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A Simple Guide To The Enneagram

I used to believe that a happy and fulfilled life was beyond my reach. That I had missed the boat. But not only did I think this to myself, I used to make sure everyone around me knew it.

"Hey look at me! I am miserable and depressed! Nothing I try ever works out! This is God's will for me! God has burdened me with this cross to bear!"

I think back to those times and I think, if only I knew then, what I know now. [Insert wistful gaze]

While pregnant with my first child I got very sick. And NO I do not mean, I had morning sickness. I mean sick, puking my brains out from morning to night, burning up from the inside, losing tons of weight, sick. (I would not wish it on my worst enemy!) I could barely function. In truth, I had nothing to give. I could barely hold my head up at work, except over a toilet. The very sight of my Sweetie made me curse all man-kind. Look, it was not a good time for me...

But, it was the most transformative time of my life.

Say wha?

It was transformative because it made me confront one of the deep seeded aspects of my ego structure - "You ain't worth shit if you are not achieving or winning." [Oh yeah, my ego swears at me... Doesn't yours?]

You see. Somewhere early in my life, 'Little Lindsey' learned that the way for her to get the love and belonging that all humans desire, she had to present an image of achievement, success, winning. And, not knowing any different, 'Little Lindsey' constructed an entire world-view, a lens, that fed this assumption about the innate workings of the world.

Can you guess how this has played out in my life?

1) A gross fear of failure

2) A persistent, if not sometimes, perverse work ethic

3) An inability to show weakness or vulnerability

4) An obsession with my "image of success," even if it means lying to maintain it

5) A fear of being incapacitated by relationships or commitments

6) A need for control over others

7) A need to be liked by others

Wow! Writing this out like this makes me feel awful. "Yuck!" as my toddler would say. But it also sets me free. Because what I learned (with my head in the toilet) is that the antidote to my obsession with my image is radical truthfulness. The more truthful I am about my shortcomings, my flaws, my weaknesses, my vulnerabilities, the more capable I am of figuring out who I am, what I want, what my greatest hopes and desires are, AND ATTAINING THEM!

What if I told you that we ALL live with a similar 'ego-lens' over our lives....?!?!? Yours may be similar to mine or it may be very different than mine. Suffice it to say, the more you learn about your lens the more realistic the practice of transformation and mindfulness will become. If I told you that there is a practice you could start doing today that would help you:

1) identify your lens 2) breakthrough common roadblocks and fears, and

3) totally transform the way you move through the world

you would jump on it right???

Welcome to the Enneagram!

So here's the thing. While I had my head in that toilet for nine months I started to study and train in the Enneagram. Google Enneagram, and you may get a thousand definitions, but for our purposes let's use this defintion:

"You are in a box.

You did not know you were in a box.

You need to get out of this box.

The Enneagram is one of many ways to learn about boxes and how to get out of them."

- Lindsey T. H. Jackson

The more you know about your box, the easier it becomes to decide when it serves you and when it doesn't. I already told you some of the ways my box has failed to serve me, but there are great aspects to my box , too- also called the Type 3 on the Enneagram -. My box has led me all around the world. It has inspired me to own my own businesses. It is has given me an innate knack to understand people and their needs. Unfortunately, it has also caused me a lot of pain.

So, no time like the present (hahahaha! There's that work-a-holic streak!) Welcome to:

Lindsey's Simple Guide To The Enneagram

(A practical guide to getting out of boxes.)

Introduction to Type 1: The Reformer

Early on in life the Little Reformer learned that love and belonging was bestowed upon those who were 'good,' 'just,' 'righteous.' The forgotten message of the Little Reformer is that we are all innately good, even though we may sometimes do bad things. (If you are rolling your eyes at this, you might want to start your Enneagram journey here)

If you are a Reformer, or know a Reformer, you might notice that their lens on the world is seen in very black and white terms. Things are either good or bad, right or wrong. There is very little room for gray. The result of this lens, this ego structure, is that The Reformer is always judging themselves and others against this merit stick. They can become very critical when they, or others, do not measure up. This in turn can produce a lot of anger or resentment for The Reformer. Anger at themselves for not meeting their high standards, or anger at others for not holding themselves to equally high standards.

Anger however is not often viewed as a 'right' or 'good' emotion, and so ironically, The Reformer is often considered to be the most cut off from their feelings of anger or resentment.

If you are a Reformer, or have a Reformer in your life, you might describe someone who is bound by duty, hardworking, always willing to help, and ethically and morally irreproachable.

