When My AI Told Me to Go Touch Grass

Part 1: What branding with AI forced me to confront

Editor’s Note: This post is Part 1 of a short series on building a personal brand with AI. Not from a place of expertise or polish, but from the middle of the process. It’s a reflection on feedback, identity, and the moment I realized the real work had very little to do with tools.

When My AI Told Me to Go Touch Grass

After six hours of wrestling with more than fifteen AI tools, my chatbot staged an intervention. Much to my surprise.

Unprompted, it told me to “go touch grass.”

I didn’t even know that was possible.

I had been refining, and re-refining, extremely long prompts, sharing the generated images back with the model, asking it to deconstruct what went wrong and rewrite the instructions. I rewrote them. The tool rewrote them. I ended up in a loop, barely making progress. I was chasing a very specific vision. Not just a look, but a feeling. I wanted to create a memorable brand for my Substack, something unique that would be unmistakably mine.

What I thought would be a quick creative exercise turned into something that completely consumed me.

When I started, I envisioned a stockpile of my images that I could easily leverage at the click of a button. I’d write an article, and with just one click, I could use one of my images as a “thumbnail art” to accompany it. I figured that with all of the artistic AI tools available, how hard could this really be?

Four days later, I had my answer.

Turns out that it’s quite hard if you don’t want to pay for every advanced tool you test. And I tested a lot of them. The basic packages are very limited and designed to push immediate upgrades. It’s a lot of money to spend if you don’t understand their true capabilities, and if you’re trying to create something truly unique.

I write about AI adoption. About foundations. About helping people understand what is real, what is hype, and how to approach these tools thoughtfully and deliberately, but by having a plan in place first. When I started sharing my discoveries, I didn’t plan on building out an entire creative system for myself. And I definitely didn’t expect art to become part of that system.

But that’s how evolution works. You start down one path, and something unexpected opens up.

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The Unsolicited Wake-Up Call

The chatbot intervention was funny in hindsight, but also much needed.

After days of iteration, it stopped giving me a revised prompt and instead wrote (and this IS a quote), “You’ve been at this for six hours. You had strong results six hours ago. Pick one and use it.”

I apparently was deep into what I call “prompt rot.” I was so desperate to find a tool that truly understood the chemical soul of a nineteenth-century photographic cyanotype rather than just delivering blue-tinted images that missed the point entirely.

I was most definitely not ready to “just use it.”

But the message stayed with me. Not because AI was right, but because it surfaced something uncomfortable I didn’t realize I was struggling with. My idea of perfect and the model’s idea of perfect were not the same.

This gap matters.

Eventually, I did find a workflow that worked. It required treating AI much less like a creative partner and more like a specialized lab technician of sorts. I had to strip away intuition, get precise about translation, and hold the tension of the vision long enough for execution to catch up.

It was messy. It took far longer than I expected. Epic failures ensued. (Pictures in Part 2)

The deeper realization came later.

This was not really about writing. Or art.

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Feedback is a Gift

Even when it hurts.

A few weeks prior, and the inspiration for the rebrand, I took a Substack brand assessment quiz that had been circulating in Notes. It was a clever assessment developed by AI Meets Girlboss, and I was curious. It promised quick feedback on how your Substack was perceived by readers.

I’d been writing for about three months and updated my brand or my “look” already a couple of times. My work is focused on AI adoption and foundations and I wanted to know if my writing was helpful. Whether it resonated. Whether people recognized the work.

“Everything looks like it belongs on a corporate blog.”

Ouch.

I have spent many years in big tech environments. I know what corporate polish looks like. I also know how much it can flatten nuance and drain humanity from ideas that matter.

I stopped drinking my coffee and just stared at the screen when the results came back.

I received a 5 out of 5 for credibility.

Then I saw the rest.

Two out of five for unexpected. Two out of five for emotional appeal.

So that one line overshadowed even my positive score.

