Chad’s Blog
Pragmatic Technologies for Life and Business Success®
If ChatGPT has felt more annoying than helpful, I get it. Today’s experiment is designed to be the opposite: fast, fun, and useful for your brand.
I want you to run a simple experiment: can ChatGPT create a caricature that actually captures the essence of who you are, not just what you look like?
Because if the result is generic, that is a signal. If it feels unmistakably you, that is also a signal. Either way, you learn something useful about your positioning and how clearly your “brand story” comes through.
I tried it. My caricature ended up blending the core parts of my identity: web and technology strategy, building the AI Insider Lab, guitar, photography, travel, presenting and even pickleball. It was fun, but the real value was this: the image forced clarity about what I want to be known for.
Why this matters, beyond the laugh
A strong brand is a pattern. People should be able to recognize you from the combination of signals you consistently put into the world. Expertise, point of view, energy, obsessions, and outcomes.
A caricature is a weirdly effective way to pressure test that pattern.
Your challenge: make ChatGPT draw “you”
Use one of the prompts below or both. Upload a clear headshot first, then paste the prompt.
Prompt 1, simple mode
Create a bold, high quality caricature style illustration of me based on my photo. The caricature should exaggerate features in a flattering way and capture the essence of who I am professionally and personally. Use everything you know about me from our conversation to choose the props, setting, and vibe. No text in the image.
Prompt 2, precision mode
Create one bold, high quality caricature style illustration of me based on my photo. Exaggerate features in a flattering way while keeping my face clearly recognizable.
Goal: capture the essence of who I am professionally and personally, not just my appearance.
Include 4 to 6 visual elements that represent:
- What I do professionally and who I serve: [fill in]
- The outcomes I create: [fill in]
- My distinctive edge or style: [fill in]
- My serious hobby or obsession: [fill in]
- A signature tool or symbol: [fill in]
- My typical environment: [fill in]
Art direction:
Style: modern, vibrant, clean lines, professional but playful.
Composition: I am central, background supports the story without clutter.
No text anywhere in the image.
Keep the face consistent with the reference photo.
After generating the image, list 5 fast refinement options I can choose from, such as face shape, expression, props, background, colors, or style.
Note: In place of any “[fill in]” section, enter [use the information you already have about me, including my Custom instructions, Occupation, and the More about you personalization details].
The point
This is not about getting a cute cartoon for your profile photo, although you will probably end up using it somewhere. It’s about testing whether your identity is clear enough that an AI can reflect it back in a way that feels specific and true.
If you try it, send me the result, plus one sentence: “What the caricature got right, and what it got wrong.” That answer is basically a free mini brand audit, delivered by a machine that never sleeps and rarely understands humans.
Behind the images: The cover image was created using Prompt 1, followed by deliberate refinement to sharpen the concept and visual alignment. The second image was generated using Prompt 2, again refined to elevate clarity and impact.
