Dear Jack: You are an Enneagram 3W4 (Achiever/Invidualist)

11 years, 10 months.

Dear Jack,

Ever since becoming certified as an Enneagram coach last December, I have had trouble getting a solid reading on you.

But as of this past week, it become clear:

You are an Enneagram 3 (The Achiever) with a dominant wing 4 (The Individualist).

Mommy and I have never put pressure on you to do well in school… nor in Taekwondo, nor in building complicated Lego sets, nor helping us build furniture we order off the Internet!

Yet you constantly excel in everything you do. While Mommy and I aren’t putting this constant “pressure to succeed” on you… you do.

What convinced me was when you came home from school last week, so proud, for certifiably excelling in all your subjects at school, in last year’s standardized test.

As proud of you that Mommy and I assured you that we were of you, it was apparent you were even prouder!

But you’re not only focusing on succeeding in life, you also like to stand out; like how you recently helped purchase your own (expensive!) Nike shoes for the new school year.

For the past couple of years now, you have openly acknowledged your goal to own a Tesla. That is what you have your sights on!

And I am confident you have what it takes… with no help from Mommy or me on that.

I wanted to surprise you with a gift to make you feel special regarding your amazing test scores. So I snuck by Marshall’s and bought you a $100 Sean Jean watch that you had recently pointed out to me.

And it because it was from Marshall’s, I only paid $20.

Either way, you are undeniably smarter than me!

I have always known you are going to go far in life. And now I realize, it’s fundamentally your personality to achieve and to be a creative individual in the process!



Dear Holly: You are an Enneagram 2W3 (Helper/Achiever)

6 years, 4 months.

Dear Holly,

We’re now a few months into me determining that you are officially an Enneagram 2- “The Helper” personality.

This past week, one particular event stood out to back this up.

Thanks to many family members across the USA, you did very well in selling magazine subscriptions as a fundraiser for your school. (That shows your dominant “3 wing- The Achiever”.)

So you got a keychain as a prize for each one sold.

But on the bus ride home from school that day, some older kids saw how many you had and asked if they could all have one.

Reluctantly, you said yes; confused, thinking they were asking to see the prizes, not keep them. But you indeed at given away three of your prizes to kids you didn’t even know.

You kept from crying, long enough to make it off the bus.

Mommy took care of you, though. She explained to your teacher what happened, so you got reimbursed the next day with new prizes.

You are a helper, and an achiever; as this story clearly demonstrates.

And as your Daddy, part of my job is to make sure you don’t help others to the point that you neglect yourself in the process.

Mommy and I are both Enneagram 6s, so we are most motivated to provide security for those we love.

You are so kind and giving- and so easy to love!

That happens to be a trait about people who are Enneagram 2- they never make you wonder if they love you.



“Maybe It’s a Dream” – Song 1 – Enneagram 6 Songwriter – Analyzing Lyrics – Themes of Belonging and Security

Since 2014, I have written over 60 songs that I have published on my YouTube channel.

This past year, I dove deep into understanding myself better than I ever have before. I became certified as an Enneagram coach, which has ultimately been my own personal equivalent of experimenting with a revealing psychedelic like ayahuasca.

I am officially a Counterphobic Enneagram 6 Wing 7, Sexual/Social Subtype.

Ultimately, here’s the breakdown: I find meaning in life by seeking security through building and maintaining relationships with people; which ultimately makes me feel like I exist. I am constantly looking for what might go wrong with the situation, so that I can either prevent it, or go down with the ship and learn from it. And despite living in constant anxiety, I face my fears head on. I am the loyal skeptic, which is ultimately a paradox: Both an introvert and extrovert; both a pessimist and an optimist.

So in addition to now understanding my fundamental psychological operating system, there is also the fact that when I write a new song, it draws out of me, subconscious thoughts I am often not aware of.

I am excited and curious to start turning my lyrics inside out. Let’s start with the very first song I published on my YouTube channel: “Maybe It’s a Dream.”

I originally wrote it on January 11th, 2014; when I was 33 years old. However, I didn’t actually record it until April 16th, 2018; just 4 days before my 37th birthday. (I’m 41 now.)

In hindsight, I don’t like the way I performed this song. The key is too low and I over-pronounce the words.

But ultimately, through this new series of unpacking the psychology of all the songs I’ve written, one by one, I want to finally focus on the true poetry of my lyrics, as opposed to simply the musical aspect.

Here are the lyrics to “Maybe It’s a Dream”:

I am a skeleton with meat on my bones – I walk around with secrets nobody knows – I am a figment of my own imagination, I bet – It’s all, it’s all, in my head – Seven billion people ride a planet that spins – A thousand miles an hour and I’m just one of them – Another stranger who’s no stranger than all the rest – It’s all, it’s all, in my head – It feels like no one knows me anymore – And I start to think that I’m safer when ignored – My head’s in the clouds but my feet are on the ground – So tell me now, where can I be found? It’s like a dream where I can’t stop falling from the bottom to the top – Maybe it’s a dream where I’m drowning out a sea – I’m coming up for air – But is this even real? My thoughts are captive and I’ve swallowed the key – I’ve locked myself out of the world so it seems – My perspective of reality will die with me – It’s all, it’s all make believe – With these distractions it’s so hard to exist – It’s survival of the mentally fittest – I’m still standing here so I guess I know that this means – It’s all, it’s all in my head 

So looking back on this song I wrote nearly a decade ago, can you see the Enneagram 6? Can you see my longing for security and confirmation of my own existence?

