Derek Sivers: Creativity, Self-Reliance, and Dropping Assumptions
“Everything you’re doing, you’re choosing to do. You need to understand that. Like never forget that you’re choosing to do this, and at any point. You can choose not to. You don’t have to. Just walk away from anything. There might be some consequences; more often, there’s not.” — DEREK SIVERS
Derek Sivers (@sivers) is a creative thinker who is quite hard to pin down when trying to explain who he is. Here’s a shortlist of what he’s a done musician, producer, circus performer, entrepreneur, TED speaker, and book publisher. If I could sum up who Derek is, I would say he’s a philosopher and introspective person looking to push his thinking in ways he hasn’t explored yet. He won’t hold any belief or assumption too tightly.
Originally a professional musician and circus clown, Derek created CD Baby in 1998. It became the largest seller of independent music online, with $100 million in sales for 150,000 musicians.
In 2008, Derek sold CD Baby for $22 million, giving the proceeds to a charitable trust for music education. He is a frequent speaker at the TED Conference, with more than 5 million views of his talks.
Connect with Derek:
Twitter: @sivers
Show Notes
[00:03:52] Derek's Background
[00:05:57] Life - Intentional and Unintentional Events
[00:07:24] Getting to Speak at TED
[00:08:46] What Did You Do Before TED
[00:10:08] Derek's Writing Process
“But with writing, I think it's the same as anything else. Like when you get stuck on something, you try to break down this big problem down into smaller, more specific problems. Right? Like I think that's the same with anything in life. Like if you're stuck in a creative problem, whether it's making music or whatever you do. There's always a way to like to flip it over and consider the opposite of whatever you're doing. It's just like a typical tool in the toolbox of people doing anything creative, it's like, let me try and reverse it. Let me try doing the opposite of whatever I'm doing. Well, let me take a 90-degree turn.
Now I want to take a 180. You get up, on the other hand, if you're having a stylistic problem like you're. Sick of the sound of your voice. And I don't mean you know you, your voice box, but I mean, whatever you're doing artistically, and you can always just pretend that you're somebody else, whether it's your role model or just something else, and you can do whatever they would do.
So for years, I was a singer, and my voice teacher would teach me like I would go in and work on a new song. He'd say like, okay, now sing it to me. Like you're sneaking up on me with a knife behind your back and about to kill me. Sorry, what? He said, okay, now sing it to me like your Grover from Sesame street, whatever.
You know, it's like you don't have to be yourself. You can be someone else when you're just doing some creative and trying to, if you're feeling stuck, you can always do it a different way.”
[00:12:11] Making Life Decisions
“I've recently found a new way of making, or getting through major life decisions when I'm feeling stuck is to describe my problem to a mentor, especially if it's someone who doesn't know me at all.
So then I have to summarize my entire context to a disinterested, right. Like, imagine You were going through a major business problem, right? And somebody says, okay, I'll give you five minutes on the phone with Richard Branson. He goes, Oh my God, Richard Branson! Oh my God, I know you're only going to have five minutes.
So now Richard Branson knows nothing about you. You have to summarize your entire situation and the problem you're going through down to like a one-minute explanation of the context and a one minute question. How would you do that? So to respect their time, you have to be as succinct as possible.
And what I found. Is that by doing this exercise, by reducing the problem down to its essence, the answer becomes clear without you having actually to contact some successful mentor, no need for Richard Branson, like just going through that exercise usually it makes the answer pretty obvious when you.”
[00:14:45] Choosing the Right Tool For The Job
[00:18:37] How Derek Views Creativity
“The people that were most surprised that I found programming creative were either people that knew nothing about it and just thought it seemed like a dumb day job.
Or people for whom it was a dumb day job that they were doing out of like just doing it for the money. Yeah. So I thought about this and realized that it's not like we, it's not like making music is creative, and programming is not creative. I think it's a matter of who you're doing it for. So if I was the assistant to a Hollywood composer, and paramount pictures was telling the composer exactly what to do, and then he was dumping it on me saying, I don't have time. You arranged the horn section, make it exactly like this. Well then that's not really creative anymore, is it? Now it's like just some stupid task I've been assigned.
