Welcome to this classic episode. Classics are my favorite episodes from the past 10 years, published once a month. These are N of 1 conversations with N of 1 people. Kevin Kelly⁠ co-founded Wired magazine and has published a number of seminal books and essays on technology over the past three decades. I have devoured everything Kevin has put out into the world and many of his ideas shape the way I live today.

Our conversation explores media, family, money, his concept of the Technium, AI, and more but the central theme of this episode is that we should be as generous and unique as possible. You will hear us refer to his latest book, Excellent Advice for Living, throughout and I highly recommend reading it if you haven’t already. Please enjoy this great conversation with Kevin Kelly.

Colossus Profile on Kevin Kelly: Flounder Mode

For the full show notes, transcript, and links to mentioned content, check out the episode page ⁠here⁠. 

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Show Notes

(00:03:05) ⁠Excellent Advice for Living⁠ - a journey towards authenticity

(00:05:05) Uncovering the essence of oneself is a lifelong journey of self-reflection

(00:06:47) What he would have done differently at 30 had he internalized this concept earlier

(00:08:51) The highest form of self-expression is being authentically unique and redefining success

(00:11:05) Conforming to others' definition of success and societal biases hinders progress

(00:13:07) Surrender and collaboration are both essential in becoming your authentic self

(00:14:38) Prototype your life to embrace imperfections and make ideas tangible

(00:17:34) Mastering cultural photography in Asia and developing a keen ability to spot trends

(00:19:59) Energy signatures reveal depth, breadth, discovery, and momentum  in events

(00:22:02) The reward for good work is more work

(00:23:42) Money is a tool for doing things, but beware its imprisoning burden

(00:28:35) Imagination can be cultivated and improved, often by challenging expectations

(00:31:38) Imaginative individuals include lateral thinkers who challenge norms

(00:34:41) Rites of passage and rituals provide stability and identity for children

(00:38:15) Mealtime without screens, family traditions, and cultivating a family identity

(00:41:44) An overview of “The three gates”

(00:43:02) Humans are naturally kind

(00:47:23) The Technium: an evolving ecosystem of interdependent tech and their tendencies

(00:52:01) Thoughts on AI

(00:55:55) Overestimating the existential threat of AI

(00:57:38) Idiosyncratic expression of creators

(00:59:48) Lessons learned about media

(01:01:34) Be the only, not the best.

(01:05:09) The kindest thing anyone has ever done for Kevin