people like yourself. So thank you for that. That was great.
Derek Sivers
Well, I feel like we’re getting quite abstract. I’m feeling bad for your audience that’s listening on a drive to just like, “Okay, they’re defining the difference between play and a game. How is this going to help me?” So let’s let’s talk about something concrete to help your audience.
Tyler
Thank you. Let’s go back to the beginning because the monomaniacal focus yourself in becoming a musician seems to be a very shaping type of experience. Tell me a little bit about that and how that actually shaped you.
Derek Sivers
At the age of 14, I was really into heavy metal guitar. I would just spend hours a day with my fingers on a fretboard, playing scales, playing arpeggios, learning guitar solos, learning how to play every note that all of my favorite guitarists played on, on all of my favorite music. I was just obsessed with being a great guitarist. After a few years of that, then I was more obsessed with making music itself, not just heavy metal, but like all kinds of music. I got obsessed with how we layer instruments to put it together. like how to make a good drum beat and how to put together a good arrangement with a bassline and a drum beat and the guitars and then how to write songs.
Derek Sivers
So somewhere in there I decided, I really, more than anything, want to be a successful musician. This is what I want. But I decided this at like 15. I’m so glad I did, because the next 15 years of my life had a purpose. Where everybody else was drifting around, not knowing what they were doing, I had this single focused purpose I’m on. I’m going to be a successful musician, and therefore I was motivated to read books on marketing, books on positioning, books on sales, books on business, books on personal development. All of this was applicable because I needed it to be a successful musician. I’m so thankful for that focus that I had.
Derek Sivers
I’d say, it doesn’t matter what you’re pursuing, as long as you have something that you’re pursuing, then everything has drive and purpose and meaning. You’re never lost. So it was really weird when I went back to my ten year high school reunion at 28 or whatever. I went back to Hinsdale, Illinois, outside of Chicago. I saw all my old high school friends that were just lost. They were just bloated and drifting. They got some job as a mid-level manager at Motorola, pushing papers from left to right, and they were just lost and drunk.
Derek Sivers
I didn’t feel successful at the time. I was a musician living hand to mouth. But I was a full time musician living in New York City. But making $300 on this gig, and $150 on that gig and I would pay my rent doing that. When I went back to my high school reunion, they were all jealous that I had followed my dreams and I was doing it and I knew what I was pursuing. So now as a parent, I look back at my former self like a different person, like a kid. I’m just so thankful that I had a thing that I was following that whole time that led me to the constant pursuit of self-improvement.
Tyler
One of the things that strikes me about that is, most people, when they’re 25 years old, ten years after you had found this really innate pursuit of mastery, many people just still don’t even have the clarity of what is actually true to their soul. Or what it is that they want to give. Or what is really screaming out to them. How were you able to encounter that so early on? Is there any advice that you might give to others who are looking to be more in alignment with their purpose?
Derek Sivers
First just forget that whole idea of purpose. Forget passion, forget purpose. You have to understand that you start down the path first and the emotions and inner feelings and representations of passion and purpose are emotions that come later after you’ve been pursuing something for years and the world is starting to reward you for it. So that’s an argument in favor of practicing your skills, let’s say. Just metaphorically getting good at anything.
Derek Sivers
Like having parents that insist that their kids pick a music instrument and then practice it every single day for an hour for ten years from the age of 6 to 16. They might not even want to do it. But for the first five years they might go and do it, and practice their skills. But after five years, well, now they’re really good at this thing and people who hear them play go, “Wow, you’re amazing.”
Derek Sivers
And they start to get that feedback and they start to get into the better stuff. The basics of anything are pretty dreary. Let’s even say computer programming. You pick up a book on computer programming, it’s going to be just a bunch of like stupid Fibonacci Series and fizz buzz. But then you’re going to get into the good stuff later, that gets really rewarding. Then that’s when you start to feel these feelings of passion and you like it enough that you think, I really want to keep doing this.
Derek Sivers
Because not only am I enjoying it because it’s fascinating and interesting, but the world is rewarding me. Now you start the feeling of purpose. So all those things come later. The problem is, like you say, somebody at 25 just lethargic going, “Oh, what’s my passion? What’s my purpose?” You can’t start from there. You just have to start doing a thing, and the feeling of passion and purpose comes later.
Tyler
That makes so much sense. It really makes me think of real estate in particular. Because it can be a very sophisticated and nuanced approach to creating wealth and creating opportunity in your life and also sharing that opportunity with other people. Because in the very beginning it’s very challenging, overwhelming, difficult to understand. But you mentioned essentially that passion comes from mastery, and it’s almost like you’ve got to commit to the fundamentals and overcoming that difficulty, getting to the other side, you start to come to an appreciation of the level of mastery that you can develop and you can create.