I have to arrange the horn section, so that's not really creative. But then say that was my day job to be an assistant to a Hollywood composer. And then at night I would go home and play with computer programming to like invent my own mobile app idea. Right. And then, in that case, computer programming would be my creative outlet, but then vice versa, of course, if I worked for a big company that was telling me exactly what to program on computers, and I was just typing out Java code to meet their specs, then programming wouldn't be very creative. And I would go home at night and play guitar as my creative outlet.”
[00:21:29] Erich's Brother's View On Creativity
Listen to Nick Wenzel here:
#49 - Nick Wenzel: Graphic Communication and Encouraging Others
#50 - Nick Wenzel: Post Graduation
[00:22:46] Is Creativity An Innate Trait?
“It's not until something is thrown at you, do you get interested in it? So I wouldn't say that's like, some people are just curious, and some people aren't. I think the people who think they're not curious, probably just haven't been in situations where they're exposed to something that they find interesting.”
[00:25:58] Curiosity is Very Specific and Personal
[00:29:27] You Don't Have To Do Anything
“Everything you’re doing, you’re choosing to do. You need to understand that. Like never forget that you’re choosing to do this, and at any point. You can choose not to. You don’t have to. Just walk away from anything. There might be some consequences; more often, there’s not.”
[00:32:23] Skill Acquisition and Skills Across Domains
[00:38:15] Self-Reliance and Accumulating Knowledge
[00:41:58] World Citizen and Being Comfortable With Travel
“So I just, I had this idea around the age of 36, and it just wouldn't leave. It's like in that one moment that one.
Probably happened in an instant. I felt like I couldn't unthink this idea, and it shaped how I wanted to live the rest of my life. That's because, to me, it's so important to keep growing and keep learning and never get stuck into habits that hold me back. So ideally, I'd like to keep moving to more and more challenging places living in each one until it feels like it makes sense.
Right? Like, I'd love to move to a place that seems completely bizarre right now, right? Like Beijing, China. Yeah. I would love to move to Beijing, and I'm sure it would be incredibly frustrating and annoying and difficult, but then give it a few years, and it would probably just start to feel like home, like, yeah, this is, it's where all my friends are. I'm sure it would make complete sense. And then. Yeah. By the time after a few years, if Beijing makes complete sense, well, then it's time to move to Rio de Janeiro to another place that doesn't make sense and then do it again. And I think that that's a great recipe to always keep your brain, like to keep pulling out the rug from under your feet, you know?
And of course, there are other ways to do it. Of course, plenty of brilliant geniuses have never left Chicago. People way smarter than me are still in their hometown.”
[00:48:38] Taking the First Step to Travel
[00:54:55] Work Visa Under 30
[00:59:19] Counteract Tribalism
[01:00:23] Don't Confuse Medium With The Message
”I think we need to drop our assumptions. don't just assume that the common pairing. Is always true, right? So they don't confuse the media and with the message. Don't confuse the tool with the goal. Don't confuse the field. Calls the vehicle with the path. In those cases, what I'm referring to is, is my company, my company was the medium, the tool, the vehicle, but don't assume that I'm interested in business or profits or investors or any often goes with it.
But you see this in other professions too, right? Like someone could be a politician. Because they're greedy and they want glory, or someone can be a politician for very selfless social justice reasons. Right. You can't assume that musicians are necessarily creative, heart driven, people that live their life in chaos and sleep until noon every day.”