So how does this get in the way of Transformation?

1) I am always doing for others but never for myself.

2) I feel bad about saying no or letting people down.

3) I am highly critical of myself and my mistakes.

4) My partner (and, or my children) tell me I am highly critical of them.

5) People tell me I appear unapproachable or distant.

6) I always take on extra work because everyone else will do it wrong if I don't do it.

7) I very rarely let loose, it would be a waste of time or too embarrassing.

8) I get burnt out a lot.

9) I try to control everything and everyone.

It's challenging to start a journey of transformation when you are so used to doing what you've been told to do, or when you are living someone else's version of what is good or right.

Daily Affirmation & Release For The Type 1:

What do you want, Dear One?

Who are you, Dear One?

You know you are sick of being loved for what you do! You know you are sick of holding yourself to these high standards.

I see you.

Put down that cross.

If you never do a 'good' or 'right' thing ever again for the rest of your life, I want you to know this:

You are good and I love you.

You are good.

I love you.

Stop trying to buy my love and belonging with your deeds. You will resent me for it anyway.

You are good and I love you.

Introduction to Type 2: The Helper

"Good character consists of recognizing the selfishness that inheres in each of us and trying to balance it against the altruism to which we should all aspire. It is a difficult balance to strike, but no definition of goodness can be complete without it."

- Alan Dershowitz

Early on in life the Little Helper learned that the way to get their needs met - love, attention, presence - was to help. The forgotten message of the Little Helper is that it is okay to have their own needs.

If you are a Helper, or know a Helper, you may notice that their attention goes toward ways to help. But this 'helping' can often come at the expense of meeting their own needs or desires.

"I'm so good at helping others. I don't have any needs of my own."

A Helper's desire to be loved can deteriorate into a desire to be needed, sometimes inadvertently pushing their help on others. When family or friends do not return their help in the same way, a Helper is left feeling angry or rejected.

"Why didn't they sense my needs and meet them like I always do for them?"

Like the quote above by, Alan Dershowitz, it is important for Helpers to recognize how 'helping' can be a selfish means of masking feelings of unworthiness. The wake up call for the Helper is learning to accept that what makes them worthy and lovable is within them, not their helping.

So how does this get in the way of Transformation?

1) I am always paying attention to other's needs but not my own

2) I am not even sure who I am or what I want

3) I am often left feeling angry or resentful of others for not meeting my needs

4) I focus on aligning myself with influential people who make me feel valuable and needed

5) I sometimes use health issues or illness to get the attention, or rest, I crave

6) I often give my value - time, money, energy, love - away to others and only realize it when it is too late

7) I have trouble setting healthy boundaries

8) I get upset when people reject or refuse my advice

9) I can be prideful and hold grudges

It's can be challenging to stay on your path toward Transformation if you do not first learn to value yourself as equally as important as every other aspect of the Universe.

Daily Affirmation & Release For The Type 2:

You are no more, or less, important than any other aspect of the Universe! You deserve to pursue your greatest hopes and desires just like the rest of us.

If you never help another person a day in your life I want you to know this:

You are worthy, Dear One.

You are wanted, Dear One.

Do you hear me?

You are worthy.

You are wanted.

Stop giving your value away to me, or anyone else. I can never give you as much as you have given me, and I never asked you to give up yourself for me. You CHOSE to do that.

So now choose to figure out who you are, what you want, and what your greatest hopes and desires are

Introduction to Type 3: The Achiever

Early on in life the Little Achiever learned that it was not okay to have their own feelings and identity. This in turn developed into a fear of being worthless, or without inherent value.

"If I am not allowed to have my own feelings and pursue my own identity, then I must be worthless."

And so the Little Achiever took on the idea that to enhance their sense of value they needed to not just achieve, they needed to succeed.

If you are an Achiever, or know an Achiever, you may notice that their attention goes to completing tasks, output, work, image. Ask an Achiever who they are and they will tell you what they do. (If Western society was an Enneagram Type it would be type 3, The Achiever.)

An Achiever's desire to achieve can deteriorate into a desire to succeed. Whatever it takes to get across the line - cutting corners, ignoring health and family, even lying - can all be justified if they help achieve the desired outcome.

The wake up call for the Little Achiever is recognizing how feelings of worthlessness are tied to their ability to achieve, do, excel.

"If I cannot contribute, then I'd rather be dead."

