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 018: How Do You Find Where You Belong?

    08/03/2017 Duration: 01h34min

    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 society. He and Gregory discuss the project’s unfortunate origins in a similarly-named fraudulent operation known as Galt’s Gulch Chile, and aspirations of everyone involved to bring the power of society back to the hands of creative individuals instead of centralized government organizations. Gabriel discusses the underlying philosophical implications of how his small team went from “Wouldn’t it be cool?” to “Let’s fucking do it!” to create a plan for their own micro-society in a world of in optimal social interactions. We cover how in a moral and reasonable society, individuals are free to form their own groups and associations based on what is appropriate for their goals. In a right society, we can build long-term relationships on trust on respect instead of taking advantage of each other for immediate gain. But this is o

  • UCWG 017: Is Your Personal Brand a Lie?

    01/03/2017 Duration: 58min

    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 great scrutiny from the mainstream financial world due to the misinformation, trickery, and illegal actions they are often associated with. Bobby shares stories from some of the less reputable contemporaries in his niche that have conned unsuspecting clients out of tens of thousands of dollars through phony passport or land buying scams. “It’s important to be ethical with your personal brand.” No matter what industry you work in or kind of life you lead, everyone is playing a character role in the narrative of life. Some get so good at telling the story of who they want the world to perceive them as that meeting after getting to know them through the false persona they create is often disappointing. The people who make the most effort to posture themselves in a certain way publically are often

  • UCWG 016: What is the Value of Human Life?

    19/02/2017 Duration: 56min

    “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 simple factors like consciousness, intelligence, or self-awareness. But what do these standards imply for the whole of human civilization? Societies are organized around collective ideas about what the purpose of life is, or their utility in life toward each other. Every time you interact with another person, it is for a specific purpose. You expect a specific type of outcome. What determines success or failure? People need to migrate to circumstances or group settings where they will be found useful. “If everyone were accountable for their own actions and nothing else, the world would be in a lot better shape.” Who owns humanity? Who makes the decisions determining its fate? A dictator? Some other governmental entity? Or is it everyday people like you and me, each living out our own rules for engagement with one another? In the end, every comes down to the

  • UCWG 015: Do You Accept Yourself?

    10/02/2017 Duration: 59min

    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?

    05/02/2017 Duration: 57min

    Travis felt 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 rewrite his own narrative however he wanted. This lead him to question what it was he would do if he had no social pressure to follow any specific path. Travis invokes the Japanese concept of “ikigai” - combining what you love, what you’re good at, what the world needs, and what you can get paid for - into something resembling a purpose for the narrative in your life. Other people often impose mental barriers on us because they are either jealous or they simply do not want to accept that the way they view things is incorrect. Gregory expresses his frustration at experiencing diminishing returns in personal growth by running out of mind-altering new experiences to pursue. He challenges Travis to challenge him. Does everything you ever do have to be part of your singular life mission? Or can it just be something you philosophically support? One of Gregory’s purpo

  • UCWG 013: Where Do You Stop Examining Your Thoughts?

    01/02/2017 Duration: 01h04min

     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 element that warrants respect and validity. To know what you think you know, you must locate your axioms of interpretation - the fundamental acceptances you use to understand everything else. They hold a sacred spot in your life beyond doubt or analysis. Michael Light (pen name of Michael Smith) is the author of the recent book Intuitive Leadership Mastery: How a CEO Doubled Profits and Halved Stress. He argues that intuition, if properly developed, can be one’s greatest tool for making effective decisions in business and life. Gregory takes the opposite approach, claiming that whatever true conclusions can be arrived at through intuition and feelings can be better refined through intense logical analysis of the factors in play. The two attempt to determine at what point it becomes impractical to continue this analy

  • UCWG 012: Will You Survive the Cultural Singularity?

    28/01/2017 Duration: 46min

    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 Northern Ireland). She works professionally to coach others looking to adopt this mentality and lifestyle. She and Gregory discuss how cultural borders (whether physical, mental, political, or technological) are growing weaker and more arbitrary with every passing year. At such an accelerating rate of change, it is conceivable that within a few generations collective cultures as we have always known them will cease to be relevant.Every aspect of human life on earth is changing at an accelerating rate. Parents will not know how to keep up with their kids who live in a multicultural new world. Individuals must choose to constantly challenge their own comfort limits if they are going to keep up with the changes. Citizenship is supposed to define your allegiance to a country, just as where you learned your cultural values i

  • UCWG 011: How Do You Choose Your Identity?