Tyler
But also in that pursuit. One of the things--you wrote the book on “Hell Yeah Or No”, it’s almost like because of that pursuit, you were saying no to everything and you’re still doing that today. We started this conversation prior to with you literally showing me exactly how you’re really focusing on making time for yourself so that you can have time to be in that making mode. So how has this evolved over the years for yourself, and do you have any advice for others who may be struggling saying no, in this world of just constant distractions?
Derek Sivers
Yeah, you have to know the story of Buridan’s donkey. It’s a fable. Buridan is spelled b-u-r-i-d-a-n, so search it up. Buridan’s Donkey is a tale of--I think it’s a philosopher that came up with this. It said imagine that there’s a donkey that’s exactly halfway between a pile of hay and a bucket of water. And he’s hungry and thirsty, but looking back and forth going, water or hay? Or water. Or hay. He can’t decide and he ends up dying of both hunger and thirst, because he couldn’t decide which to do first. So the idea is, don’t be a donkey, just pick one.
Derek Sivers
See the problem is a donkey doesn’t have foresight and imagination. It’s kind of a unique human ability. Most creatures on earth do not have foresight and imagination to imagine how something will be in future steps. We do. So you can use the future of your imagination to know that you can do one thing first. You can go to the water first, have your drink, and then saunter over to the pile of hay. Otherwise, you’re just going to die of starvation and thirst like Buridan’s donkey, if you don’t pick one and do it first and know that you’ll get to the other thing later.
Tyler
So how has that evolved for you over the years? Because at some point I’m sure you’ve fumbled your way through saying no to distractions. At this point, it seems like that is one of the lines of mastery that you’ve really engaged in. You’ve just committed to this consistent focus. And it’s about eliminating distraction. How has this evolved for you over the years?
Derek Sivers
In a lot of ways, I kind of hate the world. I hate the noise. I hate all the bullshit that’s out there. I hate all the, “You should get involved in this Web3 crypto thing.” “Hey, why don’t you do NFTs because I heard of them today.” That mindset of noise. There is so much noise. So much of it is basically advertising.
Derek Sivers
I taught my kid years ago when he was like five years old, that when we’re driving through the city and he sees all of these billboards and he’ll say, “Hey dad, why does that say you deserve a time out? I thought a time out as a punishment?” I just said, “Because they want you to give them money.” And he’s like, “They do?” I’d say, “Yeah, every one of these billboards you see, what they’re really saying is, give me your money. You earned it, we want it, give it to us. That’s all they’re saying.”
Derek Sivers
Then other times he’s like, “Why is there a picture of like a fruit inside a bottle? Because they want you to give them your money. That’s it. That’s all.” So a lot of the noise of the world when people are saying, “Hey man, you should really get into NFTs. Have you looked into Web3?” What they’re really saying is, “Give me your money.” Which is, I let somebody else convince me I should do this thing, so now I’m doing this thing and I’ll make more money if you do this thing. So you should do this thing. You should totally do this thing. Then I’ll be justified and I’ll make money, and that’s why you should do it.
Derek Sivers
I just hear this hidden message behind all of the noise of the internet. If not money, then attention. Give me your attention, validate me. I just hate it all. I have such little respect for the noise of the internet and the teeming masses telling me I should be doing what they want me to do. I just ignore it all. I’m really happy to to have books as my main source of input because they’re relatively quiet and uncorrupted by commercial concerns.
Derek Sivers
A book is almost never a way to get rich, so books are usually not corrupted by that noise. I just know the lesson from Buridan’s Donkey. That I just have to do one thing at a time and everything else is just going to have to wait. Maybe it’s because of the love of the path of mastery. Seeing how all my friends in high school that tried to do lots of different things ended up doing nothing. Whereas I was just focused on essentially a silly pursuit of just being a great guitarist. That helped me through everything, that helped me through all the noise.
Tyler
How would you give advice to someone who’s maybe building their career and they feel like at this stage in their career they need to say yes more than they say no?
Derek Sivers
The “Hell Yeah Or No” approach. Anybody listening, search my name and the phrase, “Hell Yeah Or No”. You’ll read more of what I have to say about it. It’s essentially saying that if you are overwhelmed with opportunity and if there are too many things begging for your time, you should raise the bar all the way up to like the 99%, so that only that rare 1% of a thing that makes you say not just, “Okay, yeah sure.” But like, “Oh, fuck yeah!” That would be amazing. You say no to everything but that. You lift the bar all the way up, and what it does is it gives you more free space in your life so that you have the time and space to throw yourself into that occasional rare thing.
