A detective, a librarian, and a quantum physicist walk into a bar...

The Enneagram makes visible your inner world. As you deepen in your understanding of it, you learn why human beings behave the way they do. Which makes the Enneagram an uncomfortable tool at times, but also a liberatory one.

The five: The Investigator

We begin our series with Enneagram Fives, the quintessential experts of the Enneagram. Fives investigate, observe, acquire knowledge, and develop genuine expertise in all sorts of fascinating fields and sometimes, in quite obscure fields.

Industries that are Five-ish in their behaviour and that value a Five’s expertise include:

• academia/academic research,

• librarianship,

• scientific research and development, and

• the tech industry.

 

Known for their intellectual curiosity, analytical minds, and preference for independence, Fives also show up quite a bit in storytelling. Agatha Christie’s Hercule Poirot and Arthur Conan Doyle's Sherlock Holmes exhibit classic 5 traits. Dr. Gregory House from House, M.D., Dr. Shaun Murphy from The Good Doctor, and Dr Spock from Star Trek are all examples of Fives in storytelling.

When they apply their observational skills to human behaviour, Fives also make excellent authors. Jane Austen and Henry James both exhibit Five traits in their detailed understanding of human nature, for example.

In terms of literary genres, science fiction is the most Five like in its expression, delving into theoretical and philosophical questions about the nature of reality, technology, and society.

As far as social media platforms go, Substack - as a platform for long-form writing and analysis - is very Five-ish and offers an excellent home for individuals who are Fives.

A note about typing other people

For illustrative purposes, I’ve drawn out some industries, characters, authors etc that display Five tendencies.

You’ll note that I said, ‘that display’ and not ‘that are definitively Fives’. This is because the Enneagram explores people’s motivations and uses behaviour purely as a path to understanding motivations.

Behaviour doesn’t tell you for sure what a person’s motivation is. It can only ever give you a sense of what it might be. In other words, it provides a starting point, rather than an ending point.

 

Here’s what that looks like in practice; Leonardo da Vinci is famous for many things, not least being that he’s a polymath/the quintessential Renaissance man. During his life, he explored diverse interests and intellectual pursuits across art, science, and engineering.

His curiosity and detailed understanding of different areas of expertise are Five traits. But polymaths are classically Sevens. Whilst a Five may spend their life digging deeply into one body of knowledge, Sevens love nothing more than gathering information about a diverse range of topics and experiences.

When you look at a diagram of the Enneagram (there’s one toward the top of this page), you see there’s a relationship between Fives and Sevens. That being that Fives will often draw on Seven traits and Sevens on Five traits.

Fives can slide up to Seven and adopt the more playful, extraverted characteristics of a Seven, choosing to be of the world rather than analysing it at a safe distance. And Sevens can slide down to Five and become more focused, introspective, and able to delve deeply into their interests or ideas.

So in Leonardo da Vinci, we may have a Five who draws on the polymath qualities of the Seven, or we may have a Seven who draws on the incredible focus and detailed attention of the Five.

How do Fives feel about being seen as an expert?

Fives generally exhibit pride in their intellectual knowledge and understanding and some become become arrogant about it. This is because their attention to detail and precision in thinking can lead them to underestimate other forms of wisdom and expertise.

On the flip side, they’ll doubt themselves, not when comparing their knowledge with other Enneagram points, but when comparing it with other Fives or with the knowledge they could have in a few years, when they’ve read, observed and thought some more.

A Five’s awareness of how vast a topic can be, means they’re also very conscious of the gaps in their knowledge. As Einstein, one of the world’s most famous Fives once said, ‘The more I learn, the more I realise how much I don't know.’

So a Five’s visibility blocks will often look like hesitating to speak up or share their work for fear that they may have missed an important fact. Or for fear that others will misunderstand or misinterpret them.

The other big visibility challenge for a Five is how to package their knowledge. The problem is that they have so much of it, and their almost pedantic adherence to accuracy means it’s very difficult to deliver that information succinctly without feeling like they’re missing critical details.

To Fives who are worried about being expert enough, please know this; you know more than enough to share your work with the world. 

The only expertise you need to acquire now is learning how to package and share your knowledge in a way that’s easily digestible to the people you’re trying to reach. Here are a few tips on that:

• Have a place where all of your information is housed and available. This will help you to feel at rest, knowing that you can point people there (people who are interested in the details). Then get into the habit of sharing summaries of your work in places where people are more interested in snippets of information.

• When packaging information, remember the old saying ‘A picture is worth a thousand words’ and use visual imagery where you can. Keep the importance of white space in mind, using lots of bullet points and paragraph breaks, and think about tools like infographics to convey complex ideas and processes simply.

• Consider partnering with other Enneagram points when it comes to communicating your knowledge (I know this goes against your preference for independence and autonomy so think of it as a stretch area for you). There are people who are naturally adept at packaging and sharing information. Feel free to benefit from their expertise on this one.

 

To the rest of the Enneagram, let your takeaway be this; a Five is giving you a gift when they share their knowledge with you. Being the most introverted point on the Enneagram, it benefits you to take time with the Fives in your life. To draw out their wisdom by giving them space to express themselves.

And the next time they sound overly finicky to your ears, or they start correcting you about one thing or another, know that this is not about you. Rather it’s a sign of their deep commitment to factual information and communication.

In a world where some people think fake news is legitimate news, let’s all be grateful that Fives are here to ground us in truth.

Unsure of your Enneagram type?

If you fancy taking a test, here are two I recommend. 

Eclectic Energies (free)

Integrative 9 (paid)

If you choose to take a test, do remember that Enneagram tests are not infallible. The accuracy of the test relies on the test taker's self-awareness. Also, most tests are built around traits and behaviours which can point you toward your Enneagram type but can also be misleading because certain behaviours can mask motivations that aren’t easy to discern from the outside.