World Enneagram Day, celebrated on May 25th, 2024, is an acknowledgment of the profound impact that this tool offers for helping understand human behaviour and motivation in order to transform various aspects of our lives, including the worlds of investing and business.

The Enneagram is widely regarded as a more complete and in-depth approach to understanding personality and presence than any other system. It is comprehensive, yet easy to understand and dynamic rather than static. It is arguably the oldest human development system on the planet. It doesn’t put you in a box - it shows you the way out of the box you are in.

The Enneagram is one the most effective tools I’ve found for catalysing personal and professional success. I’ve been using this powerful, transformational tool personally and professionally for more than 15 years. It has worked wonders with individual investors and business leaders. There is also an opportunity for fund managers to use the Enneagram to better understand the leaders of businesses they may invest in and encourage use of the Enneagram for leadership development.

‘Money – From Fear to Love’ using The Enneagram

In her book ‘Money: From Fear to Love – Using the Enneagram to Create Wealth, Prosperity and Love’, my friend and fellow Enneagram student Margaret Smith, Harvard PhD (Economics) and USA Certified Financial Planner, explains the importance of Enneagram in relation to money:

“The problem is that we are each asleep to our relationship to money in some way. Waking up requires intervention. We need a map of the ways in which we are asleep. This is the fundamental beginning point for improving our relationship to money. How can a person who is asleep diagnose the ways in which they are asleep? They cannot. Asking people to explore their family history with money, their childhood money messages, and their money values will bring them some distance, but not all the way. Eventually, we will hit a wall. Without a map, we cannot see ourselves more clearly. This is precisely why a system that can help people find themselves is so useful.”

From a financial perspective, by understanding your Enneagram type, you can gain profound insights into your behaviour, enhance your financial relationships, and optimise your investment strategies. This approach not only improves your satisfaction with your financial choices but also drives better outcomes. Better understanding yourself can directly impact on your financial success.

The Wisdom of the Enneagram

A great first step for exploring the Enneagram is reading ‘The Wisdom of the Enneagram: The Complete Guide to Psychological and Spiritual Growth for the Nine Personality Types’ co-authored by Russ Huson and Don Riso. This book was the first I read about the Enneagram – it was life changing and set me on a path to being trained by Don and Russ, both pioneering developers of the Enneagram system. Ten years ago, I qualified as a Riso Hudson Certified Teacher with the Enneagram Institute.

The Riso-Hudson Enneagram Type Indicator (RHETI® version 2.5) is the world’s most popular Enneagram-based test. It is a scientifically validated, forced-choice personality test with 144 paired statements. The test takes about 40 minutes to complete. It is available on The Enneagram Institute website.

The Nine Types

The Enneagram identifies nine distinct personality types, each with its own unique way of thinking, feeling, and behaving. These types influence how you approach life, including your professional and personal roles.

Applying the Riso-Hudson terminology the nine types depicted on the Enneagram symbol are:

Type 1 - The Reformer: Principled, purposeful, and self-controlled.

Type 2 - The Helper: Generous, demonstrative, and people-pleasing.

Type 3 - The Achiever: Success-oriented, pragmatic, and image-conscious.

Type 4 - The Individualist: Sensitive, expressive, and dramatic.

Type 5 - The Investigator: Perceptive, innovative, and secretive.

Type 6 - The Loyalist: Committed, security-oriented, and anxious.

Type 7 - The Enthusiast: Spontaneous, versatile, and scattered.

Type 8 - The Challenger: Self-confident, decisive, and confrontational.

Type 9 - The Peacemaker: Receptive, reassuring, and complacent.

Here is a fun depiction from Renee Baron and Elizabth Wagele of the nine types at a business meeting:

You can watch Russ Hudson explaining each type on the videos on his website homepage.

As another celebration of World Enneagram Day I’m happy to share my essay ‘Diagnosing the Personality Types of Famous People’. In this 30-page essay, I profile in-depth five famous businesspeople. I submitted this essay as part of the certification requirements to become a Certified Teacher with the Enneagram Institute. Several of my essays have been used as ‘model examples’ for students. The people I profile are:

Type One - Anita Roddick (founder of The Body Shop),
Type Two - Mary Kay Ash (founder of Mary Kay Cosmetics)
Type Three - Steve Jobs (founder of Apple)
Type Six - Andrew Grove (third employee and third CEO of Intel Corporation)
Type Nine - Ben Cohen (co-founder of Ben & Jerry’s)

This focus on businesspeople reflects my interest in understanding how professional investors can better assess leaders and encourage leadership development, by suggesting businesses tap into coaching and training that utilises the wisdom of the Enneagram.

