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How "Enneagram Investing" was Developed

Back in 2021, I began to feel restless and yearned to do something more than just managing my own portfolio, which I have enjoyed doing on a full-time basis since 2016. I wanted to break out of my Type Five shell and connect with the world in more creative ways. That was when the idea of writing a book was hatched. As a fan of self-help literature and psychology, I am always trying to unravel my psyche to understand why I am the way I am.

Coincidentally, my husband and I discovered the Enneagram at almost the same time. That was when I also realized how the Enneagram could intersect with personal investing. I proceeded to sign up for an accreditation course with Integrative Enneagram Solutions and dove deep into the theory, like a true Type Five investigator. 

In May 2022, I decided to test the idea of “Enneagram Investing” at The Atlanta Writers Conference. After sending out query letters for my book idea, I signed with Leticia Gomez of Savvy Literary Services as my agent. I was fortunate to have met her at the conference by chance, and Leticia has been been a huge supporter of my pivot into publishing. We have since sent out proposals to traditional publishers, and I continue to work on my manuscript.

Podcast Interview: June 2023

Check out my interview on The Investing for Beginners Podcast (published on June 15). Host Dave Ahern and I talk about our respective Enneagram types and how they influence our investing behaviors in the past.

My Type Five (Investigator) Personality:
Origin and Formation

My mother left soon after I was born. I will never know all the details of what happened, since she passed before I had a chance to meet her. My father did not live with me until I was a young teenager. I grew up with few privileges surrounded by caretakers who were not prepared to be guardians. Expressions of feelings were neither encouraged nor mirrored, and I remember being extremely shy as a result. Perhaps the lack of living space also deterred movement, hence the action center part of me was not nurtured. My mind became the only space I had to run free and be myself. Almost by process of elimination, a Type Five (Investigator) archetype soon emerged.

Consistent with the core trait of Type Fives, a scarcity mindset developed from a fear of losing what little I had. Hoarding – onto my father, money, time, and other seemingly non-replenishable resources – was a habit I adopted early in life. Being self-sufficient – financially, emotionally, mentally, physically – was for survival, not personal development or higher consciousness. That psyche permeated throughout all aspects of my being, until I became more self-aware with the help of the Enneagram.

Only in the last few years did I realize how my childhood experiences had impacted my mind, heart, and body. As a socially oriented Five subtype, I initially tried to fill my void with academic grades, then corporate titles, and other worldly validations. Since seeking professional help, I have addressed some difficult core issues in my life.

The way I have managed personal investing reflects the personal growth I have had. I started out investing only in government treasuries due to a real fear of taking risks, then over the years pivoted to become more open-minded, seeking an equilibrium among new learnings, higher returns, and measured prudence. Changes to my portfolio composition over the years reflect my personal evolution. With confidence growing, and inspiration from alternative perspectives, I have adopted more Type Seven (Enthusiast) and Type Eight (Challenger) traits to become bolder. No longer just motivated by fear, I want to create a different future for myself, one that is not tied to the ghost of my past but driven by a future that lies in the present hands of my inner child and mine.

Shakuntala Chandramohan, London

"I found Ben to be passionate about the (Enneagram) and applying his research to help me interpret the various Enneagram styles and understanding how I could use the conclusions from my report to develop myself"

R. Karl Hebenstreit, Ph.D., CA

"I see how (Ben) has integrated and applied all of the foundational knowledge, complemented with his natural proclivity for in-depth questioning, analysis, understanding, and action"

Reverend Michelle Thomas-Bush, NC

"The Enneagram has been key for my professional and personal development...Ben has rich insights into my type, subtype, blind spots, centers of expression and a host of other areas that have guided me along this journey"

Kevin Damaso, CO

"Benjamin Tan has rich insights into my type, subtype, blind spots, centers of expression and a host of other areas that have guided me along this journey...I am less fixated on my type and leading with more breadth and depth in my life"

About Benjamin Tan

Benjamin Tan is an investor, writer, accredited Enneagram practitioner, former investment banker at Credit Suisse and UBS, and ex-buyside at Oaktree Capital. Having previously been based in London and Singapore, he currently resides in Atlanta, Georgia, with his husband. Benjamin holds a First-Class honors degree in accounting from Nanyang Technological University (Singapore), and is currently pursuing a master’s degree in clinical mental health counseling at Mercer University. 

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