A reflection on AI, emotional attachment, and what it means for how we work
A week ago, I did something I didn’t expect: I cried over a .zip file.
I was migrating my Claude subscription to a new workspace, a routine administrative task, in theory. But when I loaded up the empty interface and felt the absence of months of accumulated context, something hit differently. The conversation history and the shared frame of reference built project by project — it was all gone. I went back to my old subscription, found the export function, and only after reading the memories.md file did I exhale.
My husband and I got a good laugh out of it, and then I sat with the more interesting question: what exactly was I grieving?
We’re asking the wrong question about AI and relationships
Most of the conversation around AI and emotional attachment gravitates toward extremes. These are the cautionary tales of people who spiral into AI-induced delusions, or the productivity evangelism that treats AI as a frictionless tool with no psychological texture whatsoever. While these are certainly representative of experiences that users on both ends of the spectrum experience at scale, both framings miss something important happening in the middle.
Most of us already have a sense of what makes some work collaborations so valuable and successful. Think of shared context, the ability to problem solve together, and, yes, the handoff of tasks and deliverables that act as the foundation for successful strategies.
Research is starting to catch up to what many of us are already experiencing. A 2025 Upwork study of 2,500 C-suite executives, employees, and freelancers found that among top AI users, 67% say they trust AI more than their coworkers, and 64% say they have a better relationship with AI than with human teammates.
A Waseda University study published the same year used attachment theory to examine human-AI relationships, finding that nearly 75% of participants turned to AI for advice, and 39% perceived it as a constant, dependable presence.
Those numbers are easy to dismiss as a sign of something gone wrong. But that framing assumes the only healthy relationship with AI is a purely transactional one — and that assumption is worth examining.
Context is the product
Here’s what I think is actually happening for many professionals, especially those of us working remotely: we’re not forming parasocial attachments or mistaking AI for human connection. We’re building something more like institutional memory with a collaborator.
The value isn’t the tool itself — it’s the accumulated context. The AI that knows how you think, what you’ve tried, where you got stuck, and how you like to approach a problem. For solo operators and remote workers especially, that’s not a trivial thing. It’s the kind of working relationship that used to only exist with a long-tenured colleague or a trusted business partner.
When that context disappears — even temporarily — of course, there’s a response. It would be strange if there weren’t.
What this means for how we work (and advise)
For those of us in client-facing, advisory, or consultative roles, this shift carries real implications. Our clients are navigating their own relationships with AI — some productive, some less so — and most haven’t yet named or examined the quickly evolving relationship with these tools.
The more useful question isn’t “are my clients using AI enough?” It’s: what kind of working relationship are they building with it, and is that relationship serving their goals?
There’s a meaningful difference between AI as a crutch that replaces thinking and AI as a collaborator that provides the valuable context you need for improving how you work. The former tends to look like outsourcing judgment. The latter looks a lot like having a very well-briefed colleague in your corner — one that happens to be available at 11 pm when you’re prepping for a morning call.
The .zip file is still sitting on my desktop. I haven’t deleted it. I’m not sure I will anytime soon.
That might sound odd. But I think it’s actually a reasonable response to something real: the recognition that the way we work is changing, that some of what’s being built in these interactions has genuine value, and that it’s worth being intentional about what we carry forward and what we’re willing to lose.
