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40: Charles Broskoski - Everything is Personal

Nicholas
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All links and transcript: dialectic.fm/cab Are.na channel for this episode: are.na/jackson-dahl/dialectic-cab Charles Broskoski (Website, Are.na, X), aka Cab, is an artist turned entrepreneur and co-founder & CEO of Are.na, a platform for collecting, connecting, and self-directed learning. I created an are.na channel for all of the references I used in preparation for this episode. Charles began as an artist before becoming a software engineer, and started Are.na with many collaborators out of a desire to replace the now defunct del.icio.us after it was acquired by Yahoo. He and a range of collaborators have been working on Are.na for nearly 15 years, and he is now focused on it full-time, thanks to the platform’s 18,000 paying subscribers. While I’m not a longtime Are.na user, I discovered Charles by way of his talk / essay, “Here for the Wrong Reasons” and was enthused by his philosophy of attention and how the things we encounter shape us. Our conversation centers on patterns of noticing and what it means to know yourself through what you pay attention to, or as Charles calls it, your radar. We discuss creativity as decision-making, self-directed learning and research, and Are.na's channels as frames for what we encounter. We also talk about personal versus performative taste, opinionated design that still gives you space, building something that lasts, and why Charles believes creative people should start deeply personal businesses.

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Uploaded May 26, 2026
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Speaker A: I think the hardest thing is like basically knowing yourself. You have to sort of like get to that place first before you can make decisions that are correct. Being creative is about problem solving. Understanding one's own perspective is about finding a way to sort of like put those puzzle pieces together. You're looking at something from this direction, you're looking at something from that direction, like what's the crossover and how do you sort of like draw something out from those two? I really stand behind that idea that it's just about decision making, especially in the past 100 years being an artist is like Duchamp, it's like about making Making decisions, that's all it is.

You can do infinite things, you have to decide what you're going to do. When someone says taste is a skill, that is annoying because you're talking about something that is personal. It's something that you develop over a long period of time, and I just think taste is synonymous with understanding of one's own self. When you talk about it like a skill, then you put it in this sort of like arena of like competition, you know? Consider the possibility that working with your friends on something that you think is cool is like the most luxurious possible thing that you can do.

The reward is the work that you get to hang out with your friends and make something cool. I have like very distinct memories of being in class, looking at a textbook, like having to be in a certain chapter and just like flipping ahead to a different chapter that I knew would not be covered just because it's like, what's over here? And I think it's part rebellion, but part just like being interested. Speaker B: Welcome to Dialectic Episode 40 with Charles Braskowski. Charles is the founder of Arena, which he spent the last near 15 years building alongside a number of collaborators and co-founders.

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