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End-of-year reflection: I’ve let messages pile up, and I want a sustainable way to maintain the relationships I care about. Most of my personal backlog is on iPhone/iMessage, and I’m looking for a mobile-first system. I’m also juggling work + personal logistics, so I need something that works in short batches vs. being “always on”. I’m looking for success/failure stories and practical setups using AI for triage + drafting across texts/email/voicemail. I’m not looking to auto-send replies—just help deciding what to reply to and drafting something I’ll send myself. Questions I’d love input on: - What workflow finally stuck (batching, queues, reminders, templates, “SLA” rules)?
- What failed (tone mismatch, hallucinations, too much friction, privacy concerns, social blowback)?
- Which tools were worth it (clients, plugins, Shortcuts, local vs cloud), and why?
- Any prompt patterns that reliably produce short, warm, context-aware replies? If you built something custom (scripts/Shortcuts/agents), I’d love the rough architecture. |