David Nebinski
host: David Nebinski
How to Live, career strategies, networking, decision-making principles, portfolio career development
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Transcript:
David
Hey friend, it’s David Dubinsky here in Brooklyn here at the Portfolio Career Podcast. We help you take ownership of your portfolio career and design the life that you want to live. Today’s conversation is with the one and only Derek Sivers to quickly introduce Derek, here’s a ten second overview by himself on his website sive.rs: I’ve been a musician, producer, circus performer, entrepreneur, TEDx speaker and book publisher, monomaniac, introvert, slow thinker and love finding a different point of view. California native. I now live in New Zealand. You can learn so much more on Derek’s website sivers.org, s-i-v-e-r-s.org. Also sive.rs, the website is full of essays, interviews and book notes of over 300 books. In this episode, you’ll primarily learn about Derek’s latest and fourth book called How to Live 27 conflicting answers and one weird conclusion published in 2021 and another book called Your Music and People, both of which I loved, and other ideas related to work, career, relationships and communication. As always, this episode with timestamp notes is available on my website at portfoliocareerpodcast.com. There you can subscribe to my newsletter called One Email Away, which has the best insights from the podcast and front source job opportunities. So excited for you to build and grow your portfolio career. Here we go. Derek, welcome to the show.
Derek Sivers
Thanks, David.
David
Thank you so much for doing this Derek. As we’re kind of warming up a little bit, I’m curious if there’s been a recent hell yeah in your life, something that has been really amazing as a piggyback off to a blog post of yours and then eventually turned into a book.
Derek Sivers
In my life, personally. Off the top of my head I can’t think of a recent one. Sorry. I should keep these on the tip of my tongue. Hell yeah or no is just a compass I’ve been using for a long time. At least ten years or so as just helping to raise the bar on what’s worth doing. You know, if something’s not making you feel like, oh, hell yeah, then say no to it. The big idea is that it leaves so much more space in your life for when that occasional hell year thing comes around. I haven’t started any new projects yet, so no, actually, I think I’m in that space right now where I’ve been saying no to everything. I’ve got the space in my life and there is no big hell yeah right now. So that’s kind of a good thing.
David
Maybe some space has opened up after writing some recent books and I want to talk about How to Live and Your Music and People. I think it’d be really fascinating to just to hear how you wrote How to Live. Tell us a little bit of that journey.
Derek Sivers
Sure. First you got to understand that it’s an homage to a strange little book called Sum spelled S-u-m by David Eagleman, which has 40 little tales about what happens when you die. Each tale disagrees with all the other ones. So one chapter will say, when you die, such and such happens, but then the very next chapter will say, when you die this other thing happens. They absolutely conflict with each other. I thought, God what a wonderful little format. Usually when you get a book, you’re expecting it to be one thing. You say, okay, this author has some kind of point of view they want to express in this book. I’m in for 300 pages of them basically saying one thing. I think that’s what a lot of us don’t like about reading books, is that you can just kind of read the back cover and maybe the first ten pages or look at the table of contents and you get the gist of what the whole book says. So you don’t want to spend 20 hours reading it. That’s what I loved about this book called Sum, I just love this format where every chapter disagrees with the rest, which I think kind of better represents the multitudes of life. Life isn’t just one thing. We have beliefs that conflict with each other. After loving this book so much and reading it a few times, one day, I just kind of had this lightning bolt of inspiration where I went, “oh my God, I want to write a book called How to Live”.
Derek Sivers
That’s going to be like the book called Sum, but each chapter is going to have a strong opinion on how you should live your life. Every chapter is going to disagree with all the rest. I’d been wanting to do for a long time try to write down everything important I’ve ever learned in my life, which I think a lot of us do. When you first have a kid, you think, “oh my God, what if I die before my kid’s a teenager? I want to write down everything I’ve ever learned so that my kid could read it if I die”. I had been wanting to do that anyway. The book called How to Live is in a much more creative format, everything I’ve ever learned in my life. At first I spent two years writing down everything I’ve ever learned, and it was 1300 pages long, nothing I would ever want anybody to actually read. Then I spent two more years chopping it down so that eliminating every unnecessary sentence so that right now what’s left in the book, How to Live, is only 115 pages. That’s the culmination of everything I’ve ever learned in my life, broken into 27 different chapters that all disagree with each other. I think it’s my masterpiece. It’s the best thing I’ve ever done.