    23/01/2017 Duration: 01h10min

    “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 (or his case non-identity) that he wants the public to associate him with. The longer he talks, the more clear it becomes that he uses generic descriptions of himself to cover the fact that he doesn’t want to limit himself through specific values and actions. He meanders from thought to thought without any consistent meaning or theme. When he talks about himself, his words are ambiguous and light hearted. Most people are so afraid to define themselves to any meaningful degree that they are forced to fall back on a generic definition they inherited. They prefer to think of themselves as being “one with the universe”, a manifestation of “God energy”, or expressing their “highest level of consciousness”. What these generic terms do is function as a safety net from real analysis of values and actions. They safeguard us from having to take real r

  • UCWG 010: Do You Own Your Darkness?

    19/01/2017 Duration: 46min

    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 great sadness, sorrow, suffering, rage, or negativity of any kind. We run from the dark side of the force. David portrays himself as an overly positive man in his thirties. But under that shiny surface in another world of emotional capacity. Among other things, he is afraid to admit he is like his father, who he resents for not being a good husband to his mother. Many of the same patterns show up in his own relationships with women, though he doesn’t equivocate them at first. He is ultimately afraid to show his negative emotions in anything other than a neutral tone and a list of synonyms to eloquently express his unhappiness. He resorts to describing his negative feelings only one word at a time in a very controlled state. “Skeletons in the closet” and “demons” are conceptions of the past that we refuse to let fade away with the natural fl

  • UCWG 009: How Does Culture Define Your Place in the World?

    14/01/2017 Duration: 01h37min

    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 traveled around the world eagerly taking jobs wherever he could find them, always finding a way to keep himself afloat and pursuing his myriad passions. This lifestyle has carried with it obvious and non-obvious challenges alike. Aside from constant acclimation to new cultures, Greg learned that he could never reintegrate back to where he came from. He experienced extreme alienation from your own peers for seeking an unconventional path. Because he dropped out of school, he would never be able to easily return to the standard education or career path. He now existed in a cultural void where there was no carved out space for him and he was free to act however he wanted, for better or for worse. We are all unconsciously shaped by the role our immediate culture carves out for us. Our skin tone, gender, attractiveness, and a million other little things contribu

  • UCWG 008: Are You Living a Non-Contradictory Existence?

    11/01/2017 Duration: 01h19min

    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 to see things accurately. Sometimes we can defy conventional categorization. We must work against the social pressure to conform to the stereotypes that other people cast for us in their limited mentalities of who we really are. Anastasia from Ukraine, who has known Gregory more intimately than most, joins the conversation to discuss how being perceived in society as beautiful has contradicted other parts of her persona, such as her fantastic intellect. She’s never felt the freedom to develop her rational mind to its fullest capacity, yet she thinks she is obligated to remain as physically attractive as possible to keep up her carved out role in society. The identity that others chose for her is crushing who she really is, and she suffers deeply as a result. Ultimately, Anastasia realizes she has a real fear of reject

  • UCWG 007: Why Do You Believe What You believe About Relationships?

    08/01/2017 Duration: 01h14min

    Simone Sauter is 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 to make meaning out of the mess of emotional turmoil these recent events have left her in. Over the course of their uncomfortable conversation, Simone gets the opportunity to reevaluate how she acquired the conceptions of relationships she has, how they are harming her, and ultimately how to replace them with something better. Join in on the conversation in your own mind as you consider the negative associations in your own life, why and how you seek companionship at all, and how to move from a place of pain to one of power. None of us has to live our lives by the standards and false beliefs of other people. External judgment is idle. Take back control of the meaning of the words you use to define yourself and your life. What are you actually looking for in a romantic partner? How quick are you to project those standards onto the suito

  • UCWG 006: Does Knowledge without Power Lead to Idle Suffering?

