Interwoven Episode 19 - From Software Engineer to Systems Thinking Advocate: Carolina Cunnington’s Leap

Before finding her footing in systems thinking, Carolina Cunnington navigated a winding and unconventional early career—dabbling first in acting, then motorcycle mechanics, and finally landing in software engineering. Although successful as a software developer and later a product manager, she often sensed a disconnect: she could see the bigger picture in organisations but struggled to communicate her insights with confidence and felt stifled by her lack of authority.

A turning point came from a chance encounter and a gifted book at the Innovation Center, which introduced her to the world of systems thinking. The discovery was profound—revealing frameworks and a language to express the interconnectedness she always sensed but lacked the means to apply. Yet, the next move wasn’t simple. When Carolina Cunnington tried to stake her claim as a systems thinking consultant, she met confusion and self-doubt; “Nobody knows what systems thinking is and why they need it…I felt like a total imposter.” Financial uncertainty and a drought of product management work heightened the pressure, until a serendipitous opportunity to teach changed her path entirely.

Stepping into education, she found meaning and energy in demystifying systems thinking for adult learners. Drawing on her own neurodiversity and past challenges, she leads with vulnerability and kindness, making complex ideas accessible and encouraging others to learn from discomfort. Her journey is a testament to the creative power in letting go of certainty, embracing mistakes, and simply starting—even while feeling unqualified.

Listeners facing their own crossroads will find reassurance in Carolina Cunnington's story: that founders aren’t born with a master plan, but rather shaped by trying, reflecting, and being open to change, uncertainty, and learning.