Derek Sivers on friendships that serve you & leaning into things you hate →

Derek Sivers has been a favorite thinker of mine for several years now, and this latest interview on The Tim Ferriss Show is no exception. Full transcript here. Two ideas I wanted to highlight:

1: Lean into things you hate (or thought you hated)

The theme is that if you feel completely averse to something, get to know it better, that whatever you feel yourself leaning away from, try leaning into. If you hate opera, then go learn more about opera. And if you hate sports, well, then go learn more about sports. It’s usually just learning about something gives you an appreciation for this thing that you used to just dismiss.

So now, it’s my — at the end of the year, last year, I just thought, “God, this has been, I think, maybe the greatest year of my life. I think this is the happiest I have ever been in my whole life.” And I think the reason why was because I had five major things in one year that I used to hate that now I love. I think, “God, this is the greatest joy.”

Derek is somewhat unique in the way he leads with curiosity. As he’s gotten older and wiser, he’s used this tendency to teach himself this lesson: if at first you dismiss something, use that as a cue to lean in and learn more about it. Worst case, you learn that it really isn’t for you. Best case, you found something new to love.

2: Find friends that challenge you

Tim Ferriss: I would actually build on that to say that I look to my close relationships, and I pause and question how I’m thinking about friendships if, in every case, there isn’t something substantial I disagree with each of those friends on.

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Tim Ferriss: I really want friends where the differences of opinion bring us closer, and make our friendships more valuable. Not the other way around.

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Derek Sivers: I thought about that in terms of the thought portfolio in our head. Any given person. So you say it with the friends you have around. But I assume, aren’t you then, by knowing your friends so well when you’re in a certain situation, you’re thinking about what to do. You don’t just have Tim’s thoughts. You also have this friend’s thoughts, and that friend’s thoughts. And it’s like, “How would this friend of mine approach this?”

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Tim Ferriss: And I think that in your new book, for instance, does a very good job of discussing perspectives, and perspective taking, and how you can read many things differently from different viewpoints. And you want friends who can help you do that, so that you don’t get trapped in your own thought loops. And furthermore, just on a very practical sense, you want to be able to speak truthfully to your friends, and you want them to be able to do the same. And if you do that, and you talk about a really wide breadth of things. If you never have conflict, one or both you is probably being dishonest.

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Tim Ferriss: And if you’re going to have some friction in the system, which you probably will if you’re really being honest. Then, you’re going to need to be good at conflict resolution, or repair, or talking about hard things. So that’s a very long stream of consciousness that I just let out. But if I look for friends who I can and will disagree with on things.

That’s a bit of a long series of quotes there but it’s just so good. When you disagree with friends and loved ones, you have an opportunity to learn, an opportunity to see the world from another perspective. To surround yourself with people who can teach you in this way, through disagreement, can give you a natural advantage when difficult or challenging or otherwise interesting things happen in your life: “how would so-and-so think about this?” That impulse to look at the world from other perspectives is like a superpower in this world of thought bubbles.

Highly recommend this episode, and every episode of Derek’s on Tim’s show. Their friendship is endearing & philosophical, and their conversations are such a joy to listen to.