Awakening 365

Awakening is about seeing, accepting, and owning each part of ourselves with curiousity, compassion, loving kindness, commitment, and – ultimately – grace. Everything is related; everything belongs. There is no part of ourselves we can remove. And as our capacity to inquire and become aware expands, we develop the strength to look at our brightest light and our darkest shadows, integrating them into who we were always meant to become. 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 engage with this new awareness? How do we apply it to daily life? There is a hidden danger here; the process of awakening is truly 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 simply don’t last. What is important is to continuously orient to commitment and intentionality to awakening, without the attachment to “getting it” or “staying there.”

One of our 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

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.“

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.

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 (IMPORTANT: Please note that we are using the word Hero in a completely gender-neutral manner). 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 soul’s 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.

There are programs and then there are “programs.” Awakened Living [previous program name] falls under the latter. As far back as I can remember, I’ve always had a burning desire to better understand who I am at my core – a mystery to solve, a code to crack. Awakened Living came at a time when I was ready to take a leap of faith, question all that I assumed to be true and surrender previously held beliefs and old ways of being that no longer served me. I sensed a longing of my soul to come home, a vague memory of a distant place I couldn’t remember and couldn’t forget, where lies the truth of what I already am, both the shadow and the light. This year long journey felt very much like a “shedding of the skin,” with one layer peeling off after the other, until what emerged was my very essence, true and pure. Throughout this entire process, the facilitators were by my side every step of the way, offering their unconditional commitment, love, and acceptance. This program is one of a kind, unique, magical, exquisite, in a league of its own. Anything less wouldn’t do it justice! – N.H. 2019

The Awakened Living [previous program name] program has been of tremendous value in my journey toward realizing who I truly am, and living in greater accordance with those realizations. It has helped me become more deeply rooted in the present moment, see the inherent worth in traveling the road that has been my life, and look forward with excitement instead of the dread that used to plague my mind and perceptions. Simon Goland, as the curator of the Awakened Living program, has created a space where a community of dedicated individuals can grow, learn, experiment, and become more attuned to themselves and the oneness of things. He, as well as my cohort, have been infallible pillars of support. Free of judgment, this space has allowed me to dig deeper into myself than I ever have before. What I have found through this has been nothing short of life changing. Through exploration of various topics such as the Enneagram of Personality, Somatic Intelligence, the Hero’s Journey, and his signature Right Livelihood Quest, this experience has been one of many instrumental factors in the evolution of the way I live. I am thankful to have had the opportunity to join this journey, and I would recommend it to anyone who wants to discover the greater intricacies of who they are, the connection they have with the world, and how to live in accordance with their unique gifts. – D.W. 2023

• "Quantum Surfing - The Innovator's Guide to Being Lucky, Aligned, and Unstoppable" by Monica Laurence
• "Deep Living - Transforming Your Relationship to Everything that Matters Through the Enneagram" by Roxanne Howe-Murphy
• "Understanding the Enneagram - the Practical Guide to Personality Types" by Don Riso and Russ Hudson
• "The Journey to Essentia" by Simon Goland (to be published in 2026)
• "The Deepest Acceptance - Radical Awakening in Ordinary Life" by Jeff Foster
• "When Things Fall Apart - Heart Advice for Difficult Times" by Pema Chodron

• The Messy Art of Navigating Transitions: Learning to Trust the In-Between
• Doors. Opening and Closing.
• In Search of the Unknown.
• A Timeless Question.

On October 13, 2025, Simon was a guest at the The Business of Expansion Podcast with Hale Shneider, where we talked about the Enneagram as a vehicle for awakening - for coaches, leaders, and entrepeneurs. You can listen to it on Spotify or on Apple Podcasts.

On July 1, 2021, Chela Davison and Simon had a rich, emergent, juicy, and heart-filled conversation on her "What is Leadership?" podcast, covering a wide territory - from Right Livelihood to presence to leadership to the Enneagram to the importance of deep inner work.

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).