Grief is a Skill, and I Don’t Have It

This article will be filled with sunshine and rainbows.

Jack Whitlock
Read or Die!
6 min readDec 9, 2023

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Someday You’ll Find Her, Charlie Brown (1981)

“Every man bears the whole stamp of the human condition.” -Michel de Montaigne

I’m not so sure, Michel. I’m a 24-year-old, and I know better than you. Look at this, I can’t even write about grief without making jokes…Yikes.

Grief is a tricky emotion. It’s not something anyone wants to feel. I’m not sad that I can’t get sad, but I guess I am kind of perplexed in a negative kind of way.

I want to be able to feel every emotion possible. I don’t prefer to go through life without one of the main emotions, but I genuinely don’t know how. If I did at one point possess the power of sadness, then it has long since left me. This is my journey of trying to find it again.

Why? Because people are supposed to be sad. It’s part of the human condition for better or worse. I want to be able to mourn and move on when sad things happen. I want to be able to empathize and become better at consoling the sadness I find in my friends and family.

When people get sad around me I kind of short-circuit. I believe being able to be sad will make me a better husband, family member and friend.

If you are reading this and thinking, “That’s just not possible everyone gets sad,” just look at Chandler Bing. He never really got sad. Emotional? Yes. Frustrated? For sure. But, he never mourned anything. I’m like that, except I also get the occasional panic attack.

Enneagram - 7

I am a seven, wing six on the Enneagram. The seven is often referred to as “The Enthusiast.” We typically are the people saying, “Let’s go out tonight” or “Who wants to go to the beach next weekend?” (while living in the midwest). We look for excitement and variety. We want to feel good all the time.

All these awesome, desirable traits land us with the profound weakness of having the lowest pain tolerance of anyone you will ever meet. I suck at sitting in mental or emotional discomfort/pain. I will writhe and wrestle by joking around or by distracting until I’m set free from a painful experience.

I can have serious conversations, but when they start to get sad or negative, my emotional gas tank immediately drops to empty. I turn into a zombie. I can’t get out of the situation fast enough. I just disassociate until it’s over.

Where Do We Get Emotions?

Are emotions nature or nurture? Do we learn to be happy, sad and angry from our parents when we are young or is it our instinct to respond to our circumstances with the emotions they provoke? I have grown up extremely lucky, there wasn’t much to be sad about, ever.

When sadness came around, I tried not to be sad. I didn’t see the point of it. Won’t I look stronger and more mature? Why be sad if I can pull off being happy all the time? I think after a while, I just made the trigger for my sadness so small that it became non-existent.

This grew to be a problem for me. Looking to dispel sadness before it had a chance to grow, I became increasingly worse at allowing others to be sad. I saw that they would come to me looking for support, only to find that their needs could not fully be met.

Imagine someone is grieving in front of you, looking for help, and the only thing running through your head is, “How can I make this funny” or “Man that sucks, wanna go get ice cream?”

If it’s a pain that I caused I can take responsibility for it, but even then, I just start looking for ways to make it better before the dust ever settles and the sadness begins. I feel a little bit like a sociopath, devoid of any emotion, just waiting until time heals all wounds.

How I Have Grown in My Grief

I started going to therapy at the beginning of 2023. It wasn’t for any of this stuff, but if you wanna hear about that, you can read this article.

Going to therapy unlocked a few more emotions than I was previously using. I started to edge my way back into being able to stand next to sadness without cringing and squirming away.

The first time I realized this was when I had to trade in my car. It was a 2012 Jeep Grand Cherokee Overland edition. It was my dad’s before it was mine, but I had it through most of high school and all of college.

I had a lot of important memories in this car. I took my wife on dates in this car, I deepened my relationship with my best friend during long drives for no reason in there.

I would go to my car to feel safe and hidden away. I felt safe in my car. It was a place where I was confident in being vulnerable. A place where a lot of personal growth and change took place.

I had to give it up for something that wasn’t mine. It hurt to do. It was necessary and exciting, but it hurt.

For the first time in my life, I challenged myself to press into this new feeling of discomfort and see what came of it. I made a playlist called Goodbye Jeep. and listened to it on my way to the dealership.

I’m surprised I didn’t crash… I was weeping, ugly crying all over an old jeep. I was a blubbering idiot for 30 minutes. I had never felt anything like it, pure unadulterated sadness overcame me. It felt horrible, but in a good way, like a deep tissue massage.

Watch the show “Shrinking” on Apple TV, it’s great. In that show, Harrison Ford’s character suggests picking a sad song and letting yourself be sad for 15 minutes.

This was some advice that I desperately needed. I gave it a try, and wow what a great idea. It gave me the space to feel sad, without thinking the world would come to an end.

I didn’t feel guilty about just quitting and feeling better after those 15 minutes were up. I could reap the benefits of being sad without feeling bad about feeling bad.

These days I still listen to Goodbye Jeep.If I feel sad or out of sorts, I give it a good listen just to test if I need to feel sad. Most of the time, it’s a false alarm, but it’s good to check just so I don’t get or build up to a panic attack. It worked a few times, to just let myself be sad for a little bit and feel a little more human in the process.

Crying Feels Good

Tears of Sadness contain stress hormones and other toxins. Crying helps expel the bad stuff from your body. This was a profound discovery for me.

Having not cried unless undergoing a full blown panic attack (after which I felt awful and usually had to take a nap), I had never experienced this post cry relief. I noticed after I cried, the next few days I would feel more clear and focused. More grounded and satisfied with my current reality.

Growing in nonpositive emotions feels so counterintuitive to me. I’ve lived so long in my “happy all the time wonderland” that half of me is screaming to stay where I am and keep any form of sadness far away, but the other half is looking to grow and change, to evolve into a better, more well adjusted person that people in crisis can depend on.

Do you have any practical tips for me to get sadder? No I’m not watching “Marley and Me”

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Jack Whitlock
Read or Die!

I want to help driven individuals thrive in the world, build confidence, survive college, and collect offer letters.