Raena Hubbell

I began my career in technology consulting. It was fast-paced, demanding, and intellectually rewarding, but over time, I became more curious about the people behind the systems. What drives us to perform, collaborate, or burn out?

That curiosity led me to LIFE XT, a Chicago-based startup focused on mindfulness and resilience training for high-stress workplaces. I worked on the operations and analytics side, supporting programs that helped professionals develop self-awareness and emotional resilience. As I watched people experience genuine transformation, I realized I didn’t just want to measure change — I wanted to help create it.

I’d already been studying the Enneagram for years at that point. I discovered it in 2008 and spent more than a decade exploring it out of pure fascination with human behavior. When I began to apply it in professional contexts, I realized it was the perfect bridge between deep personal insight and practical organizational impact, and that realization inspired me to build my own practice.

As I built that practice, I pursued certification through the Enneagram Institute, where I had the opportunity to train directly under Russ Hudson and the late Don Riso. Their work — particularly The Wisdom of the Enneagram — is what brought the Enneagram into the world of modern psychology, and studying under them shaped everything about how I facilitate today.

Since then, I’ve worked with more than 50 organizations across 20 industries — from early-stage startups to global corporations — and facilitated more than 1,000 individual consultations. What began as a curiosity about human behavior has become a calling to help people and teams show up with greater clarity and self-awareness.