[01:03:20] Acknowledge Stereotypes
[01:05:27] Separating What You Do From Who You Are
[01:06:53] Gender Stereotypes
[01:10:24] De-exaggerate the Differences
[01:14:57] Within In One Place The Differences Feel Huge, But When You Compare Big Picture It Is Small
[01:17:26] Thinking Like A Scientist Or A Sports Fan
Learn more: The Thinking Ladder
[01:20:09] Thoughts On Parenting
[01:24:37] Learning to Trust as a Parent
[01:27:03] Giving Advice To Strangers
[01:29:03] Personality Tests
[01:32:05] Time Focuses
Recommended Book: Time Paradox by Phil Zimbardo
[01:34:32] Stoicism and Minimalism
Learn More: Stoicism | Minimalism
“I mean, I mentioned this where I said that ever since then, I was a professional musician from the age of 14 until 29, so starting at the age of 14. I really knew this is what I want. I want to be a successful musician. Yeah. And because of that, I was expecting my life to be hard. Like I knew I was never going to have a job.
I was never going to have a pension or, or health insurance or any of that stuff. So I knew that this was going to be a hustle. I knew that I wanted to be a successful musician. It's almost like wanting to be an Olympic athlete. Millions wanted only a few get it. So my whole approach to life ever since I was 14 was to like constantly, preparing myself for a more difficult future.
This means never choosing the luxurious choice, always like choosing to be deliberately hard on yourself too. To keep yourself tough. So even if times are not tough right now, just assume that they're going to be tougher in the future, and you want to be prepared. So that's just kind of like my approach to life all the way from the age of 14 until whatever, like this is how I approached life.”
[01:38:42] Don't Buy Into Isms Completely
[01:39:57] Don't Hold Your Beliefs or Assumptions To Tightly
Derek provided typed answers to all the questions asked as well!
>What does your writing process look like? When you get stuck, what helps you break out of it?
Writing isn't much different than many other pursuits.
When you get stuck on something, you try to break a big problem down into a smaller more specific problem.
If it's a creative problem, flip it over, consider the opposite.
If it's a stylistic problem, you don't have to be yourself. Pretend you're someone else, like a role model, and do what they would do.
If it's a life decision problem, try to describe the problem to a mentor, especially if it's someone who doesn't know you at all, so you have to summarize the entire context to a disinterested person. To respect their time, you have to be as succinct as possible. Then usually, by doing this exercise, by reducing the problem down to its essence, the answer becomes clear without you having to actually go contact some successful mentor.
> How did you become a citizen of the world? What would help get someone comfortable with travel if they have limited exposure or experience?
Even at the age of 36, I had no desire to travel. I was living on the beach in Santa Monica California, happy as can be. You couldn't pay me to travel. No interest at all.
But then ONE TINY IDEA got into my head:
That you really only learn when you're surprised. If you're not surprised, you may be taking in more information, but your mind isn't really changing. You change your mind when you find out your previous assumptions were wrong.
So one of the best ways to keep yourself surprised daily is to live somewhere very unlike what you know. Immerse yourself in different cultural perspectives. Very different ways of looking at life, communication, expectations, and values.
That idea wouldn't leave my head. I couldn't un-think it. It shaped how I wanted to live the rest of my life. It's so important to me to keep growing, keep learning, and never get stuck into habits that hold me back. So ideally I'd like to keep moving to more and more challenging places, living in each one until it makes sense and feels like home, then moving on to the next.
OK, now, my advice?
Start with somewhere obviously different, but that speaks your language. So if you're American, don't choose Canada, England, Ireland, Australia, or New Zealand. Those don't count. The cultural differences are so minor. Instead consider Singapore, in Asia. English is the first language, but the cultural values are very different. If Europe then consider Budapest or Lisbon.
Whichever place you choose, you have to integrate. Your default is to feel that they're doing everything wrong. You'll focus on the frustrations.
You'll accidently generalize. If one person is rude to you, you'll think people in this country are rude. But you don't do that at home. If one person is rude, you don't think everyone in your country is rude. You know it's just that one person.
Try to assume that the way you grew up is wrong, and this way is right. Try to assimilate as much as possible.
Stay at least three months. Get a visa and a job, if you can. Make some ties. Make local friends. Fall in love.
> You have many skills across domains many people wouldn't recognize as being useful together, but they have paid off. How do you look at skill acquisition?
When something's important to you, you should get to know the foundations of it.
You don't want to be at the mercy of a particular person, or a particular company, if something really matters to you.
