Meet Chloe, the AI assistant that now lives inside SelfSM.

Meet Chloe, the AI assistant that now lives inside SelfSM.

She exists because I failed at something simpler. I kept trying to make onboarding easy: cut steps, redesigned the flow, moved things around. Every version worked for a while, until the product grew again, the flow gained new screens, and new users were back to guessing where to start.

The fix turned out to be the most trivial idea on the list, which is probably why I tried it last: stop simplifying the map, give people a guide.

Chloe takes you from an empty workspace to a complete brand setup, weekly content plan, and first drafts in one conversation. She asks what you do, sets up the brand, and interviews you for actual experiences and opinions before generating anything. Feed her your past posts and she'll pick up your voice from them.

Two things mattered to me. First, she has access to the whole workflow: voice, strategy, weekly plans, publishing. That's 25 tools connected to the same product actions available through the UI, so most things you can do by clicking, you can now ask for in plain language. Second, when the required material is missing, she says so. I tested this on purpose: asked for a post with nothing behind it, and she refused to write it, flat out, instead of filling the gap with something generic. Publishing still requires an explicit confirmation. Chloe cannot ship anything on her own.

The old onboarding wizard stays as a fallback. I don't know yet whether new users will prefer talking to Chloe or clicking through the screens.