Skateboarding Rules, Constraints, and Play

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.

I hope you are inspired to be generous and scrutinizing with your attention, to create things that are personal and durable, and to remember that knowing yourself is a worthy journey of a lifetime.

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Dialectic is presented by Notion. Notion is an AI-powered connected workspace where teams build their best work. Notion is also where I compile research for episodes and where you can find all links and transcripts. You can learn more at notion.com/dialectic.

Special thanks to Earshot in NYC for hosting us for this conversation.

Timestamps

• (0:00) - Opening Highlights
• (1:21) - Intro: Charles Broskoski
• (4:00) - Thanks to Notion
• (5:26) - Start: Creativity as Self-Knowledge and Problem-Solving
• (13:37) - Self-directed Learning and Casual Research
• (21:33) - Skateboarding, Being a Beginner, In Defense of Posers
• (33:26) - Contextual Patterns and Channels
• (45:54) - Nodal Points, Your Radar, and Careful Attention
• (1:04:57) - Subjectivity, Self-Knowledge, and Taste
• (1:15:09) - Performance: Here for Fame and Not Love
• (1:22:53) - Aspirational Attention
• (1:29:02) - Designing Generous Tools
• (1:42:44) - Space in a Product and Fading into the Background
• (1:50:01) - Why Creatives Should Be Entrepreneurial & Building an Independent Business Online
• (1:54:11) - Patience, Durability, and Antifragility
• (1:59:48) - Personal Businesses
• (2:10:27) - Grab Bag: Authenticity, Bohm Dialogue, Skateboarding, and Keeping Things Personal
• (2:28:28) - Thanks Again to Notion