Pathless Path
host: Paul Millerd
self-identity, personal growth, unconventional life paths, travel and its impact, parenting, career reinvention
listen: (download)
watch: (download)
Transcript:
Derek Sivers
When you book a one way flight to somewhere and go to anywhere, it could be Berlin or whatever. It changes how you see yourself. You’re like, “I am a person that did that or that does this. I am now an expat adventurously living far from home. I’m here by myself. I am courageous like it.” It changes all these internal self-representations that now you see yourself as the courageous, capable hero.
Paul
Today I am so excited to be talking to Derek Sivers, somebody I’ve been reading for years, been inspired by his ability to look at life with this very curious mindset. First principles saying “What are the possibilities here?” I feel like you, Derek, have unlocked things I never thought about in terms of how to think about life, how to live life. You’ve literally written a book about all the possible ways to live life. One of my favorite books was “Anything You Want” about just in my take injecting more play into the art of business, which I thought was really cool. Welcome to the podcast, Derek.
Derek Sivers
Thanks, Paul.
Paul
Excited to dive into all of your story today, but always start with one question, which is, what are the stories and scripts you grew up with that sort of told you, okay, Derek, this is what you’re supposed to be as an adult in the world.
Derek Sivers
Mine did not come from my parents because they were just very hands off. Like I spent most of my childhood jusT kind of nerding out in my bedroom, playing guitar, playing music, then later programming computers and then later going back into music much deeper, so much so that I really wanted to be a successful musician. So what I would do is, I would pore over every interview I could get my hands on with the legendary musicians talking about songwriting or even articles about them. So along the way there, I think I picked up a lot of stuff. Like the way that Bob Dylan, for example, was known for one thing, he was known to be this acoustic folk musician. And then at the Newport Folk Festival, he showed up with an electric band and somebody in the audience yelled, “Judas! How dare you? You betrayed us.” And that was what he needed to do to move forward creatively and he even had this lyric once that was I forget the song, but it’s the lyric is like, “She’s an artist. She don’t look back.” And I like this. So there’s little things like that would get into my soul, right? Like, okay, she’s an artist. She doesn’t look back. Artists should not look back. We should always look forward. Miles Davis kind of did the same thing, changing genres radically in his long music career, even helping to invent a new genre. David Bowie changing personas, saying, “Yeah, that was me for a while. Now I’m somebody else.” So I think these music stories and I just picked three there. But you know, add 100 more the stories of musicians and how they approached their music and how they approached their art and how they approached their long career shaped how I think about my life.
Derek Sivers
So then I went off to music school and my first major girlfriend was the daughter of hippies that had never held a job, and they just lived in a little cabin living on nothing, doing just odd jobs to pay for food. And we were together for six and a half years. You know, we were practically married. And her family was a huge influence on me. Oh, and the reason I met her is, I was in a circus at the time. So here I was, in a circus surrounded by jugglers and musicians and magicians and face painters and artists. And my girlfriend was this daughter of hippies, and these were my people and this is who I was around. And so I actually find it very alienating later when I meet normal people who had a normal life and they say things like, “How did you get the courage to quit your job?” And I look at them like, “Job? What do you mean?” So I think that I had unconventional surroundings because I was just on a different path than most. I was pursuing a life in music. Later I read Tony Robbins, and that influenced me a lot too, because I read that at a very core age of 19 and again at 21 and again at 23 and again at 25. Which is also very open ended, asking you, what do you really want from your life? Asking you to question yourself and really dive deeper into what you really want. What do you find most fulfilling? Not shallow happy, but deep happy. So the combination of all that is what shaped me.
Paul
Yeah, it’s really inspiring that people like you exist because I didn’t really feel like I had this latent. Maybe I had this Derek Sivers energy in me younger, but I just found myself on a traditional path. And when you start saying things, “Well, what if we all just quit our jobs and travel for the world?” People get really unsettled by that, right? And you kind of were early starter on that path and it seems like that’s almost your superpower too, is sort of reinventing yourself, moving on from things. Would you say that resonates?
Derek Sivers
Yeah, definitely. As much as I loved being a musician and it was so core to who I was all the way through the age of 29. My friends couldn’t believe it when I stopped making music and started running this website. Still, some of my old friends are just like, “I can’t believe you, man. You’re the best guitarist I knew. How could you give that up?” Sorry, That sounded like a what do you call that? Humble brag. I didn’t mean it like that. I’m just saying, I have old friends that are just really still mad at me that I’m not doing music anymore. But then I did CD Baby for ten years, and there are people that are upset that I’m not an entrepreneur anymore. And then I did Ted talks for a few years after that where I was just like a total Ted junkie and just got deep into that scene. And then I was done with that. There are people that still think I should be on stage speaking. And I think it’s the lesson learned from the careers of the musicians that I loved just taught me that you should keep moving on and keep challenging yourself into new fields.
Paul
And you think deeply about this. So I think for me, writing has been a good way to reflect on what I believe in and actually check myself. You’ve written about, “Oh, I’m really comfortable in this moment. This is a red flag.” How did you sort of get in tune with, “Oh, I’m this comfortable feeling and associating it with time to blow things up or time to remix life a little again.”
Derek Sivers
Okay. That comes from two things, partially from the music examples I just gave, but partially from a single paragraph in an obscure book called Personal Development for Smart People by Steve Pavlina, where--
Paul
Oh, I know his writing.
