Get Uncomfortable. Find Yourself.

Sometimes we need a little shove outside our comfort zones. Join world-traveling entrepreneur and best-selling personal development author Gregory Diehl as he leads his guests on introspective journeys about love, sexuality, relationships, drug use, travel, politics, spirituality, the meaning of life, and whatever it takes to deconstruct your fundamental sense of self. Prepare to be talked down to. Prepare to reconsider everything you thought you knew about yourself. Resolve the contradiction within you so that you can live a better life.


Latest Episode

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 April 2016 in an area between Croatia and Serbia which had been unclaimed by either country for many years. Unlike other emerging territories on Earth, there are no other claims to ownership on the land Liberland has been established on.

Founded primarily on libertarian values, the nation of Liberland is designed to cater to people who do not identify with the values of the place they were arbitrarily born into. Vít believes that people everywhere should be free to set up lives for themselves where they are free to live how they want, in line with their preferences and values. For most people in the world, their nationality and cultural values define their behavior and opportunities more than any other single factor in their lives. Without extraordinary effort to take these matters into their own hands by moving outside their culture and acquiring new nationalities, they remain slave to the social conditions of their birth.

What defines a nation today is nothing more than an arbitrary agreement among world powers of which boundaries matter and which do not. Throughout the world, there are over 100 areas which are considered disputed territories or demi-nations. Each is fighting for recognition among the leading world powers that are always in flux and generally taken for granted. The world does not have to look the way that it does, ruled by the groups that currently claim the power to make rules and raise armies to enforce their views. With changes in technology and philosophy, the layout of the world will evolve rapidly.

In its short lifespan, Liberland has acquired nearly half a million applicants for citizenship through its merit system, which will eventually award passports and citizenship to those who provide significant value for the development of the country. The team behind Liberland currently has the task of determining which of the many applicants adhere properly to the values they have declared for the nation, and which have earned the right to call themselves citizens by the time they are ready to start operating as an official part of the world political landscape.

Liberland is slowly being developed with physical structures and community activities, though it is still difficult to access the land. Currently, Croatia prevents entry into Liberland. In doing so, they are acknowledging that Liberland is a separate nation from itself. If Vít and his team go through the proper channels to establish their nationhood, Liberland will someday be respected by existing world powers as a real nation. Whether or not that ever happens, right now it still stands for an important principle of freedom and individual choice in how cultures evolve. Someday, nations will be far smaller and more personalized than the 196 monoliths we have now. Someday, they nations may be obsolete entirely.

Vít Jedlička, President of Liberland, Uncomfortable Conversations With Gregory Diehl
Vít Jedlička, President of Liberland, Uncomfortable Conversations With Gregory Diehl

Things mentioned:



Vít Jedlička



Montevideo Convention, rules for starting a country:


List of disputed territories in the world:


Artsakh, between Armenia and Azerbaijan:




Abkhazia, Georgia:






Unrepresented Nations and Peoples Organization:



Previous Episodes:

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

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

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

UCWG 037: How Can Losing Your Sight Enhance the Clarity of Your Mind? Using Blindness to Overcome Cognitive Bias with Isaac Lidsky, Author of Eyes Wide Open

Perception is never a passive process to take in the objective truth of the reality around you. In every moment, you are making educated guesses to construct an internal, conceptual

UCWG 036: Isn’t Life Coaching Kind of Bullshit? Finding the Good in an Infamous Industry with Marc Mawhinney of Natural Born Coaches.

Life coaching is an industry notoriously rampant with frauds and con artists who spout magic and creates cycles of dependency in the clients who come to them for help with

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

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

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

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

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

UCWG 30: How Do Heroes Test Their Resolve On The Mantle Of Reality? Internalizing Your Motivation and Finding the Will to Act in Any Situation.

