Enneagram and Entrepreneurship: Analysis + Tips for Success

Analyzing the relationship between Enneagram and entrepreneurship can help us understand what each Enneagram type needs to become a successful entrepreneur. Though some Enneagram types are more open to the idea of becoming their own bosses, every Enneagram type can become an entrepreneur under the right circumstances.

In this article, we’ll explore how Enneagram and entrepreneurship are connected and what inspires each type to choose such a lifestyle.

What is the Enneagram and How Does It Work?

Enneagram is a personality system developed with the mixed influences of ancient wisdom, modern philosophies, and psychological personality theories. It divides people into nine types based on their core motivation, fears, strengths, and life strategies.

Some of the core aspects of Enneagram include the following:

• Enneagram wings, which provide more flexibility to the system by introducing two subtypes for each personality type
• Enneagram arrows that offer explanations of how each type behaves when they go through healthy and unhealthy developmental stages
• Enneagram motivations that describe what drives each type’s behaviors and thought and feeling patterns

Unlike many other personality theories, the Enneagram generally focuses on inner psychological forces that shape personality types, not on their observable behavior. As a result, it is very flexible and allows for plenty of variety among the types.

How Entrepreneurial is Each Enneagram Type?

So, while each Enneagram type can be an entrepreneur, some are more naturally inclined to pursue such a career. Below, we’ll analyze how Enneagram and entrepreneurship are intertwined and how each personality type approaches their business.

Enneagram 1—The Perfectionist

Enneagram Type One is responsible, diligent, and full of initiative, so they can thrive as entrepreneurs. They also have excellent leadership skills, are well-organized, and are highly efficient—all of which are traits needed in entrepreneurship. Regardless of the business they run, it will surely be an ethical one.

In general, Ones might be more naturally inclined toward working in public service or for some kind of altruistic cause, but depending on their life circumstances, they may easily become an entrepreneur too.

In addition, Type One entrepreneurs may also be prone to revolutionizing their field of business, like Henry Ford, the founder of Ford Motor Company, whose innovations had a huge impact on the automobile industry.

Enneagram and entrepreneurship tip: Success doesn't require perfection, so don’t sweat over small flaws in your work. Staying committed to your core values without losing the big picture in mind is essential for your private business to thrive. That also means being able to delegate tasks and reduce your workload so that you can focus on your vision and not on irrelevant details.

Enneagram 2—The Helper

Type 2, the Helpers, aren’t known for their entrepreneurial spirit. In fact, they do best in service-oriented businesses where they can interact with others and provide them with help and support. They excel at building relationships with clients and partners, but they usually lack the initiative to start their own businesses.

Nevertheless, considering how responsible, committed, and diligent they are, there’s no reason for the Helper not to become an entrepreneur. As they mature and grow emotionally, they become more fond of the idea of running their own businesses. Kris Carr, author and wellness advocate, showcases Twos’ entrepreneurial tendencies perfectly.

Enneagram and entrepreneurship tip: Don’t allow your desire to help others interfere with your business goals and profit. You have every right to charge your services at the prices you set, and you should be transparent about that.

Enneagram 3—The Achiever

Threes (the Achievers) are entrepreneurs by nature. They often dream about running their own business from the early years, and their dreams are big. Their confidence and passion also make them very efficient in their work. Moreover, they are well-attuned to reality, aware of industry and marketing trends within their fields of interest, and determined to succeed.

Plus, they easily make connections, and their charisma attracts other people to follow them, so they can easily find support for their goals. Oprah Winfrey, a media mogul and one of the most successful people worldwide, is a perfect example of Three’s entrepreneurial potential.

Enneagram and entrepreneurship tip: You have a tendency to invest too much energy in marketing and public relations at the risk of neglecting the core elements of your business. Focus on long-term reputation and building a tradition, not just short-term success.

Enneagram 4—The Individualist

Enneagram Type Four is very independent and doesn’t tolerate the typical corporate culture of working 9 to 5 in an office well. Though they aren’t naturally entrepreneurial, their nonconformist spirit and need for freedom easily lead them toward entrepreneurship.

As Entrepreneurs, Fours can easily build a strong brand because they are authentic, creative, and value quality. Ralph Lauren, a famous fashion icon, is a Type Four and a great example of how Fours can be successful entrepreneurs, too!

However, they may struggle with the commercial and administrative aspects of their business, as they are reluctant to deal with tasks they find boring.

Enneagram and entrepreneurship tip: Get well-appointed with the practical aspects of your business and profit possibilities. If you’re not an expert in this, seek professional advice or hire a professional to help you set up a solid foundation for your business.