Derek Sivers
Whereas if you have said yes to too many things, then when the occasional great thing comes along, you don’t have enough time and energy to give it what it deserves. Because you’ve said yes to too many half assed things, right? So that’s the essence of “Hell Yeah Or No”. But the problem is, because I’ve talked about it publicly, a lot of people say, “Oh yeah, that’s great. I want to say hell yeah or no to everything in my life.” And I’m like, “Wait a second, no. That’s not for everything.”
Derek Sivers
It’s for a specific scenario in your life when you are overwhelmed with opportunities. But if you’re just starting out your career like you asked, hell yeah or no is not the correct philosophy. It’s not the best mindset to follow. Instead, you should say yes to everything at the beginning and work twice as hard and sleep less and do lots of things. Because what your job at the beginning is, is to see what the world’s going to reward you for.
Derek Sivers
I’ll just use my own dumb example. As a professional musician in New York City, I was saying yes to everything. Somebody needs a guitar solo on a record. I say yes. Somebody says, “Can you produce? Do you know any good recording studios?” I say, “I’m a recording studio. I’ll do that for you.” Somebody says, “I’m looking for a record producer.” I say, “I’m a record producer. I can do that.” Somebody says, “Hey, we’re looking for a jazz pianist to play at this art opening.” I say, “I’m a jazz pianist.” I can do that. So I just said yes to everything. Then I was a booking agency. I was a record label, I was recording studio, I was producer, I was a session guitarist, I was a circus clown and emcee.
Derek Sivers
Ringleader, emcee, clown for a circus, a children’s entertainer. I actually made a good living running around inside a black Lycra bag, bothering people on college campuses. I did everything. I did lots of stuff, whatever I could to make a buck. Last time I had a job was 1992. I quit my job in 1992 and I’ve just been like full time freelance everything since then. But along the way there is one little thing I did, which was I had a little web store that I sold my CD on. Then friends told friends and I started getting calls from strangers, said, “Hey, can you sell my CD? My friend Dave said, you could sell my CD.”
Derek Sivers
Pretty soon out of the 15 different things I was doing, this one took off. So I shut down the other 14, started saying no to all that, then threw everything I had into this one thing that became CD Baby. That was my big success in life, monetarily at least. But it came from saying yes to everything, trying everything and seeing what the world would reward me for.
Tyler
Being willing to go down those dead ends or those paths that didn’t lead to anywhere. But there was maybe some learning or experience that you gained from that. Or perhaps a clue that a new business could be born as a result of this. Speaking of beginning, we’re talking about saying yes versus saying no and when it may be appropriate, and I love the paradox of that thought. But you’ve written about a lot of the creativity involved in building a business through anything you want.
Tyler
One of the things that really stood out to me was this thinking tool. Again, this mindset, that starting with no money is actually an advantage rather than being a disadvantage. So I’d love for you to just expand upon that thought because a lot of people, especially in real estate, think, “Well, if I’m going to build a real estate empire, I’ve got to start with millions of dollars.” I know that you’re not specifically writing about people in real estate, but I’d love for you to just share with the listener a little bit more about why starting with no money is an advantage for any endeavor.
Derek Sivers
I think other people have probably written about this much better than I have. But my own take on it is that when you’re doing things bootstrapped, or on a shoestring, however else they say that, it means that you don’t spend a single dollar unless you’re pretty damn assured that’s going to earn you $2 back. When I first started my company, I would get calls from advertisers asking me to spend even $200 to advertise in their outlet. I’d say, “Well, can you give me the assurance that this will make me $400 by next month?” And they’d say, “No.” And I say, “All right, well then, no.”
Derek Sivers
I do not spend a dollar unless it’s going to turn into $2 almost immediately because I just don’t have extra dollars to spend. So it really makes you laser focused. Talk about just learning to say no to almost everything. Of course, as soon as you start a business, you’re going to get swarmed with flies saying--B2B flies saying, “Oh, you need to do this, and you need to have an insurance policy. You need to have a company. You need to have a terms and conditions. You need to have this.” And you go, “Nope, nope, nope, nope, nope. Because is that dollar going to earn me $2 next month? No. Then no, I’m not going to do it. I don’t care what you tell me. It’s not going to double my money in a month or two. I won’t do it.”
Derek Sivers
It just helps you get laser focused. Whereas companies who were given $50 million in investments, they just go out and do stupid things. Like they throw these big parties. They spend money on a big sign above their door or on fancy Herman Miller chairs and space age desks and infrared systems or whatever. None of it is going to double their money the next month. Because they don’t need it to. They’re just like, “Yeah, man, it’s going to build our awareness and build a brand.” Not having the money doesn’t let you--make sure that you don’t waste it.
