Dear Holly: I Finally Was Able to See You at Gymnastics!

5 years, 7 months.

Dear Holly,

When this school year started, you began gymnastics and your brother started Taekwondo. Mommy always been the one to take you to gymnastics, which happens to be at the same time as when I am taking your brother to Taekwondo.

But this week, it worked out better for me to take you instead. You being in gymnastics makes a lot of sense!

You are very energetic and daring. So for an hour, twice a week, you get to run and jump, and challenge yourself- specifically with the balance beam.

As much as I loved watching you in your dance recital earlier this year, I definitely see how gymnastics could be the better fit for you… at least for now.



Dear Holly: You are Still Planning on Marrying Brooks, From Preschool

5 years, 7 months.

Dear Holly,

Seven months ago, when you were finishing up preschool, is when I became well aware of your boyfriend (?) Brooks from your class.

He even said right in front of me one time, “Holly, remember… I’m going to marry you one day!”

Well even though you’re halfway through Kindergarten now (a different one than him), you still haven’t forgotten what he said- despite not seeing him since August.

In the mornings before school, you often like to draw pictures. This week, you drew one that made it to the fridge; as it proclaims, “Brooks and Holly Get Married.”

This is going to be hilarious if you and Brooks ever cross paths again. I don’t even know his last name!



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



Dear Jack: Maybe I’m Not Ready for You to Be Done with Plastic Toys, After All

10 years, 11 months.

Dear Jack,

This is my last letter I will write you while you’re still 10 years old. Your 11th birthday is now only a few days away!

I’ve kept it no secret from myself; how it’s not easy watching you grow up so fast, especially as you are now more of a pre-teen than a little boy.

As birthday gifts have been showing up in the mail, and as I’ve watched how you’ve used your gift cards from your birthday party, it surprised me a bit to see you choose… plastic toys.

I was thinking we were past that stage in your life.

Last year it was all about Fortnite. This year, it’s Roblox.

Yeah, I know. You’re just collecting more plastic that you’ll ultimately forget about a year from now.

But as for now, it’s proof that there’s still a little bit more “little boy” still in there.

I need there to be.