End-to-end product

PlanMap Chicago

Designed, built, and now maintain PlanMap Chicago — a planning platform helping Chicago families find park district programs that fit their real schedules — directing an AI engineering lead end to end, from spec to production.

Role: Founder, Product Designer
Timeline: 2026
Live site: planmapchicago.com ↗

Discover · Research

Microwire: an AI research agent reading years of Chicago parent discussions on Reddit — Collect — an AI research agent reads years of Chicago parent discussions across r/chicago, r/AskChicago, and r/ChicagoParents. Signed out, read-only; threads, not surveys.

Microwire: clustering parent conversations into pain themes — Cluster — conversations group into pain themes: registration-day sellouts, queue friction, opaque waitlists, price shocks.

Microwire: mapping pain themes to roadmap bets — Map — each theme traces to a roadmap bet: registration-day preparation, not another catalog.

Problem validation, AI-assisted: a research agent read four years of Chicago parent discussions across r/chicago, r/AskChicago, and r/ChicagoParents. The verdict — the pain is real and recurring, but it’s registration-day logistics that hurts, not awareness. Popular camps sell out in minutes (“the Hunger Games,” “worse than Lolla tickets”); queues punish; waitlists are opaque.
The nuance shaping the roadmap: parents don’t need another catalog — they need registration-day preparation. Wishlist prep, price and schedule aggregation, reminders: that’s the job PlanMap is built around, and it’s what the work above is aimed at.

Define · Problem

Chicago parents don’t need help discovering that park district programs exist — they need help surviving registration day. Popular camps sell out within minutes of the 9:00 AM opening; the virtual queue punishes a stray click; waitlists are opaque; and before registration, no single place shows which parks offer what, at which price, on which schedule. PlanMap is built for that job: registration-day preparation, not another catalog.

Develop · Design

Four concepts, converged from the research — each one built for the registration-day job, not the catalog.

PlanMap Chicago project thumbnail — PlanMap Chicago — independent planning tools for Chicago Park District camps and activities, built and maintained end to end.

Schedule-first discovery

Parents solve a calendar puzzle, not a catalog search — so every discovery surface leads with when. Filters open on age, free days, and time windows; result cards lead with schedule, price, and age group; and every listing is organized around its recurring schedule, parsed from official Park District data.

ActivityMap Chicago explorer with schedule-first search filters and activity categories — Filters open on the schedule puzzle — keyword, age, free days, time windows, home zip, price — with category cards carrying live program counts.

Activity search results with activity cards and a Chicago-area map — Result cards lead with schedule, price, and age group; the basemap stays light so the data stays primary.

Activity detail page with weekly schedule, season dates, fee, and registration information — Recurring schedules parsed from official data, with season dates, fee, and registration info in one place.

Your week, not the catalog

The product's information model follows the family's week — the same unit parents plan registration day around. Saved activities roll up into a 'My week' view arranged by recurring meeting day.

My week planner showing saved activities arranged by recurring meeting day — Saved activities arranged by the day they actually meet — the week is the interface.

Only promise what the data can show

Trust is the feature. The registration banner's states are gated on actual listing coverage, and 'View programs' deep-links into the filtered registration window — never a dead end. Sign-in is passwordless magic link, optional from the start; browsing works anonymously.

Registration banner announcing the Chicago Park District activity registration window — Banner states switch on real coverage data and deep-link into the exact registration window.

Passwordless magic-link sign-in page — Passwordless sign-in, never forced — and the footer says plainly what the tool is and isn't.

A hub built to grow

Two doors — CampMap and ActivityMap — each showing live listing counts, so future products slot in without restructuring the IA.

PlanMap Chicago hub with CampMap and ActivityMap entry points and live listing counts — Live counts on each door; new products slot in without IA surgery.

Deliver · Next

Park-first browsing: the word “provider” was doing double duty — naming both organizations and physical parks — so parks are becoming first-class pages at /parks, with each park’s camps and activities together in one place and permanent redirects preserving every old URL.
Save = follow: registration day is the real battleground — popular programs sell out in minutes — so saving a program is becoming a single follow gesture that subscribes you to reminders, instead of two separate systems to manage.

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