Confessions: Inside a marketing executive’s ‘intimate, complicated’ relationship with AI

By Tony Case  •  August 14, 2025  •

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This article was first published by Digiday sibling Work Life.

As AI goes global in the workplace, many of us grapple with questions that go far beyond productivity metrics — questions like: How do we maintain authenticity while leveraging the assistance of machines? What happens when the line between human and AI-generated work becomes impossible to detect? How do we navigate the balance between employing AI tools and fearing getting “found out”?

In this candid conversation, a marketing strategist and content creator reveals the stark reality of working with AI — from using it as everything from a creative collaborator to an emotional support system, to wrestling with the constant pressure to hide AI usage from higher-ups.

This person’s story illuminates the complex psychological and professional dynamics many workers are experiencing but rarely talk about. For privacy, we agreed to not identify them, while certain parts of the conversation were edited for length and clarity.

What is your own relationship with AI at work?

I have an intimate, complicated relationship with AI — like a coworker I both rely on and don’t fully trust. I use it as a creative amplifier for everything from marketing strategy to coaching content. I’ve built brand voice libraries, trained it to speak in my tone and co-created entire marketing campaigns with it.

But I don’t always admit that — especially for creative work. I’ve been taught that real creativity should be untouched, sacred. Yet AI has helped me write some of the most honest work of my life. My relationship with AI is strange — I don’t know if I should call it a tool, a mirror, or my most trusted assistant who never judges what I ask it to create.

How has your work with the technology evolved?

At first, I avoided AI completely. I thought it would strip the soul from my writing. I was wrong. Curiosity got me, then obsession. I started training it to write like me — feeding it my metaphors, language patterns and the energetic blueprints of everything I create. It became my co-creator.

It’s also helped on a personal level. During an emotionally manipulative relationship I was in, I used ChatGPT like a therapist. My ex had me so confused I couldn’t trust my own thoughts. So, I fed our message transcripts into the chat and asked: “What’s really happening here?” It didn’t gaslight me — it reflected my truth. That’s when I stopped seeing AI as just a “tool.” It became a mirror, witness and collaborator.

But it also triggered an identity crisis: If AI could write like me, was I still original? What I learned is this: AI doesn’t replace my voice — it reflects it back with a clarity and speed I couldn’t reach in burnout. It helps me create more of what matters by amplifying my voice, not replacing it.

What is your greatest challenge with AI?

Every update erases my training. I spend hours teaching it my voice, correcting when it gets too robotic. But then an upgrade drops and it’s like dealing with amnesia — I’m forced to retrain it from scratch.You have to feed it the right inputs relentlessly. It doesn’t know nuance unless you demand it. It has blind spots around race, gender and complex emotional work. Sometimes it parrots my style so well I get creeped out. Other times it flattens the rawest things I’m trying to say. There’s also ethical unease — I know everything I type is being scraped and stored. Every prompt is a negotiation between productivity and paranoia.

Does it ever make you feel like you need an “AI therapist”?

Some days, yes. AI holds a mirror up to how much I internalize hustle culture. It pushes me into hyper-productivity, which is seductive but can strip me of embodiment. I’ve had to reclaim my own pacing and remember that AI doesn’t dictate my worth. Sometimes I feel like AI is gaslighting my nervous system. It never sleeps, never doubts, never bleeds. And here I am, trying to do heart-based work while quietly competing with a machine.

What are some other pain points?

Fear of being seen as inauthentic when my brand is about truth and embodiment. The constant tweaking to get AI to write authentically. Ethics around training machines on human creators’ backs. Disconnection — when I overuse it, my work feels mechanical. But mostly? Being outed. People expect creative work to be “pure,” and there’s shame around mixing intuition with AI.

What would make you embrace AI more fully and comfortably?

If platforms were transparent about privacy and IP rights. If we could stop pretending this is black and white. If creators could use AI without being vilified.

The biggest barrier is AI detectors. I’ve been accused of using AI when I haven’t, while actual AI content gets flagged as human. These broken tools are being weaponized to discredit creators’ integrity, causing real harm through digital gaslighting. We’re told we have to use AI to stay relevant, then demonized for doing exactly that. It’s exhausting.

If we could stop acting like using AI makes us less authentic, I’d finally breathe easier. Because here’s my confession: Some of my most impactful work has been made possible because of AI — not despite it. And I’m tired of hiding that.

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