Derek Sivers
Yeah, it’s a fascinating book. There’s a lot of crap in there. I mean, fascinating crap, but a lot of it is crap. But it’s fascinating. I don’t think a book has to be perfect to enjoy it. I can read a terrible book and get a few good gems out of it. You know, that one is a surprisingly good book, but he had this one core idea in there, which is saying, we only really learn when our expectations are upended. If your expectations are not upended, then you’re not really learning anything. You’re just taking in more information, but not truly learning. And so he said, we should all read books on subjects we don’t know anything about. Or ideally move somewhere far away to a place that’s very different than what you’re used to. Then just day to day life will be upending your expectations all the time. And I went, “Ooh, yeah.” Like that resonates with me, I don’t want to plateau. I do want to constantly keep pushing myself to grow and change. So I think I equate comfort with a plateau that needs to be shattered, you know? Because of this learning and growing, saying, “Okay, I’m too much in my comfortable surrounds now. I’m not being surprised. I’m not learning and growing.” Yeah, I think more than anything, it’s the push to keep expanding as a person.
Paul
What’s the most recent plateau you’ve found yourself on?
Derek Sivers
Hmm.
Paul
For the listeners. Derek is drinking a beautiful cup of coffee or tea. What does it say on it?
Derek Sivers
Oh, actually it says, “Builder’s tea.” I like this cup. So I think right now I’m in a challenge because I was nomadic for most of my life. I had a nomadic childhood, even. And then I stayed in one place for a school years. And then as soon as I got out of high school, I started moving all around the world and I kept moving. Every year or two, I would move to a new city or even a new country all the way up until ten years ago when I moved here to New Zealand. And now I have a kid who’s turning 11 and wants to stay in one place. Actually, he doesn’t want it as much as his mom does. His mom wants to stay in one place. So I think if it were just up to me and him, we would continue traveling the world. He loves going to new places. He’s a total extrovert that just wants to meet everybody and do everything and get stimulated. So right now I’m finding it challenging to stay in one place and challenge myself. To continue to be a better writer or to take on new challenges without changing location. You know what I mean? Like, changing location was my most used tool that I would challenge myself by moving to a new location. So now I’m having to challenge myself by not moving to a new location. So that is my plateau that I’m trying to unplateau.
Paul
Yeah, travel is such a hack, it’s basically the biggest shortcut for just reawakening yourself, reconnecting with yourself. New Insights. I moved to Taiwan in 2018 and then ended up meeting my wife a month later. So it was like an explosion of possibility and at the same time I started new kinds of work. I started falling in love with writing and we moved back to the US. We just signed a ten month lease, which was like, “What are we--? This is so crazy. Is our life over?. And we’ve had to really lean into, “Okay, how can we make this interesting?” Any tricks you found from being in one place to another sort of nomad enjoyer?
Derek Sivers
No, I think it becomes internal. You have to look inward and say, “Okay, how can I change what I’m doing without changing my location.” Yeah, it’s hard.
Paul
Yeah. Why does being in new environment shift us so much?
Derek Sivers
Novelty! Your brain is filled with so much novelty. Also, you get to reinvent who you are. I think we underestimate how important our self-identity is. How you see yourself. I really want to dive deeper into this subject. I don’t mean right now, but I mean, we need to think more about. No, no, no. I mean, I need to think more about this before I can even speak wisely about it. I think it’s fascinating how some people just think of themselves as a victim in any given scenario. It’s like no matter what other objects are around them, they see themselves as below somehow. So right now I’m just thinking visually, but like they see themselves as being on the crap end of any given stick. But then there are some people like me that I’ve just always deliberately wired my brain to flip the stick. Like, if I’m given the bad end of the stick, I flip the stick and find a way to to be on top of any situation, even if it’s just my internal representation of it, right? Even if everything’s gone wrong, I can ask myself, “Well, what’s great about this?” And of course, your first impulse is to say, “Nothing, this sucks.” But then you keep thinking about it. You’re like, “Okay, come on. What’s great about this?” It’s like, “Well, I won’t make that mistake again.” It’s like, “At least I made that mistake nice and early instead of three years from now.” Okay, That’s a good thing. All right. “What else is great about this?” All right. “It helped me realize that I really don’t want that and things like that.” It’s just a self-identity to see yourself as powerful or capable. So anyway, sorry, that’s just purely internal, but sorry, I can hear you. You keep inhaling. I want to finish this thought and--
Paul
I’m just xcited about what you’re saying.
Derek Sivers
But so same with you. Like you moved to Taiwan. Holy shit. You moved to Taiwan? Even I haven’t done that. I actually wanted to move to Taiwan. My son’s mom does not. I would love for my kid to grow up in Taiwan, especially for teenage years. I think Taiwan would be an amazing place to be a teenager. He was born in Singapore and then we moved down here to New Zealand. But I’m fascinated with Taiwan. I love this-- my friends quip about Taiwan, he said, “It’s all that China without all that China.” Anyway, people in Taiwan get that joke.
Paul
We can meet up there in a couple of years because one of our dreams is to go there with our daughter. So she can really experience the culture and experience the shifting modes early in life.
Derek Sivers
Nice. Okay, so to finish off this, like internal self-identity. It’s like when you book a one way flight to somewhere and go to anywhere. It could be Berlin or whatever. It changes how you see yourself. You’re like, “I am a person that did that or that does this. I am now an expat adventurously living far from home. I’m here by myself. I am courageous.” It changes all these internal self-representations that now you see yourself as the courageous, capable hero. Whereas somebody who say stays at home and says like, “Yeah, I’d like to do that someday. Yeah, I would but my parents really kind of need me to be here.” Or, you know, I just don’t have the money yet. Just can’t, you know, sorry.” That’s an unfair one to pick on. But because it could be anything, it doesn’t have to be moving across the world. It could just be somebody who starts a website with their own name on it, like starts a personal site with your name dot com or dot org or whatever. Like now I’m a person who’s going to do this or I’m going to journal or I’m going to sign up to run a marathon, whatever it may be. It changes how you see yourself and then how you see yourself changes everything. It changes all of your actions because we’re influenced by the stories and the fictional stories we’ve heard in life. Like, we see ourselves as a certain kind of character in this play, in this movie of life, and you could see yourself not as the victim or not as the Cinderella in the ashes, but the Cinderella at the ball or whatever. And it just changes how you act. So, yeah. I’ll stop talking now.