David
Speaking of the every line and every sentence matters, I love how you start the book and it says, I think it’s read one line at a time or one sentence.
Derek Sivers
Please read slowly one line at a time. I realized later that’s how it was written, which is not how most books are. Most books have a very conversational tone like you and I are right now. How to Live, because I reduced it so much so that like every page became a sentence, meaning that 1300 page book in order to turn it into a 115 page book. I really made every sentence capture what used to be on a whole page. So they’re not meant to be read conversationally. If you try to read them conversationally and quickly, it’ll just be a blur, you know? So they’re really meant to be like one sentence at a time and take it in, like you would do with poetry.
David
You mentioned kind of everything that you learned and their conflicting ways of living. How do you think about those those principles or those ideas in kind of your decision making currently? How do you kind of decide how to live?
Derek Sivers
Ah, okay. Think of it this way, and if you’ve read the book, you’ll recognize this punch line from the end that if you are the composer for an orchestra how do you decide which instrument should play? Maybe sometimes you want the woodwinds, sometimes you want just a single trumpet, and sometimes you want like a unique combination of the viola, the clarinet and a harp. You don’t have to pick just one. If you’ve got an orchestra, you can combine them, and most importantly, you change them over time. It’s not like you need to make a decision up front which instruments are going to play. It changes like sometimes this, sometimes that. So sometimes you want to live cheaply, let’s say on the beach in Vietnam, working remotely so that you can live for $20 a day and save your money and be both hedonistic and frugal at the same time. But sometimes you want to stop everything and focus entirely on your newborn baby. Sometimes you want to get famous to say yes to every random request, live entirely for others, and leave a big legacy. What you do is you can combine them. You can combine the different ways to live, and you change them over time, like the conductor or composer for an orchestra. I think it also helps to ask yourself what’s lacking in your life right now. Because most of us have some area of our life, some need that’s being ignored. If you’re wondering what to do next, it’s usually think about what you’re lacking right now.
David
Then by having these specific sharp points of ways of living, you may be able to see another one and be like, oh, wait, maybe I am lacking in that part. I didn’t know that that was possible. Or now that you painted the whole entire kind of picture of what that looks like.
Derek Sivers
Yeah. It’s all about taking it to extremes, right? I think that most people follow norms too much. I feel bad for people who have only followed the normal path, doing what most people do and therefore getting the results that most people get, which is not great. It’s not physically any harder to do something weird. It just takes more imagination and confidence. Tomorrow, you could join a circus. You could get into the forestry business, you could move somewhere you don’t understand. You can learn strange skills or join a cult or, you know, you can live large, you can live super small. You could move to a tent or a bus. I think it’s just really helpful to explore extremes. It makes your life so much more rewarding and interesting.
David
Let’s say we’re exploring extremes. Through the book have you found any attributes or values or traits that are kind of common across many of the different ways of living that might be serve as a compass?
Derek Sivers
I think it is the one I just said. It’s about ignoring norms. I think that’s the common thread you’ll find, is that most people tend to just kind of meander through this doing whatever everybody else is doing. I think it really, really helps to do the opposite of what others are doing. There’s a chapter in there about balance. Part of the reason I had so much to say about balance, I think I often feel this need to balance out what others are saying and what others are doing. Ever since I was a kid, I found that if I found myself in a really stuffy, uptight environment, say you’re at a an awards ceremony or a funeral, I’d get really giddy and silly because everybody was being so serious. Internally, I just felt myself kind of getting goofy to balance out all this damn seriousness in the room. On the other hand, if I find myself in some kind of situation that’s too zany like Burning Man or party, it just makes me want to go to the library and read a book to counteract all this zaniness around me. I think I’ve often felt this need to do the opposite of whatever everybody else is doing. I think that can be really rewarding too. The world rewards you more for taking the path less traveled. So that’s the common theme between all of these different ways to live I talk about in the book is that almost none of them are normal. They’re all doing the opposite of what most people do.
David
When I was reading it, I would find myself like, oh, I like that one or I can see that one too. It really can spark a little bit of imagination and also sometimes emotion.
