At the very heart and soul of transdisciplinary work are imagination and creativity. Being transdisciplinary is an inherently mysterious, complex and challenging experience. It is very important to not simplify the experience especially as it begins. Complexity comes first. Elegant refinement comes later, if it ever does. As systems scientist Peter Senge (2001) wrote: “Knowledge creation is an intensely human, messy process of imagination, invention and learning from mistakes, embedded in a web of human relationships”. The creative process demands the messiest and weirdest parts. The parts that don’t make sense immediately need to be lived and embraced, patiently and collectively in order for shared understanding to occur. Many try to streamline, control, quantify or accelerate this experience too early and miss out on producing waves and resonance within the process. There are many books, articles and teaching resources with pragmatic strategies on how to innovate, produce and design. These often feel too rigid to be truly effective in the long term. Action verbs such as innovate, produce and design have underlying connotations of humans controlling what is natural. These are prototypical interactions in the early stages of the Anthropocene Age. But while we do have the power to guide natural things for our better quality of life, it might be wise to bear in mind biologist Francois Jacob’s quote “Evolution doesn’t design, it tinkers” (Jacob 1977). Things will naturally adapt to suit changing circumstances, and evolution is essentially adaptive and experimental. This means that flexibility and resilience are key. In the following chapters, I will introduce three methods for long-term substantial production of waves, resonance and shared understanding in a range or transdisciplinary and citizen social innovation projects. These are centred on moments, paradoxes and dialogues. I am developing these as I perpetually confront and embrace complexity, transience, fluidity, contradiction and uncertainty in the organically evolving creative process. They also help me focus on communicating what is truly important to the projects. I use them when I begin my transdisciplinary projects and I also use them at later stages of the projects such as reappraisals and reinvention.