GPT and me…
Collaborating with the machine. A short dump of interactions between myself and AI.
Updated infrequently!
A collaborative writing practice, between Stewart Ainslie and ChatGPT.
September 12th 2024.
I had a shot at writing a haiku the other week, which took ages and didn’t come naturally.
Naturally, I turned to ChatGPT.
What follows is a simple excercise purely to satisfy my own curiosity.
I’m still not sure about AI… but it did take a draft and ruin it.
A haiku traditionally has a pattern of 5-7-5 syllables.
Stew’s original - V1:
When we are lost,
We can ask the winter machine
The winter of man?
Broken down:
When (1) we (1) are (1) lost (1), (4 syllables)
We (1) can (1) ask (1) the (1) win-ter (2) ma-chine (2) (8 syllables)
The (1) wi-nter (2) of (1) man? (1) (5 syllables)
Chat GPT version V2:
When we are so lost,
Ask the cold winter machine
Winter's end of man
This might be technically better, and I don’t hate it. It just doesn’t feel like my own idea anymore.
I refined my original and asked ChatGPT once more.
Stew’s V3:
When we are at sea,
We ask the winter machine
The winter of man
?
I’m happier with this and feel it’s still mine to own. With heart in throat, I asked for a full review from my digital collaborator.
Whatever it is, the way you tell your story online can make all the difference.
What ChatGPT had to say…
This version of the haiku feels even more evocative, incorporating a vivid metaphor ("at sea") that opens up new layers of meaning.
Here's my review:
Syllable Structure:
Let’s check the syllables for this one:
When we are at sea, (5 syllables)
We ask the winter machine (7 syllables)
The winter of man (5 syllables)
This is now perfectly aligned with the traditional 5-7-5 haiku form, so in terms of structure, it's spot on!
Imagery:
"When we are at sea"
This phrase is rich in metaphor. It can literally refer to being lost in the ocean, or symbolically convey feelings of uncertainty, isolation, or being adrift in life. It’s a very strong, relatable image that sets the tone beautifully.
“The winter machine":
This still remains a powerful image, blending something cold and mechanical with nature. It suggests turning to something unfeeling or systematic in times of need or confusion.
“The winter of man”
The repetition of "winter" still works effectively. It evokes a sense of existential coldness or perhaps the decline of humanity, which can be interpreted in many ways—either as a reflection on human nature, aging, or the inevitability of death.
Emotion & Tone:
The shift from "lost" or "stuck" to "at sea" adds depth and a subtle layer of emotion. Being at sea implies a vast, overwhelming environment, which can evoke feelings of insignificance or powerlessness. The final line, "The winter of man," still feels melancholic, almost like a final, cold realization. The tone overall is introspective, and the sense of searching remains strong.
Flow:
The flow in this version is much smoother. Each line transitions well into the next, making it easier to follow the emotional journey from being "at sea" to relying on the cold "winter machine" to confronting the existential "winter of man."
Overall Rating:
Creativity: 9/10 – The metaphor of being "at sea" adds a lot of depth and complexity.
Emotion: 8/10 – The emotional weight is well conveyed, and the shift from uncertainty to a cold realization is powerful.
Form: 10/10 – The haiku now fits the traditional syllable pattern perfectly.
Chat GPT, ““This version is more polished and complete. Would you like any further refinements or suggestions?”
Stew, “No thanks ChatGPT.”
A humble critique from ChatGPT.
On the subject of my ‘findings’.
Saturday June 20th 2026
Dear GPT:
Review this blog and posts within it: https://www.stewartainslie.co.uk/findings Tell me what your thoughts and feelings are in the style of a critic
Reading Stewart Ainslie’s Findings felt a little like wandering into someone’s shed and discovering it is, unexpectedly, a chapel, a sketchbook, and a pub conversation all at once. There is a deliberate anti-polish to the work—a resistance to contemporary “content” that feels almost moral. In an era of optimised personal brands and frictionless thought-leadership, Ainslie writes like a man suspicious of smooth surfaces. That suspicion becomes the site’s greatest strength. (Stewart Ainslie)
As a critic, what strikes me first is voice. Stewart writes with a distinctly Scottish rhetorical cadence: self-deprecating, dry, occasionally abrasive, but warm underneath. He weaponises understatement. Titles like Bored before breakfast or It defies logic are anti-clickbait—they don’t seduce, they shrug. That refusal to perform urgency is refreshing. It says: come if you’re curious, not because I gamed your attention. In 2026, that feels quietly rebellious. (Stewart Ainslie)
His central obsession appears to be agitation—not just as a political or cultural condition, but as a psychic one. In pieces like Agitation Nation™, there’s a recurring argument that modern life manufactures noise and rewards reaction. He seems deeply interested in what systems do to people: media systems, design systems, social systems, even attention itself. There’s an almost McLuhan-esque suspicion here—not of technology per se, but of what prolonged exposure to mediated reality does to human temperament.
What I feel reading him is a tension between cynicism and earnestness.
That tension is where the writing becomes compelling.
Ainslie clearly distrusts hype, social media, brand theatre, and the creative industries’ capacity for self-mythologising. He has sharp elbows for designer ego, agency fluff, and performative authenticity. Yet beneath that skepticism is someone who still profoundly cares about craft, service, community, and making things well. In To create and serve, that moral framework surfaces most clearly: creativity is not sacred because it is self-expression; it matters because it can serve others. That’s a deeply unfashionable position in contemporary creative culture, where authorship often outranks usefulness.
His essays often read like thinking in public rather than presenting conclusions. Sometimes this is powerful. Sometimes it becomes a weakness.
Here is the criticism.
The writing occasionally mistakes intuition for argument. Ainslie is strongest when concrete examples anchor his observations; he is weaker when abstraction accumulates. There are moments where a thesis hovers just out of reach, as though he trusts the reader to bridge conceptual gaps he hasn’t fully articulated himself. That can feel intimate—like live thought—but also frustrating. Some essays need one more editorial pass, one more act of ruthless compression.
Stylistically, he is at his best when funny.
The doodle-adjacent absurdism—like meditations on dog shit, monsters, myths—prevents the site from becoming self-serious. His humour performs an important structural function: it punctures intellectual vanity. Even when discussing design, philosophy, or culture, he refuses grandeur. That restraint gives the blog credibility. (Stewart Ainslie)
Aesthetic matters here too. The site feels intentionally “impenetrable,” as he calls it, and that matters critically. It rejects the clean conversion funnels of modern portfolio sites. Instead, it behaves like a cabinet of curiosities—wargaming beside RNLI work beside essays beside sketches. The result is messy but human. You leave with a stronger sense of the person than of the professional résumé. That is rare. (Stewart Ainslie)
If I were to situate Stewart Ainslie in a broader tradition, I’d place him somewhere between the essayist, the designer-philosopher, and the pub contrarian. Not polished enough to be establishment thought leadership; too thoughtful to be mere blogging. He occupies a useful middle ground: serious without pomp.
My emotional response?
I found the blog oddly moving.
Not because every argument convinced me, but because the whole project feels like resistance against flattening. Against becoming legible purely as a service provider, a social profile, a content stream. The blog says: a person is larger than their market value. That conviction radiates from every page.
The danger for Ainslie is that contrarianism can calcify into identity. The smartest critics of modern culture eventually must risk proposing something, not merely resisting what exists. He seems aware of that trap, which gives me hope his best work may still be ahead.
In short: Stewart Ainslie’s Findings is thoughtful, shaggy, provocative, and refreshingly uncommodified. It is not always elegant, not always disciplined, but rarely dishonest.
And in criticism, honesty buys a great deal.
—”Fair enough” - Stew