Program Philosophy

Awakened Living Program Philosophy & Resources

I appreciate your interest in the Awakened Living Program. Here you will find the more theoretical and philosophical information that provides the backdrop to the program and some of its principles. You will also find resources to the Enneagram, awakening, and consciousness. Note that there are a LOT of resources on these topics available everywhere; here, we want to provide you with those that are relevant to the program through our lens, experience, and worldviews.


Awakening is about seeing, accepting, and owning each part of us through being with ourselves with curiousity, compassion, loving kindness, commitment, and grace. Everything is related, everything belongs. There is no part of ourselves we can cut out. And as our capacity of inquiring, seeing, becoming aware, and owning increases, we develop the strength to look at our darkest shadows and integrate them into who we are becoming. Awakening can be seen as uncrumpling a crumpled ball of paper, and this blog post provides a deeper glance into this concept.

We get a taste of our true nature and then we ask ourselves, how do we live this new awareness? How do we apply it in our daily life? There is a danger here, for the process of awakening is really a journey, and each day or moment will be different. Trying to hold on to a moment of awakening is a guarantee for disappointment, because such moments don’t last. The important thing here is to maintain an orientation of commitment and intentionality to awakening, without the attachment to “getting it” or “staying there.”

One of Simon’s guiding phrases is walking the spiritual path with practical shoes. It has to do with a blend of approaches, of doing the deep spiritual work and grounding it in the practicality of our daily life.

“Psychology without spirituality is arid and ultimately meaningless, while spirituality without grounding in psychological work leads to vanity and illusions.” – Russ Hudson

Additional Details

Social Learning

Awakening and enlightenment is often understood as a solitary path, whereby we picture being in a cave somewhere in the mountains in India. This is not the case with our program. We see awakening as a relational process that happens in a community of others on the path – where we are being seen, challenged, witnessed, and supported as we go through our inquiry. In fact, being in relationship with others serves as a constant mirror to us as to where we are on our journey. This program is built on the principles of social learning where we grow and develop in and through relationships.

Margaret Wheatley said it best: “For as long as we’ve been around as humans, as wandering bands of nomads or cave dwellers, we have sat together and shared experiences. We’ve painted images on rock walls, recounted dreams and visions, told stories of the day, and generally felt comforted to be in the world together. When the world became fearsome, we came together. When the world called us to explore its edges, we journeyed together. Whatever we did, we did it together.

The Enneagram

With a diverse and mysterious history, the image of the Enneagram (ennea-nine, gram-image) dates back at least 3500 years and represents within it an entire universe of dynamic rhythms, patterns, and laws that can be applied to virtually any aspect of reality.

The Enneagram of Personality is a complex psychological map that points to nine distinct personality types often called “fixations” which, when properly understood, can illuminate a myriad of unconscious behaviours and motivations operating within us that are keeping us stuck in repeating patterns and habits. When we can see these fixations for what they are, we can begin to de-identify from these predictable, unhealthy patterns of personality and ultimately connect with something far more real, essential and expansive within us.

“The Enneagram model suggests that each individual views 360 degrees of reality through a narrow slice of perception based on early coping strategies that were used to adapt to the environment in childhood. These coping strategies grow into patterns of perceiving the world and shape what we pay attention to and what we don’t pay attention to.” – Beatrice Chestnut

In our program we will use the Enneagram’s core teachings of awareness and presence to uncover and return to our pure, natural, free, and shiny being.

The Hero’s Journey

Joseph Campbell’s lifetime study of the world’s mythologies brought us the distilled essence of the movement of all our lives through what he called The Hero’s Journey, the monomyth. This is the same story that we all know intuitively and love to watch again and again in our favourite Hollywood movies or read in our favourite books. We recognize it because we are all doing it. This process of transformation through challenge and adversity seems to be a universal template for our souls evolution.

Our soul is on a journey and there are stages that we must go through for our growth and evolution. The particular predictable stages along this cyclical journey also happen to correlate with the movement around the outside of the Enneagram. Starting and completing the journey at point 9, each point on the Enneagram correlates to a process along the Hero’s Journey and so it seems that our dominant type can also be understood as a kind of stuck-ness in a particular stage of the soul’s path.


On August 21, 2023, Simon was interviewed by Kara Nance on the topics of Enneagram, deep inner work, Mankind Project and men’s work, and Awakened Living on her The Blindspot podcast series. This recording is here.

On September 23, 2018, Simon was interviewed by Geoff Bastian on the topic of purpose, meaning, and Right Livelihood Quest for his Ignited with Meaning podcast series. This recording is here (to listen and/or download).

At the Sleeping at Last podcast, Ryan O’Neal creates a beautiful song for each Enneagram type, with a lot of details and explanation of each type. Christopher Heuertz, the author of “The Sacred Enneagram” book, is a guest who provides additional wisdom and insight into the types.

The Textbooks for the Awakened Living program are:

Additionally, the following books are a valuable read, for topics of relevance and deeper exploration of “all things awakening”: