Uncomfortable Conversations With Gregory



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.


  • UCWG 040: What if You Could Design Your Own Country?

    18/08/2017 Duration: 40min

    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

  • UCWG 039: How Do You Take the First Step of the Exceptional Path?

    10/08/2017 Duration: 01h04min

    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 that as much as she knows what she doesn't want from her life, she has never seriously considered what she actually values. She has had no rational way to take the first step away from familiarity and embrace the unknown. The nature of living in a complex society is such that it seems nearly impossible to extricate your life from the constantly moving pieces of the machinery you have grown to live as part of. Stay stuck in the motion too long, and it becomes impossible to envision what your life can look like beyond its boundaries. As a result, even the people who begin to realize that there is more to their identity than what they have been told can never figure out how to take the meaningful first step away from the life they already know. They only know that that do not want to repeat the defining values they alre

  • UCWG 038: Why Do Men Today Fail to Develop Mature Masculinity?

    01/08/2017 Duration: 51min

    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 of women, just as women are losing touch with their feminine nature as they are pushed to take on masculine roles coercively. Nothing is in its right place anymore, and society suffers because we have lost the natural balance between us. Masculinity does not have to look like any one stereotypical role in society. It is an agreement which changes over time and across cultures. Every society on Earth has a somewhat different idea of how a family unit ought to function, how men must bond and work with each other, how courting and marriage works, and so on. Beyond the cultural rules of how men ought to act, there is an evolutionary generalization of traits that men tend to hold in greater quantity than women, for better or worse. The same traits applied in different ways or managed incorrectly can shift from being massive assets

  • UCWG 037: How Can Losing Your Sight Enhance the Clarity of Your Mind?

    28/07/2017 Duration: 01h07min

     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 understanding of the world. You frequently mistake this conception for the genuine article. You take this for granted. Isaac Lidsky went from being a successful teenage actor on TV to losing his sight and learning to reassess every unconscious assumption he had about life as a result. Isaac contends that going blind the way that he did is one of the best things that ever could have happened to him, as he learned to see his life beyond the illusions of his mind that would have kept him a prisoner of bad luck and circumstance. As Isaac began to lose his sight gradually over the course of more than a decade, he gained uncommon insight into the layers of meaning his mind automatically added to his perception. As micro blind spots formed in his vision, his brain would do everything it could to immediately compensate for them, often wi

  • UCWG 036: Isn’t Life Coaching Kind of Bullshit?

    21/07/2017 Duration: 54min

    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 their personal problems. They rarely teach systematic solutions and genuinely help people reach new levels of independent thinking. Their income depends on their clients coming back to them over and over for more coaching, instead of moving on to greater things. Marc Mawhinney is a coach who coaches coaches, helping them build better business models and promote themselves in their quests to tell other people how to live. He joins Gregory to discuss what’s right and what’s wrong with this strange and modern industry.   According to Marc, a professional coach is just someone who helps someone else accomplish a specific goal. Marc believes that coaches who offer real value in the attainment of strategic goals should price their services on packages related to those goals, not act as an ongoing crutch for emotional support. Lesser-known life co

  • UCWG 035: How Does Looking at the World as a Single Destination Transform You?

    15/07/2017 Duration: 01h05min

    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 earth as though it were a single destination, beyond arbitrary national and cultural borders. His book, and Gregory's own Travel As Transformation, are a rare type of book to explore the philosophical implications and profound personal transformation made possible only by travel. Though Gregory and Nicos agree on many things, there is still a world of differentiated nuance in the conclusions their respective journeys have brought them to. Gregory’s book is written from the perspective of a naïve young Californian man rapidly coming to realize how much bigger the world is than he was ever led to believe. Nicos’ book is written by a man approaching middle age who already had a wealth of practical and philosophical expertise on the world. Both books are predominantly philosophy books, presented through the categorical structure of travel experiences. They a

  • UCWG 034: Why Should Anyone Give a Damn About Spiritual Enlightenment?

    07/07/2017 Duration: 02h09min

     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 Without Power Lead to Idle Suffering? to carry the dialogue on from their first conversation about being bold enough to pursue the interests of great intellect. The conversation this time around gets much more personal to both Gregory and Alexander’s unique perspectives on themselves and interaction with the people of the world, eventually coming to a head for the purpose of meditation and enlightenment. The world is composed of only two things: experiences you are prepared to handle and experiences you are not prepared to handle. When an event that is outside your unconscious expectations comes into your life, you shift your conscious attention toward it so that you can figure it out and learn how to apply it in your life. This necessarily slows down your thought processes, however. Whenever t

  • UCWG 033: Are Disruptive Events Essential to an Exceptional Life?

