“You’re an eight, aren’t you?”
Students took turns guessing their friends’ enneagram type as they sipped their complementary Penny’s drinks and awaited the start of Career Service’s “Enneagram and Your Career” presentation. Hillsdale has no lack of enneagram enthusiasts, and the coffee shop buzzed with excitement about learning how to apply one’s type to their career goals.
Career coaches senior Anna Katherine Daley, an eight, and junior Andy Walker, a four, opened the event with the history of the enneagram test.
“We know it came from South America in the 1950s, and then was taken up by the Jesuits, and then came to America in the ’80s, and has progressed from there,” Walker said.
They took a quick survey of the types in the room, revealing mostly ones, threes, and nines.
Then, Daley and Walker offered a brief description of how each type looks in the workplace, including communication and management styles as well as strengths and weaknesses.
Starting with the body center, eights are called “the challenger,” causing them to challenge authority, and prefer self-employment and direct communication. Nines, “the peacemaker,” tend to see all points of views and be encouraging and unassertive, leading through diplomacy and inclusiveness. Ones, “the perfectionist,” tend to be detail oriented, ethical, and methodical, viewing the world as black and white and preferring matter-of-fact communication and clear expectations in the workplace.
Moving to the heart center, twos, “the helper,” have intuitive interpersonal skills and a dedication to relationships, motivating others through positive encouragement and support. Threes, “the achiever,” are motivated by success, causing them to be ambitious and productive in the workplace. Fours are “the individualist.” They strive to be unique and connect with people based on authenticity, leading in the workplace through creativity.
In the head center, fives, “the investigator,” seek to accumulate knowledge, communicating formally and managing with objectivity and expertise. Sixes, called “the loyalist,” seek careers which offer safety and security, leading responsibly and analytically. Sevens, “the enthusiast,” manage and communicate with enthusiasm, creativity, and energy, enjoying engaging with others in the workplace.
Daley and Walker announced two focuses for the evening: “an inward focus of how to approach a career based on enneagram type, and an outward focus of how self-knowledge can help in interviews and lead to understanding of one’s dream career.”
They encouraged attendees to break into groups and discuss strengths and weaknesses, career goals, leadership preferences, and core motivations.
“It was helpful to reconsider my enneagram type in the context of a work environment,” freshman Claire Hipkins said. “I appreciated thinking through and discussing the implications of the enneagram on more tangible details with my group, such as leadership style, style of workplace, et cetera.”
Comparing and contrasting motivations and career goals with their groups helped the students better understand how to work well with people of other types.
Walker reviewed the common motivations of each type, such as a nine’s desire to be at peace, and a one’s desire to be morally good. They made connections between which motivations complement which types of work environments. For example, because they are motivated by competition, threes thrive when working in teams.
“I had never before connected my enneagram with my future career, but the event inspired me to think about my work environment, career path, and dream job in a way that kept my 3‑wing-2-ness in mind,” freshman Luke Hollister said.
Daley proposed several questions each type should consider when choosing a career path.
“Do you do your best work in a group, or as an individual? Do you prefer to meet expectations or exceed them? Do you want variety in your work? Are you a perfectionist, or are you more results-oriented? How much stress do you enjoy?” she asked.
Daley and Walker shared the way they have applied their enneagrams to their career plans as they reach the end of their Hilldale education.
Daley described how she identified her dream job in relation to her type.
“My dream route was to work at a PR agency and I’m actually currently applying for jobs at PR agencies, and that relates to my motivations and my type.”
They recommended several resources for further enneagram exploration, such as “The Road Back to You” by Ian Morgan Cron and Suzanne Stabile, “The Complete Enneagram” by Beatrice Chestnut, and the “Sleeping at Last” podcasts on Spotify.
Walker provided a disclaimer regarding his enneagram expertise.
“I would like to emphasize that the enneagram is, as Ian Morgan Cron often says, ‘a low-resolution picture’ that can be helpful, but it certainly isn’t everything,” Walker said. “It is really easy to weaponize the enneagram by putting others or even yourself into the box associated with your type. Hopefully, we were able to communicate that the enneagram is an interesting and helpful way to look at future careers, but like any other system of personality, is subject to interpretation.”
Attendees said the presentation increased their self-awareness and prepared them to apply the enneagram to their career choices as they move closer to entering the workplace.
“I thought it was a really great way to start thinking about how individual personalities can benefit the workplace,” freshman Elizabeth Speck said. “It was also interesting to hear people of my own type sharing about their tendencies, strengths, and weaknesses and being able to recognize them in myself and relate to what they were saying.”