The origin of the Enneagram is rather mysterious and still the subject of substantial debate.

The word Enneagram is from the Greek and means "nine points". The original teaching may go back as far as 2500 B.C. to the kingdoms of Babylonia, and the wisdom school of the Sarmoun Brotherhood. In the 14th and 15th centuries it was passed on to Islamic mathematicians who incorporated it into their mystical teachings. Traditionally it has been a part of the secret oral tradition of the Sufi Brotherhoods, being revealed only in part to any but the masters.

Because the Enneagram has been a secret oral teaching, no written records of it exist until it's introduction to the West. The earliest appearance in the historic record dates to a Greek man named Georges Gurdjieff (1866-1949). He was interested in the meaning of life and traveled around North Africa and Asia learning various spiritual traditions. Allegedly, one of these was called 'The Work' which supposedly had been passed down from teacher to pupil for thousands of years. The Work made such an impression on Gurdjieff that he made it his life mission to teach it to the western world.

Gurdjieff was initiated into the use of the Enneagram by his Sufi teachers, and he alluded to it as a device which he used to recognize his student's aptitude for certain types of inner life training. Gurdjieff did not transmit the Enneagram to his students in full, making reference to the fact that it was not yet the right time for it to be revealed. His students did however, study the mathematical properties of the Enneagram, and used it's symbology in non-verbal movement designed to teach the rhythm of process through the physical body.

The evolution of The Work into the Enneagram of today is attributed to a Chilean named Oscar Ichazo, the founder of the Arica Institute. He received training into the system by Sufi teachers in Afganistan and incorporated it into his system of human development. In the 1960s, Ichazo developed a theory of nine personality types corresponding to the nine points of the Enneagram (although he claims total originality of this concept). In 1971, Ichazo brought his teaching from Chile to the United States, where John Lilly and the Chilean psychologist Claudio Naranjo encountered it at the Esalen Institute. Naranjo reframed the Enneagram into the language of modern western psychology and taught his system (called the Enneagram of Fixations) in America during the 1970s. Through Naranjo, a Jesuit priest named Bob Ochs introduced the system to his community, where, as the "Sufi Numbers" it is widely taught and used as a tool for spiritual development, prayer, and living in community.

In the 1980s, Naranjo's Enneagram of Fixations was popularized as a psychological profiling system by authors Helen Palmer and Don Richard Riso. Don Richard Riso is a former Jesuit who learned the system through his order, and after leaving the Jesuits, developed material on it's secular, psychological aspects. Helen Palmer was a student of Naranjo who has pursued the aspects of attention and intuition for the types.

Because this system is best taught orally, there are many other teachers who can only be found through word of mouth.

Today, the Enneagram is widely used in clinical psychology and corporate America and is also very popular among Jesuit and Catholic priests.