Conversation with David Cain

David Cain, the mind behind the popular blog Raptitude, is a writer I’ve looked up to since my first days in the blogging world. It’s not surprising at all to see his philosophies and musings get more and more exposure as time goes by. He’s one of the deepest and kindest thinkers online.

David and I have known each other for years now, but we never got a chance to have a good, long conversation about philosophy. That’s why I was elated when he agreed to record one on Skype for my site. This conversation is simply spectacular, and it gets better and better as we start exploring and connecting more topics. I had this call for the selfish reason of getting some quality time with David, but the product is something anyone that thinks about life and humanity can enjoy. 100% recommended.

Some of the topics we discuss:

• David’s famous 30-days self-improvement experiments, and his thoughts on habit implementation.
• Our thoughts on bucket lists as a way to measure someone’s life, and as a motivational tool.
• Our philosophies on stuff, things, and the material.
• Why I don’t have a car or know how to drive.
• Our thoughts on the stress/distraction of technology, and how to cripple it.
• Our thoughts on why people don’t do what they love: attachment to security, lack of clarity, and the connection between clarity, incentives and security.
• The problem with fluffy self-development.
• Why David believes that us and our friends dying is a good thing, plus a great mental exercise on appreciation.
• Thoughts on taking things for granted, stoicism and negative visualization. The connection between our stoic philosophies with the way we think about stuff and things.
• The connection between our dissatisfaction and evolution. Appreciation goes against our biology.
• The problem with believing in evil.
• Why I believe misrelating is the biggest problem in the world, and the biggest disappointment of adulthood.
• Simplicity as an obstacle for our learning process.
• Our solution to save the world: Self-examination.
• The problem with labels: simplification of complex individuals, communities, cultures, etc. People not liking to be replaced by patterns or symbols.
• On society’s dislike to see some questions asked.
• The effect society’s design has on our decisions. We’re not allowed to think independently because of poor design.
• World’s complexity and our need for safety makes us resort to simplifications, despite of the terrible effects.

More about David:

David’s blog: Raptitude
David’s Experiments
David’s Bucket List
David on Twitter