    29/06/2017 Duration: 44min

    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 the bravery required to act on their leadership qualities. They need an inspirational influence. They need a catalyst to awaken them to the powerful actions of which they are capable. JC Preston runs New Inceptions and the Angles of Lattitude podcast, where he shows young people how to acquire the qualities of leadership and self-direction in life. Most people have their leadership qualities suppressed by the traditional Prussion educational model almost everyone goes through in children. Society breeds followers and conformity, making those who do not naturally follow suffer immensely throughout life. Evolution on a sociological level happens much slower than it can on the level of the individual, so there will always be resistance when the two do not align in their acceleration or trajectory. Without hope, individuals are almost certain to succ

  • UCWG 032: When Does Personal Development Evolve into Interpersonal Development?

    24/06/2017 Duration: 01h13min

    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 archetype, and then unconsciously model it in our own lives. Useful as this type of path is, and even a necessary starting step, what comes next in the heroic journey? The lone warrior must eventually learn how to deal with other people. He must form a tribe of ideas and perspectives that complement his own. He must be humble enough to know that however capable he is on his own, he will be more capable with the help of others. This humility only comes after he has earned healthy pride. Parker Harris runs Junto Global, a networking organization for high-performing, high-ambition entrepreneurs dedicated to creating massive change in their lives and the world. Inspired by Benjamin Franklin’s meetings about 12 of his most respected and intelligent peers, Junto aims to enable individuals to act beyond their solo potential. This is a step that many capable indi

  • UCWG 031: Do You Dare To Follow Your Hero’s Journey to Find Self-Actualization?

    16/06/2017 Duration: 01h08min

    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 mythological principles of the Hero’s Journey, and what on earth all of that has to do with the path to finding one’s true self in life. Most people attempt to solve existential level problems with superficial ego-serving solutions that, at best, temporarily alleviate the symptoms of being non-actualized. They ignore the existential cause of deep suffering. Spirituality is reduced to emotionally jarring clickbait titles because real analysis challenges the ego instead of feeding it. Most marketing is design to appeal to the ego, therefore distracting from raw truth. Self-help authors prey on the weaknesses and fears of their audience. They don’t promote true growth and self-actualization. People stay stuck at one level of development and are never able to go after what they really want in life. Without solving the surface lev

  • UCWG 030: How Do Heroes Test Their Resolve On The Mantle Of Reality?

    09/06/2017 Duration: 01h04min

    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 circumstance. But you can only reach this point through painful self-discovery. Veronica Kirin is an entrepreneurial success coach for women, an anthropologist, and the creator of an upcoming book featuring the life lessons of the “greatest generation” who grew up before our present technological abundance. Veronica and Gregory embark on a journey of understanding why we act the way we do, and how we use the tools of our world to get what we want. The new Wonder Woman movie tells the story of an idealistic hero whose motivations are faulty because she has no real world experience to test them against. By the end of the movie, after suffering great misery and having her motivations tested through trials, she realizes she now acts for a different reason. She isn’t acting to save other people for their sake or because they deserv

  • UCWG 029: How do Neuroatypicals Function in an Ordinary Society?

    03/06/2017 Duration: 01h25min

    Natalie Marsh joins Uncomfortable Conversations to discuss the problems of unconventional, exceptional thinkers trying to thrive in a conventional world. Neuro atypicals, including those with Low Latent Inhibition (LLI), Autism, ADHD, and so on, must learn to construct their own societies in a world not made for how they naturally are, in spite of their great gifts.   From the episode of Prison Break where Michael Scofield is diagnosed with Low Latent Inhibition: "People who suffer from low latent inhibition see everyday things like your or I do…but where we just process the image…they process everything. Their brains are more open to incoming stimuli and the surrounding environment. Other people’s brains, yours and mine, shut out the same information. We have to do it in order to keep our sanity. If someone with a low IQ has low latent inhibition, it almost always results in mental illness. But, if someone has a high IQ, it almost always results in creative genius." A genius is someone who is able to push th

  • UCWG 028: How Do You Find Closure With Your Emotional Baggage?

    27/05/2017 Duration: 01h03min

    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 as various events remind her of the event. Painful memories continue to haunt her without resolution because she has not learned to fulfill the expectations which had been cut short by his untimely death. The great struggle Katharina must go through now is to examine the arbitrary associations she has adopt with her past trauma. Specific people, dates, and symbols only serve to bring back the negative emotions that keep her trapped in pain. She must learn to see things as they are and replace harmful associations with useful ones. It is necessary for every truth-seeking person to become highly aware of the meaning they add to their observations in the realm of their minds. No matter what you do, you are adding meaning to experience. You need to figure out how to optimize your meanings and make them work for you instead of against yo

  • UCWG 027: Are You Self-Aware Enough to Parent Your Own Offspring?

