MilestoneMap

MilestoneMap is a mobile + web app for people who set long-term goals but rarely translate them into concrete, time-bound steps. Instead of another to-do list, it forces a “goal math” workflow: define a 1–10 year outcome, break it into measurable milestones, then assign realistic quarterly and weekly commitments. It includes a friction-heavy reality check: time budget, money budget, and trade-off prompts (what you will stop doing). A lightweight AI assistant can suggest milestone structures and identify missing dependencies, but the user must approve every step. Progress is tracked via evidence uploads (screenshots, receipts, certificates) and periodic reviews. The app also supports accountability contracts: share a read-only roadmap with a friend/mentor and schedule recurring check-ins. It’s not motivational fluff; it’s a planning and follow-through system designed to expose wishful thinking early.