So how does this get in the way of Transformation?

1) I find it hard to be present. I can always find something else to do, but never fully enjoy what is.

2) I find it hard to slow down and enjoy life. I start to get antsy when on holiday or with my family.

3) There are lots of things I want to try or experience but they might get in the way of work or other important commitments.

4) I come home exhausted and burnt out. On the weekend I just want to stay in bed and eat junk food.

5) I'm so tired of keeping up appearances. I'm afraid no one will accept me for who I am, especially if I show any weakness.

6) I'm always trying to figure out what people want from me, I can easily adapt myself to be what others need or want.

7) I get upset when people slow me down, or get in my way.

8) People tell me I can appear detached. Emotions get in the way of getting stuff done.

9) It doesn't matter how I feel, as long as I maintain my image of success and perfection.

It can be challenging to stay on the path toward transformation if you are lying to yourself, but first you have to accept just how much energy you waste on keeping up this appearance of success and perfection.

It must be exhausting.

Daily Affirmation & Release For The Type 3:

Dear One, you are loved for yourself. Your true self is acceptable, worthy and worthwhile. You are precious to me.

You are worthy, Dear One.

You are valuable, Dear One.

You are worthy.

Introduction to Type 4: The Romantic

Early on in life the Little Romantic learned that the best way to get attention and love was to be bigger, better or different. Fearful of being without personal significance or identity the Little Romantic learns to indulge in the self, they enhance those attributes that make them standout, including but not limited to, dress, artistic abilities, emotional depth, enhanced language skills.

The Romantic, more than any other type in the Enneagram, wants to be themselves, but may never develop a true sense of just who or what that is. Instead, a fear of being mediocre or just like everyone else may take over and keep the Romantic from allowing feelings of peace and happiness in.

If you are a Romantic, or know a Romantic, you might describe someone who is passionate, artistic, creative, and dramatic. But you might also describe someone who is prone to melancholy, depression, negative comparisons and envy of what they perceive others to have.

So how does this get in the way of transformation?

1) I believe my 'pain story' is what makes me interesting.

2) As soon as I start to feel happy or content I sabotage it. It's not okay to be too functional or too happy. Then I will be insignificant.

3) I fall in love hard. But it tends to fizzle out as soon as I get close to the person.

4) I am never satisfied with my artistic creations. I cannot communicate everything I think and feel.

5) No one truly understands me or listens to me. I feel isolated and alone.

6) I always tend to identify with whatever group I am. I will alter my dress and beliefs to fit in.

7) I feel every emotion at 110%. I cannot turn them on and off like a switch. Some people call this dramatic but that's just how I've always been.

8) When I get in arguments with my partner or family they tell me to be practical, or rational, or to detach from my emotions. Without my emotions I do not know who or what I am.

9) I have difficulty seeing the positives around me. My attention goes toward the negative.

It can be challenging to start your path toward transformation when you believe that you are what you think and feel.

Daily Affirmation & Release For The Type 4:

You are not solely what you think and feel.

You, the real you, exists before thought, feeling and action. You know the truth in this. You have felt it. You have experienced it. You've just been too afraid to own it.

You are seen for who you are, Dear One.

Have the courage to be yourself, Dear One.

Stop trying to impress me, or captivate me, or dazzle me. Just sit here with me in silence knowing that you are enough. You, just as you are, are significant and important to me.

You are significant and important to me.

And, I love you.

You are significant and important to me.

And, I love you.

Shhhhhh, Dear One. Can you just sit here silently for once receiving this love...!

Introduction to Type 5: The Observer

Early on in life the Little Observer took on the idea that the best way to get their needs met was to do it themselves. Fearful of being useless, incapable or incompetent the Little Observer becomes intent on being competent and knowledgeable - avid collectors, researchers and hoarders of information - which if left unchecked can deteriorate into useless specialization into areas of interest.

The Observer, thinking that is not okay to be comfortable in the world, desperately needs to know that his or her needs are not a problem. (For example there innocent need to explore a subject deeply, to question, to take a break from big parties, or deep emotionally draining conversations)

If you are an Observer, or know an Observer, you might describe someone who presents as an introvert, but suddenly becomes the life of the party when feeling comfortable. But you might also describe someone who gets emotionally drained easily, and would rather retreat to the confines of a good book then stay and have an emotionally confronting conversation. Or if pushed, use logic to stay emotionally distant and cold.

So how does this get in the way of transformation?

