We open the Head Triad portion of our Enneagram ConvoCast series with YOBcast regular, Will! Will shares his motivations, fears, stress, and security as a Type Five (the Investigator or Intellectualist). As a member of our YOB community, how does his Five-ness manifest in the realms of sexuality, masculinity, and relating with other men?

Fives are heady types, supreme thinkers and philosophers, as Will confirms his “endless curiosity” for books and learning, and returning to school whenever he hits an existential crisis. Enneagram expert Ian Cron describes Fives as the most misunderstood type, people with emotions beneath their intellectual exterior, and Will confirms his journey with processing difficult emotions. He shares the appeal of intellectual attraction versus physical attraction for the Five, and he explains how his problem-solving nature wanted to “fix” his “gay problem” in adolescence. During stress Will admits getting disorganized and clingy, but during security he’s passionate about strengthening the people around him — where, as a pastor, his Five-ness particularly shines. During times of doubt and questions, Will returns to the Gospels and his love for how Jesus makes sense of this world.

Listen to our full Enneagram conversation, and be sure to follow us these last few weeks as we finish dialing around the Enneagram with the remaining types in our community!



Are you an Enneagram Five? How have you grown as a Five in relation to your sexuality and masculinity?


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