Derek Sivers
Cool. As I was writing it, every single chapter would convince me while I was writing it that, you know what? Forget the rest. This is actually the real one like this, you know, chapter nine, and we’re getting chapter nine. I’m like, “you know what? I know this is a book with 27 chapters, but honestly, this is really the way that everyone should live. I mean, this is really the best. It’s just the most sense. It’s the most effective, the most powerful”. Then the next day, I’d be working on chapter ten, and I’d be like, “you know what? Actually, this is the one”. Each time I’d convince myself that this chapter is it. I wanted to give that experience to the reader to, like, while you’re reading it, you’re really supposed to be convinced by each chapter that, forget the rest, this is actually it. Then the next chapter ideally flips you around, and that’s the desired effect. It’s not your typical nonfiction book that thinks it has the answers.
David
I think after the first time I read it, I emailed you and I was like, “I love this, I’m still processing it, but I just want to let you know that I love this and I’m still processing it”. It’s a very dynamic book. What chapters or ways of living in the book do you think apply to people’s careers? We talked about maybe like extreme lifestyles.
Derek Sivers
I’d like to break people out of the thinking that your career. Needs to be a common thing. I try to make sure that I never forget the experience of that little shack on the beach that will rent you a snorkel and mask to go swimming in the ocean, that they they’ll rent you a snorkel and mask for $5 it’s just a shack on the beach, and they have no privacy policy or terms and conditions. They have no HR department. It’s just a person on the beach that will rent you a thing. That’s a valid business. You can live your life that way, if that’s what you want. We all have different values. Some people just seem to never be happy to have enough. They don’t like the feeling of enough. They like pushing and pushing and driving for more. So they finally make $1,000,000. Now it’s not enough, I want to make $10 million. They get $10 million and it’s not enough. They’re pushing for more and some people enjoy that drive. There’s actually a weird term for it. We all know what stress is.
Derek Sivers
Then there’s distress, which is negative disaster stress. But then there’s eustress spelled e-u-s-t-r-e-s-s, which is positive stress, which is the thing I’m describing. Some people want the feeling of eustress to push for more all the time, but some people don’t. They just want to relax and be comfortable. You have to know your own preferences at the time because these can change in life too. You might be completely driven and ambitious in your twenties and then suddenly at the age of 37 you feel like, “you know what? I just had a baby. I just want to chill and do nothing and just collect the passive income from the business I worked on for 15 years”. That might be the path for you and you might have people telling you how to drive and push more, but you can just turn that all off. You can say, nope, I’m not driven, I’m not pushing. I’m happy to collect my $10,000 or something. That’s enough for me. It pays my cost of living. That’s enough. So no I wouldn’t say that there is a path that anyone should follow for their career.
David
In terms of work. Talk to us a little bit about why or how people may think about the importance of choosing opportunity over existing work obligation, the norms say, you should work two years before, it will look bad on your resume if you leave before two years, or stay till the third year. There’s these norms. I think in some of your work I’ve seen about this idea of kind of choosing opportunity sometimes at the cost of certain things. Can you talk to us a little bit about that?
Derek Sivers
Sure. Have you talked about the book called So Good They Can’t Ignore you?
David
I have, I’ve read it.
Derek Sivers
For anybody listening, if you haven’t read it and you’re a fan of this podcast, go read it. So good They Can’t Ignore you by Cal Newport. I think it addresses a lot of what you talk about. I mean, it just seems right up your alley for this show. One of my favorite points in the book was when he talked about the two different stories of two lawyers who wanted to quit their job. And he found real people that had done it. He found two lawyers that had quit their job and got two very different results. One wanted to be a ski instructor and one wanted to be a yoga instructor. Both of them quit their job as a lawyer and switched to a new career. But they did it in two very different ways and one was a horrible failure and one was a huge success. The success was the one who gradually transitioned and cashed in the career capital, he calls it, that they had built up their reputation, their connections, the people they knew and brought them into the ski instructing business slowly over a couple of years, very strategically. The whole time, starting to come into the office four days a week instead of five and starting to kind of bring all your clients out on ski trips and then let each one of them know repeatedly that you could help them get better at skiing.
