#29 I think I'm going through the five stages of grief with AI

How I moved my operations workflows through Claude Cowork — and why it's better than me at most of what I do

👋 Hi Optimists,

Telling my operations friends about how I work now feels like time traveling. I describe my week and they look at me like in disbelief.

Over the past few weeks, I’ve moved my entire workflow through AI, specifically Claude’s Cowork, and I need to be honest with you: it’s better than me at most of what I do. Work I’ve spent years learning, refining, getting good at. The document prep. The research. Financial modeling. Things I considered my craft. The AI does them faster, often more thoroughly, and doesn’t need a coffee break.

Ironically, I think I've been going through the five stages of grief — denial, anger, bargaining, depression, acceptance — the classic framework for processing loss, except in this case what I'm losing is the illusion that my years of operational expertise made me irreplaceable. I've landed somewhere between bargaining and acceptance.

Here’s what actually changed

This isn’t abstract “AI will transform everything” talk. Let me tell you what my actual week looks like now.

Legal and tax. I have a project where Cowork’s legal plugin opines on tax structuring questions and regulatory compliance. It doesn’t replace counsel — but it gets me 80% of the way to a first draft that used to take a full day of research. I bring sharper questions to our lawyers now instead of starting from zero.

Board prep and finance. Preparing for our last board meeting felt like a completely different exercise. I had a finance sidekick cleaning up messy data, summarizing P&L by quarter, and flagging the variances worth talking about. What used to be a week of spreadsheet wrestling became an afternoon of strategic thinking.

Email and calendar. The Chrome extension handles inbox triage and structures my calendar. Small thing? Maybe. But reclaiming 45 minutes a day from email compounds fast.

Hiring and recruiting. Someone reached out last week with a cold email offering recruitment services. My honest first thought was: why would we add headcount right now? AI has raised our per-person output so dramatically that the math on new hires looks completely different than it did six months ago. We’re not alone in feeling this — Spotify recently said some of its best engineers haven’t written a line of code since December. They’re directing AI instead.

The shift most operators are missing

Engineering is seeing this first because their tools got there first. But here’s what I want the Operations community to hear: legal, finance, and operations are next. Not in some vague future. This year.

The models that dropped in early 2026 weren’t just faster or cheaper. They crossed a threshold. They started making decisions that felt like they had something resembling judgment — not just following instructions, but understanding context, weighing tradeoffs, and producing work that didn’t need to be rebuilt from scratch. That’s a fundamentally different tool than what we had even six months ago.

The uncomfortable truth

I’m going to say the thing I think some of you don’t want to hear.

If you are still on the free tier of any AI tool and your verdict is “it’s not that useful” — you haven’t actually tried it. The free versions are a demos of the past. The paid tiers with real agent capabilities are a completely different product.

And if you’re an operator who hasn’t meaningfully integrated AI into your daily work yet — I say this with love — you are working with stone tools in a steel age. Not because you’re bad at your job. But because the floor of what “good” looks like just got raised, and it’s rising every week.

This isn’t a trend. It’s not a fad. It’s the biggest shift in how knowledge work gets done, possibly ever. And the good thing is, we are all in the same boat of figuring out how to use it best.

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I’d love to hear: have you started using AI meaningfully in your ops work? Do share your use cases and let’s learn together!

Until next time,

Diana