There comes a narrative turning point in the life of the person who makes their development their highest priority. When you find your internal motivation, your actions become immune to

UCWG 029: How do Neuroatypicals Function in an Ordinary Society? Low Latent Inhibition, Divergent Thinking, and the Problem of Social Integration.

Natalie Marsh joins Uncomfortable Conversations With Gregory to discuss the problems of unconventional, exceptional thinkers trying to thrive in a conventional world. Neuro atypicals, including those with Low Latent Inhibition

UCWG 028: How Do You Find Closure With Your Emotional Baggage? Moving On From A Decade of Negative Associations And Unfulfilled Expectations.

At 17, Katharina Knoll experienced the brutal murder of her boyfriend – a traumatic experience that has lasted with her the last 11 years, coming back into her psyche periodically

UCWG 027: Are You Self-Aware Enough to Parent Your Own Offspring? Unschooling and Unconventional Child Rearing in Vilcabamba, Ecuador.

At age 33, Antonio Pondichi had gone from growing up poor in communist Romania, to move a comfortably luxurious life in New York City as an adult where everything he

UCWG 026: How Do You Experience Intimacy with the Various People in Your Life? Consciously Forming the Right Kinds of Relationships with Simone Sauter.

Simone Sauter is a veteran of Uncomfortable Conversations With Gregory. After her last appearance in UCWG 007: Why Do You Believe What You Believe About Relationships? she is back to

UCWG 025: What Would it Take to Destroy You? Breaking Out of the Prison of Comfort with Stacy Cross and The Comfort Killers.

The necessary first step to personal development is removing yourself from comfort, but very few so-called personal development leaders acknowledge this in their methodology. They keep their devotees steeped in

UCWG 024: What are the Processes and Objectives of Your Transformational Journey? 10 years and 100 Life Goals Accomplished by Tal Gur.

Tal Gur is an author and personal development professional who recently completed a transformational journey of spending 10 years accomplishing 100 specific goals around the world. He started at 31,

UCWG 023: Can Your Empathy Be Rational? Deconstructing Sociopaths and the False Dichotomy of Intellect and Emotion.

The guest today is a self-professed sociopath who believes that the more self-aware you are, the fewer emotions you feel. He claims that almost everyone with an IQ over 140

UCWG 022: What Would It Take for You to Kill Yourself? The Futility of Trying to be Bigger than Your Own Death.

Danny Flood is a writer, entrepreneur, and world traveler who chronicles useful information about life through his website, Open World Magazine. He joins Gregory to discuss two recent deaths: a

UCWG 021: How Can Life Be Happy, Perfect, Magical, Wonderful, and Comfortable All the Time? Feeling Good No Matter What Shitty Choices You Make.

Welcome to Comfortable Conversations With Gregory! On today’s extra special episode, we talk about how special and important you are and how to stay comfortable in any situation. Make sure

UCWG 020: Does Your Profession Align with Your Purpose? Matching Actions with Identity.

Alexa Glo is a 28-year-old multinational seeker of identity and meaning in life. She and Gregory discuss the importance of putting down roots and solidifying your identity on earth through

UCWG 019: Are You Accountable for Your Subjective Preferences? Identifying and Living Out Your Principles.

Today’s guest, Rolf from Germany, is a strategic consultant for expensive professional problems. Ironically, he does not trust his own subjective evaluation on some of life’s most important topics, such

UCWG 018: How Do You Find Where You Belong? Decentralizing the Powers of Society at Fort Galt.

Gabriel Scheare is one of the co-founders of Fort Galt, an intentional community project in Valdivia, Chile that seeks to give its inhabitants optimal freedom over how they participate in

UCWG 017: Is Your Personal Brand a Lie? Showing the World Who You Really Are.

Bobby Casey works in the controversial “offshore services” industry helping people structure their business and manage their money with little-known opportunities around the world. These kinds of activities have earned

UCWG 016: What is the Value of Human Life? Knowing Your Worth and the Fate of Society.

