UCWG Uncomfortable Conversations With Gregory Diehl Podcast Square

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 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 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 level needs of ordinary human desires, they will not ascend to the profound truth of their existence.

People frequently get stuck in lifestyle loops resolving the same problems and addressing the same needs time and again. They chase the wrong things in the wrong ways. Even if they are aware enough to know they want more sex or more money, they don’t know how to get these things. If no one ever introduces the idea of higher level goals, we do not move on. Popular media, more often than not, keeps us chasing our tails for the duration of our lives.

A human mind can only contain a certain quantity of problems to solve. A problem is simple any time your mind desires something to be different than it is. If it does not succeed it its desired change or accept the way things are, it cannot move on to higher level problems to change. You are always being manipulated by your brain to achieve what it sees as its survival needs.

Without outside influences to guide you to higher truths, you must have a deeply inquiring nature that forces you to move beyond what you already know. No experiences is inherently good or bad. It matters what meaning your mind adds to it: what you get from it. It can distract or serve as progression, such as watching a powerful movie or having sex.

Existential personal development is about moving beyond the realm of physical needs and mental beliefs. It’s about identifying yourself as what you are before any stimulation or value judgment. It is present in every single moment, always unchanging. Most religions and forms of spirituality think of this as a Godly presence, but it is only the authentic you.

Underneath the world of our gross physical experiences lies the subtle realm of what happens within us. It is underneath our thoughts and emotions even. Most people consider their spirituality a series of thoughts and beliefs, and therefore it only serves to distract them from the subtle truth of what they really are. They are setting themselves up for an unending trap of distraction from the truth. They must learn to stay grounded in the subtle unchanging part of reality, regardless of what problems they encounter.

The Hero’s Journey is about facing your deepest fears, even your physical death, and emerging on the other side in a higher state of existence. The Dark Night of the Soul is the lowest point on the Hero’s Journey where one must face the parts of themselves they have been avoiding their entire lives. They experience painful separation from the experiences they are most psychologically attached to. It is the only way to move into the subtle realm of their identity. Emotional release only comes when the loss is complete.

The Hero must learn to break away from the stories of his culture to follow his own path. He cannot act in resistance to what other people choose. He must place his own development as his highest priority above all other forms of ego gratification. Our education system, our politicians, and our popular culture are misleading almost everyone to pursue fruitless ends instead of knowing the truth about themselves.

Parents pass along the emotional loop they get stuck in to their children, getting them to value the same thing they arbitrarily picked up during their own lives. Almost no one teaches their offspring the fundamental values of the pursuit of self-knowledge from an early age. They remain forever unfulfilled, even if they acquire what they thought they wanted.

Every experience you ever have is biased by constantly changing chemical imbalances in your brain. Psychedelics and other substances can instantly show a person a radically different manner of experiencing reality, but there is no neutral control group even when a person is totally sober. The perspective of vast new experiences shows us the filter through which we see things, and a gateway to the subtle ongoing experience underneath everything.

In most Hero’s Journey stories, a mentor who has already completed their own journey guides the hero with the lessons they have already learned by overcoming their trials. Young people today lack adequate mentors because education and parenting are generalized for the masses. It is difficult to find someone uniquely suited to guide you on your quest. You need someone to show you what is possible if you stay on the path before you. Knowing that something can be done is what makes it viable to the uninitiated.

Negative emotions by themselves can be the starting point for major changing actions, but they cannot exist alone. They must be complemented by inspiration and a positive desire for greatness. Everyone needs a vision for their life to become everything they are capable of being.

Leo Gura, Actualized.org - Uncomfortable Conversations With Gregory Diehl
Leo Gura, Actualized.org – Uncomfortable Conversations With Gregory Diehl

Websites mentioned:

Actualized.org by Leo Gura:


Highest Hero’s Journey video:


Leo Gura’s YouTube channel:


Leo Gura’s Life Purpose Course:


Previous Episodes:

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.

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.

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