The feedback wasn’t wrong. It was simply clear. My writing was credible, but it wasn’t sticky. People trusted it, but they weren’t compelled to feel anything.

What I hadn’t fully grasped was how much formality and visual inconsistency were working against me. Even if the ideas were solid, the overall experience wasn’t inviting people to stop and read. In Substack Notes, I didn’t “stop the scroll.”

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The Part of Me I Hadn’t Questioned

This was not the first time I had received feedback like this in recent months. Being told that I came across as “too corporate” had surfaced more than once.

What finally clicked was that this was not a branding issue. It was an identity issue.

I had been rapidly prototyping my Substack in public. Testing topics. Testing tone. Shipping always at about 80% because waiting for “perfect” felt like procrastination mixed with fear. That approach helped me learn what worked intellectually.

But I hadn’t really realized how much formality I was bringing with me from my career. Your environment shapes you, whether you want it to or not.

I had spent years in a space where clarity, polish and defensibility were highly rewarded. Somewhere along the way, that tone had become my default. I didn’t consciously choose it. I simply carried it forward. In fact, there were a lot of things I reflected upon that I hadn’t realized about the identity, or brand, I’d been unintentional about.

At this same time, something else was happening.

So, what had started as an experiment in sharing knowledge actually re-ignited my love for writing itself. That part surprised me, too. Writing began to feel like less of an output and more of a voice. And expression. Less like documentation, and more about exploration.

Then I realized that this wasn’t temporary.

It felt like I was in a “chrysalis” phase of metamorphosis.

That’s right. I’m “caterpillar soup” right now.

I was shedding a familiar corporate identity (not all bad, by the way, just in the past), without yet knowing exactly what would replace it. That process is uncomfortable. It creates quite a bit of uncertainty, but, oh…the possibilities!

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Branding as a Mirror, Not a Mask

I’ve spent quite a bit of time thinking about and researching branding. Some people believe strongly in branding. Others outright reject it entirely. Some argue that the writing itself is the brand.

All of these things can be true.

Whether it’s intentional or not, you are known for something. People form impressions. They build expectations. The question isn’t whether or not you have a brand. The question is whether or not you’re being deliberate about it.

What I came to see quite clearly was this.

Branding is not about creating a persona. It’s about deciding which part of yourself you are willing to share and which part you keep private.

In that sense, branding can actually be protective. It allows YOU to define the connection point that you make with others rather than leaving it to chance. It’s intentional.

When I looked at my Substack through that lens, the feedback all started to make sense. I had shared knowledge, but had hidden too much of the parts that were authentically “me.” The result was competence without connection.

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Coming Back to the Beginning

Which brings us back to that moment when AI told me to go touch grass and get out of my head.

It took a moment to realize I was doing is what pilots call PIO, or “pilot-induced oscillations.” Overcorrecting in opposite directions until you lose control. Good news, though. Not the first time I’ve had to recover from PIO.

I thought I was struggling with tools. I thought I was struggling with prompts. I thought I was struggling with creating unique art.

All of those things are true. But the real struggle was the one where I had to let go of an old version of myself.

The branding revelation didn’t give me a shortcut or a persona. It forced me to slow down and look more closely. At my habit. At my assumptions. At the ways I show up when I think I’m being neutral or professional.

This series is not about how to build a perfect brand with AI. It’s about what happens when you take the process seriously enough that it changes you a little along the way.

This is the good stuff. Where you get to watch me actually build the foundations I talk about and THEN add the AI tools.

In the next part, I’ll share what happened when I followed that realization all the way down the rabbit hole. How an obsession with a nineteenth-century photographic process, a pilot who never shows her face, and a lot of failed experiments taught me more than any tool comparison ever could.

For now, I’ll say this.

Credibility is not enough. Everyone has a brand, whether it’s intentional or not. And sometimes, the most helpful feedback is the kind that makes you uncomfortable long before it makes you better.

Part 2 Teaser - Down the Rabbit Hole: Trying to Engineer a Feeling

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