Feel free to leave a comment. I’d love to hear your thoughts!

And now you can listen to the song, below, if you wish:


Dear Holly: I Now Realize You are an Enneagram 2, “The Helper”

6 years, 1 month.

Dear Holly,

Up until this past week, I didn’t question you being an Enneagram 7, the Scattered Enthusiast.

But then I discovered a few of your notes that you thoughtfully wrote for your brother and let in his room.

That’s when it hit me: It couldn’t be any more obvious that you are an Enneagram 2, The Helper:

Empathetic, sincere, warm-hearted.

One of the notes you proactively wrote for your brother was because he “cleaned out the junk” in his room… and gave it to you!

I almost feel silly not realizing this until now…

Because something I always say to you is, “Holly’s such a good little helper!”

You’ve been an Enneagram 2 the entire time.





That Awkward Moment You Realize How Embarrassed You are By Who You Were 10 Years Ago

I’ll start by pointing out the obvious. This is 2022. Nobody reads blogs anymore. I know that.

And that very fact likely reveals how much time has passed between the version of myself I do not wish to remind anyone of (though ironically, that’s what I am doing here), and the now 40 year-old version of myself who is finally beginning to process the shame, fear, and anger that I didn’t realize has been here this whole time.

Would it be silly for me to apologize to everyone who knew me during the most challenging and darkest time of my life? I can if you need me to.

Because trust me- I don’t like that guy from a decade ago!

He came across as very self-righteous, eager to prove others wrong, and way too caught up in conspiracy theories.

At the time, I was Parents magazine’s official Daddy Blogger; a side hustle that lasted a solid 4 years. During that time, the plant-based trend was really picking up. So naturally, I found myself exploiting the fact I was a hard core vegan, in my blog posts. Sure, it helped my views. But my vegan lifestyle also served as an avatar to reveal my anger and confusion.

If it wasn’t me being a vegan, it would have been something else. My subconscious would have found an alter-ego to demonstrate what is completely obvious to me now:

I was not at peace. I was reaching.

I was reaching for the idea that I could be in control of… something.

Because during that time, I felt like my life was out of control.

My wife and I had moved from Nashville (where we had decent jobs) with our newborn son, back to my hometown in Alabama. Keep in mind, this was shortly following the Financial Crisis of 2008. And not knowing better, we moved there without securing jobs first.

Unlike now, where people my age are migrating back to their hometowns because so many of us are working remotely anyway, it proved impossible back then to find a decent job where I could support my wife and newborn son.

So after nine stormy months, we had to swallow what was left of our pride and ask for our old jobs back.

We moved to Nashville again, but not before our car broke down on the way up.

And of course, we had been living off our savings the whole time we were jobless in Alabama.

That means we returned to our life in Nashville, with no savings- and for me personally, very little dignity. Starting over.

I couldn’t have known it at the time, but I was very angry and was living in much fear; in addition to the shame I felt, for years following our move back to Nashville.

It was about four years ago that I began to wake up from the fog. The company I had been working for all those years shut down their branch where I worked, which forced me to find a new job.

That new job as a recruiter, where I still work today, would prove to be the best place I have ever worked. I became part of a team for the first time. I polished my leadership skills. I felt good about my life again, finally.

Subconsciously, I was beginning to find my inner peace again.

The biggest epiphany began to present itself a just few months ago, after I became inspired to earn my certification as an Enneagram coach.

I learned that I am an Enneagram 7. I am the optimist and the extrovert, out of the 9 Enneagram personalities.

The downside is, my specific fear as an Enneagram 7 is that my time is being wasted, so I constantly feel I have to keep myself busy all the time- and I have to feel like I’m being productive.

Otherwise, the anxiety kicks in. And I realized that the unsuccessful move to Alabama changed my Enneagram wing of a practical 6, to an aggressive and often angry 8.

I will say- it means I’m really good at my job: Convincing people what to do all day; thanks to my aggressive, energetic edge.

But outside of the character I play at work, it can be challenging for me to feel relaxed. Because I have this angry, anxious energy running through my veins.

For me, this is a year of focusing on mental health. I feel like a lot of people have been saying the same thing, here recently.

As an Enneagram 7, my “growth personality” is an Enneagram 5. In other words, the best version of myself is when I am a more analytical and balanced introvert.

Contrary to that is who I was a decade ago, the self-righteous vegan. That was me in my “stress personality”, which is an Enneagram 1, the Perfectionist. That was the worst version of me, on public display.

Thanks to my new insight, I am able to see progress begin.

As recent as… yesterday, actually… I actually began crying tears of sadness, anger, and shame; as I came to terms with the emotions I repressed for over a decade, from the move to Alabama not working out.

This past weekend, I joined what I am ultimately going to call a “Men’s Support Group”; some of us are specifically there to sort out our repressed anger issues.

And while I haven’t been a vegan for years now, I have been secretly going to the gym 6 days a week each morning before work, to help my mental focus before any other challenges can present themselves.

I’m focused on my mental health, my physical health, and my spiritual health.

My anger, my shame, and my fear from a decade ago are still inside of me; yes.

But I am learning how to unpack all of that. How to manage it. And slowly, to release it and redirect it.

And you guessed it: My typing these thousand words here now is part of the therapy for me.

You’re witnessing the beginning of the release.