Caldecott was born in New Westminster, British Columbia and graduated from University Hill Secondary School in Vancouver in 1987. That same year, Caldecott won best actor in a Vancouver Theatre Festival for his performance in a play by Sheldon Rosen called The Box. Shortly thereafter Caldecott, also known as Todd Shaffer, obtained an agent, and began working in the film and television industry, guest-starring in several television shows including Wiseguy, 21 Jump Street, Danger Bay, Northwood and Bordertown. He also acted in a number of made for TV movies including Mother May I Sleep With Danger and One Boy, One Wolf, One Summer, and the feature films Fear and Jason Takes Manhattan.

After becoming disillusioned with the film industry, Caldecott traveled to India and West Asia in 1990 for a year long trip on a budget of only a "few dollars a day". During this year he studied Indian classical music in Chennai and Varanasi, India and buddhist meditation in Bodhgaya, India and Nilambe, Sri Lanka. During his travel and study he became very ill, at one point suffering from both bacillary and amoebic dysentery. After leaving India he traveled in a weakened state to the Northern Area of Pakistan, including Gilgit, the Hunza valley and Pasu. It was in these areas, renown for their long-lived inhabitants, healthy food and glacial water that he "partially recovered" from his illness. He then went on to travel throughout Iran, spending several weeks as the guest of a Sufi master in Shiraz.

Returning to Canada, Caldecott sought relief from what now had become a chronic digestive disorder, and found success in the treatments of an Ayurvedic physician. This would prove to have an enormous influence on his life path, and shortly thereafter Caldecott enrolled and graduated from a three year, full-time clinical program in Western Herbal Medicine at the Coastal Mountain College in Vancouver. After graduating, Caldecott immediately traveled back to India to study Ayurvedic medicine in Coimbatore, India over a five month period, and then returned to Canada to begin practicing, writing and teaching. In 1999, Caldecott relocated to Calgary, Alberta, where he eventually became clinical director of the Wild Rose College of Natural Healing. Here Caldecott developed, administered and taught a three year clinical program in Western Herbal Medicine. During this time Caldecott completed the manuscript for a textbook called "Ayurveda: The Divine Science of Life", which was subsequently published by Elsevier in 2006.