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Famous Enneagram Sixes: Woody Allen, Jennifer Aniston, and Richard Branson

WORLDVIEW: The world is a volatile, unpredictable, and fearful place; I must find meaning and certainty.

SIXES have insightful minds and create anticipatory or worst-case scenarios to help themselves feel prepared in case something goes wrong. Some Sixes, called counterphobic Sixes, do not appear fearful because they move directly into the fearful situation to prove they are not afraid.

Sharp minded, insightful, and loyal, Sixes are issue identifiers and problem solvers, with a mental-emotional antenna that is finely attuned to anticipate problems before they occur so that alternative paths and contingency plans can be created to try to ensure the best outcome and prevent the worst from happening. Although the above description applies to all Sixes, Sixes are complex individuals who run the gamut from phobic Sixes such as Woody Allen, who are overtly and palpably fearful, to counterphobic Sixes such as Richard Branson, who often mask their fear by taking huge risks that adrenalize them and prove to them, at least for the moment, that they are not fearful. And then there are Sixes who are in the middle of the phobic-counterphobic continuum – for example, Jennifer Aniston.

All Sixes worry as a habit of mind, although some Sixes call it instantaneous anticipatory planning or problem solving and other Sixes do this so naturally that they no longer notice it. There are also key differences among Sixes.  Some Sixes deal with their concerns by becoming warm, inviting, and by developing strong and loyal social alliances as a way to feel safe; other Sixes become extraordinarily dutiful and try to know and adhere to the “rules” as a way to not get in trouble by going astray; and still other Sixes – the highly counterphobic ones – unconsciously turn against their fear with demonstrations of strength as a way to convince themselves and others of their bravery. In reality, most phobic Sixes have some counterphobic qualities – for example, they can become aggressive toward authority or authority figures – and most counterphobic Sixes do display fears and concerns to those they trust or through their non-verbal behavior.

In the following YouTube segments, you will see three short clips of famous Sixes: one clip illustrates the phobic Six (Woody Allen), another illuminates the counterphobic Six (Richard Branson), and a third shows a Six with equal amounts of phobia and counterphobia (Jennifer Aniston). Among the three clips, you can see the similarities in interpersonal style, as well as observe their common warmth, genuineness (relative lack of pretentiousness), candor, agility in expressing concerns, and willingness to talk truthfully about themselves. 

Remember: While we can all worry, be insightful, and want to feel well-prepared for the various scenarios life offers, for Sixes, the pursuit of meaning, certainty, and trust, and the avoidance of negative scenarios is their primary, persistent, and driving motivation.

Woody Allen (phobic)Click here to see clip

In this interview, Woody Allen is more serious than funny — although he is still amusing in certain segments — as he talks about his life concerns, his view of the world, and his career ups and downs. He even talks about how his life must be good because it isn’t bad!

Jennifer Aniston (mixed phobic counterphobic)Click here to see clip

In this interview with Diane Sawyer, one that predates her divorce from Brad Pitt, Aniston reveals her questioning orientation, her fears and sweetness, and her highly active mind.

Richard Branson (counterphobic)Click here to see clip

In this interview, Branson describes his life as one of extremes, his survival instincts, and his willingness and pleasure in facing somewhat daunting circumstances.  

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