Getting Out of The Box Series: A Conversation with a High-Mastery Enneagram Type 2

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Getting Out of The Box Series: A Conversation with a High-Mastery Enneagram Type 2

Type 2 aka The Helper are the kind of people who possess a heart that’s always ready to give love and care for anyone who needs it. Undoubtedly, they can be the most giving person and almost selfless to a point. This is their Achilles heel – they fear being rejected, be worthless or dispensable, so they feel that they must give, empathise, help, or sacrifice to be accepted and loved by others.

For a less self-aware Type 2, they can get very sensitive when they feel that others are not reciprocating the love and efforts they give to others. Neediness and emotional manipulation may come into play in times of heightened stress when their love tank becomes empty.

Meet Jason — when my laptop screen finally showed his face, I was greeted with a very warm smile and I felt his positive energy transcending virtually.

This conversation is special—although I’ve known him for a couple of years now. We are diving deep about his journey, the steps that he took to get to where he is now – a content and confident individual who aims to create a tribe of helpers to propagate the spirit of helping.

He shared with me the biggest lessons he learned in his self-discovery journey through the help of Enneagram.


  1. Always pause.

Jason said he used to put himself last and quickly jumps into helping others without even thinking whether he could actually help the other person or not. Being highly sensitive, he takes energy from others which he, later on, realised to be not sustainable or healthy on his part. This led him to be frustrated and have “emotional explosion” when things get stressful. Also, he didn’t recognise the times he’s actually stressed – he would find himself easily agitated and full of negative energy. Jason said it wasn’t an easy transition to practice being mindful at all times – he experienced a lot of resistance to take a pause since it was in his nature to quickly jump into things. But through perseverance and wanting to be better, he eventually got into the habit of taking a pause.

After learning about the Enneagram, he can catch himself when he is feeling stressed and not let it take over him. He learned that by being mindful, he could let go of his frustrations of not being able to help others or when he feels taken for granted. He said “I make sure that I pause first before I help someone else. And if I realise that I cannot help the person – that’s okay.”


  1. Help unconditionally.

“I want to be a helper who is grounded and focused.” Jason learned the hard way that people may not always give him the acknowledgement that he craved for. Type 2s wants to be seen and acknowledged for their help and contribution. He struggled a lot with wanting to help but at the same time expecting something in return and also constantly feeling that he’s being taken for granted. Throughout his journey, he made peace with the fact that people won’t always satisfy his needs of being thanked and acknowledged and that this doesn’t mean that his efforts were wasted. He said that having self-awareness is the key in managing his expectations and to be able to help unconditionally. Giving and helping shouldn’t be transactional, especially when we are expecting that the other person will help or give something back in the future.

He also learned the importance of studying all the other Enneagram types. He is now better at building a connection with each and reading body language.  He said that learning about the different Enneagram types also enabled him to successfully empathise with their struggles and help them in a better way – a way which they wish to be/not be helped.


  1. Help yourself first.

This may sound easy for some Types, but for a Type 2, it is totally against the identity they are trying to build. Type 2s are extremely sensitive to others’ needs but tend to neglect their own. Because 2s do not get any validation for anyone for helping themselves, and asking to be helped is contradicting to their identity as a helper to others.


Jason now recognised that most of his (unnecessary) frustrations that he experienced were due to lack of self-understanding. When he finally learned about his Enneagram Type, he worked on being self-sufficient—to not take it upon others to fulfil his needs because he is capable of loving and providing it for himself. He said in order to help himself, he needs to understand his needs, wants, and desires and be OK to acknowledge them. He learned that to give/help others, he needs to first be able to do it for himself.


Jason’s transformation was far from being easy— he went through 3 consecutive life-changing events which became the catalyst for change. He made a decision to go on a self-discovery journey and from then on, started on making conscious changes within himself. He started working on self-discovery and once he had sufficient “information” to work on, he consciously and constantly makes changes.

He mentioned that identifying what to change is important. Many stopped or dropped their journey towards mastery, because of the initial pain they are facing. However, this pain is necessary. It’s like a cleansing process for a cancer patient going through chemo. The pain transforms us into a new, better us!


Wrapping up my conversation with him; he calls for other Type 2s to help one another and build a network of Type 2s to help others, especially during this trying period.



Curious about your Enneagram type? Here’s a quick overview of the 9 Types. I know reading through these descriptions can be confusing. So save yourself from second-guessing and figure out your type with the help of our online test.


Cindy Leong
Cindy Leong
Cindy Leong is a sought after bilingual (English and Mandarin) Enneagram Personality Coach and Corporate Trainer in Asia, who can help you make sense of your professional and personal relationships. She is a member of International Coach Federation (ICF) and Singapore Psychological Society (SPS). Besides a Bachelor Degree in Psychology (majoring in Communications), she also has a Diploma in Business and has done in-depth research and studies in the areas of Organisational Behaviour and Gender Communications, both in Singapore and Taiwan. Through her expertise in corporate executive coaching, personal development, and relationship coaching, she has helped many professionals in their walk through challenging times, particularly in the areas of identity searching, relationship building and career breakthrough. Aside from being a published author of 2 books, she has also been invited by several radio stations and magazines as an expert guest speaker to provide insights into Enneagram, workplace conflicts and relationships.
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