Planner.ai

Designing and launching an AI coaching system for follow-through

Details

Role:Product design, strategy, and build

Timeline:3 months

Team:Solo 0-to-1 build

Overview

I designed, built, and launched Planner AI, a live web app that turns vague goals into realistic daily action. It gives people a system to create a plan, keep it alive through reminders and calendar sync, and update it through conversation instead of starting over.

Problem

People often had a goal in mind and looked online for advice, but existing tools did not help them stay accountable.

Discord post asking for help deciding what to focus on next. — People asked Reddit or Discord for help with a goal, but many posts received little or no response.

ChatGPT response generating a generic health and fitness action plan. — AI could generate an actionable plan, but it lived as a one-time chat with no accountability.

Challenge 1

Because the first version jumped from one prompt straight to a generated action plan, the action items felt generic. Users often did not want to do them, could not do them, or simply disliked them.

The first version started with a broad goal and very little context.

Solution

Ask a short set of coaching questions about preferences, constraints, and timeline before generating the plan.

Outcome

The output felt more grounded in the user’s real situation instead of sounding like generic advice.

Planner AI coaching conversation asking focused questions before generating a plan.

A few focused coaching questions made the generated plan feel far more grounded.

Challenge 2

The AI generated unnecessary extra planner layers that users did not need, wasting AI tokens.

Early Planner AI interface showing daily habits, weekly goals, and long-term goals as separate layers.

Daily habits, weekly goals, and long-term goals all at once.

Solution

Collapse the output into one weekly plan made of concrete daily action items.

Outcome

Users preferred the simpler plan because the AI only produced the daily actions they cared about.

Refined Planner AI weekly plan focused on concrete daily action items.

A simpler weekly plan focused on concrete daily action.

Challenge 3

It was hard for users to remember to come back to the Planner AI site to see their action plan and actually follow it.

Planner AI empty app state showing the planner site open in a browser.

Email reminders bring the plan back into the user's day.

Solution

Push the plan into email reminders and Google Calendar instead of leaving it inside Planner AI alone.

Outcome

The plan surfaced in tools users already check, making it easier to act on and less likely to be forgotten.

Planner AI tasks synced into Google Calendar.

Planner AI email reminder showing daily habits.

Tasks can move directly into the tools people already check.

Challenge 4

Per-task chats were hard to manage and limited the AI to one action item at a time.

Planner AI interface showing per-task chats attached to individual action items.

One continue conversation button gave users a single place to revisit and update the full plan.

Solution

Move plan editing into one global continue conversation entry point with access to the full action plan.

Outcome

Users had one place to manage changes, and the AI could turn requests into structured proposal cards with full-plan context for review before applying.

Planner AI interface showing one global continue conversation entry point with full-plan context.

The AI could use full-plan context to propose reviewable changes and add tasks globally before anything was applied.

Outcome

I designed and launched an end-to-end AI planning experience that helps users generate structured plans, save them through Google sign-in, and share them with others through public links.

Learnings

After 2,800 iterations in Figma Make, I learned that AI-generated UI is only useful when paired with strong product judgment. Vibe coding helped me turn ideas into interactive experiences quickly, test them with real users, and refine the product around what they actually valued.