What ChatGPT Taught Me About Myself (and My Work)

I asked ChatGPT a strange question recently:

“Tell me something about myself I probably don’t know.”

I didn’t expect a real answer. But it surprised me. It told me I think like a systems architect. That I don't just advise clients—I design invisible infrastructure across the HR and benefits tech ecosystem.

And you know what? It was right.

When I first started using AI, I assumed it would help with the basics: writing faster emails, clarifying messy notes, running quick estimates.

But it’s evolved into something more essential:
A collaborator in how I think through complexity.

I work across benefits admin, HR tech, insurtech, and increasingly with platforms and investors trying to stitch it all together. Middleware layers, decision support tools, public-sector market dynamics—every partnership, model, or integration path I build needs a clear mental blueprint.

ChatGPT has become part of how I sketch that out.

I use it to:

• Pressure-test integration strategies (e.g., can X plug into Y via middleware like Ideon or Finch?)

• Explore TAM for new offerings in niche verticals

• Enrich provider data with real-world context (not just what's on the website)

• Refine the story behind a pitch or partnership, depending on who’s in the room

But more than anything, I use it to interrogate my assumptions.
To stop and ask: “Am I actually seeing the full picture?”

It doesn’t make me work faster. It makes me work clearer.

It doesn’t do my thinking. It sharpens it.

It’s not a shortcut. It’s a mirror.

And sometimes, it reflects something back that reshapes how I view my own value.

If you're building or navigating the HR/benefits/insurtech ecosystem—and thinking about partnerships, integration strategy, or go-to-market alignment—I'd love to connect.

Yes, ChatGPT will probably be in the room with us. Yes, ChatGPT helped me write this Blog.
No, it won't replace the hard work. But it will help us see it more clearly.