Why the last round felt dystopian, the rules that fix it, and five characters built on those rules.
The bubble buddy is the one: a warm orange speech bubble with a happy face, whose little tail is a pen nib. It says "talk to me, I'll write it" without any device in sight, it is instantly friendly to a public audience, and it is simple enough to be the app icon at 16 pixels.
Use 5, the letter face as the quiet version for places that need to look grown-up (invoices, the pitch deck footer), and 2, the notepad pal as the mascot for onboarding and social.