The Enneagram and Entrepreneurship: Which Types Are Most (and Least) Likely to Be Self-Employed

In her book Scaling with Soul: How I Built and Sold a $25 Million Tech Company Without Being an A**hole, Sharon Gillenwater describes her path from working as a restaurant waitress to becoming the CEO of a tech startup that she eventually sold for $25 million. She doesn't sugarcoat or romanticize the experience. The book starts with the harrowing final hours of the sale transaction and how much is riding on it. It turns out a lot is, because she and her husband had racked up over $500,000 in debt to banks, credit cards and family members during her startup journey. I took special interest in her story because I worked with Sharon in the 1990s, back when she had a stable marketing job at a language company in downtown San Francisco.  

Sharon’s story is inspirational, and it begs the question–why did she abandon her secure future to bet the farm by starting a company? What makes some people take bold risks while others opt for the security of a regular paycheck?  To explore this question, I turned to my favorite tool to decipher human motivation: the Enneagram. Unlike other personality systems, the Enneagram dives deeper than character traits and looks at the root cause of behavior: our motivation. 

Who Becomes an Entrepreneur?

The Oxford Dictionary defines an entrepreneur as “a person who sets up a business, taking on financial risks in the hope of profit.” While this is the technical definition, the psychological profile is much more complex. 

According to Cornell University’s article “The Science of Startups”, studies show that successful startup founders often share some core personality traits: 

• They have a thirst for variety and a drive to start new things. 

• They are high in energy and exuberance. They believe in a positive future.
• They get things done and run on high octane.  
• They exhibit low levels of modesty. These are typically folks who don’t mind the spotlight and don’t shy away from being the center of attention.

With these traits in mind, let’s explore which Enneagram types are most naturally drawn to the entrepreneurial path.

Which Enneagram Types Have the Entrepreneurial Mindset?

It is important to stress that any Enneagram type has the potential to be a successful entrepreneur, and no one type corners the market on risk-taking or innovation. There are theories that SpaceX’s Elon Musk might be a Type 5 Investigator, or perhaps a Type 1 Perfectionist, that Ben Cohen of Ben and Jerry’s Ice Cream is a Type 2 Giver, that Apple Computer co-founder Steve Jobs was a Type 4 Individualist, and the list goes on. You will see entrepreneurs of all Enneagram types.

But when studying the most common traits of successful entrepreneurs, it isn’t hard to see how Type 3 Achievers, Type 7 Enthusiasts and Type 8 Challengers easily fit into the entrepreneurial mold.  Let’s take a closer look at why.

Type 3 Achiever: The Ambitious Founder

With a habit of attention to success and achievement, the entrepreneurial world is a natural fit for Type 3s. From entertainment to technology, you’ll find them trail blazing in all areas of the business world. Here are just a few Type 3 traits that help them succeed in the startup realm:

• Goal-oriented and results driven:  Type 3s love competing and winning. Crushing their goals energizes this personality style, and new businesses offer an endless amount of practical goals to achieve. Rather than get drained by the demands of a startup, Type 3s get energized by them.
• Adaptable and image-savvy:  Like it or not, image matters in a nascent new business, and the Achievers of the Enneagram make sure their business initiatives have good public relations potential.  Startups need to change and morph, and the ever-adaptable Type 3 personality can change form as needed. 
• Motivated by success and recognition: The entrepreneurial path offers the recognition that Type 3s crave.  As outlined above, a lack of modesty is one of the common factors for successful entrepreneurs, and this intersects neatly with the Type 3 drive for recognition.

Blind spots to watch:  While Type 3s love success, they hate failure.  If it seems like the startup is going badly for too long, this personality style might have a harder time doubling down and powering through the difficult periods.  Type 3s do best when they do some inner work to recognize their own feelings of shame and to stay a little longer, even when things are tough.

Type 7 Enthusiast: The Optimistic Founder

With a habit of attention that tilts to the positive and drive to try new things, it is no surprise that Type 7s are often found leading new companies. Naturally exuberant and more open to risk than many personality types, their belief in a better future fuels the grit and resilience needed to succeed in a business startup.  Specifically, the Type 7 traits that make them likely entrepreneurs are:

• Natural innovators: The Type 7 mind features non-linear thinking and has an innate ability to make unique connections. This leads Type 7s to be creative thinkers and natural innovators. It is often a Type 7 brainstorm that leads to a new business idea or solves a thorny business problem.
• High energy and optimism: Known as the “rose-colored lenses” of the Enneagram, Type 7s constantly see the glass half full. They truly believe in a better future, and this optimism is contagious, often carrying their colleagues through darker times by lighting the candle of hope.
• A love of personal freedom:  Personal freedom is a fundamental value for most Type 7s which is why the traditional business world doesn’t always work so well for them.  In entrepreneurial roles, they have the freedom and flexibility to do things their own way and at their own pace. This less structured environment is extremely appealing to most Type 7s and often feeds their creativity.

