In Episode 44 of The Incredible Machines Podcast, hosts Jon Oliff and Luke Holden are joined by Colleen Wilson, a Human Navigator, Enneagram practitioner, writer, speaker and guide who has dedicated her life to helping people better understand themselves and navigate life with more intention.
This episode is a deeply honest human conversation about pain, purpose, and personal responsibility. Colleen takes us through a life shaped by contrast: a privileged, joy filled upbringing followed by a second half defined by struggle, chronic illness, loss and hard-won wisdom. Along the way, she unpacks how suffering can become a teacher, how self-knowledge is the foundation of everything, and how the Enneagram offers a powerful map back to ourselves.
Whether you are a parent, a leader, an entrepreneur or simply a human being trying to figure it all out, this episode is a reminder that life will give you both suffering and splendour, and that the real work is learning how to meet both with courage, clarity and self-awareness.
At nineteen, Colleen experienced one of the most devastating events imaginable. A boyfriend took his own life on the night that she broke up with him. Far from hardening her, this experience sparked a lifelong fascination with human behaviour, what drives us and how we navigate the most difficult moments of existence.
Later, the challenge of parenting pushed her even deeper into the science and art of human development. In 2015, she flew to Los Angeles to study under Dr. Dan Siegel, building frameworks that she now uses in her work.
"I take my pain to purpose. I experience things, I distill them, I translate them, and then I teach others."
One of the most powerful concepts Colleen introduces is the lens of the nervous system. What drives our personality? The answer, she says, lies in how regulated or dysregulated our nervous systems are.
"Whether I show up as this version of myself or that version of myself is dependent on how regulated my nervous system is."
She encourages people to use their senses as a daily regulating tool. Small, intentional moments build credit in the nervous system and create a more grounded way of being.
Colleen is a passionate Enneagram practitioner. Unlike assessments that box people into a type and leave them there, the Enneagram reveals both our light and our shadow.
As a Five on the Enneagram, with strong wings into Four and Nine and lines to Seven and Eight, Colleen is deeply introspective, analytical and capable of profound isolation. Understanding this about herself has been transformative, not because it gave her an excuse, but because it gave her a choice.
She works with individuals, families, and corporate teams through a framework of three core principles: Know Yourself. Grow Yourself. Show Yourself. Self-awareness, self-development, and self-expression, in that order.
Colleen’s self-described role as a Human Navigator is not just a brand. It is a lived philosophy. Her three sub brands reflect the full arc of her work.
The Nest is a safe space for parents navigating the complexities of raising children, particularly those dealing with mental health challenges. It is built on Enneagram, family strategy, and compassionate coaching.
Abode is a personal development programme focused on coming home to yourself. It is designed for those who have played so many roles for so long that they have lost touch with who they are.
And Nine is Enneagram based work in the commercial space, grounded in the belief that when people do better personally, businesses do better financially.
Every hardship is here to teach us how to dance with this life. (So when some semblance of failure rises up, remember what it means to shine your light)”
~ Elena Brower as referenced by Colleen Wilson.
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.
Watch the PlayStation Double Life Advert
Colleen Wilson’s story is not a highlight reel. It is a testament to what becomes possible when we stop running from the hard parts of being human and start learning from them. Through chronic illness, grief, parenthood, marriage and the daily discipline of self-knowledge, she has built a body of work that is equal parts of science and soul.
Her message is not that life gets easier. It is that we can get better at living it.
If you are a parent navigating complexity, a leader trying to build something meaningful, an entrepreneur questioning whether you are on the right path or simply a human being who wants to show up better; this episode is for you.
Who is Colleen Wilson?
Colleen Wilson is a Durban-based human navigator, Enneagram practitioner, writer, and speaker. She works with individuals, families, and organisations through three sub-brands;
What is Enneagram?
The Enneagram is a dynamic personality framework that maps nine interconnected types, each with their own core motivations, fears, and patterns of behaviour. Unlike static personality tests, the Enneagram reveals both our light and shadow sides and offers a pathway to genuine self-awareness and growth.
What is the Incredible Machines Podcast?
The Incredible Machines Podcast is a thought leadership series produced by Tim Africa, featuring conversations with visionary entrepreneurs, leaders, and change-makers from across the continent.
Where can I listen to the full episode with Colleen Wilson?
You can listen on all major platforms including:
🎧 Spotify
🍎 Apple Podcast
🌐 Tim Africa Podcast Hub
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.