I've been around long enough to watch companies disappear. Companies that people were depending on, that people had uploaded all of their stuff to. Next market crash, they're gone.
I've also felt the pain of being helpless when I was depending on an expert that was the only person who knew how to do something I needed, and that person disappeared.
So, I tend to learn things that give me self-sufficiency and independence where it matters most.
These things are different for everyone.
I don't depend on my car or my bike, so I'm happy to just pay someone to fix those when they break. They don't matter to me enough.
But I'm self-publishing my books, and don't want to be dependent on a graphic designer to do the layout, so I'm learning the core language behind that now.
For someone else, it might be vice-versa.
Learn the foundations of the things that are important to you.
> Writing a song isn't that different from writing computer code. It's all just having a little vision or spark of an idea, then seeing how you can make it happen — for its own sake».
> As an engineer and analytically minded, I hadn't viewed myself as a creative until recently.
> How do you re-frame creativity to able to categorize music and coding into similar spaces? I've also seen musicians in my field who are adept at understanding electrical circuits; it is fascinating.
Maybe it's a matter of who you're working for.
If I was the assistant to a Hollywood composer, then my boring uncreative day job might be writing music to match his specific requirements.
Then at night I might go home and play with computer programming to invent my own mobile app idea.
Or vice-versa. If I worked for a big company telling me exactly what to program, and I was just typing code, meeting specs, then maybe that wouldn't be very creative.
But going home at night and playing guitar would be.
For me, I do both for myself, so it all feels kind of the same. I have an idea for something I want to exist, then I go figure out how to make it happen.
I guess you could say the same about:
Architecture, building a house or furniture.
Accounting, figuring out how to structure accounts for a business.
Gardening, Landscaping, etc.
If you're doing it for yourself, making a vision come true, it feels as creative as anything.
If you're doing it for others, following strict instructions, not so much.
> What are your definitions of creativity and problem-solving problems for fun?
Sorry, no definition. Whatever seems fun. My kid wanted a Rubik's Cube a few days ago, so I bought it, then had to watch a video explaining how to solve it. I found it fun and fascinating, and a fun memorization exercise, so now I can solve a Rubik's Cube in 3 minutes.
A couple years ago I learned to speak Esperanto. Last week I learned a book typesetting programming language.
Even situations like this interview. You throw strange questions at me. I think about them, and try to come up with an answer that's interesting to both me and your audience.
> Now that I think creativity and curiosity seem like puzzle pieces that fit together
>How do you think of curiosity, is it something we can train?
No. Curiosity is very specific and situational.
My advice is if you feel even a hint of interest about something, go learn more about it. Because the more you learn, the more interesting it gets.
When you know nothing about a subject, it's hard to be curious because you have no questions yet.
But once you start learning, and have more context, you start having questions.
It helps to have a real need. Even a tiny one. Like I had no interest in Rubik's Cube, but then my kid bought one, so now I have it here, and have to solve it, so now I find it interesting.
This is a great argument for why people should get out of their comfort zones, and go do random different things, exposing yourself to completely different inputs.
> The quote at the end caught my attention:
“Don't confuse the medium with the message.
Don't confuse the tool with the goal
Don't confuse the vehicle with the path.”
> This is something I've been thinking about a lot over the last few months. I'm currently reading Amusing Ourselves to Death by Neil Postman and seems to fit right in with his thinking. How would unpack this passage?
I haven't read that book, but in my case I wrote that because:
Yes I ran a business, got surprisingly lucky, and made millions. But don't assume I was doing it for the money, or even wanted to have a business. Neither is true.
Drop your assumptions.
Don't assume the common pairing is always true.
"Don't confuse the medium with the message."
"Don't confuse the tool with the goal."
"Don't confuse the vehicle with the path."
In my case, my company was the medium, the tool, the vehicle. But don't assume I'm interested in business, profits, investors, or any of the stuff that often goes with it.
You see this in other professions, too.
Someone can be a politician for the greed and glory, or for selfless social justice.
Don't assume musicians are creative, heart-driven people that sleep in.
