Enneagram Pairing Type 5 & 6

5 - The Investigative Thinker

Investigator, Observer, Expert, Scientist, Analyst, Specialist, Hermit

6 - The Loyal Guardian

Loyal Skeptic, Trooper, Trouble Shooter, Defender, Guardian, Questioner, Devil's Advocate


Core Pattern

Fives and Sixes are both in the Thinking triad. Fives are objective, analytical, rational, observant, and mentally agile. Sixes are also mental but tend to have strong emotions as well.

They are loyal, skeptical, questioning, and warm. Both Fives and Sixes have a deep need for safety and security.

Sixes tend to be obsessed with considering danger or catastrophe, while Fives tend to be more curious about what could go wrong and how. Five’s core wound is around feeling neglected and misunderstood by the world, and thus retreating to their mental sanctuary. Sixes core wound is around feeling unsafe in a dangerous world, and thus creating connections and making choices that promote comfort and security.

Shared Values

These two will share a love of knowledge and mental acuity. They’ll probably share a love of brain games, intellectual challenges, and puzzles. Each other’s perspectives will fascinate them, especially when it comes to ideas about world issues, strategies for problem-solving, and theories of change or progress.

Both Fives and Sixes use their many mental skills and intellectual abilities to more deeply understand, and thus help solve, the problems in the world around them. They tend to value penetrating conversation, skepticism, objectivity, and cogent analysis. They also appreciate expertise, hard work, and they place a high premium on people who work to become excellent at something.

How You Complement Each Other

This is an intellectually symbiotic relationship, although Fives and Sixes tend to be very different emotionally. Intellectually, they can share their musings on current events, problems, theories, decisions, doubts, and questions on basically any topic. There will be an almost continual questioning and answering between these two that will feel fruitful, deep, and stimulating. Emotionally, Sixes tend to be more charged and passionate than Fives, both in that they have stronger feelings and exhibit a more outward expression of them.

They tend to be very anxious and often have extreme ways of coping with their feelings of fear. Sixes also have firmly held beliefs and values, which is one of the ways they defend against the insecurity of the world. Fives, on the other hand, tend to reject conventional values and commonly agreed upon systems instead of their own, autonomous authority.

To this relationship, Fives bring calm, detached objectivity, their keenly observant mind, and ample curiosity. Sixes bring their passion and loyalty, genuinely heartfelt values, and very human feelings of insecurity and doubt. Sixes will retain a sense of warmth and softness throughout the relationship, while Fives will provide a grounded, reasonable voice to quell Sixes many fears.

How You Can Get Into Trouble

The major trouble spot for these two, whether professionally or personally connected, is in their shared tendency to focus on what could go wrong and all of the obstacles in their way, instead of using their discriminating minds to find solutions and focus on what’s working. This kind of thinking will cause them to be hesitant and risk-avoidant, which means they will likely struggle to get projects off the ground or make moves toward shared goals or visions.

Fives and Sixes also tend to be opposed to how they think about things, even though it’s a fact they both think a lot about everything. They will often come to completely different, if not opposing, conclusions after pondering a problem or course of action, which can pose problems if they need to work together somehow. The Sixes tend to be much more emotional than Fives, and will typically rely on precedents and set standards to guide their thinking and shape their understanding of a given situation.

Fives tend to be unemotional, even detached and objective, when considering an external reality (also when considering their inner reality, for that matter). They rely less on consensus and popular wisdom, opting to discover their truth and way of engaging something. Sixes us their intellect and sharp thinking mind to gather information, clarify others’ intentions, and determine what’s going on so that they can feel safe and secure in the world, whereas Fives employ their vast intellect to deepen their understanding of truth, whether or not it leads to feelings of security.

Fives also tend to keep information to themselves, which can make a Six feel threatened or fearful. Fives have a vivid imagination for catastrophe, and they tend not to shy away from the darkness in the world, which can cause a Six to feel even more fearful or anxious in Five’s presence.

The coupling of Six's catastrophizing and Five’s seemingly limitless imagination for what could go wrong can result in both parties feeling hopeless and powerless in the face of inevitable calamity. It will be easy for these two to become mired in the sense of fear and scarcity, even while they continue to explore lofty meta-ideas.

