Welcome to Episode 44 of The Incredible Machines Podcast! In this thought-provoking conversation, Jon Oliff and Luke Holden sit down with Colleen Wilson, a Durban-based transformational consultant, coach, speaker, trainer and mentor whose work brings together the Enneagram, nervous system literacy, parenting support, personal development and team dynamics.
From growing up in Durban and reflecting on a privileged, steady childhood, to experiencing early loss, complex relationships, chronic illness, motherhood, entrepreneurship and personal reinvention, Colleen shares the life experiences that shaped her path into human development. Colleen describes herself as an Enneagram 5, and her work is rooted in helping people understand themselves more clearly, navigate life more consciously and show up with greater honesty, steadiness and humanity.
They explore the extraordinary within ordinary life, the cost and gift of struggle, what it means to be “okay in the not okay”, and why self-awareness is not a luxury but a practical tool for better relationships, better leadership and better living.
This episode moves through themes of grief, parenting, the Enneagram, nervous system regulation, and the ongoing work of becoming more at home in yourself. Whether you’re a parent, leader, entrepreneur, or simply someone trying to navigate life with more grace, this conversation offers a powerful invitation: know yourself, grow yourself and show yourself.
⏱ Timestamped Overview
02:43 – Introduction to Kevin and a Remarkably Ordinary Life
05:06 – A Life of Two Halves
09:13 – First Encounter with Hardship
12:35 – Pivoting from Commerce to Human Behavior
16:36 – The Journey into Parenting
20:19 – The Science of Human Relationships
23:05 – Family Background and Early Lessons
28:09 – Early Career and Entrepreneurial Ventures
33:22 – Meeting Her Husband and a 20-Year Health Journey
38:50 – Daily Practices for Well-being
49:26 – Passion for the Enneagram
54:46 – Being Open About Your Enneagram Type
01:00:37 – Coming Home to Yourself
01:04:25 – PlayStation Ad Discussion
01:09:53 – The Importance of Authenticity
01:12:18 – Finding Your True Self
01:18:42 – The Meaning of "Human Navigator"
01:35:55 – Giving Up Alcohol
01:38:54 – Working with Individuals vs. Groups
01:39:35 – Colleen's Outlines Her Three Brands
💬 Quote of the Episode
" I really wanted to like myself. I really wanted to get to that point where I liked who I was, as a wife, as a leader, as a mum, as a daughter, as a friend.” – Colleen Wilson
🧠 Related Campaign Example
PlayStation Double Life Advert: This is not the kind of advert Colleen Wilson would typically choose, but that’s exactly why it stands out. What resonated with her is how it challenges the way we define ourselves. We’re often quick to label who we are, but through her work with the Enneagram, she encourages a shift from saying I am to I can be. Identity isn’t fixed, it’s fluid, shaped by context, environment, and experience.
Colleen values how the advert reflects the full range of who we are, including the parts we tend to avoid. By embracing both the visible and shadow sides of our personality, we move closer to wholeness rather than limiting ourselves to a single identity. At its core, it speaks to her belief in knowing yourself fully, not just the parts that are easy to accept.
PlayStation Double Life Advert: https://youtu.be/QIW4HMl81hw
👣 Relevant Links & Mentions
Colleen Wilson’s LinkedIn: https://www.linkedin.com/in/colleen-wilson-982a6a6/
Colleen Wilson’s Instagram: https://www.instagram.com/colleen_wilson_contemplative/
Colleen Wilson’s Facebook: https://www.facebook.com/colleenwilsoncoach/
Colleen Wilson’s YouTube: https://www.youtube.com/@colleenwilsoncoaching101
Colleen Wilson’s Spotify: https://open.spotify.com/show/1q7FEuwxRu8e2AOVnex5z1
Colleen Wilson’s Website: https://colleenwilson.co/
Colleen Wilson’s Speaker Profile: https://redjacketspeakers.co.za/colleen-wilson
The Enneagram: Colleen describes the Enneagram as a powerful framework for understanding personality, unconscious patterns and the pathway towards healthier self-expression. Her own site describes it as a tool that offers insight into why we behave as we do and how we can move towards the highest expression of ourselves. View our package for teams: https://colleenwilson.co/at-work/leadership-team-enneagram-discovery-journey/
Odyssey Magazine: Colleen mentions writing for Odyssey Magazine and sharing work around coming home to yourself. Odyssey has also featured Colleen in conversation around the Enneagram, healing and navigating life’s threshold moments.
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