Butterfly Possibilities
- Catherine Addor
- Nov 30, 2025
- 3 min read
Innovation rarely begins with a breakthrough. More often, it begins with a quiet shift; an internal decision to step into the chrysalis and do the unseen work of transformation. A quote I encountered recently said, “You can’t have butterfly conversations with caterpillar people.” It echoed years of watching students raise caterpillars in the classroom: the energy, the uncertainty, the patience, and finally the moment of release.
In leadership, the same is true. People grow at different rates. Some are still crawling along the surface, seeing only what is directly in front of them. Others are ready to rise, look beyond the obvious, and imagine what could be. Cultivating an innovation mindset means meeting people exactly where they are, honoring the work happening inside the chrysalis, and creating conditions where transformation is not only possible but inevitable.
Why Caterpillars ≠ Butterflies (Yet)
Caterpillars see surfaces. They navigate the world step by step, focused on the immediate and the familiar. Innovation feels risky because it lifts them off known ground.
The chrysalis is the hard part. Real transformation happens in the quiet; the rewiring of habits, the letting go of old assumptions, the messy middle we rarely name out loud.
Butterflies rise. They see patterns, connections, and possibilities that only become visible once you move beyond the surface.
A strong innovation culture recognizes all three stages. It values the journey, not just the emergence.
Self-Reflection Questions for Leaders and Innovators
Use these questions to assess your readiness (and the readiness of your team) to move from caterpillar thinking to butterfly vision:
Where am I still clinging to the “surface” (focusing on tasks and routines) when the work calls me to lift my eyes toward wider possibilities?
What part of my practice is currently in the chrysalis stage (messy, uncomfortable, or unclear) but necessary for growth?
Who on my team is ready to take flight, and who do I need to support through their chrysalis rather than pushing them prematurely into the sky?
Actionable Steps to Develop an Innovation Mindset
Transformation doesn’t happen by accident; it happens through intentional habits that slowly shift how we think, create, and lead. These steps utilize the caterpillar-to-butterfly journey as a guide to help individuals and teams transition from surface-level routines to elevated, visionary practices.
1. Create “Chrysalis Time” for Deep Work: Just as caterpillars need protected space to transform, people need uninterrupted time for reflection, learning, and experimentation.
Block intentional time for inquiry and skill growth.
Protect it as fiercely as instructional minutes.
2. Design Experiences That Lift People Off the Surface: Butterflies gain insight by rising above the ground.
Utilize protocols that shift perspective, such as shadowing students, cross-team walkthroughs, and empathy interviews.
Regularly ask, “What can we see from above that we couldn’t see from the ground?”
3. Normalize the Messy Middle: Transformation dissolves the old form, allowing the new one to emerge.
Celebrate drafts, attempts, and iterations.
Adopt language that acknowledges growth as non-linear.
4. Match Your Conversations to Readiness: You cannot hold butterfly-level strategic conversations when someone is still learning to trust the chrysalis.
Notice and honor each person’s stage.
Scaffold for some, stretch for others, and release when wings appear.
5. Release and Trust the Flight: Once butterflies emerge, you must let them go.
Offer autonomy to pilot solutions and test ideas.
Avoid over-directing; trust the wings you helped strengthen.
Every transformation begins with a willingness to see beyond the surface. Innovation does not ask us to abandon who we were; it asks us to become more of who we are capable of being. Like the caterpillar that instinctively knows when it’s time to build the chrysalis, we each reach a moment when the old way of working no longer fits. The edges begin to feel tight. The routines feel too small. The view feels too narrow.
Leaders who cultivate an innovation mindset recognize these moments in themselves and in others. They create environments where people feel safe enough to dissolve old assumptions, brave enough to imagine something new, and supported enough to spread their wings when the moment arrives.
The butterfly is not "better" than the caterpillar; it is simply the next version, the one with greater perspective, range, and possibility. Innovation works the same way. It is the natural evolution of individuals and systems that are willing to step into discomfort, embrace curiosity, and rise toward a broader horizon.
As you move forward, ask yourself:
Where am I still crawling?
Where am I transforming?
Where am I finally ready to fly?
The answers to these questions will guide your next steps; your next chrysalis, your next emergence, your next flight.
Innovation begins the moment we choose to emerge. Once we lift off, the sky becomes our curriculum.
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