Derek Sivers
But the other one that wanted to be a yoga instructor at a certain point had just had it. She said, okay, today is my last day. Tomorrow I’m starting a new thing. Goodbye, everybody. And she started this yoga studio, but she didn’t use her existing network and connections. So her new yoga studio was a was a failure because she didn’t cash in this career capital she had built up. I don’t think there’s any set number of years to show on a resume or anything like that. I think all of that is superstition. I come from the music business where people would say, “if you want to be a success in the music business, will you have to tour?”. There would be lots of hip hop artists who never toured and were a huge success, and they’d say, “well, if you want to be successful, you have to have a great recording”. There are plenty that didn’t have a great recording and were huge success.
Derek Sivers
You know, you have to look good and there are plenty that didn’t look good and were a huge success. I’m sure it’s the same in every industry where you have well-meaning people telling you what must be, but it’s all disproven and you can be the one to disprove it again if you want. This thing about two years requirement or whatever, I think it just depends on what you’re after. I mean being strategic about it and making the move. There’s one more metaphor I should share at this time that I heard is the Tarzan metaphor that when Tarzan is swinging through the jungle, like swinging on the vines through the jungle, notice that he doesn’t let go of the old vine until the new one is supporting his weight. So you swing through the jungle, you grab the new vine, and once you feel it’s strong enough, then you let go of the old vine and swing on to the next. I think it’s really cute and memorable metaphor for our career changes, is don’t don’t leap off the old thing until you sure. Until you can make sure that the new thing is supporting you.
David
As a follow up to that, I think it’s in Your Music and People. One of the ideas that I’ve had kind with the show is like how we’re kind of like one email away from a new opportunity. I think the line in Your Music and People and I’d love to hear you talk about it a little bit more is make sure the quote is right. But it’s the difference between success and failure can be as simple as keeping in touch. Can you talk to us a little bit about that as someone who is extremely open, very inviting, encourages people to email them, stuff like that. Can you talk about this this idea around like how just keeping it in touch can lead to new opportunities and how it could be the difference.
Derek Sivers
It is such an interesting rule that I’ve found about human nature is the recency and proximity effect of contacting someone over and over and over and over again. In my career, I found that the best opportunities were given to me by someone that I had just recently talked to, like the day before or the week before. So often it would happen that I would talk to somebody, whether it was somebody I had known for years or somebody I had just recently met. Let’s say I talk to them on a Tuesday, whether we meet up for lunch or just have a phone call or maybe even an email, though ideally something that uses more of the senses is better than just being yet another email in the inbox. Then so many times I’d get some kind of opportunity like the next day from them that they’d be like, “hey, I was just thinking about what we talked about yesterday and a friend of mine is making this movie and he’s looking for such and such, you know, for this film. I thought you’d be a good person to talk to, so here, Derek, meet Tracy”. This kind of thing happened so many times that I realized that there’s something to this that wasn’t just a fluke. The first few times it felt like a fluke. But then I realized it’s human nature that when you talk to somebody, that person’s on your mind that day and the next day, but usually gone like a week later, at most, a week later. Usually within a day or two, they kind of slip out of your mind again.
Derek Sivers
So opportunities tend to come your way from the people that you’ve just recently spoken with because you’re still on their mind. Next time they encounter somebody doing something that’s looking for something, they go, oh, I was actually just talking with David yesterday. Here I know somebody that’s good for you. When you’re looking for more opportunities in life, I think the single most important thing you can do. Is to reach out and talk with. Ideally meet up with at very least to talk with the people that you think could open doors for you. Even if it’s just an old friend or an agent or a well connected somebody, it could be just a random contact. You cold call somebody, which is always painful, but it usually pays off, especially if you persist. There are people that were very cold to me at the first contact, but then by the second or third contact they warmed up to me and ended up becoming friends. Yeah, the proximity effect, the recency of opportunities come to you usually just within a couple of days after you’ve spoken with somebody.
David
It’s always connected to people. I think another line kind of following up to Your Music and People is also that like every breakthrough is connected to like a person.
Derek Sivers
Everything great in your career comes from someone you know, everything that has ever happened in my life. I think almost everybody’s , it almost always comes from someone you know, someone you know makes that little connection or tosses something your way or refers somebody to you. That’s how everything happens.
David
Like when you were building CD Baby. You kind of started it for yourself. Then some other people were interested in it and then it started to grow from there.