Paul
No, I love this. It sounds like this is a very alive thread for you. I think you wrote recently, “Beliefs are a means to improve actions.” And I think you’re actually underselling it here. So when you experience this, it’s sort of like changes your life in a single moment. When I was like, “Oh, I’m going to go move abroad and live in Taiwan.” You’re suddenly realizing, “Oh, I’m the person that tells people I’m doing this.” And then you end up start looking for more opportunities. You see possibilities. Oh, I could just move to another country, too. And it’s so subtle, but it’s so wild that I didn’t think to do this earlier in life. And the scary side of that is I could have gone another 10, 15, 20 years in a different possible future where I just didn’t go. And that’s kind of crazy because that seems very realistic to me as well. What are some other examples you’ve seen of this of sort of beliefs as a means to improve actions? Because I think you actually do this really well in your writing. You’ll sort of claim something and then you I sort of sense you’re trying to meme yourself into that new mindset or approach.
Derek Sivers
Hold on. Let’s go back one step. Yeah. I’m asking the thing you said about you booked the trip to Taiwan. When I look back at my life about these major things that I’ve done, what’s amazing is that the moment of making that change is so simple and so small and so easy. So when I left America forever, I mean, I had only lived in America really until the age of 40, right? Maybe I was 38. Yeah, I was 38. So at the age of 38, I had never really left America except for a couple of quick short trips. And so I was just considering it. I was like, “Huh, what if I were to go to London?” I was like, “Well, let me just look at the prices of the flights.” So I was living in Portland, Oregon at the time, so I typed, PDX LHR prices. I was like, “Okay, I have to pick a date. I don’t know, how about three months from now?” So I just picked a date three months from now and said, “Oh, it wants a return trip. Okay, well, how about nine months after that?” Okay, so there. But I just considered those to be like dummy dates, right? So I did a search for the price. And it was shockingly low. It was like $420 round trip from Portland to London. I was like, “Whoa! Holy crap, that’s cheap”. I was like, “Huh? You know what, tick, tick, tick. Type 16 digits. Expiration date, cvv code.” Boop, boop. I was like, “Whoa! I just booked it.
Derek Sivers
Holy shit. I’m going to London for nine months.” Simple as that. Wow, okay. I just did that, it just happened in one minute I just did the thing. But then I think that’s happened so many other times where I’m like at the TED conference and they say, “Any volunteers?” I’m like, “Huh?” I raised my hand and they say, “Derek, come on up on stage.” I’m like, “Whoa, okay. I just did that. Whew. Okay”. Heart racing. Now I’m standing up on stage. All right, time to talk. I mean, even entrepreneur wise, I’m selling my CD just off my own website in 1997, and my friend says, “Huh, could you sell my CD too”? I say, “Yeah. All right.” It’s like, “All right, that’ll take me about an hour. Yeah, I’ll set that up.” And suddenly I’ve started a business selling people’s music, and it just grew from there. It started with that one little action. And so I think that so many people these days listen to so many podcasts and read so many articles and books, and they’re taking in and in and in. And they don’t just do the one little action that changes everything. So I think we should all err on the side of just book the flight. Raise your hand. Join the thing. Start the thing. And just take that one little action that gets it rolling.
Paul
Yeah. People will say to me, “Oh, you’re different, Paul. You don’t understand. I’m not like you.” And I’m sure people say that even more to me, “Oh, Derek Sivers is just so much more extraordinary.” But I think the more weird the paths you take in life, you start to realize all these other people taking weird paths, they’re basically doing the same thing, which is constantly grappling with the uncertainty and unknown of the world and starting to see the logic in existing in such a relationship to their lives. Is there a question you’ve found that like helps plant possibility or curiosity about people’s lives? I mean, you’ve written a book called “How to Live”, which is many possible framings of this, but I’m wondering if you’ve found any interesting questions for people to ponder.
Derek Sivers
No, I just get to know people. Yeah. Whether through email or through the phone or just people in front of me. And I start to glean different approaches to life. My friends are often very unlike me. One of my best friends is a very conservative Mormon. And he’s fascinating. He and I have the best conversations. We disagree about some stuff, but we agree on a lot of stuff. And yeah, two of my best friends are Muslim and grew up with a very different set of beliefs than I did, and it’s just really cool, like just getting to know each other and our different worldviews. So I think a lot when you see me writing a book like “How to Live”, a lot of those, “Here’s how to live” I’m kind of taking on a persona of somebody I know well, or I’ve read a book or 2 or 10 prescribing a certain kind of way of seeing the world. And what I did with that book called “How to Live” is then each chapter was adopting one of these outlooks and taking it all the way to its logical conclusion, like going deep into one point of view, knowing the very next chapter was going to have a completely different point of view when they were deliberately conflicting. And that was so much fun to write and so useful to read, to remember that any approach to life is not right or wrong. It’s just one approach that you could use for a certain outcome.
Paul
What’s the most interesting sort of default path you’ve seen around the world? So by default path it’s like, okay, in the US, the common and you didn’t even sort of follow this path. But I mean, in Singapore I know there’s a very rigid default path. In New Zealand, I don’t even know what it is, but it’s always some form of work, school, things like that. Have you been surprised by any that are interesting?
