Enneagram Five: The Observer


Mar 15

A Five is motivated by preparation and feeling capable out of a fear of being helpless or caught off guard.

Welcome to part five of the Enneagram series! If you are a Type Five, this post is meant to offer some clarity into your personality and ideas for improving your work life. If you are not a Type Five, chances are you know one. My hope is that this gives you greater compassion and appreciation for the Observers 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 our own story of a fictional Type Five named Rebecca. Keep in mind that the point of this story is to notice the patterns of motivation, not the specific circumstances or behavior.

“Rebecca is a 33-year-old restaurant critic living in the Bay area. She enjoys weekend trips to the surrounding vineyards to go on tastings, tending to her modest herb garden, and reading through her vast library of cookbooks.”

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


The Sleeping At Last “Five” 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 prepared and capable

Basic Fear – fear of being helpless

Rebecca has a natural ability to absorb information and experiences in an objective way. Her sharp eye and refined palette make her one of the top food critics in the saturated restaurant world of San Francisco. As a child growing up in southern Oregon, Rebecca enjoyed taking walks through the woods and discovering native plants. She imagined intricate worlds for these silent living things and became fascinated with the many tastes and textures of vegetation. As an adult, she brings her impressive knowledge and extensive experience to the food scene and makes remarkable connections between dishes and chefs that make her column one of the most anticipated articles online each week. She enjoys having a job that celebrates her expertise and allows her to communicate with the world through a computer screen. As a writer, she is able to share her vast imagination and unique perspective with the world.

Rebecca’s Unfolding Story

Rebecca’s ability to make subtle connections makes her a captivating critic. She is incredibly knowledgeable and her objective feedback is respected by chefs and appreciated by her readers. She often makes bold leaps in her reviews to add context and flavor to the dining experience, encouraging others to keep an open mind to food.

When Rebecca feels prepared to review a restaurant and clear about her perspective, she can produce inspiring stories and entertaining dialogue. She enjoys going down the rabbit hole to provide context to the restaurant’s concept.

But when Rebecca feels misunderstood or incapable of explaining her ideas, she can slip into an average or unhealthy state. When she can’t organize her thoughts, she’ll retreat back into her mind and isolate from those around her. Because she often lives within her head, chefs find her impossible to read and difficult to connect with. Feeling increasingly disconnected, she loses direction and misses her deadlines, disconnecting from her work and others.

If left unchecked, Rebecca can become reclusive and mentally unstable. What was once seen as brilliance now appears eccentric and bizarre. Fearing her own thoughts and limitations, Rebecca can begin to feel trapped by her thoughts and imprisoned by her mind. This mental spiral leaves her feeling limited and helpless.


In states of stress, Fives take on the characteristics of an unhealthy and scattered Type Seven. When they feel burned out from deep focus, Fives seek out stimulation and excitement in the world.

When stress progresses, they become socially detached and retreat further into their mind. Feeling fearful that they cannot do things as well as others, they become increasingly eccentric and reclusive, losing touch with those around them and obsessing over their ideas.

how to counteract stress for a type five

1. Be mindful of times when you retreat into your mind and disconnect with the people around you. Stay connected to your present circumstances.

When Rebecca starts to feel overwhelmed by her many contradicting ideas, she takes a moment to be still, calm her mind, and then move forward by observing her thoughts without feeling enslaved by them. She’s found it helpful to spend a few moments writing about her current environment, the taste of her coffee, the feel of her chair, the sounds outside her window. By connecting to her physicality, she’s able to calm and declutter her mind.

2. Find a way to ease your nervousness and mental chatter by calming your mind without numbing it.

Instead of releasing tension with a glass of wine at night, Rebecca now goes on a jog around her neighborhood. This physical practice allows her to slow down her nervous mental energy so that she can sort through her thoughts about the day with peace and clarity.

