Intro to Enneagram for Entrepreneurs Pt. 1

If there is any one secret of success, it lies in the ability to get the other person’s point of view and see things from that person’s angle as well as from your own.
— Henry Ford

This April will mark four years for Drop Cap, and each year I learn something new about the branding process - specifically about personal and small business branding. It’s entirely different from working with corporations, often creating a more intimate and collaborative experience. The more I work on personal brands, the more I realize how important it is to cultivate self-awareness as an entrepreneur.

I heard about the Enneagram a few years ago, took the quiz, and filed the results alongside the Myers-Briggs and StrengthFinders tests. But this year, I felt a pull to get back to the root of why I started Drop Cap, and more specifically, where it’s going. So I went back to my test results from personality tests past to see if I had changed. When I got to the Enneagram… things began to get interesting.

Suddenly it was like a world of understanding unfolded before me. I saw that nothing was accidental and that my strengths and inspirations were more than inclinations. All of it tied to who I was and how I specifically viewed the world. I went down a rabbit hole in finding out more about why I thought and felt the way I do, and what it means for my business as an extension of me.

As I found my way out of the hole and back up to the light, clinging to my new self-awareness, I saw how many opportunities this strikingly helpful tool was in the business world. For example…

  • It gave me a foundation for knowing who to add to my team.

  • It gave me compassion for others in conflict-resolution situations

  • It allows me to understand my audience and clients in a new way

  • It gave me the self-awareness to know which opportunities were best suited to my strengths

  • It gave me an awareness of where I need to be held accountable

Over the next few months, I’ll be revealing each number in depth as it relates to work and entrepreneurship. My hope is that this serves as a tool for understanding yourself and creating a business that allows your natural strengths to shine and best serve your audience.

But first… an introduction.

What is the Enneagram?

The Enneagram is a mysterious nine-point model whose roots seem to come from Asia and the Middle East dating back thousands of years ago. The Enneagram is startlingly accurate and gives insight into how people feel, think, and behave. It has deep psychological and spiritual complexities and has historically been used in the context of counseling and mentorship.

Teachers of the Enneagram hailed from Bolivia, Europe, and Chile in the early 1900’s when the model began to circulate outside of philosophy and theology schools. The amazing thing about this model is that it gives insight into enduring truths about the human character, from every culture and background. It’s a tool for relating to anyone and better understanding yourself.

How to Find Your Type

Contrary to other personality tests, the Enneagram doesn’t involve just taking a quiz and reading the results. The best way to identify your type is by studying each number. You’ll know when you find yours. You’ll feel as if someone read your mind and exposed all your hidden motivations. And if you don’t, ask your friends, family, or a therapist to help you identify your motivations and deep-set desires.

The Enneagram is all about motivations, not behavior. Instead of focusing on how you express yourself, focus on why you hold certain beliefs and perspectives. Each number has layers of complexities, so think of it as a starting point: each number acts like a color - with various shades and tones on the scale.

While I’ll be taking a deep dive into each personality type in this series, I first want to help you identify your number.

Summary of the Nine Types

Type One • "The Perfectionist"

dedicated, purposeful, & self-controlled

With a strong sense of right and wrong, Ones are natural teachers who are on a mission to improve things, but afraid of making a mistake. They maintain very high standards, and can often be critical of themselves and others. They are responsible, hardworking, and disciplined. It can be hard for them to allow things to be “good enough.”

Ones are well-organized and conscientious. Their biggest fear is being defective, and their biggest desire is to be balanced. They want to avoid fault and improve the world.

Type Two • "The Giver"

generous, people-pleasing, possessive

With an optimistic outlook, Twos are natural helpers who excel in communication. They anticipate the needs of others and are highly empathetic, but struggle with establishing personal boundaries. They are generous and sincere, but can also become people-pleasers in the process.

Twos are warm and caring. Their biggest fear is being unwanted, and their biggest desire is to be needed. They want to be appreciated by others and avoid acknowledging their own needs.

