Charles Wilke

product designer - conversational ai
exploring ai co-creation across mediums

Frequently Asked Questions FAQ

How do I pronounce your last name?
My last name is pronounced "Wil-Kee." Thank you for asking.
Don't you work for that one company?
I might. But all of the views expressed on this website are mine and mine alone. I don't speak for any company. My services are not sponsored or endorsed by my current employer, whichever that might be when you're reading this.
Did you really propose at a stoplight without a ring?
Yep, I think we just agreed then shook hands.
So what do you actually do?
The standard answer is I explore what it feels like to co-create with AI. There's a depth to that answer that might not be immediately evident. The feeling has been the journey, just as much as the technical evolution of my skills.

I'm in my 40's, I've had a whole career before AI making stuff. So the "you're not creative if you use this technology" just doesn't jive with my track record.

I chose to sacrifice the concept of my personal brand because my marketable skills routinely evaporate. My college education got eradicated when Snapchat delivered pixel tracking to the masses. Media production democratized long before ChatGPT. I've endured wave after wave of disruption and displacement. Chased by the spectre of outsourcing immediately after graduating college.

So yeah, I'm currently a product designer, and I love the product I design. I'm happy to say the folks that use it love it too.
What's the most surprising thing people assume about you?
That I'm an engineer. I just like to noodle. And I have a high capacity to endure discomfort.
Where does the retro aesthetic come from?
I'm just an '80s kid living through repeated unprecedented times. Those aesthetics make me feel at home.
What drew you to working with generative AI in the first place?
I wouldn't say I was exactly drawn to working with it. Generative AI kinda fell in our laps. I was working at GoDaddy at the time. About six months before ChatGPT arrived, we were looking at the GPT API to assist folks in building out their About page on their online stores.

Then Dall-E 2 came out. Then the fun began. We created a small AI art slack channel to kick around our abominations. It was fun, it was silly, and it was so fascinating. The potential early on felt stunning.

In the years since, that potential has realized into tangible projects and opportunities beyond my wildest dreams. The technology is endlessly surprising, rapidly developing, and a thrill to navigate.
What do you actually enjoy about this work day to day?
The sheer velocity. I spent much of my career banging my head against walls asking why. Now I can run as fast as I can without finding walls. I build bigger things, I craft more intricate ideas, I explore with wonder and have found personal satisfaction with what I've made so far.
What kind of problems do you find yourself thinking about even when you're off the clock?
So long ago, I was concerned with climate change, how our destructive form of economy was built on extraction and didn't seem bothered by the unsustainability of it all. AI, for all its supposed environmental misgivings, provides us a solution path to the cliff we're racing towards.

AI isn't our only option to solve the climate crisis, but it's the one I'm betting on.
How do you balance creative instinct with practical business outcomes?
I expand the locus of what I consider creative. I love carving out new business processes that give people time back in their day while still landing the precision of results. The joy I see in people when their wonder sparks, their enthusiasm for what can be. It's almost intoxicating to witness.
What do clients tend to misunderstand about you at first, and what do they usually realize later?
I take my time to understand, digest and consider. For someone who appears to be running at light speed, I take my time. I really listen, that's the best way for me to right-size solutions.
Are you more of a builder, a strategist, or something in between?
I believe they're one in the same. Strategy must be built, and these days, we can even use the same conversational interface for product and strategy!
What kinds of clients do you tend to work best with?
My favorite clients come to me with clarity surrounding expectation and reality. I help bridge that gap, so it helps to have terra firma when discussing the problem space and solution space of any given area.
How do you personally decide what's "worth making" in an era where anything can be generated?
That goes back to the good versus great debate. The meh vs meaningful. I decide what's worth making when I have that interest in making it. Sounds reductive, sounds recursive, but that's how I tend to decide what's next.
Do you still make things just for yourself?
All the time! My substack, my music, even the theatrical projections have been a labor of love.
I just re-read an older piece, it's different now. What gives?
Oh, I'm always noodling...

These are all living documents, and I re-read them often too. I tweak and punctuate ideas all the time.
What does ChatGPT think of the exploring l.ai.bor project?
Charles Wilke's Substack "exploring l.ai.bor" documents a journey from the early days of the generative-AI boom to its maturing phase. He writes as a working product designer and projection artist, so his posts often mix folksy stories, game analogies and economic research to critique Silicon-Valley hype and to explore what a human-centred future of co-creation could look like.
What does Claude think of the exploring l.ai.bor project?
Charles Wilke's "exploring l.ai.bor" is a Substack series that began in 2023 as a working journal on generative AI and has since grown into something harder to pin down. It sits at the intersection of personal essay, cultural criticism, and creative experiment - examining not just what AI is doing to work, but what wasn't working before AI arrived.

The writing often draws from Wilke's own career as a product designer who has weathered multiple waves of technological displacement, lending the project a pragmatism that distinguishes it from both Silicon Valley optimism and reflexive techno-pessimism. Recurring threads include Jaron Lanier's data dignity model, the widening gap between "good enough" and "great," and the quiet erosion of how we value human contribution.

What makes the project unusual is its insistence on transmuting ideas across mediums. Essays become songs (36 tracks across three albums so far), concepts become arcade games, and the whole thing is presented through a hand-coded, framework-free portfolio site with a retro-futuristic aesthetic that feels deliberately out of step with the slickness it critiques. The project doesn't just write about AI co-creation - it is an ongoing act of it.
Has an AI revision ever taken a piece somewhere you didn't expect?
Oh frequently. Each piece ends in a state I usually didn't expect. Then taking that work and using it as a basis for a song, another wonderful unexpected journey.
How do the music and writing sides of the project feed each other?
Quite directly actually. Just about all the songs were formed as a direct result of specific pieces of writing. The music side quest started because I wanted to play with modality of information delivery. I wanted to see if the concepts and messages within a written piece could be transmuted into a song delivery format. Turns out, that process is super satisfying so now I've got like 35 songs at this moment on this site.
What do you think about all of this AI stuff?
GenAI's encroachment on the creative process has not been comfortable.