Derek Sivers
I think the default path is never that interesting except. Except in relation to you growing up with a different default path. Right. So I grew up not just in America, but in California. America is already individualistic, but say Kansas is less individualistic than California. Those California people are like off the chart individualistic. Right. And those are my people. So then when I went to Singapore, at first I felt everyone here is wrong. Everybody’s talking about deliberately giving up their dreams to do what would make their parents happy. And I’m like, “No, no, no, no, no, that’s so wrong.” But then after making some really dear Singaporean friends that we got to know each other really well and spent many, many hours over many months and years together, that Singaporean mindset really started to sink in like, okay, I get it. It’s just a different approach, it’s not wrong that I think doing what’s best for your family, doing what’s best for your community, even your country, is a totally valid way of approaching life, too. In that sense, I started thinking of it as like meditation. It’s like I want to be a musician, right? Like, you can have that be a desire. But with meditation, we kind of learn to sit still and let the feelings come in and go right back out again. You know the feeling that you want to scratch your neck comes and then it goes back out again. A wave of sadness comes over you and then it goes back out again. And it’s like the desire to be a musician. It can come into you and it can go right back out again. And instead you can let it pass and do what your higher self believes is best for higher self or your collective self. Your family, your community feels is best for the group and do that instead, which gives you a deeper joy than if you had followed your personal whims. Damn, that was a very different way of thinking for me and very enlightening to understand it more deeply.
Paul
What’s the most interesting thing you’ve written down now in your possible futures folder?
Derek Sivers
All I can think about is the one that is most interesting to me right now. Which is after two years of living somewhat locked down here in New Zealand. I mean, our borders were literally closed. Only New Zealand citizens were allowed in for two years. And therefore you weren’t really allowed out because if you left the country, it would be like a month long queue to go back into quarantine upon re-entry. So it’s like we couldn’t leave and nobody could come in. So I’m really looking forward to travel. But also hosting events or rather throwing parties, however you want to describe them. I was initially looking to see-- I kind of missed going to conferences. So I was initially looking to see, “Hey, what conferences are going on out there that I could attend.” But most of a conference is a bunch of bullshit that doesn’t matter to me. All this kind of like so many people with walkie talkies and clipboards and organizing things where it’s like, really? We could all just show up to a place. You could just put out the call and say, “Hey, everybody, show up to this hotel in Stockholm for these two days. Meet you in the lobby. See you there.” And everybody could just sort out their own trip. Just show up and we’ll get together to talk. We don’t need to have organized sessions or name tags. In fact, we don’t need to pay an admission. The thing doesn’t even have to have a name. Just everybody show up here to this hotel for these two days. Let’s hang. So I think that’s what I’m going to be doing and that’s exciting to me right now.
Paul
I love that. It could be called anything you want.
Derek Sivers
Oh, God. That’s funny. That’s why I didn’t even choose that title. I wanted to call that book “The music of business” as a play on the words, the business of music, which is a popular music business book. I wanted to call it The Music of Business. And Seth Godin said, “No, too cheesy. We’re going to call it Anything You Want.” I went, “It’s too generic. Whatever. All right. Your book. You’re the publisher. Go for it.”
Paul
So he’s a good person to listen to?
Derek Sivers
Yeah, exactly. Yeah, “You know best. I don’t know shit about selling books.”
Paul
You wrote, “We all underestimate our ability to massively change our life when it’s gone off track.” I thought if this is Derek’s ability to channel optimism, this is impressive. But you sort of wrote when you had this really rough year, I think it was around the age of 30 or so. And you sort of underestimated how that led to a lot of positive changes from that. How can people think about some of the down things in their life leading to interesting, positive upsides?
Derek Sivers
Oh, the thing I said earlier, if you just ask yourself in any given situation. Okay, what’s great about this? What could could come of this? You can get yourself into that mindset. Any question you ask of yourself, your subconscious is going to answer. So if you ask yourself, “Ah, why am I such an idiot? Why do I always sabotage everything I do? God, why do I suck so bad?” Then your subconscious is going to answer that, “Well, the reason you suck so bad is you always do everything wrong.”
Derek Sivers
But if you ask yourself what’s great about this, your subconscious will answer even if it resists it first. But you know, moving is a great hack. It doesn’t even have to be moving to a country far away like we’re talking about. Just moving to another town. A few miles away just to get a slightly different perspective. Moving to a different kind of place. If you’ve been living in a house, you just get rid of most of your stuff and you move to a little apartment or live in a motor home for a while. Moving helps so much because of all the novelty and moving helps keep you future focused. I find it really hard-- if you have a major breakup to stay in the same place. So it’s like everywhere you go is the same place you were with your ex. That is so hard. It just keeps you focused on the past. Whereas almost every time I’ve had a big breakup, I just move literally the next day I’m like, “I’m out of here.” Like, go to a new place and it just gets me future focused. It’s such a simple hack. It’s almost as blunt as the one is when somebody says the best way to get over an ex is to just get with somebody new right away. Even if they’re not great. It helps scramble your brain. It helps get the old person out of your brain a bit. A rebound. That’s the verb. Go ahead and rebound. It sounds like a blunt hack, but it works, right? And so I think of those two rebounding versus moving, I think moving is even healthier to go make that change that you’ve wanted to make in your life. Those things that you’ve been saying to yourself, “I want to do those.” Well, just move to a new place and now you are the person that is doing those things and just be that new person. That’s my favorite one.
Paul
I had an experience in Mexico. We were living in Puerto Escondido and we lived in three different places in three months. And I kept changing my behavior every time. And I’m just thinking, wow, one, our human bodies are so sort of dumb. We just adapt to our new environment. I’m closer to the beach now. I go to the beach every day. But yeah, that really changed my mindset around how important it is to kind of change the environment, keep reshuffling and be in places that make me happy instead of trying to be happy with my thoughts or something like that.
Paul
How have you thought about travel? Obviously you’ve been a little more in one place with your son. How have you thought about traveling with kids? If there’s one thing, I’m about to have a daughter. People say, “Oh, you can live your life, Paul but now you got kids. You have to get serious. You got to get a house.” And I’m just seeing the scripts around kids is like an even more deeper story people tell themselves than work. So let’s dive in.