Acknowledge stereotypes, then unbraid them.
They're often not true.
Disconnect the outer action, appearance, or profession with your assumption about that person's inner motives.
> I would love to elaborate further on what being a parent has taught you and how you are raising him.
I don't have much to say about this. Again, it's all so situational.
I've seen friends who have three kids, and two are angels and one is Satan. A surprising amount of who people are is just DNA.
For me, being with my kid is like meditation. When I'm with him, I shut down my needs, and enter his world. He leads. I follow.
> Going back to parenting: How would you let a child explore the world?
> This we can make more general apply it more broadly. *How you encourage a student to explore the world?
There are some tiny techniques. Like anything they're physically capable of doing, let them do themselves.
When he was 5, I gave him some money to go across the street to our usual corner store by himself, to get something.
When he was 6, and we were living in a little enclosed neighborhood, I'd let him run off with the neighbors, and I didn't know where he was for an hour at a time.
Last week, at the age of 7, he started a fire in the fireplace without me knowing it, while I was making dinner. But he knew how to do it carefully because I'd taught him how.
All of these involve trust. First, preparation. Then optimistic trust that it's going to be OK.
It's a little scary but that's my problem, not his. I teach him that the world isn't scary. That he's capable.
> Personality Tests : One of the few categories you have on your website is Introvert, which is linked to - INTJ (I also fall into this category myself). *What are your thoughts on Meyers-Briggs and other personality assessments? (Big 5 Personality, Character Strengths, etc.)
Not much. It helps me understand others, though, by comparison.
I couldn't understand why anyone would want to run a marathon on the big day, with all the fuss, all the noise, the crowds, the clipboards, the walkie-talkies, when they could have just done that same run by themselves in wonderful peaceful solitude the day before. Then an extrovert explained to me how they get charged up by having all those people around.
Same with the time-focus. Some people are present-focused, and think mostly of today and this week. Others are future-focused, and live mostly in service of their future self.
It's really interesting to realize which sounds like you, then use it to compare to someone else's point of view.
> You self discovered minimalism and Stoicism as guiding philosophies and are one for healthy skepticism as well. *How did it feel that realizing you hadn't created something new?
(( First, re-tell context. Lived this way for 25 years before finding out it was a philosophy with a name. ))
But I wasn't trying to create something new. I just felt I was the only weirdo who approaches life this way. So to find out that there were ancient weirdos who pioneered it, and it's supposedly a desirable way to be, was kinda nice. But honestly no big deal.
I've never wanted to be part of a group. I would never subscribe to an ism. I can't relate to how some people go all-in on something, like they start doing yoga, and then start saying "namaste" and putting on a stereotypical tone of voice.
Even Stoicism. I read a couple books about it, got some good insights, but that's that. I'm not going to say it's my life philosophy.
> how you keep yourself from holding on to your views too tightly?
I'm disloyal to my past views, almost to a fault.
Whenever I learn more, I update my worldview. If it invalidates everything I've ever said or done in the past, that's fine. I don't mind. I don't care if people think I'm flaky.
In fact, I think it's pretty cool. It means I'm learning and changing, and that's ideal.
It's a top importance to me to challenge my old beliefs, and make sure I'm not stuck with old beliefs out of habit.
> I find your take on gender stereotypes illuminating because it cuts through much of BS when people bicker about silly things. *Elaborate on treating genders the same way. Has having more female friends ever thrown people off, or why do you think you have more female best friends?
(( First, re-tell context. Friend that says, "Oh you know how MEN are, always blah blah." ))
Social psychologists found that the differences AMONG men, and AMONG women are much greater than the differences BETWEEN men and women in general.
They also found that we have a natural human nature to tend to EXAGGERATE the differences BETWEEN groups, like that.
So, to think clearer, DE-EXAGGERATE the differences. Or take it all the way and assume ther're the same, knowing your human nature won't let you assume that all the way.
It's like throwing a frisbee, when you notice it always goes to the right, you deliberately aim to the left of where you want.
Over-compensate, to compensate.
