Derek Sivers ( @dereksivers) has been a musician, producer, circus performer, successful entrepreneur, TED speaker, and book publisher. He has lived worldwide and never let himself be too comfortable – constantly changing and following his inner ambition.
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- Embracing Change and Self-Perception: how taking bold steps like booking a one-way flight to a new place can change your self-perception. You start seeing yourself as a courageous, capable individual who can live adventurously far from home.
- Travel as a Means of Self-Discovery: how travel can lead to new insights and Self-discovery.
- Challenging Conventional Paths: his unconventional path of pursuing a life in music and how it shaped him. He also mentions how he was influenced by Tony Robbins’ open-ended questions about what one really wants from life.
- Beliefs as a Means to Improve Actions: Derek discusses the idea of adopting certain beliefs not because they are necessarily true, but because they are useful in improving actions and achieving desired outcomes.
- Embracing Randomness: his influence by Brian Eno’s “oblique strategies,” a deck of cards with creative challenges that encourage embracing randomness and injecting it into one’s life.
- Redefining Ambition and Retirement: redefining ambition as the desire to be the ideal version of oneself and retirement as not working for money. He emphasizes the importance of internal growth and self-improvement over external validation and material success.
- Parenting and Lifestyle: the stress associated with parenting often comes from trying to fit a child into an adult schedule. He advocates for a more flexible approach to life when raising children.
- Useful Not True: Derek talks about his upcoming book, “Useful Not True,” which challenges the idea of clinging to beliefs because they are true and instead adopting beliefs because they are useful.
Derek’s Definition of Ambition Doesn’t Factor In “Other People” but is also because people “gave up” on him at 14
I asked Derek how he thinks about ambition, and Derek shared pretty openly about how he thinks about ambition and how that might have come from people “giving up” on him at 14:
Paul: I’ve also called it legible versus legible ambition. Huh? So legible ambition. My definition is your parents can tell their friends about what you’re up to. Legible 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: See, in all of my hours of thinking about this, I have never brought in. The subject of others. Who cares about others? Why? Why, why care what anybody else thinks? I’d honestly never even thought about it.
Paul: I’m much longer on the default path, Derek.
Derek: Well now it’s funny that you just mentioned this just now and I went like, Hmm. I was like taken aback…like others. So your parents, who cares what somebody else thinks?
No. 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.
Like, okay, let me put this into the second person. If you think about the skills that you really want to have, the talents you really wanna 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, um, 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. Um, you wanna be somebody that can stand up on stage and command a room. You wanna be somebody that can sit down in front of a blank computer terminal and make an app out of thin air from scratch? 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, especially if you take action towards it.
That’s ambitious to me. Like any idiot can buy a Ferrari, get a credit card, you go down to the shop and you hand them the card and they hand you the car and then you pay the debt. That takes no skill. To me. It’s, 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. 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?
Derek: 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 I always think that too, because I think I, in high school, grew up in an upper-middle-class suburb of Chicago. Um, and all the people around me were all in like that college pre-prep kind of course. And I was like; I’m not even going to college. I just wanna be a musician.
And they were all neat and proper and dressed nicely. And I had super long hair and denim jackets and Ozzie Osborne Iron Maiden heavy metal patches on my denim jacket. Um, so people gave up on me long ago, and that was great. They’re just like, Ugh, Derek, you know, like, he’s just gonna be a musician. Uh, so people gave up on me.
Nobody was expecting anything of me. Um, even my parents just gave up on me just like, oh, well he’s just gonna be a musician and. Maybe that’s why I, you know, since the age of 14, it’s like what anybody else thinks is, is moot.
Nobody’s expecting anything of me.
Derek’s Upcoming Book Is About Understanding That Things Don’t Have To Be True to Be Useful
Derek: I’m fascinated with this idea of believing, 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.
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 clinging onto that and you, because you feel it’s right and it’s true. Instead, I think we should abandon that whole categorization of truth 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, kinda like we said earlier about how some books can be deeply flawed and the author can be a jerk, and there can be misquoted, badly attributed 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. 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 know, you need to go to college. No, that’s not true.
You need to stay near your parents. Not true.
You need to 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 you can feel better about yourself or you can hire a nanny to help, whatever. That’s just a belief that you found useful.
It’s not true, and it just, this, this, to me, it, it also helps me break the rules in life. When people said things like I dunno 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 gonna work for me.
I just like went straight in through the back door and found my way in and got the gig and, and there are 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, you know, 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.
33k+ Sold! (Top 1% Book) The Pathless Path is Paul's book about walking away from a "perfect" job with a promising future and starting over again. Through painstaking experiments, living in different countries, and a deep dive into the history of our work beliefs, Paul pieces together a set of ideas and principles that guide him from unfulfilled and burned out to what he calls "the pathless path" - a new story for thinking about work in our lives. Learn More & Buy The Book Here