Tyler
Well, what I also loved about this thought that you shared was that you don’t need money to start helping people. And when you really build it down to the base level. When you break it down to the base level, business is about helping other people. Investing is the same. It’s about having an abundance mindset, and serving and adding value to others. So I just loved that thought. At the end of the day, if you really bring it down to the base level, it’s about adding value to whoever your customer is, whoever--in the real estate business it maybe a partner or maybe a resident, maybe a tenant, but it’s thinking about, “Well, instead of how can I bloat my business, it’s how can I help other people?”
Derek Sivers
It helps me to constantly remember nobody cares about you, and they shouldn’t. Why should anybody care about you? They shouldn’t. So when you go out into the world and you say, I want to make some money, the world says, “Fuck you, we don’t care.” That is moot to us that you want to make some money. But on the other hand, if you say I want to help people lose weight. Or I want to help people fall in love. Or whatever the thing that you’re--or I want you to help people taste the difference between bad chocolate and good chocolate. Whatever it may be. Now, you can have a mission that people will care about.
Derek Sivers
If you say I’m on a mission to help people taste the difference between bad chocolate and good chocolate, you’ll get some ears perked and going, “Hmm, there’s a difference? Okay, I’m curious.” Whereas if you go into the world and you say, I want to make some money, the world looks at you with a scowl.
Tyler
Absolutely, and ultimately it comes down, in my opinion, I really believe this, it comes down to a mindset of abundance. When you think about--and you’ve shared this as well, is that when you’re adding that value to someone else, if we’re just thinking about what do we get in exchange, it’s that mindset of scarcity. I think that you cut yourself off from so much upside if you’re only just focused on yourself.
Tyler
I mean, you’ve got to be focused on other people and you even share this. At the end of the day, it comes down to adding value, but ultimately it is a delivering of service. I think about, you go out to a restaurant, I don’t know about you, but man, I get blown away by great service. Poor or even average or even slightly above average service to me is like, I just don’t have an interest in going back. There is such a big difference because when you have this mindset of generosity and abundance, I think that’s when you start to experience exponential growth. Does that resonate with you?
Derek Sivers
I think it can go either way. I think what I’ve learned traveling the world, which by the way, after I sold CD Baby, I realized I’d spent the first 40 years of my life in America, so I wanted to spend the next 40 out. I wanted to understand different perspectives on the world. Different ways of seeing life. I wanted to do that in an immersive way, not just reading a book.
Derek Sivers
So I made myself move to places that I knew nothing about in order to understand their perspective on the world. So when you say, I think the key to everything is a mindset of abundance, yeah, could be. That’s one way that works. On the other hand, if you ever, especially with your interest in real estate, you someday should take a business expense educational two week trip to Singapore or Hong Kong and see the way the real estate market works in these places, which is very different.
Derek Sivers
And it very much comes from a scarcity, cutthroat mindset. It was just one little, tiny story that shocked me. I haven’t even thought that much about this. This might mean more to your listeners than it did to me. When I lived in Singapore, I found out it’s very common to list your property for sale, and then when you get an offer for, say you list it for 650,000, and then somebody offers you 650,000, you then say no and you remove it from the market and you listed it 660,000 now. You keep doing that. You keep refusing the offers and raising your price until you finally find an amount that nobody’s willing to pay and they just want to pay you a little under.
Derek Sivers
Then you finally say yes, because only then do you know that you’ve found the maximum price. So there’s this patience and this cutthroat, ruthless thing that it’s somewhat ignoring social norms, you know what I mean? It’s kind of offensive. The first time I heard it, I was like, That’s just evil. That’s just wrong. But well, it’s rational. Okay, all right, I get it.
Derek Sivers
Even the way the agents work there. There is no--two things different with America. There is no buyer’s agent. Every person is just left to fend for themselves, and there’s no exclusive seller’s agent. So you can have one home and like every agent in town will represent it. But because of that, it’s actually a downside nobody wants to put any effort into--they don’t do those things like staging and presenting or getting a 3D camera to take really nice photos of a place. Because since there’s no exclusivity, why bother putting forth a big effort?
Derek Sivers
So instead, it’s just this free marketplace of properties for sale. It’s a lot of chaos. It’s just such a different way of approaching it. So sorry when you say something like, the key to everything is a mindset of abundance. My initial instinct is to agree with you, but then I have to catch myself and go, “Wait, that is just one way of thinking of it.”
