Stu­dents joined Career Ser­vices at Penny’s to study the enneagram and its impact on work rela­tion­ships.
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“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.”