UCWG 040: What if You Could Design Your Own Country? Starting a Sovereign Nation from Scratch with Vít Jedlička, President of Liberland.

  Vít Jedlička is the president of the world’s youngest country. His new micronation, the Free Republic of Liberland, is only three square miles in size. It was established in

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UCWG 039: How Do You Take the First Step of the Exceptional Path? Overcoming the Burden of Lifestyle Choice and Arriving at Your Own Authentic Values.

A regular listener of Uncomfortable Conversations With Gregory joins the show to have an emotionally vulnerable discussion about breaking away from the ordinary life she is trapped in. She learns

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UCWG 038: Why Do Men Today Fail to Develop Mature Masculinity? Reclaiming the Masculine Essence with Nate Lind of Legendary-Man.com

Today, more than ever, there seems to be a growing culture war between masculinity and femininity in society. Men are starting to feel threatened by the growing presence and empowerment

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UCWG 035: How Does Looking at the World as a Single Destination Transform You? Developing a New Philosophy of Travel with Nicos Hadjicostis, Author of Destination Earth.

Nicos Hadjicostis wrote the book Destination Earth after traveling to more than 70 countries in 6 years in his 40’s. His goal was to learn to look at all of

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UCWG 034: Why Should Anyone Give a Damn About Spiritual Enlightenment? How Meditation, Meta-Cognition, and Linguistic Relativity Shape the Egoic Self.

Alexander, a young man struggling to express himself fully after reading Gregory’s book (Travel As Transformation), returns to Uncomfortable Conversations With Gregory after his appearance in UCWG 006: Does Knowledge

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UCWG 033: Are Disruptive Events Essential to an Exceptional Life? Young People Escaping Conventional Career Paths with JC Preston of New Inceptions.

There are two kinds of people in the world: those with the qualities of leaders and those with the qualities of followers. Many who are naturally leaders do not have

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UCWG 032: When Does Personal Development Evolve into Interpersonal Development? Collaboration Among Those Who Share Your Values with Parker Harris of Junto Global.

  Our culture loves telling the story of one man taking on the world, working hard to do everything for himself. We build our movies and our myths around this

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UCWG 031: Do You Dare To Follow Your Hero’s Journey to Find Self-Actualization? Life Purpose As The Highest Priority With Leo Gura of Actualized.org

Leo Gura is the founder of www.actualized.org, and the host of a popular Youtube channel on finding your life’s purposes and deep spirituality beyond stories. Leo and Gregory discuss the

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Shatter the flow of your unfulfilled life.

You cannot solve the problems of your existence with superficial pursuits that perpetuate the life you already know. The existential cause of deep suffering is a profound life spent without

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Challenge how others categorize you.

An ordinary person is so afraid to define himself that he stumbles accidentally into whatever social function resists him the least. Never going too far in any direction provides safe

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