3. Find at least one person you trust that you can confide in when you’re trying to make a difficult decision.

Rebecca knows that she has a habit of isolating from her friends and family when she feels helpless or paralyzed by a decision. However, she also knows that pulling back can leave her vulnerable to uncontrolled negative thoughts and emotions. Now, she has a friend she has given permission to show up unannounced and check in throughout the week. Rebecca tries her hardest to share openly about her thoughts and feelings.

4. Make sure you are spending your mental energy on worthwhile pursuits and that you are focusing on subjects that improve your view of yourself and others.

Rebecca makes it a point to sit down once a month and read back through her reviews, making note of any assignments that did not seem to add value or direction to her career. Although she has several obscure areas of expertise, she realizes she must limit her pursuits to focus on ideas and opportunities that truly matter. She also feels a renewed dedication to represent and support chefs and restaurants that make a positive and meaningful contribution to her city.

5. Learn to accept conflict as a healthy component of close relationships, not as a way to affirm your suspicion and distrust of people.

Rebecca has begun to learn how to differentiate between the hurtful comments from readers on her reviews and the constructive criticism of her friends and trusted colleagues. She now understands that tension can spark growth and further understanding, as well as strengthen friendships and collaborations.

Work Environment

The most important thing for a Type Five to experience at work is depth. As a Type Five entrepreneur, it is crucial that you have permission to follow a lead and go deep in your area of expertise. Here are three other ideas for incorporating your Type Five strengths in your business:

  1. You will greatly benefit from a support group. Whether it’s a mastermind, a weekly lunch group, or just a close friend in your industry, make it a point to find your people and build meaningful connections. This will contribute to your self-confidence and give you an opportunity to feel understood, valued, and capable of doing your job.

  2. You can become easily frustrated working with others. Consider finding a partner in your business or hiring a virtual assistant who can manage customer and client communication. It’s easy for you get overwhelmed when others seem to be making demands of you or not understanding your ideas. This communication buffer will protect you from retreating into your mind.

  3. Lead with your niche specialty. You have a particular strength in taking in lots of information and making connections that others do not see. Let your customers and clients see that you are constantly learning new things about your area of focus, and going deeper than others to solve specific problems.

When we first met Rebecca, she was a renowned food critic who loved sharing her expertise and opinions with the world through her reviews. Her sharp mind and quick wit strengthened her writing and gave her a unique voice in the industry. As a researcher and observer, Rebecca was celebrated for her obscure ideas and niche specialty. However, the pressure to quickly organize her thoughts and deliver comprehensive summaries was leaving her feeling mentally scattered and overwhelmed.

By gaining a deeper understanding of herself and how she handles stress, Rebecca will be able to recognize her reclusive tendencies and mental paralysis. When she is cultivating a practice of meditation and awareness of her physical surroundings, she is able to calm her mind in a healthy way without turning to substances to numb her avalanche of thoughts. By calming her mind and bringing awareness to the present moment, Rebecca can enjoy her curiosity without feeling enslaved by it. Her best friend helps her to navigate mental spirals and connect with the outside world.

Although Rebecca will always struggle with connection, she will develop stronger relationships when she makes it a point to share her thoughts and ideas with a few people she trusts. When she is able to distance herself from her thought life and connect with her present experiences, she will become a more balanced and articulate writer, being able to sort through her many ideas and cling only to the relevant ones. Instead of retreating when she feels burdened by her need for help, Rebecca turns to the one person she can trust to speak the truth back to her.

It turns out her greatest contribution is her mind’s depth and her natural ability to challenge assumptions and pursue her curiosity. By seeing her thoughts as a natural vessel for shared experience, she allows others to go along on her mental journey of curiosity and imagination, already possessing everything she could ever need.

“How do you like this new series? Do you identify as an Enneagram Type Five? 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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  1. K says:

    I love this! Thanks for sharing!

  2. Cheryl Springer says:

    This was great! I’m a 5 and I’m learning about how to make that a good thing instead of a constant challenge. This helped a lot. Thank you!