Blind spots to watch: While Type 7s are gifted as seeing what could go right, they are less skilled at identifying what could go wrong.  This “trapped in sunshine” mentality can lead them to gloss over or miss entirely the problems of the business. Type 7s do best when they do some inner work to be more balanced in their view of what could go wrong.

Type 8 Challenger: The Bold Founder

With a habit of attention that seeks power and avoids vulnerability, Type 8s embody many of the characteristics necessary to build a new company. Bold, decisive and resourceful, this personality style isn’t afraid to be disruptive.  Specific traits that help Type 8s in the entrepreneurial world include:

• Expansive leadership vision:  Type 8s don’t build companies–they build empires. Some Type 8s even talk about the company as their kingdom. This is someone who is expansive and broad in their vision of what is possible.  The Type 8 mind is constantly pushing the company to the next phase, which is why they tend to be great in startup environments and less effective when the goal is to maintain a smoothly running business environment.
• Decisive and action-oriented:  Starting a new business venture requires literally thousands of decisions and often, founders are sailing through uncharted waters. It isn’t for the faint of heart, and this is where the Type 8 mentality is a huge asset. The Challengers of the Enneagram aren’t afraid to make tough decisions and even when they don’t know what to do, they move into action. These traits mean their startups rarely stall out or fade away. They might not always be moving in the right direction, but they are always moving.
• Resilient: Type 8s are mentally tough. This toughness keeps them resilient for the ups and downs of entrepreneurship and serves them well when the going gets tough. The warriors of the Enneagram have to be careful they don’t sacrifice their health in the pursuit of success for their startup.

Blind spot to watch:  When they feel vulnerable, Type 8s often respond by becoming more controlling or domineering. This is a natural defense against vulnerability, but it doesn’t always land well with the company employees, and it isn’t always what is best for business. Type 8s do best when they do some inner work to recognize and regulate their response to vulnerability.

The Enneagram Types Less Obviously Aligned with Entrepreneurship

While the Type 3, 7 and 8 personality styles are well suited for entrepreneurship, there are also a few who you might see less often.

It is pretty easy to imagine why Type 6 Skeptics might shy away from the risk-taking world of entrepreneurship. With a habit of attention that focuses on what could go wrong and with a strong drive for security, this type seems at odds with the startup world. In the mind of many Type 6s, it can be hard to justify the risk-reward equation inherent in a new business.

The same might be said for Type 9s. With a habit of attention that seeks harmony and a drive to avoid conflict, the Peacemakers of the Enneagram don’t seem like an obvious match for the fast-paced, often contentious task of getting a new business off the ground. With procrastination and a go-with-the-flow attitude as core traits, it can be hard to imagine what would inspire a Type 9 enough to take all the necessary actions to begin an entrepreneurial pursuit.

But while statistically it may be true that Type 6s and Type 9s are less likely to start companies, anecdotally, it isn’t as true. I was the Chief Financial Officer of a venture capital firm that had a Type 6 as the founding partner. And I was the head of finance for an interactive agency that had a Type 9 co-founder as the CEO. Any Enneagram type is capable of being an entrepreneur, although Types 3, 7 and 8 are probably the most likely personality styles to start new businesses.

I asked Sharon what she thinks are the core personality traits of entrepreneurs. She said,  “Curiosity. Resilience. Decisiveness. Discipline. Hard-headed determination and a distrust of conventional wisdom. I have also come to realize that I often show signs of hypervigilance. This is not a comfortable way to live, but it is a helpful trait for entrepreneurs.”  

And then I asked her to take an Enneagram assessment. Her result:  Type 8, the Challenger. Read her book and you’ll find out why there is no surprise there!

Entrepreneurship is a Calling

Sharon’s journey from waitress to multimillion-dollar founder shows us that, beyond having the “right” character traits to launch a business, founders need the courage to follow a deeper drive. While Types 3, 7 and 8 may be naturally wired for the rollercoaster of entrepreneurship, every Enneagram style brings something essential to the table. In the end, your willingness to know yourself, face discomfort and stay committed when things get hard is probably the most important trait when starting a new venture.

The question might not be “Which Enneagram type is most likely to become an entrepreneur?” but rather, “What kind of entrepreneur could you become once you understand your own motivation?” If you are ready to find out, start by learning your Enneagram type.