    05/01/2017 Duration: 01h43min

    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 learn to branch out and pursue what makes them happy in greater landscapes around them. Gregory is joined today by a reader of one of his books (Travel As Transformation) who is seeking new sources of personal growth and fulfillment in his life. Alexander feels frustrated because he does not know where the next great challenge for him lays, and he grows increasingly bored with the tools he has grown accustomed to in his ordinary world. One of the topics we lay the foundation for the conversation with is Low Latent Inhibition (LLI), which is a set of psychological traits that make certain people attuned to taking in more working information from the world than others, thus increasing their ability to conceptualize all the different ways that things could be. Most famously, the character Michael Scofield from the TV show Prison Break wa

  • UCWG 005: Are You Willing to Abandon Your Sacred Cows at Any Age?

    03/01/2017 Duration: 01h11min

    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 major revelations and paradigms shifts must happen very early in life before our mindsets solidify. Jonathan Lockwood, a world-renowned voiceover artist and lover of premium Mexican mescal, was raised a Jehovah’s Witness. Despite being a reasonably intelligent man, he even became a cult elder at age 29. For some reason, at age 38 he decided it was all kind of bullshit and weaned himself away from the only social structure he had ever known. With the exception of his 17-year-old daughter, he was excommunicated from his entire family and most of his friends. Now at age 50, he feels mentally youthful and ready to question every remaining foundational belief in his own mind. Join our uncomfortable conversation, as we delve into the origins of cognitive dissonance and why people will defend pre-existing beliefs to the death before ever questioning why they thi

  • UCWG 004: How Do Artists and Intellectuals Love and Create Differently?

    30/12/2016 Duration: 01h57min

    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 no more obvious than when looking the distinction between those who identify as artists vs. those who identify as intellectuals. If the two are not actively seeking to communicate with open minds and empathy, it can be impossible to find any common ground at all. This means sacrificing the benefits beholden by the other side. This show’s guest, Luciano, shares his insights into how the creative process affects him, articulating thoughts many of us have had better that most are able to. The conversation evolves over the course of three hours and a pitifully short poker game into themes of knowing the limits of your physical body, experiencing love as a shared sense of identity, lustful attraction vs. emotional attraction, sex with friends and strangers, the difference between a want and a need, why it is essential for adults to spend

  • UCWG 003: Is Your Identity Strong Enough to Overcome the Stories That Consume You?

    26/12/2016 Duration: 01h53min

    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 around you? This show’s guest, Mariza, talks about how the aftermath of Donald Trump’s presidential election have affected her emotionally, even though no measureable difference has been made in her life. This leads into a broader discussion about how we let stories - not actual events - control our mindset and actions more than anything else. We all must take responsibility for what we care about, and not succumb to idle action for the sake of action, such as the case with those who protest or complain with no realize mechanism in place for getting what they want. Mariza will share her story of how she left her former life behind to travel the world and pursue what she really wanted after an impassioned viewing of Eat Pray Love. The ultimate goal of the person identified with a mission or principle is to become the superhuman embodiment of that idea.

  • UCWG 002: What is the Opportunity Cost of Wanting to Experience Everything?

    23/12/2016 Duration: 01h20min

    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 experiences as “wanting to fuck all of life”, and it doesn’t just apply to her sexuality. She ultimately has to realize how to become confident in why she does what she does, even if it means sacrificing other options. But no matter what you choose, your time and other resources are always finite. You cannot be the best at everything, or anything at all, if you never specialize. To someone in Asha’s position, that could mean being the best at monogamy and dedication to a single partner. It could mean living in one country and devoting herself to a smaller set of passions. A person must first be mature enough to make such big decisions. What does it really choose your own goals? Do you know who you really are if you don't know what you really want?

  • UCWG 001: How Many Dicks Would You Have to Suck to Know You Weren’t Gay?

    21/12/2016 Duration: 01h23min

    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 open-mindedness? How does this apply to other unconventional romantic relationship structures like polyamorous marriage? Or just other forms of unconventional lifestyle exploration? This show’s guest, a young man named Eddy, talks without reservation about how the most difficult experience of his life, his father’s suicide, helped him grow more than anything else. The family anchor he lost opened new horizons. As a result, he built new standards and values for himself. He had to find out through experimentation what would make him the happier version of himself. He didn’t want to live his life for someone else. Yet, he still longed for deep love and devotion without obligation. What are the limits of self-exploration in the context of your own life? Can anyone really say they are a happy person without extending their limits and feeling

  • UCG 000: Introduction to Uncomfortable Conversations

    05/12/2016 Duration: 03min

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