    22/05/2017 Duration: 01h16min

    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 ever needed was planned for him. One day, as his daughter reached age 5, he began to realize that many of the things he had been taught about how to live and raise her weren’t true. He moved his family and his life to the valley of Vilcabamba, Ecuador to explore unconventional ways of living that would allow all of them to find their happiness. Many parents don’t realize that they are giving away the majority of their children’s upbringing to strangers who run the arbitrary schooling institutions of their culture. Schooling trains people in what to think, whereas a true education teaches people how thinking works. We can either acquire knowledge through inheritance from other sources or observing and reasoning it ourselves. The social environment of schooling is frequently destructive to self-esteem and normal bonding habits. Segregating children

  • UCWG 025: What Would it Take to Destroy You?

    07/05/2017 Duration: 50min

    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 comfort and enthusiasm. What many people miss is that the willingness to be unhappy is what increases your overall capacity for happiness. Stacy Cross is a personal and entrepreneurial development coach who founded The Comfort killers. Stacy received an email one day from a stranger deriding her for all the lifestyle mistakes she was making. That email became the seed for rapid personal transformation. She has embraced discomfort as a lifestyle and used it as a tool to overcome gambling addiction and change her entire lifestyle. Now she helps other people do the same with their own lives. Social cohesion can be the enemy to personal development if you allow other people’s stories about you to replace your own self-awareness. Social sacrifices must be made to embrace one’s own development as their highe

  • UCWG 024: What are the Processes and Objectives of Your Transformational Journey?

    28/04/2017 Duration: 53min

    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, and is now ready to share what he learned in his upcoming autobiographical book, The Art of Fully Living: One Man, Ten Years, a Hundred Life Goals. Tal devoted each year of his decade-long journey to a different aspect of his personal transformation. He learned that going to uncomfortable extremes could teach him more than staying in the comfortable middle of any domain. Transformation is not random or spontaneous. It is cumulative and logical. We move in sequence from one change to another according to patterns and rules. Most people are not in tune with their own minds, bodies, and emotions, so they do not know the right path for themselves. Tal had to learn through his many trials how to get in tune with himself to find his authentic core. Not everyone has to spend 10 years pursuing 100 goals to find themselves

  • UCWG 023: Can Your Empathy Be Rational?

    18/04/2017 Duration: 01h10min

    The guest today is a self-professed sociopath who believes that the more self-aware you are, the less you emotions you feel. He claims that almost everyone with an IQ over 140 will have symptoms of an antisocial disorder like sociopathy. Sociopaths are superior because they have greater awareness of their emotions. Psychopaths are inferior because they are slaves to their emotions. A psychopath’s emotions are defined by violence and destruction. That is how they achieve ecstasy. There is a difference between being unable to feel something and simply not finding it useful. Generals in wartime have somehow recalibrated their emotions to justify the killing of soldiers. People who think they rely entirely on reason to dictate their actions fail to see the reason behind their most powerful emotions. Reason only matters when you’ve defined a goal. Change your goal and the validity of your actions changes too. Emotions are not social constructs. They are not imaginary, counterproductive, or unimportant. What matter

  • UCWG 022: What Would It Take for You to Kill Yourself?

    11/04/2017 Duration: 01h12min

    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 suicide by Gregory’s hometown friend and an adventurer named Justin Alexander who never made it back from one of his more dangerous trips. Hope is the belief in random, positive change – the idea that the unknown future can be better than what you currently have. If you’re at the end of your rope, why not throw yourself into an experience you’ve never had before? What have you got to lose? Our culture of death is to bury and get away from it as fast as possible because we cannot stand the reality of it. It doesn’t matter what people say about you when you are gone. It only matters how you perceive your own life. A better question to ask yourself is how the world will be different because you ever existed. You forget 99.999% of the things that ever happen to you. Only the memories with strong emotional ties remain in yo

  • UCWG 020: Does Your Profession Align with Your Purpose?

    27/03/2017 Duration: 53min

    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 your actions, which often means your professional path in life. Home is where you feel most like yourself. Being outside your home is what gives you the perspective to know your home. The contrast of being something other than what you are is ultimately what shows you what you are. Purpose is a principle, not a specific task you perform. Tasks are defined by your culture, which is always changing. There is always another way to express your purpose. You perform your purpose because of the energy it gives you, not to fulfill a social role. You have to give people what they are ready for. They can only be ready for so much as any given time. Professions are outdated concepts. There is no law of nature that says you have to spend your entire life in one kind of productive role, just as you do not have to live your whole life i

  • UCWG 019: Are You Accountable for Your Subjective Preferences?

    19/03/2017 Duration: 01h38min

    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 as the worth of specific human lives. He states that he would rather flip a coin on certain life and death situations that be the one to make important decisions and live with the consequences. Yet, in other more menial areas he has no qualm about choosing and standing by his decisions. In the political domain people frequently use words like “human rights” to defer responsibility away from their opinions and acting as though their preference were a natural law. Thus, nearly everyone is constantly at odds with everyone else about their idea of the natural order of things, and conflicts go forever unresolved. If instead they could own their statements as merely their own preferences, a common solution would become more obvious and available to everyone seeking something different. Accuracy is not always the sam

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