Derek Sivers
It’s such bullshit. It’s such projecting of values to say, “Oh, yeah, well, you’ve had your fun, but no kids needs stability.” I think I’ve heard those three words next to each other in that order so many times. “Kids need stability.”
Derek Sivers
You know what kids need? Kids need to feel safe. But you can teach them to feel safe in Timbuktu. You can teach them to feel safe anywhere. You can teach them that they can get off a plane in Istanbul and be safe and they can get off a plane in Australia and be safe. That they are loved anywhere. And especially if you’re with them, then they feel safe. And I think you’re doing your kids a great service by continuing to travel to show them that this whole world is their home, not just Lawrenceville, Kansas, and that’s it, but anywhere in the world that Mongolia can be their home and Estonia can be their home and people can love them and they can love people in all of these places and they can be connected. So I think that traveling with kids is so much easier than people say. In fact, I think it is the best way to travel. In fact, I’d almost recommend doing the opposite. If I were to design somebody’s life for them, I’d say, “Go ahead and have a kid nice and early.” Have a kid when you’re 23, and then when the kid is born, then start 12 years of nomadic life from the age of 23 to 35. Stay on the road with your kid. Oh, I guess there’s the money issue. Sorry. We’ll figure out a way to get. Learn a very valuable skill before the age of 23. Then have a kid and do your valuable skill on the road. But the point is that traveling with kids is better than traveling without. I wrote a whole article about this. So if you go to sive.rs/tk, get it? “Travel with kids.” sive.rs/tk. People connect with you more, strangers that don’t even speak your language will come up and just want to interact with your baby or your kid. Your kid will play with other kids. You get to see the world through your kid’s eyes who does not have the prejudices that you have. If you’ve been told that Russia is evil or Pakistan, everybody’s terrorists there.
Derek Sivers
Your kid’s never heard these things. So you can get on a plane to Karachi, Pakistan, with your kid and just see the warm and wonderful people through your kid’s eyes that hasn’t been bogged down with this prejudice. And then by seeing it through your kid’s eyes, you realize that it’s just some crap that you’ve heard that you can now dismiss anyway. Yeah, it’s so much easier than people say. The only friction I’ve seen. That’s in common with all the people that say that parenting is hard. Are the people that are trying to force a kid into an adult schedule. So that’s just like a round peg square hole.
Paul
This is a key thing because that’s almost 100% overlap with the people that seem to be super stressed with kids, is a lot of it is around orienting sleep around a dual income 9 to 5 knowledge work schedule. And then you have to layer on nannies on that childcare, cars commutes. I think this was the biggest motivator for me to quit my job because I didn’t want to do that. I don’t think people believe me. Maybe now that I’m having a kid, I was like, “I’m quitting my job and lowering my income so it will be easier to have kids.”
Derek Sivers
Okay, wait. I’ll kind of come back to Honduras in a second. But yeah, I can’t emphasize this point enough. If anybody listening to this, especially, you know, Paul’s had a lot of talk lately about the upcoming baby. And I know that there will be talk about the existing baby in a month and a half or so. So if you’re thinking about baby stuff, anybody, my number one advice is never try to force your kid into an adult schedule. Instead, when you have a kid, it’s just your time to adjust your life to fit a kid’s schedule. Which means, for example, you nap when the kid naps. If your kid takes a nap at 2:00, you sing her a lullaby. And you know what? You’re going to get damn sleepy, too. Just let yourself sleep. Don’t go run away and check email in those moments. Just let yourself sleep. Just change your life in such a way so that you can fit your life to the kid’s life. Which I mean, in so many ways you may decide to go somewhere. And then she wants to stay just sitting in the grass for five hours. And it’s like instead of being like, “No, come on, we need to go now.” Just sit in the grass with her for five hours. Just change your life to match the kids schedule. Okay, so Honduras, that first major girlfriend of mine that I mentioned earlier with the hippie parents. She grew up with no money at all in a log cabin in rural Massachusetts that her parents were basically given for nothing for doing some odd jobs. It was like a rickety little log cabin. They just kind of, in their spare time, did odd things to improve it.
Derek Sivers
And when somebody would discard a dishwasher, they would take it or somebody would discard an old fence, they would go take it. And so they just built this house out of nothing, raised her with no money. Ended up putting her through college because of scholarship, because they had no money. And then when this woman my now ex girlfriend when she was. 30 or so and decided she wanted to have a kid. She moved to Honduras and lived in a little village, living on basically nothing, living on like $5 a day, basically that she just kind of made through some odd online work or I think she worked for a while on a fishing boat and saved up some money. And then she went down to Honduras and was able to live for nothing and had her baby down there in a community full of people that she loved and raised her kid for many years, also for no money at all. You know, again, maybe who knows, whatever, 8 to $10,000 a year. I think she said at one point that she was living on down there. So kids don’t need to cost any money. You can adjust your life to match the kids schedule, and it makes for a happier kid and it makes for a happier you. Parenting is just love and joy. When you just stop with this schedule thing and you just join their life and you’re just seeing the world through their eyes, you’re just living fully in the present with your kid. It’s so much easier than people say it is. It’s just to me, it was just like being in love. It’s so nice.
Paul
I love that. Yeah. I’m very much looking forward to it with a similar mindset, I would say to people,” I’m going to nap when they nap.” And people say, “Oh, you can’t do that, too much stuff.” So I’m very reassured. There are going to be some naps for sure. I imagine when you’re traveling too, people are more excited and willing to help you, right? If you’re going around with a little kid, people are not going to let you struggle or suffer. Have you been on the receiving end of anything that was sort of moving or took a six month old baby?
