This is my old Substack photo that I used for the first 3 months of this newsletter until today.
You may be wondering, what am I even looking at? That’s a blurry photo my housemate took of me at 23, DJing on my laptop in the Halifax student housing we lived in. It’s statistically likely that I was high out of my mind at the time the photo was taken. There’s a lot I treasure about this picture and my life at the time. Weed and psychadelics had helped me break through the herd mentality and fear of not fitting in that kept me emotionally, academically, and creatively constipated as a teenager. DJing allowed me to conceive of myself as a creative person for the first time and develop my capacities to conceptualize and improvise.
But I’m almost 40 now. The attitudes and trips of that era have long ceased doing more good than harm. So what would compel me to use this photo for a project in 2025, 15 years after it was taken?
The Background and Theory Behind Being Sad
All this talk about the Enneagram in my newsletter and I think I’ve only ever shared my own type in one partially paywalled post. I am a type Four. Riso and Hudson call type Fours Individualists, The Narrative Enneagram tradition calls us Romantics. I can identify with both, particularly Romantic in the sense of having deep feelings and longings. As to why that would lead to odd, counterproductive choices of social media profile pictures, that actually goes pretty deep…
Each Enneagram type falls into one of three different triads. Types Two, Three, and Four comprise the Feeling Triad or Heart Triad.

To ruthlessly summarize the shared characteristics of this triad, Feeling types tend to lose touch with their hearts and feelings. A strong sense of shame or grief tends to accompany this loss of connection. Feeling types try to compensate for this by building up a false identity, identifying with it themselves, and then presenting it to others. This is done in the hopes the false identity will attract the affirmation that the Feeling Type is not getting from within due to their alienation from their own hearts. This is almost entirely unconscious and borderline-instinctual at first. Resolving it is unfortunately not as simple as telling yourself not to be disconnected from your own heart or trying to stop pretending for the affirmation of others. The conscious mind might genuinely want to stop behaving in these engrained ways, but these ways of being are be deeply rooted in the body and nervous system.
Types Two, Three, and Four all live out different variations of this pattern until they become conscious of it and begin to work through it. The type Four variation is to maintain a false identity based on feelings, fantasies and past hurts. No one gets through childhood, or even infancy, without hurts. I wrote an earlier post exploring different theories about the important of hurts and disappointment in early life being core to the formation of ego and personality. The specific Type Four habit is to overidentify with these past hurts and see ourselves “as victims and prisoners of [our] pasts.”1 This is not to say that any given type Four did not experience legitimate pain or even trauma in the past. The challenge is in how the centrality of past stories shapes the Four personality and keeps it locked in place.
Look At Me. Don’t Look At Me
I haven’t forgotten about my outdated, cryptic photo. One of the unsolvable dilemmas of the type Four personality is the sense that we need to be seen by others in order to be perceived as unique and special. However, there is an equal drive to not be seen for fear that we will be seen as something other than unique and special. This unwinnable situation is emblematic of the absurdity of outsourcing one’s sense of worth to the opinions of others. .
That’s one way you end up with bohemian half-measures like my Halifax photo. I could write anonymously or with no photo, but part of me wants to be seen. I could use a regular or professional-looking photo, but part of me doesn’t want to be seen as too ordinary.
My day job is in marketing. Intellectually, I grasp the importance of seeing someone’s face online, and how it plants the seeds for a sense of trust and connection. If someone else were to ask me what photo they should use for their new Substack, I would tell them to pick a photo where they look natural and like someone who might know what they’re talking about.
This understanding but not doing is rather instructive of how Enneagram types work. I have a firm cognitive grasp on the photo I should choose for my Substack, but then my type takes over and convinces me: Nah, fuck that. You’re, like, an artist man. Pick one where they can’t even see who you are or what you’re doing ‘cause it’s so, like, deep and mysterious. They’ll be blown away by how deep and mysterious you are. What can I say, at least I caught myself three months later.
Waking Up
It would be quite sad to learn and recognize all of this in myself and then continue to move forward trapped by the same patterns. Perhaps even sadder than unwittingly being in the thrall of these habits. To me, the value of all of this introspection and capacity to write essays on my own foibles is to be able to catch these patterns as they start to happen and make conscious choices to operate outside of them.
One thing I have found that works for me is to go slow and be as vulnerable and out there as I can with faith that, little by little, the next steps will become possible. I knew I wanted to write (perhaps needed to write) and I knew I would dread putting a face to my writing. Instead of waiting until I felt ready to share my face or until the perfect picture of me had been taken, I just went ahead a wrote and published with no pictures. A few weeks after that, I felt ready to add the blurry bohemian Halifax picture to my Substack. Now, a few months after that, I feel ready to show up with a more professional picture that feels more aligned with the seriousness with which I take the Enneagram and my writing. Here it is:
Don Richard Riso, and Russ Hudson. Wisdom of the Enneagram: The Complete Guide to Psychological and Spiritual Growth for the Nine Personality Types. Bantam, 1999. Page 56