“The only way you can determine who deserves to live or die is to know what the point of life is.” Many have defined humanity’s essence or unique value by

UCWG 015: Do You Accept Yourself? Seeking Approval and Fearing Rejection from Others.

A young woman learns that the rejection she feared so much from other people was only a mask for her own missing self-worth.

UCWG 014: What Keeps You Engaged in Reality? Finding Your Authentic Narrative.

Travis Barton is a life coach from California. He felt that he was trapped on a singular path as a young adult, until he discovered that he was about to

UCWG 013: Where Do You Stop Examining Your Thoughts? Intuition and Rational Analysis.

Is intuition just unexamined thought? Or something beyond rational analysis? Many believe that when we get a strong feeling, a “deep inner knowing” about something that is contains a supernatural

UCWG 012: Will You Survive the Cultural Singularity? Third Culture Kids and Embracing Cultural Homelessness.

Gaby Kamp is a “third culture kid”, originally from the Netherlands, who grew up living in many countries throughout the world full time (most recently including Nigeria, Argentina, China, and

UCWG 011: How Do You Choose Your Identity? Influencing and Letting Yourself Be Influenced.

“As soon as I use words to describe myself, I limit myself.” Today’s guest, a young man named Josh Plotkin, enters the conversation with a prepared script of the identity

UCWG 010: Do You Own Your Darkness? Bringing Skeletons and Demons into the Light.

We live in a world that encourages us to acknowledge only the bright and positive parts of ourselves. We are trained to ignore or outright deny anything capable of causing

UCWG 009: How Does Culture Define Your Place in the World? Sacrificing Conventionality for Unconventional Fulfillment.

Greg Curtin left America in his twenties to see what the world could offer him with hardly a plan to means to sustain himself. Now in his thirties, he has

UCWG 008: Are You Living a Non-Contradictory Existence? Breaking Free From Your Idealized Conception of Self.

We all conceive of the world through generalizations and broad categories. It’s necessary for us to function as rational beings. But sometimes the categories we inherit actually hurt our ability

UCWG 007: Why Do You Believe What You Believe About Relationships? Resetting Conceptions About Love and Romance.

Simone Sauter is a life coach specializing in getting over heartbreak. She joins Gregory to discuss a recent bout of heartbreak that took even her by surprise. Together, they try

UCWG 006: Does Knowledge without Power Lead to Idle Suffering? Matching Intellect with Boldness of Action.

Very often, our greatest suffering stems from our ability to conceive of things we cannot obtain. The explorers who feel this great pain must either suffer with it internally or

UCWG 005: Are You Willing to Abandon Your Sacred Cows at Any Age? Leaving the Jehovah’s Witness Cult and Your Own Family at 38.

Are You Willing to Abandon Your Sacred Cows at Any Age? Leaving the Jehovah’s Witness Cult and Your Own Family at 38. It’s often the case that we assume any

UCWG 004: How Do Artists and Intellectuals Love and Create Differently? Finding the Common Ground in Dichotomous Ideologies.

The more familiar we get with one way of seeing things or interpreting information, the easier it is to forget that not everyone shares our perspective. This difference is perhaps

UCWG 003: Is Your Identity Strong Enough to Overcome the Stories That Consume You? Making Peace with Trump’s Presidency and Other Negative Interpretations.

Do you know what you care about? Are you so sure in you principles, mission, and values that you are immune to interference from the chaotic events of the world

UCWG 002: What is the Opportunity Cost of Wanting to Experience Everything? The Consequences of Spreading Yourself Too Thin.

Asha, the wife of guest Eddy from last show, continues the conversation about polyamorous marriage from the female side of the equation. She describes her lust for new experience as

UCWG 001: How Many Dicks Would You Have to Suck to Know You Weren’t Gay? The Practical Limits of Exploration.

There’s an ongoing debate around the world about the nature of homosexuality. Are you born a certain way? Is it possible to turn yourself straight or gay through willpower and