DLGP

Doctor of Leadership in Global Perspectives: Crafting Ministry in an Interconnected World

The Enneagram, Free Will, and Good Character

Written by: on September 11, 2024

One of the primary reasons the concepts behind the Enneagram first resonated with me can be summed up in the words of Paul in Romans 7:18b-19: “For I have the desire to do what is good, but I cannot carry it out. For I do not do the good I want to do, but the evil I do not want to do–this I keep on doing.” (NIV)

I realized that the strengths I have always leaned into–being organized, being driven to get things done and to do them well (when I was in my 30s my mother told me that I had always been driven, even as a child and a teen), to take charge when there is a vacuum of leadership, and to feel comfortable being in the spotlight (actually desiring to be in the spotlight…)–well, those strengths also sometimes got me into trouble. They still do.

And I don’t want to get myself into trouble. I don’t want my strengths to turn into challenges or even liabilities. I really want to do the right thing in every situation.

But too often… I just don’t. 

I couldn’t understand why that kept happening. 

Until I discovered the Enneagram.

If you know anything about it, I’m sure you can guess toward which number I lean most strongly. 

Yes, I most often live with the personality patterns of the Three. Though I also lean almost as much toward Two.

If you read the description above, you can probably imagine when and how those personality tendencies can be positive and helpful… and when and how they may lead to problems when not managed effectively. Miscommunication. Misunderstandings. Misalignment of direction. You get the idea. 

Self-awareness is the name of the game. That’s when you can step back, almost like you’re hovering over yourself, and say, “Oh look! I’m doing that again!”

But self-awareness isn’t enough. You then need to move into self-knowledge. That’s when you can say, “Yes, I noticed it’s that same trigger that caused me to do that again. Now I can prepare for it so I can choose to do something different next time.”

Free Will… or Not?

That last comment is really the point of this essay. We get to choose our actions. As leaders, it is incumbent on us to use the free will God has given us to choose well. 

In Meditations by Marcus Aurelius (circa 170-180 AD), the author frequently writes about the three disciplines of Stoicism. He describes them this way (with side comments by translator, Gregory Hays):

Everywhere, at each moment, you have the option:

    • To accept this event with humility [will]
    • To treat this person as he should be treated [action]
    • To approach this thought with care, so that nothing irrational creeps in. [perception] (7.54) [1]    

Gregory Hays explains that for the Stoics, 

“…perhaps the most important [worldview] is the unwavering conviction that the world  is organized in a rational and coherent way. More specifically, it is controlled and directed by an all-pervading force that the stoics designated by the term logos… (When the author of John’s Gospel tells us that ‘the Word’–logos–was with God and is to be identified with God, he is borrowing Stoic terminology.)… All events are determined by the logos, and follow in an unbreakable chain of cause and effect.” [2]

Hays explains that Stoics get around the apparent lack of free will by “defining free will as a voluntary accommodation to what is in any case inevitable.” [3] 

That certainly resonates with many Christians, I’m sure, who also struggle with the dichotomy between the free will given to us by God, and our belief that God is all-knowing. 

About human free will, Dallas Willard wrote, 

“The will, or heart, is the executive center of the self. Thus the center point of the spiritual in humans as well as in God is self-determination, also called freedom and creativity… Every human being has a will, or willpower. It is our inclination and capacity to act on our own and to produce what we find to be good–to be freely creative. Because we have will we are not things. We have in us the capacity to be self-determined to some significant degree. Without will we would have no life that is recognizably human… It is the human spirit, and the only thing in us that God will accept as the basis of our relationship to him.”   [4]

Good Character

Marcus Aurelius also discusses what it means to be the best version of yourself:

The human soul degrades itself:

II. When it turns its back on another person or sets out to do it harm, as the souls of the angry do.

III. When it is overpowered by pleasure or pain.

IV. When it puts on a mask and does or says something artificial or false.

V. When it allows its action and impulse to be without a purpose, to be random and disconnected: even the smallest things ought to be directed toward a goal. But the goal of rational beings is to follow the rule and law of the most ancient of communities and states. (2:16)  [5]

At another point, Aurelius writes, “I was once a fortunate man but at some point fortune abandoned me. But true good fortune is what you make for yourself. Good fortune: good character, good intentions, and good actions. (5.37)” [6]

Good character is something we look for in leaders; we don’t want to follow degraded souls. Good character is a critical element without which we cannot trust our leaders to do the right thing. 

But what is character? A simple definition is this: what you would do without thinking, when no one is watching

Our character is formed by our personality patterns, our attachment patterns, our experiences, and our circumstances. It’s an integration of internal and external influences.

So why do we struggle with building good character?

