Enneagram Eight: The Challenger


Apr 5

An Eight wants to be in control, but fears being controlled by others.

Welcome to part eight of the Enneagram series! If you are a Type Eight, this post is meant to offer some clarity into your personality and ideas for improving your work life. If you are not a Type Eight, chances are you know one. My hope is that this gives you greater compassion and appreciation for the challengers in your life.

In this series, we will be heavily referencing The Modern Enneagram, which was one of the options for #dropcapbookclub on Instagram. Because the votes were tied, we will be going through Gary Vaynerchuk’s Crushing It in book club, but I will be doing this blog series on the Enneagram for those of you who want to learn more about this wonderful personality tool. You can grab a copy of The Modern Enneagram on Amazon, which will give you additional thoughts and insights into your type and how it plays with others.

We’re going to focus on each personality in the context of a work environment. Our lives are incredibly complex, and The Modern Enneagram explores family dynamics, romantic relationships, and personal development, but we won’t be exploring those issues in this series.

In each type’s post, you’ll learn:




The Modern Enneagram starts with a story of “Julia” (who is a Type Seven) and I found it extremely helpful in understanding how the Enneagram model might be applied to a real person. So let’s start with a story of a fictional Type Eight named Anne. Keep in mind that the point of this story is to notice the patterns of motivation, not the specific circumstances or behavior.

“Anne is a 30-year-old campaign manager for a local politician. She loves being a part of the high-energy atmosphere of local politics and playing an active role in influencing her city and community.”

We’ll use Anne as an example of a Type Eight as we dive into the deeper personality and core motivations of this type.

The Sleeping At Last “Eight” song has not yet released. I will link to the song and podcast here as soon as it becomes available.

Core Motivation

Motivation – to be in control

Basic Fear – fear of being controlled by others

Anne is a naturally influential person. Growing up, she was always the leader of her social group and the girl others looked to for advice. From an early age, Anne developed a thick skin when it came to relationships, and always felt comfortable taking the lead and speaking her mind. In college, she was encouraged to join SGA where she could be surrounded by other assertive go-getters who wanted to make things happen. Instead of being told to tone it down, her intense personality was celebrated as an inspiration to others.

Anne’s Unfolding Story

Anne’s confidence and can-do attitude make her an inspiring campaign manager. She is known for her ability to jump into a crisis and handle the most stressful moments on the road. The politician she supports has absolute trust in Anne to get the job done and lead the rest of the team to victory. She’s able to assemble a capable team, inspire action, and maintain the platform and message from beginning to end.

When Anne begins a new campaign season, she is in her element – recruiting volunteers, speaking to the press, and strategizing the platform with her candidate. She enjoys the leadership opportunity and extreme energy it takes to run a successful campaign. 

But tensions rise in the final months before election day, when no one is getting adequate sleep and debates are in full force. She starts to question the commitment of the campaign volunteers and build resentment towards the opposing party. As the stakes get higher, Anne gets aggressive towards the media and suspicious of her team’s loyalty. Many of the seasonal volunteers become irritated with Anne’s tone and confrontational leadership style, and Anne picks up on their lack of respect – which does not help the situation.

If left unchecked, Anne will start to act like a campaign dictator as she struggles to maintain control over the race. Once she begins questioning the loyalty of those around her, she may start to attack from within, killing the moral and leaving her exhausted from fighting both the opposition and her own team.


In states of stress, Eights take on the characteristics of an unhealthy and secretive Type Five. Fearing the motivations of others, self-confident Eights become withdrawn, planning their next move.

When stress progresses, they can become paranoid and project their own narratives and insecurities onto others. Acting strategically, they can become ruthless in their pursuit of power.

how to counteract stress for a type eight

1. Redefine power as the ability to lift others up, not force them to comply with your agenda.

As an experienced campaign manager, Anne is now able to anticipate problems and stressful moments ahead of time. Instead of fighting for respect, she finds leaders within the volunteer groups and empowers them to keep up the moral and productivity of the whole group. She has learned that her greatest influence comes when she takes a mentorship approach to a few rather than being the sole leader of many.

2. Understand that you cannot control a situation, only your reaction to it. By dominating others, you sacrifice the potential to build meaningful relationships.