Enneagram 5—The Investigator

Fives excel in industries that require in-depth knowledge and expertise in specific fields. They are analytical thinkers with the fascinating ability to acquire a large amount of information quickly and come up with innovative solutions and ideas.

Like Fours, Fives don’t thrive in a typical corporate environment and prefer to work independently. For this reason, despite the fact that they are not naturally inclined toward entrepreneurship, Fives are often entrepreneurs and usually run businesses based on highly specific services.

In addition, Elon Musk, with his innovative business, is a great example of the type of Entrepreneur the Enneagram Type Five (the Investigator) can be.

Enneagram and entrepreneurship tip: Don’t hold on too tightly to your comfort zone. You have great analytical skills and are more than capable of taking smart, well-calculated risks. In addition, focus more on networking and building relationships within your field of expertise to expand your business and build recognition.

Enneagram 6—The Loyalist

Enneagram Type 6, otherwise known as the Loyalist, is probably the least entrepreneurial Enneagram type because Sixes prefer stable, predictable, and traditional business environments. Plus, they tend to rely on others for guidance and direction and aren’t likely to pursue leadership roles despite having many leadership qualities.

So, if they are inspired to start a business, Sixes will first ensure they have at least one backup plan should their business fail. In addition, they can easily succeed in industries focused on stability and security, requiring attention to detail, control, and organization. Larry Page, the co-founder of Google, is proof that Loyalists can thrive as entrepreneurs.

Enneagram and entrepreneurship tip: You have the knowledge, expertise, skills, and experience needed for entrepreneurship. However, despite all of this, you tend to doubt yourself and your decisions. So, to become a successful entrepreneur, you need to focus on building healthy self-confidence and boosting your leadership ability.

Enneagram 7—The Enthusiast

Sevens, the Enthusiasts, are highly inclined toward entrepreneurship because they aren’t afraid of taking risks and thrive in dynamic environments with ample intellectual stimulation and challenges. They are creative, communicative, and innovative, often becoming pioneers in their fields of interest.

However, while they usually start off with great success, their lack of focus and consistency may threaten their success in the long run. Richard Branson, founder of Virgin Group, exemplifies Seven’s adventurous and visionary entrepreneurship style.

Enneagram and entrepreneurship tip: Create a long-term business strategy before you announce your private business. Following your intuition and inspiration is a great way to start, but you also need to set practical goals and stick to them. Learn to prioritize tasks and seek professional advice for administrative aspects of your business.

Enneagram 8—The Challenger

The strong, independent Eights are determined to be in control of their lives in every possible way, so entrepreneurship is a common career choice for them. Plus, they are natural leaders who aren’t afraid to take risks, fail, and start again, grinding relentlessly toward their goals.

Assertive, focused, and efficient, Challengers are usually the personality type behind huge corporations and renowned worldwide companies. Donald Trump and his career path are a perfect example of Type Eight’s entrepreneurial nature and leadership ability.

Enneagram and entrepreneurship tip: The most important skill you need to learn is to delegate work. This requires you to overcome your trust issues but provides you with more time and energy to devote to your more important goals.

Enneagram 9—The Peacemaker

The easygoing Nines aren’t naturally interested in entrepreneurship, as they are more focused on relationships in their lives. Due to their strong focus on others, they develop many useful skills like negotiation, mediating, resolving conflicts, and building relationships.

So, if they decide to become entrepreneurs, their business is most likely to be based on providing services to others. Reed Hastings, the co-founder and CEO of Netflix, is a great example of a Type Nine entrepreneur known for his laid-back leadership style and adaptability.

Enneagram and entrepreneurship tip: You focus on long-term stability and prefer a non-aggressive approach to business, which is great in many ways. However, sometimes, you must be more assertive and efficient in making decisions. Don’t be afraid to impose your authority; you are in charge of your business.

Is your Enneagram type a natural entrepreneur?

Take our free Enneagram test and find out!

Key Takeaways

So, if you have the will and the idea, no one can stop you from becoming a great entrepreneur, especially if you allow Enneagram to help you map your entrepreneurial strengths and overcome your weaknesses!

With that in mind, let’s round off with some key insights about Enneagram and entrepreneurship:

• Ones, Threes, and Eights are the most natural entrepreneurs because of their ambition, determination, and leadership skills.
• Fours, Fives, and Sevens are fond of entrepreneurship because they like to work independently and follow their own vision.

Twos, Nines, and Sixes aren’t inspired by the idea of entrepreneurship, but as they mature, they become more aware of their entrepreneurial spirit and potential and are more likely to engage in such ventures.