1) I prefer to observe my emotions through a calm and logical lens.

2) I get emotionally drained easily and feel like retreating.

3) I feel disconnected from the world and people in my life.

4) I sometimes feel like being reclusive and cutting of ties with people.

5) People in my life have told me that I can be 'holier than thou' and not allow them to express their feelings.

6) I often miss things that are going on around me, especially subtle body language and emotional cues.

7) I prefer to observe other people, watching all the games they play and the way they interact with one another.

It can be difficult to start your path toward transformation when you are sitting on the sidelines of your life. It's scary as hell, Dear One, but you've got to get out there and participate in your own life.

Daily Affirmation & Release For The Type 5:

You will not be overwhelmed by your emotions. You will find the energy you need to stay present.

Your needs are not a problem, Dear One.

You don't have to be capable and competent all the time, Dear One.

I don't need to know the ins and outs of the latest book you read. I want to know the ins and outs of you! What makes you laugh? What takes your breath away? Who broke your heart?

I want to connect with YOU! Let me in!

Can you let me give you this love!?

You are useful, capable and confident.

You are useful, capable and confident.

Introduction to Type 6: The Loyal Skeptic

Early on the little Loyal Skeptic lost connection with their inner guide. In an environment that either was, or was perceived to be, dangerous the little Loyal Skeptic took on the belief that the world is not a safe place and therefore learned to look outwardly for a sense of security and trust. The forgotten message for the Loyal Skeptic is that it is not okay to trust oneself.

If you are a Loyal Skeptic, or now a Loyal Skeptic, you might describe someone who is very loyal and steadfast but also looks for the holes in any argument, is skeptical of new ideas or leaders, and leans towards pessimism. However for the Loyal Skeptic, skepticism and pessimism are all effective tools for making sense of a potentially dangerous or ambiguous landscape.

So how does this get in the way of transformation:

1) Does not like uncertainty. Would rather deny our true feelings than create a situation that would result in uncertainty.

2) Skepticism and pessimism, although useful tools for gathering information, can be alienating and off-putting.

3) Afraid of change.

4) Does not know their own feelings. Looks to others for emotions.

5) Looking for security they become wary of new thoughts or beliefs

6) Become dependent upon others -parents, significant other, work - for sense of security or protection.

7) Only allows safe or acceptable emotions to surface.

It can be difficult to start or stick to your path toward transformation when you have not yet learned to listen to your self, your inner guide . Stop looking outside of yourself for help, support, courage. It starts from within. You know what you want. Trust yourself.

Daily Affirmation & Release For The Type 6:

You are courageous beyond your wildest dreams.

You are courageous beyond your wildest dreams.

Speak up.

Speak out.

Live your life, Dear One.

The thing, place, or person you are hoping will be your everything, will fill the void within you, they cannot do that for you. You have to do it, Dear One. You have to fill that void yourself or else they will always let you down.

You are safe and secure.

Stop depending on something outside of yourself.

You are safe and secure.

Stop depending on something outside of yourself.

Introduction to Type 7: The Enthusiast

Early on the Little Enthusiast took on the idea that it was not okay to depend on anyone or anything. And so they learned to provide for themselves by learning to avoid pain and/or deprivation. In fact, what scares The Enthusiast most is the thought of being trapped in pain or deprivation of any kind - physical, emotional, spatial.

Naturally tuned towards opportunities for adventure, pleasure and fun, you may recognize an Enthusiast by their outgoing and playful nature. They are known for being the life of any party. However, you might also recognize how their desire to be "happy" can quickly deteriorate into their desire to escape situations that are perceived to be overly deep, emotional, or painful.

So how does this get in the way of transformation:

1) You are constantly planning what "fun" thing you will do next. You have difficulty staying present with what is.

2) You have difficulty trusting others and are always testing them. You already have a plan in place in the event that things get too hard or don't go the way you want them to go.

3) You fall in and out of love easily.

4) It is a challenge to stay in a job, relationship or country once the initial buzz has worn off. Things become dull.

5) You have trouble asking for help or support.

6) You tend to do things in excess. You have difficulty finding balance.

What if I told you that sitting with your painful emotions would make you enjoy life more, not less. It's hard to know the day if you have never known the night. Just like it is hard to know real joy and rapture if you have never known their counterparts.

Daily Affirmation & Release For The Type 7:

Stop running.

Stop running.

Sit here with me. Hold my hand.

Breathe in.

Breathe out.