Derek Sivers
No. Maybe he was like three months old at the time. When I took him to Thailand. I was living in Singapore. He was born in Singapore. So going to Thailand was just a short little 90 minute hop away, went to Thailand for a week and a few different times we’d go into a restaurant, just a tiny little restaurant in the middle of nowhere, cheap little place, the plastic tables. The waitress would just be like, “Oh, give me baby.” And she’d like, pick up the baby and just walk away. And then we learned that this is okay. So they’ll take the baby out to the back and they’ll just sit there, a couple of women will like, play with your baby while mom and dad enjoy your meal. And that’s like really common. And of course, you know, like my ex that moved to Honduras, you could actually just find yourself in a community.
Derek Sivers
God, I met this guy, fascinating guy once that lived in I think it’s called Pai in Northern Thailand.
Paul
Yeah I’ve been to Pai.
Derek Sivers
You have? With the Ferris wheel, was a wooden Ferris wheel still there?
Paul
So no. There’s a lot of interesting stuff there.
Derek Sivers
But okay, there’s a little neighborhood in Pai with a human powered Ferris wheel. You actually have to kind of climb it and pull it with gravity. It has no engine.
Derek Sivers
People sit in the seats. Anyway, he lived in that little community in Pai. That’s where his wife was from. He met her while nomadic, and they fell in love and moved back to her village. It’s like, you know, the classic what “It takes a village to raise a child.” They had children just raised by the whole village and what a paradise life.
Derek Sivers
And was able to live there for no money at all. So sorry. This is like a recurring theme, right? Like my my girlfriend’s hippie parents living on no money. Then she went and had a baby in Honduras for no money. So the digital nomad moves to Pai, Thailand and raises a couple of kids in Pai for no money.
Derek Sivers
Again, I’m going to equate money with the adult schedule thing this necessity. They’re like, “Oh no no. Having a kid is the hardest thing in the world. You’re going to be exhausted.” And they say all these things. It’s because they’re trying to live this scheduled rat race life and make a kid fit into that. You can’t do that. You just have to change your life if you’re going to have a kid or just shrug it off and say, “Oh, well.” And just have your kids raised by nannies, which is not the worst thing.
Paul
Yeah, this sort of ties to your definition of retirement, which resonated a lot with me. I’ve been telling people I’m retired from working in coercive wage jobs which basically just requires enough to like hack a living each year and not go broke, which I think is easier than people imagine. But you define it as not working for money, which I think is sort of the same thing. It’s basically a principle of like, I am going to follow my creative urges, my curiosity, things like that. Yeah. So you’re retired. Congrats, Derek.
Derek Sivers
Well, it was a there’s a funny story about that. It was a border visa border control guy that told me that I was retired because I was in Belgium about to get on the Eurostar train into London. And they do the visa check stuff. And he said, “All right, why are you coming to the UK?” And I said, “Oh, just hanging out.” And he said, “What do you do?” I said, “Oh, nothing, this and that.” He said, “Who do you work for?” I said, “Oh, nobody.” And he said, “Well, how long are you coming for?” I said, “Not sure. Come on, let me in. The train’s leaving soon.”
Derek Sivers
And he said, “All right, you know, mate, I’m not going to let you on this train. It sounds to me like you’re coming in here to take a job. So unless you can prove to me that you’re not secretly coming in here to take a job, I’m not going to let you on this train.” So I leaned down to the glass, spoken to the little part of the glass so nobody around me could hear me. And I said, “All right, look, you can search the web. I sold my company for $22 million. I don’t need money ever again. I’m not taking anybody’s job.” And he goes, “Oh, why didn’t you say so?” He goes, “Look, from now on, when you do these forms, just make it easier on all of us and just admit that you’re retired.” And I went, “Okay, thanks.” And I took the form and I got on the train and I thought about that like, just admit you’re retired. So from the visa border guy, point of view retired just means you’re not working for anybody. You don’t have a job. So you could just be an author selling ebooks. And as far as the world is concerned, you’re retired. If you’re just living off the money from your ebooks that you’re writing, if you’ve done something in the past and you saved your money even just for a couple of years, from their point of view of the visa border control guys, you’re retired.
Derek Sivers
But then that actually made me think about a belief I’ve held ever since the very beginning as a teenager. It’s like. I never want to work for money. And I’ve held true to that for my whole life. Nothing I’ve ever done has been for the money. It always had a deeper purpose. So even if I was driving six hours to do a gig for $200 as a musician. Yes, I wanted the money and the money was my barometer or as part of the challenge. But I was doing it for the experience. I was doing it to be a better musician. I was doing it to be a professional musician. I was doing it for the people I was going to meet while doing it. I was doing it to try out a new song. I was doing it because I had never been to that part of Pennsylvania before. I was doing it for so many other reasons. And I made the money. And I think we should all aim to do that with whatever we’re doing. Yeah, you might make some money, but if you find that you’re doing something just for the money then I think you should either stop or question yourself a little deeper and find another reason that you’re doing this. That’s not just for the money. And turn up the volume on that reason so that the money is always secondary. It’s never the reason.
Paul
Yeah, it’s funny how that relates to the border guard. Our sort of conception of work is funneled through a job and employment now in so many places of the world. And this is something I explore in my book. It was so fascinating to me. And this still happens even though I’m making money, people will say, “Oh, Paul’s unemployed.” And this is just so interesting. I got through the defensiveness phase that you inevitably go through. But yeah, this is so interesting and you start to realize a lot of this comes back to what you were saying before, which is that we need to change our beliefs to change our actions and ambition as well. Right? Ambition is something that I grew up somebody called me not ambitious because I didn’t want to work at a gas station growing up right. And I love how you define ambition as creating and learning. But for a lot of people, people would say, “Oh, Derek is leaving things on the table. He could do more. He could build another company, he could do all these things.” But yeah, that to me, I feel like we need new words for, like work, ambition. What do you think?
Derek Sivers
Yeah, well, ambition. Maybe it’s a shallow ambition versus deep ambition. Shallow ambition is--
Paul
I’ve called it all ambition to halt. I don’t have the right word. I’m struggling.