Tyler
I think it’s a very valuable perspective and really thinking about everything and saying, “Well, there’s two sides of this coin, or maybe even three sides of the coin as Robert Kiyosaki talks about it.” There’s one side, there’s the other side, and there’s the edge. And so understanding that, I think is a path towards intelligence and perspective and recognizing that just because you’ve experienced one set of rules or norms doesn’t mean that it couldn’t actually be flipped on its head.
Tyler
One of the things that is really interesting about immersing myself in your world is that you’ve immersed yourself in this world of learning through immersion like that. You’ve just been exploring the different side of every coin. It almost seems like that’s been a pathway towards your creativity and your curiosity. Does that make sense, or am I on the right path there?
Derek Sivers
Yeah, that’s my common thread in life. Essentially, that’s what I’ve been doing. No, I shouldn’t say the whole time. That’s what I’ve been doing since I sold CD Baby in 2008, let’s say, that’s been my main common thread. Is looking for a different point of view. In fact, I’ve done a few TED talks, but if you want to know my favorite one, it was the one--I think it’s called The opposite May Also Be True. Where I found that--Oh, I love this example.
Derek Sivers
In Japan, I was asking somebody for the name of a street and I said, “What is this street called?” And they just looked at me weird. I said, “Well, this street, what is this street called?” And they said, “Well, that’s block number seven. That’s block number 13.” I went, “Okay, but what is this street?” He just didn’t understand my question. Then I finally found out what it is. That in in America or in most of the Western world, actually probably most places except Japan, we think of streets as having names and the blocks as being the unnamed spaces in between the streets.
Derek Sivers
In Japan, it’s the opposite. The blocks have numbers and the streets are thought of as the unnamed spaces in between blocks. That blew my mind. It’s just like, “You know what? That is equally valid.” I thought that, of course, streets have names and of course the land in between streets is just land. Then I was in Australia and as I was at the airport leaving, I saw a map of the world upside down.
Derek Sivers
So Australia was on top and there were a bunch of countries scattered at the bottom like the US and Europe. And I went, “Oh, that’s right.” The earth is a circle--it’s a sphere, I should say. So that’s equally valid. We’re used to thinking of Europe and the US and the northern Hemisphere on top, but it works equally well if you’re looking at it from the south. Then I just kept looking for perspectives like this. What other things in life have I been thinking of from one perspective, where the opposite is just as true?
Derek Sivers
So my first TED Talk was about that, and it’s still my favorite one. Because I think it’s still my favorite subject. It’s constantly looking for another point of view. And not just stopping it, flipping the coin once or even stopping it looking at the edge. You could keep going. There’s still other ways that you can think of anything. And they’re often very beneficial. Whether it’s to give you a competitive edge in a marketplace. Whether it’s to help your own personal productivity or just to help your peace of mind, to think of something in a different way.
Derek Sivers
Like when I used to think that all of my employees had wronged me. And I thought, “Wait a minute, what could be the opposite? Maybe I wronged them.” I was like, “Ah, this feels better.” This is a more resourceful, powerful state of mind. So sometimes, even just for your own happiness and effectiveness on life, it helps to keep looking for another point of view.
Tyler
This is why I think it’s important for us as investors to be having conversations more so rather than the how to. The execution of finding deals, optimizing those properties, managing the manager. All the things that we deal with on a day to day basis, because I think that opening and expanding our gaze can be extremely powerful. It’s a pathway to joy as far as I’m concerned, personally. From a growth perspective and just a learning perspective. Because I think there’s a lot to be said about what happens when you understand that, “Wow, my little bubble is just that. It’s just a little bubble.”
Tyler
There’s so many other perspectives out there. There are so many other different cultures out there. The description of the blocks in Japan and the streets in the United States and many other cultures, I think is an interesting one. It almost makes me think of, if you’re brushing your teeth with your right hand every single day, try brushing your teeth with your left hand. It’s a weird experience.
Tyler
It’s a very simple, weird experience, but it’s the opposite. And it’s like, “Well wait a minute. Maybe there’s a pathway in my brain that can start to be carved as a result of something as simple as that.” When you think about your learning and your growth and your expansion, it almost seems like you’re trying to flip everything on its head. Trying to explore the opposite of of every thought.
Tyler
You’re talking about a competitive advantage or perhaps just an expansion of the way that you are empathetic towards other people? What else does this type of life give you? Is this something that is expanding? Is it changing the way that you are just--and obviously, you’re living in New Zealand now and you’re immersing yourself in that, a different type of culture in itself. But how is this evolving or changing as you continue to grow older yourself?