As clearly laid out in his book, Live No Lies, John Mark Comer reiterates the age-old understanding of why we sin: the devil, the flesh, and the world. He says, “the devil’s primary strategem to drive the soul and society into ruin is deceptive ideas that play to disordered desires, which are normalized in a sinful society.”  [7]

Comer quotes Ignatius of Loyola, the founder of the Jesuit order: sin is the “unwillingness to trust that what God wants for me is only my deepest happiness.” [8]

Authentic Leadership

And that is how all these threads can be brought together: as leaders, we must continually grow in our trust of God’s goodness and be willing to allow the sometimes challenging pruning of our character that God knows is best for us.

Embracing the fullness of our identity as beloved children of God, warts and all, is essential for cultivating good character and making wise choices. The journey of self-awareness and self-knowledge, as illuminated by the Enneagram, allows us to recognize our strengths and weaknesses. It helps us see where we are deceiving ourselves as well as others, by wearing that false mask of which Aurelius wrote. As Comer invites, “live no lies.”

By exercising our God-given free will, we can align our actions with our true selves, creating a life that reflects the goodness and purpose God intended for us.

As we strive to be all that God created us to be, we must remember that character is not simply about avoiding wrong actions but actively choosing good ones. 

It is about being authentic, pursuing humility, and treating others with love and respect. When leaders commit to this path, we inspire those around us to follow suit, fostering a community grounded in trust and integrity. 

It’s a tall order, one we can’t possibly achieve on our own without the grace and power of the Holy Spirit to guide us.

We can only be the beacons of light Jesus wants us to be in an often dark world, by growing in character–becoming more like Jesus–through daily spiritual disciplines that come from good choices and actions… and a lot of prayer. 


[1] Marcus Aurelius, Meditations, trans. Gregory Hays (New York: The Modern Library, 2003), 93.

[2] Aurelius,  xx.

[3] Aurelius, xx.

[4] Dallas Willard, The Divine Conspiracy: Rediscovering Our Hidden Life in God (San Francisco: Harper Collins, 1998), 80-81.

[5] Aurelius, 22.

[6] Aurelius, 65.

[7] John Mark Comer, Live No Lies: Recognize and Resist the Three Enemies That Sabotage Your Peace (Colorado Springs: WaterBrook, 2021), 57.

[8] Comer, 61.

About the Author

Debbie Owen

Deborah C. Owen is an experienced spiritual director, Neuro-based Enneagram executive and life coach, disciple maker, professional writer, senior librarian, and long-time church Music Director and lay leader. She has earned the award of National Board Certification for teaching excellence, and a podcasting award, and is pursuing a Doctor of Leadership degree through Portland Seminary at George Fox University. She lives in the backwoods of Maine with her husband and flat-coated retriever. She spends as much time as she can with their 3 grown children, daughter-in-law, and 2 small grandchildren. Find her online at InsideOutMinistries.info.

15 responses to “The Enneagram, Free Will, and Good Character”

  1. Adam Cheney says:

    Debbie,
    Thanks for the insight into Marcus Aurelius, Willard, and Comer. I know that you do coaching for Enneagram. What drew you to Meditations?

  2. mm Glyn Barrett says:

    Thank you for your thoughts, Debbie. I appreciated how you tied in Scripture, Stoicism, and authors like Willard to explore the complexity of free will and character. Practically speaking, how do you personally balance trusting God’s will and exercising free will, especially in leadership moments that require quick decisions?

    • mm Kari says:

      Glyn beat me to this question, Debbie. So I’m going to tag on here as I’m also interested in your answer to this question.

    • Debbie Owen says:

      Glyn, good question. Wish I had a really good answer. 🙂

      I believe that faith is an internal way of being. It’s a combination of emotional, spiritual, and intellectual understanding that God wants what is best for each of us.

      I believe that trust is the external, physical action that manifests my faith. In other words, if I have faith that God wants what is best for me, my trust in choosing a particular path of action is the result, the manifestation of my faith.

      If my faith is based on believing God’s will for me is always good, even when the ship sinks (so to speak), I also know that God invites me to be my best self in choosing what I do.

      As I indicated in the post, there is a great mystery between believing God is all-knowing and yet we have free will. The Stoics struggled with this too. I didn’t include it in the post, but the translator said it’s like tying a dog to the back of a cart. The cart is going forward and the dog can choose whether or not to trot along. Essentially, the dog gets to choose to walk on his own four feet or get dragged. I’d rather not have God drag me into the future! I’d rather walk there with God beside me, on my own two feet!

  3. Elysse Burns says:

    Hi Debbie, I appreciated your thoughts on Marcus Aurelius’ philosophy of good character, which you then tied to authentic leadership and aligning our actions with our true selves. In my blog post, I also focused on figures serving in the Roman Empire. However, I found it challenging to write anything meaningful because I felt apprehensive about “supporting” their leadership, given the harshness of the Empire and my lack of historical knowledge. You did an excellent job in presenting Aurelius’ ideas. Besides the Enneagram, have you found any other tools to help you on your self-knowledge journey?