Type Three • "The Performer"

driven, image-conscious, adaptive

With a charming disposition, Threes are self-assured achievers who excel in competitive settings and productivity, but can often become overly concerned with how they are perceived by others. They have problems with workaholism, and are constantly looking for ways to advance beyond and impress others. They are naturally poised and diplomatic, able to adapt to any situation.

Threes are motivated and competent. Their biggest fear is worthlessness, and their biggest desire is to feel valuable. They want to be admired by others and avoid failure.

Type Four • "The Artist"

withdrawn, sensitive, individualistic

With an emotionally-honest awareness, Fours are creative romantics who want to be understood. They are sensitive and expressive, but can withhold from others to avoid vulnerability. They have immense feelings and can tend to be idealistic. They have problems with self-indulgence and moodiness, but are creative dreamers who deeply want to be unique.

Fours are self-aware and personal. Their biggest fear is settling, and their biggest desire to feel significant. They want to be understood by others, while tending to their own emotional needs.

Type Five • "The Researcher"

perceptive, innovative, isolated

With an analytical perspective, Fives are focused investigators who love to satisfy their curiosity. They are alert and insightful, but tend to be private, valuing their independence from others. They often display an intensity in their ideas and interests, and can have problems with eccentricity and isolation. They are innovative thinkers who want to absorb information.

Fives are inventive and focused. Their biggest fear is feeling helpless, and their biggest desire is to feel competent. They want to understand their surroundings and defend themselves with knowledge to ward off the unpredictable.

Type Six • "The Loyalist"

witty, responsible, anxious

With a practical mindset, Sixes are reliable troubleshooters who cling to security. They are committed and hard-working, but can often run on stress while complaining about it. They are gifted at foreseeing potential problems and encouraging cooperation. They are cautious workers who want to find a safe zone, while maintaining extreme loyalty and dedication to their relationships, systems, and beliefs.

Sixes are loyal and trustworthy. Their biggest fear is the lack of support, and their biggest desire is security. They want to feel reassured by others, while avoiding insecurity.

Type Seven • "The Enthusiast"

spontaneous, excited, scattered

With a spontaneous attitude, Sevens are fun-loving adventurers who seek happiness. They are extroverted and optimistic, but can often become scattered and undisciplined. They are high-spirited and playful, constantly seeking new experiences to the point of exhaustion. They struggle with impatience and impulsive behavior in their addiction to excitement.

Sevens are extroverted and energetic. Their biggest fear is being deprived, and their biggest desire is contentment. They want maintain their freedom, while staying occupied and avoiding painful situations.

Type Eight • "The Challenger"

confident, decisive, confrontational

With an intense communication style, Eights are commanding and take-charge personalities. They are protective and assertive, able to solve problems resourcefully and handle a situation. However, they can also be controlling and close-minded in their pursuit of power. They are strong-willed and self-confident in their pursuit of justice.

Eights are intimidating and effective. Their biggest fear is being controlled, and their biggest desire is to protect themselves and others. They want influence over others, while avoiding their own vulnerability.

Type Nine • "The Peacemaker"

reassuring, agreeable, receptive

With a strong desire for peace, Nines are pleasant and laid back. They are supportive and trusting of others, able to naturally see others’ perspectives and easily mediate conflict. While they keep things going smoothly, they can often be too accommodating in order to keep the peace. They are stable and optimistic, while minimizing anything negative or upsetting.

Nines are compassionate and understanding. Their biggest fear is separation, and their biggest desire is stability and peace. They want harmony from others, while avoiding tension or conflict.

The Enneagram is a powerful tool for understanding yourself and relating to others. I have read several helpful books about the Enneagram, each one giving me further insight into how the model works.

This is not an affiliate link, but I would suggest starting with Ian Cron & Suzanne Stabile’s book The Road Back to You. This book gives a lot of insight into how the Enneagram plays out in your personal life and relationships. However, in this series, we will take a look at how the Enneagram can be a tool for business and entrepreneurship. Once you’ve discovered your number, let me know which one you are in the comments below!

**I’m a Three :)