Derek Sivers On Real Ambition | Pathless Path Podcast

Hey all - just wanted to send a quick note about the podcast episode I dropped this morning. Also wanted to reshare this link that wasn’t working a couple of weeks ago in case people wanted to try again:

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Derek Sivers Doesn’t Like Following The Rules

I had a delightful conversation with Derek Sivers a few weeks ago. Derek has long been an inspiration with the way he seems to find secret portals to interesting ways to approach life. He also seems to be fully alive and excited about what he is creating, which is rare in today’s world.

We riffed on a number of topics including moving to a different country, ambition, looking to comfort as a cue to shake things up, why Brian Eno inspires him, and his theory on why parenting seems so hard.

Before the interview, Derek shared that he had watched Angie and my episode we recorded a couple of months ago which was pretty cool. When I first met Angie, Derek’s book Anything You Want was one of the first books we talked about in our first week of dating. It’s usually a good signal that we’ll get along if you like how Derek thinks.

I thought I’d share two of those things that stuck with me upon relistening today:

1. Derek’s definition of “real ambition” and why it’s easy not to care what others think

2. Why he thinks more people should focus on ideas that are “useful, not true” (also the name of his next book)

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#1 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, I grew up in like 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.

#2 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.