    P.S. I am an Enneagram Type: 1.

    • Debbie Owen says:

      Elysse, I understand your predicament. I figured I’d just identify the good things I could find in the book.

      Yes, I also know a good bit about attachment theory, which can easily accompany the Enneagram as a tool for increasing self-knowledge (which, as we know, is critical to ongoing spiritual formation). I also read everything I can get my hands on from Curt Thompson and Dan Siegel, both of whom also talk about interpersonal neurobiology (how we relate to each other). And I read Jim Wilder, Peter Scazerro, and some others. I’m also in a coaching certification course where we’re learning about the Jungian archetypes, which are extremely helpful.

      I aim to integrate all of this together as I support people through life transitions and challenges (as a coach, retreat leader, and spiritual director). I’m putting all of this together (or much of it, anyway) in an upcoming retreat which you can read about at the end of this article about Enneagram Ones. 😉

      https://open.substack.com/pub/debbieowen/p/pursuing-excellence-understanding?r=1m6dv&utm_campaign=post&utm_medium=web&showWelcomeOnShare=true

  4. Chad Warren says:

    Debbie, along with a few other comments, I appreciate how you combine the ideas of Marcus Aurelius, Willard, and Comer into one conversation. How do you see this discussion resonating with your research towards Discipleship and your NPO?

    • Debbie Owen says:

      Chad, my NPO has had to leave discipleship a little to the side, unfortunately. But I’m eager to incorporate how growing in self-awareness and self-knowledge is a critical aspect of supporting people through life transitions, relationships, and other challenges.

      I’m not waiting 3 years to integrate what I’m learning into my NPO. I’m trying things out right now, especially in the upcoming retreat I’m leading here on the coast of Maine next month. I think you’ll see some of these themes resonating in the text on this page: https://owen-reconnect.my.canva.site/leading-with-life-in-balance

      What does this have to do with free will? I believe it comes down to discernment. God wants what is best for us because God is only good. And… we get to choose how we respond to what happens in our lives. Actually, we can react without a lot of thought, or we can respond based on growing self-knowledge.

  5. Christy says:

    Hi Debbie, thanks for your post. I’m an enneagram 8 but a very close second is 3 (I might even go back and forth in testing) – so I get it!

    Do you know the environments that allows for a healthy 3 vs. the environments that bring you to an unhealthy place?

    I used to struggle with the paradox of free will vs. God’s sovereignty. Today, I’m much more satisfied knowing that both can be true simultaneously, and it’s just part of the mystery of God.

    • Debbie Owen says:

      Christy, you might be interested in this article I wrote recently about Enneagram 8s.
      https://debbieowen.substack.com/p/guardians-of-justice-how-enneagram?r=1m6dv

      Excellent question about how to navigate the challenges between healthy and less healthy. It comes down to observing the triggers that cause me to do what I don’t want to do.

      For me, it includes: when someone claims credit for something I said already, or just doesn’t credit me; when there is a vacuum in leadership and I have to decide if it’s best to keep waiting, or if it’s time to plunge in; when I feel like someone is trying to tell me what to do and I already feel pretty competent on the topic; when there are 4 things that need to get done, all of which I can totally do, but I know I need to delegate or make space for others to contribute…

      I didn’t used to know these things about myself (and that’s just the start of it!). I am grateful God has gently allowed me to grow in honoring him by allowing others to increase while – sometimes – I decrease.

      I have a long way to go though, by the power and grace of Jesus’s Holy Spirit…

  6. Daren Jaime says:

    Hi Debbie. Thank you for sharing your thoughts as I am now reflecting on authentic leadership. This is hard to see modeled as we are saddled with the plight of so many fallen leaders in recent times. What would you describe as the biggest obstacle to this authenticity, and how do you practice this for yourself?

  7. Debbie Owen says:

    Great question Daren, thank you. Personally, there are a few things I notice (about myself sometimes, and about other leaders too). These include:
    — A lack of willingness to be honest about one’s strengths and challenges.
    — A lack of true self-awareness and self-knowledge (see some of my other responses).
    — A lack of recognizing that one person doesn’t have all the answers and it’s always better to work in a team (lack of humility).
    — Forgetting that leadership isn’t about YOU, it’s about those whom you serve. With an emphasis on SERVE.
    — The temptations of power and control. Why would someone be fully authentic when the exertion of power and control requires you to be just a bit inauthentic?
    — A lack of adhering to one’s values.

    I could go on, I’m sure.

    I intend to practice authenticity by constantly trying to be honest with myself about my challenges, and by remaining true to my values. These things are often not easy…

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