Performance Management Blog

Caterpillars Can Fly
A Stone about caterpillars flying set in Petra, Jordan

For three decades, I have been using the idea of caterpillars and butterflies to focus on themes of change and personal growth. Here are ideas.

The metamorphosis metaphor is simple and excellent — people really like it. And I have generated a knowledge base around these animals and their amazing transformations. This is a short overview and an excuse to share my new image done in Perplexity.

The metaphor has really nice links to personal growth and change and also to ideas for involving and engaging people in an organizational change process. You can find some of my best blog posts below:

Leading Change – “Teaching The Caterpillar to Fly”

https://performancemanagementcompany.com/2026/01/06/leading-change-teaching-the-caterpillar-to-fly/
Uses the caterpillar-to-butterfly metaphor to show that real change is about enabling metamorphosis—releasing existing potential—rather than bolting on external “best practices.”

Teaching The Caterpillar to Fly – Thoughts on Change – Part One

https://performancemanagementcompany.com/2013/07/02/teaching-the-caterpillar-to-fly-thoughts-on-change-part-one/
Explores why change is inevitable, why caterpillars resist wings, and how leaders can help people move through the discomfort of metamorphosis.

Scott Simmerman on “Teaching the Caterpillar to Fly”

https://performancemanagementcompany.com/2025/01/11/scott-simmerman-on-teaching-the-caterpillar-to-fly/
Frames the two‑caterpillar story and punchline as a humorous but sharp lens on resistance to change and fear of the unknown in organizations.

Teaching the Caterpillar to Fly – A poem about a Work in Progress

https://performancemanagementcompany.com/2013/07/09/teaching-the-caterpillar-to-fly-a-poem-about-a-work-in-progress/
Presents a poetic take on the caterpillar-to-butterfly journey to highlight that many aspects of change unfold beyond anyone’s direct control.

Reality of Change: dealing w/ resistance / driving innovation

https://performancemanagementcompany.com/2014/06/13/reality-of-change-innovation-and-engagement/
Uses your caterpillar/butterfly imagery to kick off conversations about resistance, innovation, and how to better involve people in real change.

My impetus for generating this post was to share a new image that I created in a new style that I am playing with. The idea is to create a memorable visual anchor and to get into the timelessness of the idea, so I set this to be in Petra, Jordan, an amazing place.

I hope you like this,

A Stone about caterpillars flying set in Petra, Jordan

The idea is one of paradox. Caterpillars DO lighten up as they go through the transformation to a butterfly and their perspective on the world certainly changes. It would be real that they will see that the round wheels are already in the wagon and that the team might choose to do some things differently. 

Take a look at one of the articles above if you want to find some ideas and tools you can use. And know that you can grab the Square Wheels One image for FREE from me by clicking on the image below:

Download the FREE Square Wheels One image under Creative Commons licensing BY-ND 4.0

Click to download the FREE Square Wheels® One image and instructor’s guide under a Creative Commons license.

For the FUN of It!

Dr. Scott Simmerman, designer of The Search for The Lost Dutchman's Gold Mine teambuilding game.Dr. Scott Simmerman is a designer of team building games and organization improvement tools.
Managing Partner of Performance Management Company since 1984, he is an experienced presenter and consultant who is trying to retire!! He now lives in Cuenca, Ecuador.

You can reach Scott at scott@squarewheels.com
Learn more about Scott at his LinkedIn site.

Note that I often use Perplexity AI to help research and generate ideas for my posts.

Square Wheels® are a registered trademark of Simmulations, LLC
and images have been copyrighted since 1993,

© Simmulations, LLC 1993 – 2026

What I’m About:

My Square Wheels blog and website exist to help leaders, trainers, and facilitators make work smoother, more engaging, and more human. I focus on practical tools for process improvement, organizational change, and workplace collaboration that spark insight and deliver measurable results.

And I am convinced, after 30+ years of using Square Wheels®, that it is the best facilitation toolset in the world. One can use it to involve and engage people in designing workplace improvements and building engagement and collaboration. It is a unique metaphorical approach to performance improvement and we can easily license your organization to use these images and approaches.

By blending proven facilitation methods, creative problem-solving, and engaging team activities, my mission is to support organizations in building energized, sustainable cultures of involvement and innovation.

Through accessible — and often free — resources and virtual facilitation tools, I aim to help teams everywhere collaborate more effectively, innovate continuously, and take ownership of their improvement journey.

#SquareWheels  #InnovationAtWork  #TeamEngagement  #FacilitationTools  #WorkplaceImprovement  #EmployeeEngagement  #CreativeProblemSolving  #OrganizationalDevelopment  #LeadershipTools #collaboration #leadership #motivation #communications #enablement #leadership #CreativeCommons #enablingperformance #teamwork #storytelling #storyasking

Dr. Scott Simmerman

Dr. Scott Simmerman is a designer of the amazing Lost Dutchman's Gold Mine team building game and the Square Wheels facilitation and engagement tools. Managing Partner of Performance Management Company since 1984, he is an experienced global presenter. -- You can reach Scott at scott@squarewheels.com and a detailed profile is here: https://www.linkedin.com/in/scottsimmerman/ -- Scott is the original designer of The Search for The Lost Dutchman's Gold Mine teambuilding game and the Square Wheels® images for organizational development.

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