Derek Sivers
Well, I’ve noticed recently--this is actually the subject of my next book is called “Useful Not True”. Because I noticed that whenever anybody starts a sentence by saying I believe such and such, whatever follows that word believe is not true. Because if it was true, we wouldn’t use the word believe. We don’t say, I believe in carrots. Carrots just exist. It’s just a fact. There it is. It’s a carrot. You don’t have to believe in it. But it’s when--I think earlier you said something like, “I believe that abundance is the key.” Or the mindset of abundance is the key to everything.
Derek Sivers
Well, that’s one way of looking at it, but that’s not objectively true. The reason you said, I believe, is because you’re choosing to adopt that perspective. I think it’s fascinating then to realize that all of our beliefs are not true. That we’re choosing them and we’re choosing them because they work for us. And because we’re choosing them, we can choose different ones if the ones we’ve adopted are not working for us.
Derek Sivers
Or maybe they were just hand-me-downs that you didn’t choose. Your parents gave you some clothing and said, “Here, these were my parents clothes. You wear them.” And you can tell I’m speaking metaphorically. The beliefs that we have that we’re just handed down from our parents that might not be working for us. We assume that they’re true. But when you realize, “Whoa, wait, none of these are true.” It was all just a certain perspective that maybe this perspective worked for my grandparents when they came over from Italy in 1890. Sorry, I guess that would be great grandparents.
Derek Sivers
But now this is not applicable to 2022 in my current situation, living in New York City. So it’s really helpful to remember that all these things you believe are not true and you can adopt them. And the things that other people insist are true, and that’s what’s funny, the difference between kids and grownups. It’s like when kids play make believe, even if they’re sitting there with mud saying, “I’m making dinner now. Look, here’s a fresh chicken out of the oven.” They know that it’s not actually a fresh chicken and that’s not actually an oven. They know that it’s mud and sticks.
Derek Sivers
So why is it that when we get older, we insist that the only reason we believe something is because it’s true? I think we should acknowledge that these are all still make-believe, and we’re choosing to believe them and we can let them go in an instant.
Tyler
Do you think it’s the lack of awareness that most people don’t realize that beliefs are chosen? If the argument is that most people know that beliefs are chosen, they choose to be average. Or they choose to be below average, they don’t choose the path of mastery. What is the difference?
Derek Sivers
The reason I’m calling the book “Useful Not true”, is because I think the beliefs we hold are useful for some purpose. Like the story that somebody wronged you is useful because it let’s you feel like the noble hero of that tragedy. It lets you feel like there was nothing you could have done, that you did your best, damn it, because they just wronged you. That story is useful to you to feel good about yourself, to feel good about the past. Whereas acknowledging actually it was my fault that there were people selling drugs in my apartment.
Derek Sivers
I was reading your story about real estate turned out to be tougher than you expected at first. Frozen pipes and drug dealers or whatnot. If you acknowledge--I’m sure the first reaction would have been, “Oh, God damn it, those idiots, those jerks.” But instead, if you’re like, “Actually, this is my fault. I let this happen.” At first it doesn’t let you tell that tale anymore. That felt good for a while. That was useful to you. But then you realize, this new belief system, it doesn’t feel good at first, but it’s going to help to get me where I want to go. Why do people believe things that aren’t true? I think it’s because they have been useful to them to believe that.
Tyler
Because a lot of times being average or the useful belief of, “Hey, I can’t do that or I shouldn’t do that, or if I do that, I might fail.” It’s the use for--the utility of that thought, and I’d love to hear your thoughts on this, is perhaps that’s protecting them or it’s keeping them safe. What are your thoughts on that? That’s a useful--
Derek Sivers
Gets them off the hook. You don’t need to work. Hey, you know what? You are totally justified in just sitting and watching TV tonight. In fact, every night, you are totally justified to just take it easy. You don’t need to try too hard. You don’t need to read those books. Just relax. Let’s just watch this game tonight, instead. You’re totally justified doing that. Because, hey, you know what? All we can really do in life is get by, and that’s all anyone can expect. That belief is useful for relaxing, but it gets people off the hook.
Tyler
You just described the standard average American thought. That’s what that is.
Derek Sivers
It’s standard everywhere. Here in New Zealand--it’s funny, New Zealand is quite a paradise. You’ll notice that places that are like paradise usually don’t have very many ambitious people in them. You go to Fiji, go to Tahiti, there’s not a lot of ambition there. Because they’re in paradise and New Zealand’s kind of the same way. It’s the places that are not super comfortable to live in. You go to maybe Warsaw or Hong Kong, you’ll meet a lot of ambition, because there are a lot of people very driven to get out of these places and go to paradise where they can stop being ambitious.