The Levels of Development

In one of their many unique contributions to the Enneagram literature, Riso and Hudson introduced the idea of Levels of Development. At a training I attended Russ Hudson mapped the territory of developmental levels by drawing a circle with eight other circles around that first circle. The inner circle, he said, is “The Journey as Presence” (Level One); and the first two circles (Levels Two and Three) are “The Journey with Presence”. Levels Four to Six are “The Journey to Presence”, also described as the “Average” Levels. Levels Seven to Nine are the “Unhealthy” Levels. Riso and Hudson depict these levels as follows:

FREEDOM — OPENNESS — EXPANSION

CONSTRICTION — REACTION — OBSESSION

Riso and Hudson teach that we are each one dominant Enneagram type and that the levels help explain individual differences. Each level is distinct and interrelated. They maintain that the levels are a measure of our how asleep we are at any given moment. Riso invites us to ‘wake up’ so that ‘our lives can be a miraculous unfolding of beauty and joy’.

For Riso and Hudson the personality is a tiny part of our potential, which includes mere imitations of the real qualities of Essential Nature such as joy, love, peace, compassion, strength, and understanding. The personality is constantly reacting, whereas when present we are grounded and receptive. In becoming free from the negative (lower level) aspects of personality, our Essence develops, and we move to more positive (Levels 1 to 3) aspects of personality: ‘Ego no longer controls us: Essence speaks through our personality’.

Expressed another way, there is a broad spectrum between immature and mature. In this context, an immature person is trapped within themself. In contrast, the mature person is free.

Escaping Prison

One of the Enneagram’s core metaphors is the analogy of being in prison, which illustrates how individuals are often trapped by their own habitual patterns of thinking, feeling, and behaving. Here's how this analogy works and how the Enneagram offers a path to escape.

How we are all imprisoned

Trapped in Habitual Patterns
Each of the nine distinct personality types, has its own set of core fears, desires, and defence mechanisms. These patterns are like the walls of a prison, limiting how individuals perceive and interact with the world.
Locked in Unconscious Behaviours
People often operate on autopilot, unaware of how their type's habitual patterns dictate their responses to various situations. This lack of awareness is akin to being locked in a cell without realising there is a way out.
Clinging to a False Sense of Security
The prison provides a false sense of security. Individuals might cling to their patterns because they offer familiarity and predictability, even if they are ultimately limiting and self-defeating.

The Path to Escape

Self-Awareness
The first step to escaping the prison is recognising that one is trapped. The Enneagram encourages self-observation and mindfulness, helping individuals become aware of their automatic responses and underlying motivations.
For example, a Type 2 (The Helper) might notice their tendency to seek approval through acts of service and begin to understand how this pattern limits their own needs and well-being.
Understanding Patterns
The Enneagram provides insights into each type's patterns, explaining why they developed and how they manifest in daily life. This understanding is like finding the key to the prison cell.
A Type 3 (The Achiever) might learn that their relentless pursuit of success is driven by a fear of worthlessness and begin to see how this impacts their relationships and sense of self.
Growth and Transformation
The Enneagram outlines paths for growth for each type, showing how individuals can move from unhealthy, automatic behaviours to healthier, more conscious choices.
A Type 4 (The Individualist) might work on embracing their inherent worth and finding balance between their emotional intensity and the present moment, leading to a richer, more fulfilling life.
Integration and Wholeness
True escape from the prison comes from integrating the positive aspects of all nine types. This process involves embracing the strengths of one's own type while also cultivating the virtues of other types.
A Type 5 (The Investigator), for instance, might develop the warmth and sociability of a Type 2, the practicality and action-orientation of a Type 8, and the optimism of a Type 7.

By using the Enneagram, individuals can gain a deeper understanding of themselves and others, breaking free from the constraints of their personality's ‘prison’ and moving towards greater self-awareness, authenticity, and personal freedom.

Conclusion

Exploring the Enneagram can offer profound benefits for personal investors and business people, as it fosters a deep understanding of intrinsic motivations, strengths, and potential pitfalls. By recognising their own personality patterns, individuals can make more informed decisions, enhance their emotional intelligence, and improve interpersonal relationships. Personal investors can leverage the self-awareness offered by the Enneagram to mitigate biases and make more strategic financial choices. For business leaders, the Enneagram provides a framework for better understanding themselves and others, leading to more effective management and collaboration. Ultimately, the Enneagram serves as a powerful tool for personal and professional growth, enabling individuals to unlock their full potential and achieve greater success and fulfilment in their endeavours.

Catalysing Success - Celebrating World Enneagram Day