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.
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Uncomfortable Conversations with Gregory



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Jul 15, 2017

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 are not typical “travel” books.

Nicos compares the choices a traveler makes in the way he chooses where to go and what to do in a new country to the choices we make for how we structure every aspect of our lives and identities. There is always more to see and to do than we are capable of accomplishing with limited time. Diminishing returns also quickly become a factor in any new activity. Every traveler must choose for themselves when it is optimal to move on to the next location or activity, just as each of us must decide when to move on to a new stage of our personal development.

If you were to travel back in time to any ancient culture on Earth, you would be unable to understand the cultural mindset that existed back then to explain the dominant behaviors of any group of people. The same principle applies even many of the modern cultures that currently exist. The further away you step from your home country, the more flexible you are going to have to become in your analysis of why people act the ways they do. You must eventually accept that everyone has their own reasons for doing what they do, not matter how strange or offensive you might find their behavior to be.

The more you experience as you travel, and the older you are when you have these experiences, the harder it will be to reconcile the new knowledge you have acquired with your old interpretations of life. Nicos explains that travel engenders more travel. He originally planned to only travel for two years, but sooner after setting off he realized that the world was much bigger than he anticipated. There were so many more things to see and do than he could have guessed when he began.

People can only derive the principles of their identity by having a wide berth of incidental experiences that show them what is possible and how they respond to everything that can happen. If you work many different types of jobs in your life, you will quickly see what you like or dislike about each one.


Being proud of one’s nation necessarily divides the human race along arbitrary lines, pitting us against each other when we could all be working together for common goals. When national pride can expand to become global pride, we can evolve past our present sociological problems. World travel breaks down the identification barriers in an individual mind, and perhaps then may be a necessary part of the process of fixing the world’s dualistic problems of fighting against its own interests. Individuals can begin taking strategic steps now to start living the life of a global citizen now, even if the rest of the world isn’t ready. Your group identification ends only where you allow it to.

Moving into the unknown is a function of your will to act when you don’t know what’s going to happen. If you can master your fear, everything else in the journey begins to fall into place. It has nothing to do with how well you plan or what you think you want. Take the first step, and then be ready to take the next.



Things mentioned:

Nicos Hadjicostis website:


Destination Earth by Nicos Hadjicostis:

Travel As Transformation by Gregory V. Diehl:

Vagabonding by Rolf Potts:

The Four-Hour Workweek by Tim Ferriss:

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

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