Tyler
It is interesting. I spent a period of time in Hawaii and I noticed that myself. That there was not a lot of ambition on the island of Maui. I think that there’s something to be said about pursuing something. But the bigger part of that, and I feel like it’s something that you’ve really shown, is that it’s who you become. It’s not about what you attain or obtain through that path of mastery. It is truly who you become, which is such an unbelievable realization.
Derek Sivers
You know, I was really into Tony Robbins. Was “Rich Dad, Poor Dad” the book that made the biggest difference in your life?
Tyler
It was a catalyst for me to open my mind to the way that wealthy people think. And it really was a transformation because I came from a middle class background and that was a huge catalyst for me, for sure.
Derek Sivers
Okay, so I got that impression. That “Rich Dad, Poor Dad” was a big turnaround for you. For me it was “Awaken The Giant Within” by Tony Robbins. When I read “Awaken The Giant Within”, it was just mind blowing. But it also resonated with something that was already inside me, but also just helped me think of life in a different way.
Derek Sivers
In there he has this chapter where he’s trying to spark your desire, and your drive by talking about all the things you could own. Do you want to own your own private jet? Wouldn’t you love to have a mansion on the beach? Wouldn’t you love to have a swimming pool? Do you want your own personal chef? I just remember reading, this both then and every moment since. Every time I go back to that, I have this sneer on my face. No, that sounds awful. I don’t want a Ferrari. That’s embarrassing. You couldn’t pay me to own a Ferrari. I don’t want a mansion. Think of what a pain that would be to live in a mansion.
Derek Sivers
Who the hell needs nine bedrooms? What stuff would I put in that? I realized it was always--even as a teenager. Still to me it’s been about who I want to be. I want to be the person that makes myself proud. I want to challenge myself to try to master this craft that I’m pursuing. I want to challenge myself to learn this subject I’m tackling. It’s all about who I want to be, not what to have. I feel like any idiot can own a Ferrari. Just go put it on your credit card and worry about the bills later. But it takes no--it’s not impressive to own a thing, but it is impressive to be a thing.
Tyler
My goodness, you’re dropping sound bite after sound bite, Derek. That is a really, really great reminder for all of us. That when we’re setting goals, it’s not about what we want to have. It’s what we want to be, who we want to be. Who we want to become. I think that’s why it’s so important for us to dive into work, like what you’ve been gifting to the world for so many years, Derek. So you’ve been extremely generous with your time, with your wisdom today. So I just want to thank you so much.
Tyler
I want to transition into the rapid fire section of the podcast. We call it the rare-air questionnaire. The life that you’ve lived, and that you continue to live, and you continue to set the example for, is one that is rare, it’s uncommon. But you’re living the uncommon fruits of that labor. I think there are so many clues in our conversation today. But I’d love to ask you a few questions. If you had to point to two or three of the most impactful books that you have read over the past few years, what would those be and why?
Derek Sivers
Okay. If you’re limiting it to just the last few years, “The Courage To Be Disliked”, it’s got a Japanese author. Let me think what else? You know what, the real answer will forever be at this word go to sive.rs/book. I take detailed notes on every book I’ve read since 2007. I started this habit. I read hundreds of books before 2007, but starting in 2007, every book I read, I take copious notes. I highlight all of my favorite ideas from this book. I write a description of. Then most useful to you, the listener, I give everything a 0 to 10 rating on how much I would recommend it to others.
Derek Sivers
There have been some books that were personally useful to me but wouldn’t apply to most people, books on programming, or understanding Swiss culture. I would give those a low rating even though I liked them. But if you go to sive.rs/book, I always put my most recommended books at the top. So there’s my real answer. Go to that URL and you will always see my favorite books of the last year.
Tyler
I love that and we will definitely put a link in the show notes as to where the listeners can find that, just to make it really simple. I wanted to ask you a quick follow up on that. Because one of the things that really stood out to me as I was getting prepared for our conversation was, you talked about your affinity for journaling and how all of your learning happens there. Could you talk a little bit about your practice for journaling and what that actually looks like for you?
Derek Sivers
The details don’t really matter. I get some people saying, “Well, which piece of software should I use?” It doesn’t matter. Grab a pen and paper or just open a plain text file. Well, I recommend not getting subscribed to some monthly fee software or even being bound to a cloud because you might have a time in your life when you’re offline. If you suddenly have no access to your diaries when you’re offline or oops, if Google deletes your account, you don’t want to be screwed.
Derek Sivers
The most important thing to me is, we can hear facts and information and we can even hear perspectives and mindsets in shows like yours. But it’s not until you apply it to your own life. You say, Tyler mentioned this really interesting mindset today. Let me think about how I could apply this to my life. It’s in that reflection that you really internalize something. Until then, it’s just information that’s out there. It’s only when you stop and put aside the time to reflect, turn off the videos, turn off YouTube, turn off the Internet, and reflect on how what you’ve heard today could apply to your own life and how you could apply this. How you could change it. What are your own thoughts on it?