Derek Sivers
Yeah even that. I’m sure there was just somebody I knew, there was specifically a bassist named Marco that gave me the idea for CD Baby accidentally because he said, “oh, wow, you built that thing to sell your CD. Could I sell my CD through that?”. I went, “oh I hadn’t thought about that but sure, so Marco from Finland made CD Baby happen. I’m even thinking of the other ones like before that, because once CD Baby started that just filled a niche in the marketplace that was just very needed. Nobody else was doing it. But for the other things, like all my years as a professional musician, all the best gigs I got were just from some random contact. My roommate opened a certain door for me in a huge way or some random person that had just been to my recording studio a couple of days earlier suddenly called me and said, “hey, there’s this TV show looking for music”, and it just always happens like that. It’s just somebody that you were just talking with. Always the people that you know, that will open the doors.
David
Can you talk about the idea around being like considerate in communication? Let’s say you’re reaching out to someone like you said, like you’re kind of cold calling someone or you’re emailing somebody. Ideally, you’re probably not just saying like, “hey, hire me”. Maybe you might want to think about someone else’s point of view. I think also in Your Music and People, you talked a lot about the importance of being considerate to the people that you’re communicating to and would love to hear you talk a little bit more about that.
Derek Sivers
Sure. It should just be human nature. But for a lot of it’s not because our needs are kind of drowning out the needs for the consideration of the other person you’re talking with. I always try when talking with anybody to think as hard as I can about what their life must be like right now and what their problems are, what they’re struggling with, what they’re looking for. Sometimes just straight up asking them, though, if you were to ask that directly, it sounds a little too calculated and said it usually just kind of comes up in conversation. Sometimes you just catch a little word in a sentence and you can say, well, what do you mean? Like why did you mention that? What’s an example of that? Then you might hear that they are having trouble with their kid. Their kid is seven years old and still doesn’t know how to read. You might send somebody their way that can help with that. I remember like I met with somebody in the music industry that was a pretty powerful dude in the music industry. That was like complaining about his laptop, how it didn’t work. I noticed it was a really old laptop. So the next day I kind of sent him this thing that said like, okay, the three best laptops you can buy today. And I said, “hey, you know, I think your laptop problems might come from the fact that yours is pretty old. And, you know, here’s the best ones. And as a techie, I can recommend two”.
Derek Sivers
So it’s just thinking of things from their point of view, which goes for anything. I mean, hell, even if you’re looking for a job. When I was an employer, you know, I had 85 employees. This happened twice, I believe if I remember correct, somebody came to me and said, “I know you’re not hiring for this role, but I know CD baby and I think I can do this for you. And I think you’re leaving money on the table in this way. And I can I can take charge of that and I can find you some new income here and I can do this if you let me. You don’t even have to pay me at first. Let me do this for free for a couple of weeks, and if you’re impressed, put me in charge of it”. I did it twice. I wasn’t even hiring, but somebody came to me with a proposal to where they could improve my business because they had looked at it from my point of view. They had looked at the internals of what they could tell CD Baby was doing and found a way to make a job for themselves. I have a page on my website called Get Hired. If you go to sive.rs/gethired, I believe is the URL. That’s my advice on how to get hired, coming from the point of view as somebody who hired 90 times.
David
Another thing that I think that you’ve been thinking about over the years is around this idea, around like directives and was curious, is there some directives or in kind of the directives project and what you were thinking about there and if there was another directive or some directives that people should consider as they’re moving forward in their career in 2022?
Derek Sivers
The Directives project is what became the How to Live book. If you heard my interview I did on Tim Ferriss show in the beginning of 2016, I believe. I talked a lot because my current obsession was going through everything I had learned, which is often talked about in a kind of third person informational kind of way. I would think, “how can I turn this into a do this style sentence?”. Not necessarily to others, even just to myself, you know, do this, do that. Instead of talking around a subject, let’s just focus on the actual action I should be taking. That’s why you’ll notice that the How to Live book is written in that style, very unapologetically saying, do this, do that. Because it is the culmination of the do this directives project, directives for somebody making a career change. Was that your question? If I were to offer one tip that isn’t said enough, I think it’s the thing I just mentioned, the thing that I just the story I told 2 minutes ago about the people that would come to me. And create a job for themselves. I thought, I’ll give you a concrete example. I saw it for the first time. At the last job I ever held, which was working for Warner Brothers Music publishing in New York City. It was a small office. It was only 12 people. Our job was to earn more profits from the copyrights that the company owned.