When Anne is tempted to confront her candidate or the team, she reminds herself that it is more important to diplomatically handle disputes and take a team-building approach to problems. Instead of creating enemies within, she actively works to build genuine friendships with those around her.

3. Remember that the world is not against you. By alienating others, you confirm your own fears. Usually people are not as bad as they seem.

At times, Anne has felt isolated from the rest of the group. While everyone else is passing out stickers and ordering pizza, Anne is usually the one responding to articles and putting out fires. Instead of creating the story that others are intentionally leaving her out of the fun to do the dirty work, she remembers that her position may make it difficult for others to approach her, and now makes an effort to reach out first.

4. Your autonomy is an illusion. You depend on people more than you realize, and have much to risk by pushing others away.

During one particularly difficult campaign, Anne was reminded by her candidate that she depended on his nomination for her own job, and that she also depended on the inspired participation of the volunteers to be successful. Since then, it has stuck with Anne that she is not the only person steering the ship, and heavily relies on everyone, which softens her perspective when things go wrong.

5. Understand that those who are only attracted to you for your power do not love you for yourself. Power is overrated, especially when it is gained by manipulating or bullying others.

When Anne is tempted to intimidate a new reporter, she remembers that forceful power is not the same as earned respect. The only way that she will maintain her influence in the end is to earn the trust and respect of those around her, even if it takes longer.

Work Environment

The most important thing for a Type Eight to experience at work is influence. As a Type Eight entrepreneur, it is important for you to see the positive impact that your business has on your audience. Here are three other ideas for incorporating your Type Eight strengths in your business:

  1. You tend to react quickly and intensely to situations, even before you fully understand what’s going on. The best thing you can do when you’re triggered and angry is to sleep on it. Either wait until the next day, meditate, or take a nap before responding. Make a 24-hour email response policy with your customers and clients to give you space to react when you’re under stress and pressure.

  2. You tend to think you’re autonomous, so it’s important for you to have a form of accountability and support in your life. Give a few people permission to speak to you honestly about your thoughts and reactions, keeping you aware of your own mistakes and weaknesses so that you can grow. A mastermind or business coach is a great way to do this.

  3. It’s important for you to assume the best in your customer and team. Being able to connect with your audience is the number one way to build influence. Take a moment once a month or quarter to connect with your customers, audience, and team in a genuine way. Begin to learn their stories and recognize their positive attributes.

When we first met Anne, she was an intense campaign manager, with a reputation for being able to handle any situation. Her self-confidence and natural leadership made her an invaluable asset in assembling a team and inspiring action. As a campaign manager, she also had the opportunity to directly impact her city and gain respect from important politicians who owed her their success. However, as election day approached, Anne often found herself feeling stressed and aggressive towards the rest of her team, and unnecessarily confrontational with the media.

By gaining a deeper understanding of herself and how she handles stress, Anne will be able to gain some perspective when her stress rises. Instead of attacking her perceived enemies inside the campaign and on the opposing side, Anne has learned just how much she depends on each person involved in politics to keep her job as a campaign manager. She has understood the difference between forced respect and earned admiration – preferring to deserve the influence she gains.

Although Anne will always struggle to keep her aggression in check, she will be able to do more good when she learns to be diplomatic in a confrontation. She religiously meets with her therapist during the most intense months of a campaign to vent about her frustration so that she doesn’t take it out on others, and has found that a cooperative approach gets her much further than a controlling tone. She makes it a point to let loose with the volunteers more often and enjoy the thrill of a successful rally, building love and support as their fearless leader.

It turns out that her confidence and intensity are the reason the volunteers want to be on her side. By keeping perspective on what she’s actually fighting for (her candidate’s success and to propel certain issues and policies forward), she inspires action and becomes a voice for the beliefs of an entire team, which results in more influence and genuine respect than she ever imagined.

“How do you like this new series? Do you identify as an Enneagram Type Eight? Comment below with your own story!”

If you enjoy learning more about the Enneagram and are curious about how to lead with your personality in your business, you may enjoy participating in our Enneagram for Entrepreneurs course. Click the link below to find out more!

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