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.


Dear Holly: You’re So Chatty! (And Likely an Enneagram 7, Like Me)

5 years, 7 months.

Dear Holly,

This morning when I woke up at 5:55 AM to go to the gym (which was later than normal for me), you were coming down the stairs.

Normally, I give you a big hug, then you run into the bedroom to talk to Mommy.

But today, you immediately initiated would what become an hour long conversation with me, and would ultimately be the reason why today would be my one day off from the gym this week.

While the majority of your questions for me were light-hearted and hilarious (like, “Daddy, how many bucks will the Tooth Fairy even give me, though?”), I noticed some of them had a darker undertone, alluding to fear and anxiety.

As I’ve begun my certification training this week to become an Enneagram coach, I recognize your behavior, because it’s the same as mine! I think you may be an Enneagram 7 like me.

“Daddy, when I lose a tooth, will it hurt?”

“Daddy, if my toe breaks off, will it grow back?”

“Daddy, how can a skeleton believe in Jesus?” (This makes the 2nd time you’ve asked me this one.)

“Daddy, what can break a board? A person’s hand?”

“Daddy, what can break open a person’s head? Maybe if a house falls on them?”

You are an unbelievably bright, sunny, and optimistic person. You make people laugh and you are constantly moving- and talking!

Ultimately, if you’re like me, this is an attempt to outrun our secret anxieties and fears about how the world actually works.

We’re in this together! I know exactly what it’s like to have a brain that works like yours!

Enneagram Type Seven

The Busy, Variety-Seeking Type:
Spontaneous, Versatile, Acquisitive, and Scattered

Sevens are extroverted, optimistic, versatile, and spontaneous. Playful, high-spirited, and practical, they can also misapply their many talents, becoming over-extended, scattered, and undisciplined. They constantly seek new and exciting experiences, but can become distracted and exhausted by staying on the go. They typically have problems with impatience and impulsiveness. At their Best: they focus their talents on worthwhile goals, becoming appreciative, joyous, and satisfied.

  • Basic Fear: Of being deprived and in pain
  • Basic Desire: To be satisfied and content—to have their needs fulfilled



Dear Jack: You are One Talented Kid! (And an Enneagram 4)

11 years old.

Dear Jack,

It’s not lost on me that you are incredibly smart, as well as talented. You’re the kind of person who is able to turn any project into gold.

Whether its your dedication to Taekwando, or you running and being voted as the Student Council Representative last year, or your ability to barely study yet still get straight A’s.

Selfishly, I’ll admit. That’s one less thing I have to worry about as a parent- knowing that you are an incredibly productive, and creative, person. I don’t have to motivate you- you’re already motivated!

I understand that there’s balance in everything. That especially right now as you are in your pre-teen years, one of the things I need to help you focus on is managing your emotions.

Fortunately, I enrolled this week to begin my training to become a certified Enneagram coach. Or as I like to call it- a cheaper version of a therapist!

I figure… everybody can use a little bit of therapy. I’m already learning how to be a better parent though what I’ve learned about your personality: An Enneagram 4- The Invidualist.

The Sensitive, Introspective Type:
Expressive, Dramatic, Self-Absorbed, and Temperamental

Fours are self-aware, sensitive, and reserved. They are emotionally honest, creative, and personal, but can also be moody and self-conscious. Withholding themselves from others due to feeling vulnerable and defective, they can also feel disdainful and exempt from ordinary ways of living. They typically have problems with melancholy, self-indulgence, and self-pity. At their Best: inspired and highly creative, they are able to renew themselves and transform their experiences.

  • Basic Fear: That they have no identity or personal significance
  • Basic Desire: To find themselves and their significance (to create an