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Interesting how the topic begins with how aesthetics are tied to relevance & medium.
I'm not concerned with relevance to an abstract or hypothetical mass of would-be converts, or readership, but these are still personal concerns.

"Do you keep up?"

By mere circumstance of being in time, in some ways more than others, only proactively in very few ways. I'm not trying to catch up, but curiosity does lead to some of that.

"So how flexible is your aesthetic?"

I play around with the aesthetics that seem fun to me at the moment, I don't commit to a singular aesthetic forever, though I'm drawn to similar elements, traits, genres, tropes, typologies throughout time. In speaking & forming narratives & thoughts, & in moral judgment, one paints everything with an aesthetic, whether unaware of it, or very deliberately. Mixing and conflating our senses and notions of good & bad with ugly & pretty. Is ripe fruit pretty & a rotten fruit ugly? Is a healthy person beautiful & a rotting corpse with maggots, flies & cockroaches horrible? Our brains developed instinctual aversion to "gross" things that might cause illness, in a similar way that fear conditions responses to threats, and not quite unrelated to how physical appearance relates to inciting lust.

I find some aesthetics infatuating, others repulsive, but the great majority is meh & easy to ignore & overlook, in the same way that all the skyscrapers in cities scream out their style to deaf ears of most people who don't give a fuck about architecture. It's just the interchangeable background to the petty dramas of their daily life. But people love making themselves pretty & getting pretty things, it's the economy, status & aesthetics are inextricable. You don't give a fuck about the font of a billboard unless graphic design is your passion, & increasingly more people are freelance or makeshift graphic designers because everyone uses the internet & makes websites & memes. Not to mention the bloated population with art or design degrees etc. Images, spectacle, your mom.

What's attractive to me, what appeals to my senses, overrides concerns of being relevant or not, or the opinions of others. I enjoy these things, but I'm also wary that it may be used against me. Among what's repulsive to me, there's a little bit of the phenomena described as juvenoia & "cringe" thrown in the mix.

"Do you jump into the pool & play when new mediums like TikTok come around, or are you more prone to holding to what you've been doing and letting “those who know” come to you?"

I'm not opposed to novelty in mediums. I don't like TikTok in particular. I don't want anyone to come to me, I want them to stay away and leave me alone. Selectively alternating (when you give a fuck) between assuming and presenting different aesthetics, including but not limited to pleasant, innocuous, the unremarkable, unappealing, and the outright repulsive, can help keep people at bay. Nothing new about scare tactics or shock factor, sometimes that's even used for attraction, a lot depends on context. I'm not engaged with seduction, nor marketing, nor some outward facing publicity stunt. Other people are, therefore hone their aesthetics to suit their goals.

"How do you do your own thing without becoming dated or out of touch, or how do you embrace the new without getting lost in the static?"

I'm always-already becoming-dated and out of touch. I'm lost in the static. I'm not being poetic, just answering the question by sticking to its terms. What I'm mean is that I'm getting older and I'm often out of the loop, increasingly so, and I don't care. I'm fine with dying and being forgotten. I don't mind not being able to relate, if there's reciprocity in how off-putting others find me and my choice or lack of aesthetics, it's fair. Although becoming senile or getting Alzheimer's is scary and very normal these days, hopefully I don't get that.