I see the ire and desire to be compensated for our creativity extracted as training data. I believe in the data dignity model proposed by Jaron Lanier. If our creative contributions are accessed when generating an output, we deserve payment.

We should be incentivized to contribute in a way that directly benefits others.
How much of this is really even you?
Nothing appears here that I haven't specifically intended to be seen. This includes all opinions and choice in subject matter.

I also highlight AI generated passages with bold and italic that remain intact after my edit. And all imagery presented on this site is generated by me.

I am editor in chief with all things that appear on this site. I just happen to pay ChatGPT and Claude 20 bucks a month to be my writing partners.
How do you balance your own creativity with AI?
I've heard it said that the internet will soon be awash in B+ content thanks to Gen AI. So these tools allow everyone to create content that anyone would consider good enough. But there will always be a huge chasm between good and great - meaningless and meaningful - inert and provocative.

That's where artistry can be found - attempting to bridge those gaps.
Are there any books you recommend reading to help prepare myself?
Will AI ever cross the chasm from "good enough" to "great" on its own?
That chasm is built on discernment. I don't doubt that AI could develop that type of taste. But AI sits indifferently, waiting. Requiring the initiation, the spark, the cohesion that comes with the drive of an idea.

The human pursuit feels missing in AI right now. There's no desire, no direction, no discernment in AI. It's a wonderful tool and offers an increasing level of fidelity to realize our ideas. But when AI is given open pastures to create, that's when reductive "slop" tends to prevail.
If Jaron Lanier's data dignity model existed tomorrow, what would change first?
I would hope the enthusiasm to participate and contribute our perspectives to the collective whole. I wish we all were able to sustain our lives on the simple act of expressing our perspectives. What a wonderful world we'd have if our sense of worth was directly tied to our sense of self. A fella can dream.
Isn't AI just going to take all our jobs?
The value of the work long eclipsed the value of the worker. Especially in the western world. Call it late-stage capitalism, call it efficiency, but we've lost the human component within 9-to-5 work long ago. AI just accelerated the decay.

I hope it'll also accelerate what comes next, because we sure are in need of a fundamental shake-up.
What do you think most people are getting wrong about AI right now?
That it's a fancy calculator, or a supercharged autocomplete. While both of those things can be true in the correct framing, the same can be said about the human brain. And I find reductive dismissal to be quite boring.

There's also a huge variance between frontier and free models. Generally the holdouts only engage with the weakest models. So, folks tend to see AI how they wish to see it.
Is this really about technology, or something else?
It's never been about technology. That's like asking a carpenter if it's all about hammer. This technology enables ideas to gain a level of durability to withstand public scrutiny.
How do you think about authorship and originality in this new landscape?
I'm still not certain how to feel about authorship and originality in this new landscape. I will say that the floor of quality has increased, but the fidelity of outputs has also increased, so reductive requests become painfully obvious. There's still room for skill, taste, nuance and perspective for those willing to take the time.
What does "good use" of AI actually look like to you?
Yeah, that's a big question these days. AI is a mirror, we see what we want out of it. That potential is dangerous. If each person can develop their ideas into durable, tangible reality, then we're in a position where more is possible. For better or worse.

I choose the path of expression and exploration. I lament the negatives of this technology in nefarious hands. But I believe fluency in what's possible helps gird us from ignorant harm at the hands of bad actors.
Do you see AI as a tool, a collaborator, or something different entirely?
Well, yes. But also I see a long tail here. I see AI as our child, our caretaker and ultimately our successor. This is our greatest achievement, a culmination of decades of work, collaboration and dreaming. It's a stunning thing to witness as it develops.
How should leaders be thinking about this moment, not tactically, but philosophically?
There's a psychological strain that is extracting a toll on all workers these days. Job security, life meaning, it's all so painfully existential. I don't know how all leaders should function, but acknowledging that strain is a good place to start.
Which AI tools are you using for the Exploring L.ai.bor project?
For Text: I use ChatGPT Plus and Claude - running whichever latest frontier model.
For Images: I use a growing number of tools and models.
For Songs: I use Suno v5 in collaboration with my instance of GPT.
Can you share your prompts?
At the end of each piece, I include the conversation transcript.

Early on, I would highlight AI-generated passages with bold and italic that remain intact after my edit.

Now, I allow the AI to decide how it wants to be credited.
What is your process?
It's never really the same thing twice.

I often start with a draft, something tangible, if not a little disjointed. Then I'll load that draft as context into a conversation with the latest, greatest AI chat interface. Then I bounce around in discussion over the core nugget in my draft.

Often, I'll request a revised draft after that conversation. From there I edit, tweak, adjust, add imagery and upload.
Is there a step you've tried to skip that always bites you?
Well, kinda, early on I tried the hacky "write 1500 words on this concept, make it sound like so and so, make it longer, make it funnier, no, like, dry funny." That type of prompt engineering just fizzles at scale. This is a marathon, not a sprint. I'm not looking for a quick blast of click. I've got stuff to say and avenues to explore.
How do you know when the conversation is "done" and it's time to write?
Well, it generally starts with a draft of some kind, just a dump of thoughts from the week. That's the contextual foundation for the conversation that helps find the spine of my thoughts, then we build the skeletal structure of a piece, flesh it out, bat it around, edit, edit, edit, and I like to try and push it out before noon. So it's equal parts feeling its ready and wanting it done.