What Each Type Needs To Be Aware Of

As part of the Thinking triad, both Five and Sixes are also fear types, although this fear manifests in each of them differently. Both will have a highly developed sense of what’s dangerous, as well as a tendency toward worst-case-scenario thinking; aspects that could be heightened by each other’s presence.

That being said, Fives will use this awareness of what could go wrong to stoke their fires of curiosity, and might even let their imaginations run wild with their negativistic thinking. Sixes, on the other hand, will aim to keep the bad thoughts at bay and will do everything in their power to make themselves feel safe, secure, and out of harm’s way.

Generally speaking, these two will have different needs when it comes to physical and emotional contact, as well. Sixes appreciate more intimacy and connection, so Fives should keep in mind that making an extra effort in this arena will go a long way. Fives require more solitude and uninterrupted thinking time, which might send a more paranoid Six into a tailspin: keep in mind, Five’s retreat is typically not personal and usually has nothing to do with their relationships.

How You Can Support One Another

Communication, friendliness, and clarity are going to prove crucial to these two. As Sixes are easily threatened and often feel suspicious of others, it is vital that Fives initiate conversations, provide reassurance, and freely offer information. Conversely, Sixes can support Fives by allowing them plenty of space and time to tackle their projects, while also remaining clear and precise in word and action.

Fives dislike imprecision. There is a danger that Fives will view prying Sixes as interfering, or that suspicious Sixes will see Fives as secretive and withholding. To avoid this confusion, best to maintain regularly scheduled meetings or open dialogue about each other’s needs and progress on shared projects.

In more personal connections, these two will be best for each other if they can keep their catastrophizing to a minimum, and instead use the strength of their combined intellects to vision a positive future, solve problems, and map out successful plans. Sixes can support Fives by exemplifying warmth and social engagement, something Fives often struggle with, and Fives can support Sixes by providing rational, objective truth when they get lost in their fears.

In A Romantic Context

This connection likely starts as a friendship or work relationship and develops slowly over time, as the pair learns more and more about their shared interests and intellectual hobbies. The slow pace will also stem from the fact that it takes a long time for Sixes to trust people and a long time for Fives to expose details about their personal lives to others. As a result, this could be a relationship that stems from a long-time friendship.

It will be characterized by a high level of respect for one another’s minds, with both parties relishing in the other’s ability to observe and report details accurately and without personal bias, persevere through stressful situations, and develop expertise in their chosen fields. Fives benefit from Six’s devotion, warmth, and consistent care, while Sixes gain a lot from Five’s ability to remain grounded through their vacillating needs for independence and connection. When these two find themselves in a trusting and communicative relationship, they’ll experience the joy of truly knowing the inside of another person’s mind.

As both Fives and Sixes are part of the Thinking triad, and therefore prone to fear and anxiety, it is imperative these two have a strong, trusting bond, lest one or both parties become suspicious and paranoid. If the trust does erode, the relationship can slip into confusion, misinterpretation, assumption, and doubt very quickly.

Once communication and trust break down, Sixes will become nervous and hyper-vigilant, always on guard about making a mistake around their partner (who will likely criticize them). They will view their Five counterparts as willfully obstinate and unnecessarily independent, traits which will frighten them and shake their beliefs to the very core.

Conversely, Fives will become reticent and withdrawn, while starting to see their partner as overly conservative, indecisive, and pandering to authority. The respect these two once had for each other can turn into shadowy projections, wherein both parties feel threatened and triggered by the other.

They discover they are opposed in how they relate to the world, namely the Six needs to believe in something to feel secure in an incomprehensible world, while the Five has an insatiable need to obtain the objective truth, whether or not it leads to security. This fundamental difference can put these two at insurmountable odds, making them feel more like enemies on opposite sides of the line than lovers on the same team. A genuine fear and distrust can permeate their connection, causing a rupture wherein neither party is sure what went wrong or how they got there.

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Max Marmer

Max Marmer is a Multidimensional Entrepreneur, Investor, Writer, Coach, Biohacker and Systems Theorist dedicated to supporting and enabling the flourishing of humanity in the 21st century.


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