I haven't known your pain, but I've known pain.

I will sit here and take care of you.

You are taken care of, Dear One.

You are safe, and you are taken care of.

I am imperfect in many ways, but I can take care of you, at least for this moment.

Lay your burden down at my feet and rest your head upon my lap.

Introduction to Type 8: The Challenger

The Little Challenger learned early on in life that it was not okay to be vulnerable or to trust anyone. They learned to be hyper-vigilant to circumstances or people that might cause them harm, or attempt to control and/or limit them,

If you are a Challenger, or know a Challenger, you might describe someone who is proactive, takes charge when necessary, and enjoys seeing a job through to completion. But you might also describe someone who is combative, quick-tempered, and who's 'my way or the highway' approach leaves others in their wake.

So how does this get in the way of transformation:

1) You can't understand why people always get in your way. You hate yelling but sometimes it is the only way to get people to listen.

2) You thrive on stress, but your heart doesn't. Your Doctor is concerned about the risk of heart attack or aneurysm if something doesn't change.

3) Your partner is always harping on about opening up and being more vulnerable but you know she/he would use it against you if you did. No one really respects weakness.

4) When things get tough I've learned to bend people to my will. I don't even recognize when I am doing it. It's usually after the fact that I notice this Jekyll and Hyde side of me.

5) Just because I always appear strong at work or out in the world, sometimes it feels like a mask I have to put on. I wish someone could see the real me. I wish someone could see beyond all this blustering.

I do.

I see you, Dear One.

You are not so scary...

But don't worry. It can be our little secret.

Daily Affirmation & Release For The Type 8:

I know you feel like you have to protect yourself, and those around you, but you have become like Don Quixote: You make ferocious giants out of windmills.

Stop fighting.

I will not betray you.

Stop fighting.

I will not betray you.

No matter how you attempt to bend us or this world to your will, we are not yours to control. You must learn to judge each new person and each new experience with the innocence of a child, open and ready to be loved and protected by another.

Introduction to Type 9: The Mediator

The Little Mediator learned early on that it was not okay to assert themselves. So they learned how to get along, to go with the flow. The biggest fear for the Little Mediator is loss of connection, so they became very adept at adapting their needs to that of the parent, group or loved one.

If you are a Mediator, or happen to know one, you might describe someone who is naturally open-minded, laid back and comforting. But you might also depict a very stubborn silent time, prone to bouts of passive-aggression, who when asked "what's wrong?," will reply with a curt "I'M FINE!" as they retreat to the couch for an extended vege-fest.

Sound like someone you know?

So how does this get in the way of transformation:

1) Hiding from life on your couch/office/behind that extra body fat is not living

2) Just because you've learned to know what people want or need before they even ask does not mean that they are as attentive to your needs. You have to learn to ask for what you want or need.

3) The silent treatment is not winning you any points. You are the one that is suffering.

4) People have stopped asking for your opinion because you never seemed to have one. If you are ready to make a change then stop waiting for an invitation. Oh! And some people are not going to like it, you suddenly having a voice and opinion... Tell them, respectfully, to get used to it.

5) Avoiding arguments and tough situations is not peace. Most rainbows show up after the storm.

6) You have feelings, no matter how much you try to ignore them, and despite what you think they are written all over you.

Daily Affirmation & Release For The Type 9:

Dear One, your presence matters.

Your opinions, thoughts, feelings, they all matter.

You and I both know you never stopped having them, no matter how hard you tried to shove them down, hide them, or sometimes eat them.

You are here.

You are alive.

You are deserving of the space you take up in the world.

Your presence matters, Dear One.

Stop pretending you are not affected by what is going on around you.

Your presence matters, Dear One.

Stop going along with what everyone else says, or does, or wants.

What do you want? Or better yet, what do you not want? Who are you not? That passive-aggressive streak in you, that is your road-map to who you are and what you want.

If you are ready to be the strongest, fittest, and happiest version of yourself it is very important that you learn to recognize all the ways that your personality type, your box, is both your greatest gift and your greatest limitation.

I can help you with that...

If you are ready to take bold steps in the direction of your greatest life, to break with fear and self-doubt. and to instead embrace courage and joy, then now is the time for action.

Contact me HERE to set up a complimentary one-on-one Discovery Phone Call. At the end of our chat you will know more about your Enneagram Type, your personal box, and you will walk away with key tools to help you break free.

Contact me at, right now to get started on your journey forward.


xx Lindsey

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