Derek Sivers
Because maybe you disagree, after some reflection you think, “Actually, Tyler said that this is the key, but I think it’s just one of the ways, in fact, the opposite might be more true.” That to me is where I feel like I’ve learned everything. I read a lot of books, but it’s not until I stop and reflect on them later that I feel like I’ve really internalized it and learned it.
Tyler
That’s great stuff. So aside from our discussion today, Derek, what’s the biggest way that you elevate your life on a daily basis? It may be journaling, but it may be something else. Is there anything else that you would point to?
Derek Sivers
No, it’s journaling. It really is.That to me is just everything. I spent at least an hour, often 3 hours a day, just writing, just fingers flying, just thinking. The most important thing I think is questioning. Asking myself questions, answering those questions, but then questioning my answers. I really enjoy doubting everything I think. So let’s just say, I’ll ask myself, “What’s the best thing I could do today? Well, I think the best thing I could do today is to work on such and such. Is that really? Why do I say that? What’s the real purpose of that? Well, because then I’ll get it done. Why do I think I want to get it done? Just because I started it? Is this actually going to help people? Yes, it is. Wait, is it really? Is this something that--there are lots of other people helping people with this thing? Am I really needed for this? What is my unique contribution here? What’s something that I’m doing that other people don’t seem to be doing? Is there a reason other people aren’t doing it?”
Derek Sivers
This sounds like navel gazing. It is, but I think it’s really useful to constantly question what you’re doing and make sure that you know why you’re doing it. Often it will give you some completely new insight. It’s honestly why I left America. I left America for good in 2010, because I loved it so much. I was living in Santa Monica, California, on the beach, and I absolutely loved it. It was paradise to me. I was so happy. I even had--at the time I had a girlfriend from Sweden. We’d been together for six years and she wanted to travel the world with me.
Derek Sivers
I said, I don’t want to travel. Look, we live in paradise. Why would we go anywhere else? This is the best place on earth. She was frustrated with me that I didn’t want to travel. It wasn’t until after we broke up and I was like, “All right, we broke up. Blank slate. What do I want to do now?” Well, the most important thing to me is learning and growing. It always is. And somewhere in that journaling process I was like, “Wait, then why am I sitting in the same place I’ve been for ten years? If learning and growing is important to me--how do we learn? We learn when something surprises our expectations.”
Derek Sivers
We learn when we’re surprised. If you’re not surprised, then you’re just taking in more information that fits with what you know. You’re only really learning when you’re surprised. Well, what’s a good way to be surprised, on a daily basis? It’s to live somewhere that is completely different to where you grew up. So that just on a moment to moment the little things--like my story about how people price their their homes for sale in Singapore makes you go, “What? That’s crazy, huh? That is so weird. Well, I guess that works.” The streets in Japan, the whatnot.
Derek Sivers
That’s a way to be surprised on a constant basis. It’s to keep yourself living in places that are strange to you. I was like, “Oh, that’s congruent with who I am. I want to constantly be learning and growing. I need to leave America now.” Those things, those big realizations that may change your life for the better, don’t come unless you spend some time reflecting and questioning, doubting your own answers.
Tyler
I’ll tell you what, I’ve been surprised by this conversation. I feel like I’ve learned so much because, you always anticipate the way that a conversation is going to go and the insights that you’re going to gain. But I tell you what, you’ve been a great pattern-interrupt today. I will tell you, just out of gratitude, that I’ve learned so much today and there are so many takeaways from our conversation. Before I let you go, I have two very quick questions. One of the last two is, what’s the biggest way that you elevate others around you, Derek?
Derek Sivers
Probably just answering emails. It doesn’t sound like a big thing, but I get emails from strangers every day. Yesterday, the highlight was a very ambitious 24 year old in Uzbekistan emailed me. It ended up leading to a 90 minute conversation. That was fascinating. I really enjoy hearing from strangers around the world. So anybody that’s listened to this whole podcast, go to my website. Go to sive.rs, and make sure you just send me an email and introduce yourself. It’s really my favorite part of the job. Kind of see that as my community service. People are always surprised that I answer every email, but this is my giving back. But I also find it fascinating.
Tyler
I can attest to that because this conversation came from exactly what you just described there. So the listeners can find you on your website. Is there anywhere else where they can find you?
Derek Sivers
In my house. I don’t do social media, really. So go to sive.rs. Everything is there.