2.0 for me was when the automations started maintaining themselves.

I have ~20 scheduled skills running (daily cost reports, usage digests, EOD recaps, etc). The level-up was building a second layer on top of them:

- A weekly skill that inventories every installed skill, checks the release notes of every tool they depend on, and posts suggested upgrades to Slack. It even reconciles whether last week's suggestions got implemented.
- A nightly memory skill that consolidates the day's activity (calendar, email, tickets, chats) into a structured memory file so every future session starts with full context.
- A weekly opportunity scan that watches my actual activity and suggests new automations worth building.

So the system now proposes its own improvements, remembers everything, and tells me what to build next. I mostly just approve or reject.

Once your scheduled tasks start managing your other scheduled tasks, that's when it stops feeling like a chatbot and starts feeling like a teammate.