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Enneagram Stances: Meet Entrepreneur & Enneagram Expert, Dr. Jon Singletary

The Reformer. The Helper. The Achiever. The Individualist. The Investigator. The Loyalist. The Enthusiast. The Challenger. The Peacemaker.

Do these titles sound familiar to you? If so, you’ve probably heard of the Enneagram.

Based on ancient oral tradition and adopted as a means of self exploration in the mid-20th century, the Enneagram has quickly risen in popularity thanks to its undeniable accuracy and the self-reflection it allows. The Enneagram is defined as, “a nine-sided figure used in a particular system of analysis to represent the spectrum of possible personality types.” We want to be clear – the Enneagram is so much more than your typical personality test. The in-depth insights of each number contribute to self-awareness and self-understanding, bettering individuals and relationships.

As we quickly became advocates for the Enneagram and watched our community show extreme interest, we decided to meet up with Waco’s own Enneagram expert – Dr. Jon Singletary. Dr. Singletary is dean and professor at the Diana R. Garland School of Social Work at Baylor University, and a bonafide Enneagram expert.

Singletary began his Enneagram journey through relationships, and soon realized the importance of leaders having a deep understanding of the Enneagram. This sparked his passion to change the way leadership is approached through his own entrepreneurial venture.

Singletary’s perspective of the Enneagram includes two distinct applications – relationships and leadership.

“Most of my journey with the Enneagram and how I want to use it is split between the two – How people understand it for relationships and what it means for leadership,” Singletary said. “Really I think the value of the Enneagram is best realized at the intersection of the two.”

As a leader, there can be a preconceived notion that you must constantly be strong-willed, fast-paced, emotionless and not let anything intrude on the success of achieving a goal. Singletary explains the importance of how relationships and leadership work together. In an environment where productivity dominates relationships, it never fails to backfire in one way or another.

For Singletary, the Enneagram equipped him with the skills to connect to feelings that all leaders experience. As leaders, it’s not a option to keep feelings in check, it’s a requirement. In order to reach success, leaders must effectively balance thinking, feeling and doing, because a large part of leadership is paying attention to one’s own feelings, as well as the feelings of those being led.

“People matter in our work, and they aren’t just cogs in a wheel, they really are relational beings who need to connect, and it’s only in the connection that we create a really meaningful team that is able to do the work,” said Singletary.

Leaders tend to be externally focused, and living in that mindset can get them in trouble. Though it can be somewhat like telling a leader to go in reverse, they must take the time to pay attention to the feeling aspect of leadership and learn to be inward focused. Singletary expresses how essential it is for leaders to be reflective and introspective.

Through his own side hustle, Enneagram Stances, Singletary works to help others understand and implement the Enneagram in their daily and working lives. When asked about his approach to teach someone to be a better leader, he explains they must recognize their own struggles in leadership, they have to “see the mess in their own backyard.” It’s often times difficult for leaders to recognize they have feelings, pay attention to them and honor them.

“Relationships and the fact that we all bring our personal lives with us to work, means that feelings come along, and we have to find ways to pay attention to them,” said Singletary.  

In a company or working group, you always strive to find the Enneagram balance among your team, but with that balance comes diversity and learning how to respect a diversity of personalities. For all leaders, Singletary recommends practicing consistent self-reflection – something he lives by. Adopting nonjudgemental self-observation and relinquishing self criticism benefits an individual leader, and those being led.

“Good leaders know the value of caring for others. It doesn’t mean you’re a feeling person, you have to go beyond just caring for others in order to practice self care. You really do have to put your oxygen mask on first,” said Singletary. “You have to learn to love yourself as much as you love your neighbor. You have to find ways to really honor the things in yourself that you think are good enough. It’s hard to really stop – and to do those as a part of the work experience.”

Through Enneagram Stances, Singletary tunes into all numbers, whether they be aggressive, withdrawing or dependent, and lead them to a healthy understanding of themselves while teaching the importance of self-care. Each number has a different answer to the questions: ‘What am I feeling? What am I thinking? What am I doing?’

Connection in the heart of leadership is where Singletary resides, and where he strives to lead others.

“I love providing support to local leaders in our community. It is always an honor to get to be a part of this work and walking alongside the amazing people in Waco doing great things.”

To connect with Dr. Singletary, visit