Derek Sivers
Maybe I’d rather reframe it as, fake ambition and real ambition. How about that? Fake ambition is wanting to buy a thing or like.
Paul
But I’ve also called it legible versus illegible ambition.
Paul
So legible ambition. My definition is, your parents can tell their friends about what you’re up to. Illegible ambition is really hard to explain to others, even yourself. But is this sort of deeper journey that is more in the heart than in the brain.
Derek Sivers
Interesting. See in all of my hours of thinking about this, I have never brought in the subject of others. Who cares about others? Why do they care what anybody else thinks? I honestly never even thought about--
Paul
I spent much longer on the default path, Derek.
Derek Sivers
Well, it’s funny that you just mentioned this just now, and I went “Mmmh”. I was taken aback like others? Your parents? Who cares what somebody else thinks. Now, that’s funny that you mentioned that. I honestly hadn’t considered that. That in all my years of calling myself ambitious, it’s always been for the self. It’s always been about being the ideal me.
Derek Sivers
Okay, let me put this into second person if you think about. The skills that you really want to have, the talents you really want to have, or the kind of person you really want to be. Say like you’ve spent some time once with somebody that was a great listener and you think like, “God, I’d love to be that present and that great of a listener.” Or “I’d love to be that graceful.” Or maybe you met somebody that really had their shit together that knows exactly where they’re going in life and exactly how to get there. And they say no to everything else and they’re driven and focused. And you think, I’d like to be like that? And you really work towards it. To me, this is ambitious. You want to be somebody that can stand up on stage and command a room. You want to be somebody that can sit down in front of a blank computer terminal and make an app out of thin air from scratch.
Derek Sivers
Or somebody that can sing wonderfully or somebody that can write a poem that can move you. To me, to yearn to be that person you want to be is ambitious and especially if you take actions towards it. That’s ambitious to me. Like any idiot can buy a Ferrari, get a credit card, go down to the shop and you hand him the card and they hand you the car and then you pay the debt. That takes no skill. To me, it’s that internal stuff that’s what takes the real work. That’s real ambition to me.
Paul
Yeah, and I totally align with that. I think the process for me was stripping away the outside view. Right. I think that’s the script, the story of what you’re supposed to be. And the only work you can commit to, actually comes from within. Do you resonate with that? Like in terms of--
Derek Sivers
Yeah just because you’re asking me some personal questions about my past. You just made me wonder why am I like this? And I think it’s because--
Paul
I always think that too.
Derek Sivers
Because I think-- in high school, I grew up in like an upper middle class suburb of Chicago. All the people around me were all like that college pre-prep kind of course. And I was like, “I’m not even going to college. I just want to be a musician.” And they were all neat and proper and dressing nicely. And I had super long hair and denim jackets and Ozzy Osbourne, Iron Maiden heavy metal patches on my denim jacket. So people gave up on me long ago and that was great. They’re just like, “Oh, Derek, he’s just going to be a musician.”
Derek Sivers
So people gave up on me. Nobody was expecting anything of me. Even my parents just gave up on me just like, “Oh, well, he’s just going to be a musician.” And maybe that’s why since the age of 14, it’s like what anybody else thinks is moot. Nobody’s expecting anything of me.
Paul
That’s very freeing. Are you going to give up on your son in the same sort of empowering way?
Derek Sivers
Oh, good one. Good question.
Paul
I think you know what I mean. But yeah.
Derek Sivers
Yeah, that’s a fun twist on it, though. You know, the best thing you can do for your kids is to give up on them.
Paul
Yeah, well, and I sense a lot of anxiety about parenting comes from enormous expectations. We haven’t even had the child yet. And people are asking me if we’re thinking about college. It’s like, I don’t know.
Derek Sivers
Oh God! College won’t exist in 20 years.
Paul
Yeah, mostly just thinking about feeding and diaper changes, the basics. Yeah. You don’t think college will exist in 20 years?
Derek Sivers
Oh, no, no. I don’t say that I’m predicting that. You can always do the thought experiment of saying it might not.
Paul
Who are your path role models?
Derek Sivers
We kind of started with that, didn’t we? The musicians that changed their career many times. I don’t even mean specifically Bob Dylan. It was just one that came to mind. But just a lot of the musicians, even like Brian Eno, if you don’t know about Brian Eno and his oblique strategies, search the web for that. It’s fun. Brian Eno is a very creative record producer of bands that you’ve heard of, and he’s got a very philosophical approach to producing music. And one of the things he did is, he made a deck of cards with what he called oblique strategies, such as you shuffle the cards and pull one out and it may say cut an essential thread. And his challenge to himself as a record producer is whenever he was not quite sure what to do or just felt like a little random input, he’d shuffle the deck, pull out a card and must obey what it commands. So he’d make himself do things to the music that he wouldn’t have ordinarily done. So it’s like a creative challenge. It was a huge influence on me to think of the randomness that we can instill into our life.
Derek Sivers
Kind of like that example I said of just like, “I wonder what it would cost to to move across the world on a one way flight. Let me just find out. Oh, that’s pretty cheap. I’m going to just book it right now.” Like that’s celebrating randomness in a way. You know, like, I didn’t have this idea this morning, but now I’ve booked it or the raising your hand at the TED conference or something to get up on stage. These things can just kind of be random influences. And I think that Brian Eno’s oblique strategies influenced me that direction. Yeah, the careers of artists have been very inspiring to me in general because they take that same creative spirit and apply it to their life actually. Brian Eno in particular. I remember at one point he moved his family to Saint Petersburg, Russia for one year.