Derek Sivers
Just the song copyrights, not the recordings, but just the songs underneath it. For example, Warner Brothers owns the copyright to the song Happy Birthday. So if somebody sings Happy Birthday in a movie, Warner Brothers get some copyright income from that. This guy named Allen came to the company one day and said, “you’re not doing enough to get music into commercials. I’ve worked in advertising for a couple of years and nobody from Warner Brothers ever called me to try to put one of your songs into a commercial. You’re missing a huge opportunity. You should be doing this”. He kind of said, “if you give me a desk and a phone, I can generate some commercial income from you or for you, you don’t even have to pay me. Let me just show you what I can do”. For a couple of weeks, the company said, alright, fine. You are now Alan Tepper, commercial licensing at Warner Chappell Music Publishing. But we’re not going to pay you. You’re not on the payroll, we’ll say that you work for us. You can represent us and show us what you can do. He did for two weeks and suddenly got one of our songs in a Budweiser commercial and then another one in like a Ford truck commercial, just calling on his old contacts. The company was impressed and he became one of the most successful people at the company, one of the top paid people, because he just came in and made a job for himself.
Derek Sivers
Warner Bros was not hiring. He made that job on the creative side. Similar story I saw back at that time too, there was a songwriter that had no success to his name, no credits, no nothing, but he just kind of found some kind of in to the company, which is kind of hang around where things were happening and just listen to like who’s doing what, who’s going into the studio and who might be looking for a song and just found a way to put himself in there where things were happening. Didn’t wait for somebody to say, we are looking for such and such. He just looked at the scene and found where he could put himself and kept pushing and saying, “here, I got a song for that. Here, let me write lyrics for that here that’s a great track. Let me let me put a melody to it. I’ll bring it back to you tomorrow”. Also ended up becoming one of Warner Bros most successful songwriters. It was amazing for me as a 21 year old at the time to just watch that happen in a year. Watch this guy that was like hanging around looking for opportunities, made opportunities for himself instead of waiting for them to be handed to him, and then became the biggest songwriter of the year within two years or something like that.
David
Wow. Crazy.
Derek Sivers
It only sounds crazy if, going back to where we started at the when you asked about the common theme between chapters in How to Live, it only sounds crazy if you’re used to just kind of doing the normal thing that everybody else does. And well, let’s look to see who’s hiring. Well, I’ll apply for this. Just stick it out here even though I’m not happy. It’s like the normal path gets you normal results, which are not great. So you really have to do what seems unusual at first if you want to get unusually good results.
David
Love it. Is there anything else you want to share or how people can follow up and stay in touch and keep learning from you?
Derek Sivers
Oh, well, email me. The reason I do these interviews is because of the people I meet afterwards. I don’t really care about selling more books. I just give all the money to charity anyway, so I’m not here to sell my book. Really, the reason I do podcasts like this is because of the people that reach out afterwards, and I meet some of the coolest people I’ve met in my life just in my inbox. I often like to find out where people are and when I travel somewhere in the world, like I went to Finland for the first time. I emailed, you know, the 15 people I knew that were in Finland, and I met up with like six of them. It was some of the most interesting conversations I’ve ever had. What a great way to get to know Finland through people that had emailed me. If you’re listening to this, send me an email, go to my website sive.rs and you’ll see the big email me, contact me link there and send me an email and just introduce yourself and say hello.
David
Amazing. Thank you so much, Derek. I really appreciate it.
Derek Sivers
Cool. Thanks, David.
David
Hey friend, thank you for tuning in to this special episode of Portfolio Career Podcast. We’d love to hear what you learned and what you enjoyed. You can find me on Twitter, LinkedIn, Instagram, whatever is best for you. As a reminder, I’m just one email away as well. This episode with Timestamp Notes is available on my website at portfoliocareerpodcast.com. There you can subscribe to my newsletter called One Email Away, which includes the best insights from the podcast and sourced opportunities. So excited for you to build and grow your portfolio career. Thank you so much.