Derek Sivers
Why? Because he’d never lived in Saint Petersburg, Russia. So he said, let’s just shake things up a bit. Let’s live in Russia for a year. And so he did. Joi Ito is an interesting guy that has done something similar. I never heard the follow up, but at one point he said, “You know what, I know a lot about the rest of the world. I really don’t know anything about the Middle East. I’ve traveled a lot but don’t know the Middle East. I’m moving to Dubai.” And he moved to Dubai for a year. And I just love that kind of spirit about taking the same creative approach that a songwriter would take to their song or a painter would take to their canvas and just use it on your life and say, “Let’s try this. I’m going to do this thing.”
Paul
Looks like he’s living in Japan now, teaching at a university there. Or he might have been in Boston.
Derek Sivers
But, yeah, he’s from Japan. Or he’s a Japanese family at least. But I know he was living in Boston recently.
Paul
What has been inspiring to you? Something you’ve consumed, read, listened to in the last 6 to 12 months that has been on your mind?
Derek Sivers
I thought you were going to say last 6 to 12 hours. And I was going to talk about my very inspiring conversation this morning with my Sicilian friend who’s living in a van on the Canary Islands right now.
Paul
Oh, amazing. I love the Canary.
Derek Sivers
We just had a very-- oh, I haven’t been there. But yeah, we just had a very inspiring conversation just three hours ago. So sorry. When you said 6 to 12, my brain was like, okay, last 6 to 12 hours. And then you said months. Okay, months. My next book is called “Useful Not True” because I’m fascinated with this idea of adopting beliefs because they’re useful, not because they’re true. And in fact, I start out by challenging that we need to stop trying to think of anything as true. Stop trying to apply that filter because it gets you into a dangerous, stuck place of beliefs that you grew up with and not challenging those. Or clinging on too quickly to one because you read a particular self-help book that has a certain point of view and you say, “Ah, this, this is the way to live.” You cling on to that because you feel it’s right and it’s true. Instead, I think we should abandon that whole categorization of true and just look at everything as whether it’s useful or not to you right now. So a certain self-help book might be useful to you right now. You don’t even have to ever think of it as true. And then you can just adopt some of it, which then means kind of like we said earlier about some books can be deeply flawed. And the author can be a jerk and there can be misquoted lines in there. And there could be quoting psychology tests that have since been disproven. And yet the book can still be incredibly useful to you. An absolute wreck of a person lying face down in a gutter could say something to you that could be really useful to you. It doesn’t matter the source. It doesn’t matter whether a philosophy is congruently true through and through.
Derek Sivers
Same with religions or whatever. You can pluck the bits that you want to use that are useful to you right now. And even then, you don’t need to turn an idea into an ideology and subscribe to it. Declare yourself to be a follower of this ideology. Instead you just be opportunistic and you just take an idea. And say, I can use this now and then maybe next week. You don’t need that idea anymore because it served its purpose it was useful to you. This approach to life for me has been so helpful, so effective. It’s kind of related to all the things we talked about today, not following the rule book, “You need to go to college.” Now that’s not true. “You need to stay near your parents.” Not true. “You need to follow this path.” Nope, not true. “Having kids is really, really hard.” Nope, not true. Apparently that belief is useful to you so that you can validate yourself while you’re stressed or whatever. But that’s not true. That’s just a useful belief for you right now. So that you can feel better about yourself. Or you can hire a nanny to help or whatever. That’s just a belief that you found useful. It’s not true. And it just--
Derek Sivers
This to me. It also helps me break the rules in life when people have said things like--. When I when I started as a gigging musician, I started to get into the university circuit and people said, “Well, you need to do things this way. You need to submit your application and then wait six months and you’ll get approved.” I was like, “No, I don’t think so. I don’t think that’s going to work for me.” And I just like went straight in through the back door and found my way in and got the gig. And there’s so many things in life that people can kind of try to hold you down through telling you to do things the normal way. And you need to be able to say like, “No, you’re stating that like it’s the truth. But that’s not true. That’s just that’s something that you believe that’s useful for you to believe that because you have a job that pays you to believe that. But that’s not true.” So this is what my next book is about.
Paul
I love this title. It’s so good. A lot of people when I was writing my book said, “You have to have a framework and you have to tell people how to do stuff.” So I literally tried to write the book and at the beginning I’m like, “There are no how to’s in here. I will not give you next steps.” And what I realized I was doing, was giving people things that were useful, hopefully useful for me, but probably not true for you. So I love that framing that’s so powerful.
Paul
Where do you want to steer people to follow along? I love what you’re doing with your books, by the way. You have people buy them once and then they can pay $4 for future copies as well. That’s such a great model. Once you’re out of the frame of what only Amazon lets you do. But yeah.
Derek Sivers
To me the contents of the book, and the paper it’s printed on are two separate things. So you only need to buy the contents of the book from me once ever. Once you’ve paid me the $15 for the contents of the book, you’ve got it in any format for life. Even in the future. There are some digital holograms that will implant the book directly into your brain. You will get that format for free as well. If you want the paper, you just pay me the break even cost of the paper itself. But yeah, if you go to my website sive.rs
Derek Sivers
That is my name with a dot in it. Everything is there. I don’t really do social media so much. I don’t trust it. I don’t believe it will stick around forever. So I put everything of value on my website. So just go to my website and email me. Anybody who’s listening to this should know that the main reason I do interviews like this is because of the people I meet. When I do them, I get emails from cool, interesting people from around the world. So if you listened all the way to the end of this, you should go to my website and send me an email and say hello.
Paul
He replies.
Derek Sivers
I reply to every single email.
Derek Sivers
I love that part of the day. I put aside an hour a day and I reply to everything.
Paul
I love it. Thank you so much, Derek. And you’ve been an inspiration on my path and I really just appreciate everything you continue to do. Keep following your ambition.
Derek Sivers
Thanks and thanks for the fun, thoughtful questions. It was a really, really interesting conversation. I really love your questions, so thanks for having me.