Lee-Way

Overview

Plan like a human.

Most productivity tools are built for ideal conditions — they assume you'll follow the plan, stay on schedule, and feel motivated every day. But real life doesn't work that way. For students managing coursework, jobs, social obligations, and their own mental health, rigid planning systems don't just fail — they actively make things worse.

Lee-Way is a planning and scheduling assistant that expects you to mess up. It uses AI to automatically plan your day, allocate time for tasks, adjust when life happens, remember the little things, and track your goals — so you can spend more time living than planning.

Part 01 — The Problem

Rigid planning tools create shame, not structure.

The problem isn't that students don't want to plan — it's that the tools they use punish them when plans inevitably change. Everyday disruptions turn into shame spirals, and once the spiral starts, basics like hygiene, meals, and sleep get deprioritized entirely.

01

Disconnect between planning and real life. It's impossible to predict what will actually happen. When plans break down, the tool offers no grace — just an overdue list.

02

Basics get deprioritized. As students scramble to catch up on missed work and deadlines, non-academic essentials — eating, sleeping, hygiene — fall off the list entirely.

03

Goal: Replace rigidity with forgiving structure — tools that adapt to real humans, not the other way around.

38%

of college students report positive mental health — meaning 62% do not (Healthy Minds Study 2024–25)

37%

of college students are experiencing some form of depression (PHQ-9)

2–8%

of college students have ADHD; at least 25% of students with disabilities are diagnosed with it

Part 02 — Findings & Analysis

Listening to students who gave up on planning.

The research phase combined qualitative interviews, an empathy video exercise observing students struggling in real time, and an accessibility lens scavenger hunt — a structured observation method to uncover everyday frictions that contribute to the problem.

"I've given up on trying to plan out my days and tasks… I just try to remember deadlines and be productive when possible, but with multiple responsibilities outside of school, it's really stressful."

— Anonymous Tandon Student

The scavenger hunt broadened the lens — observing not just what tools are present, but what they're missing. The key insight: friction compounds. It's harder to start laundry when the machines are faulty or the space is crowded. Environmental and cognitive barriers stack, and planning tools rarely account for that.

However, this phase also revealed a trap: thinking too broadly about every influencing interaction risked straying from the original problem. The lesson — good HCD requires narrowing the lens without losing the human context.

Theoretical Framework

Design is never neutral.

Two theoretical lenses grounded the design direction and helped identify what existing tools were quietly doing to their users.

Paul-Michel Foucault

Power / Knowledge · Non-Neutral Design

Discipline: Streaks, badges, and red flags act as micro-punishments and rewards — training users to feel shame when they "fail" the system.
Surveillance: Activity logs and data tracking can reveal patterns and build self-awareness — or create anxiety about performance.

Jacques Rancière

Distribution of the Sensible · Rethink HCD

Accessibility: Visual-only schedules privilege certain attention styles. Removing difficulty from planning means meeting users where they actually are.
Expand planning: What if a schedule could include energy, mood, and recovery — not just tasks?

Part 03 — Ideation

Affinity mapping: from chaos to clarity.

The ideation phase used affinity mapping to move from broad, messy brainstorming toward a focused design direction. The process ran in three stages.

Stage 1

Divergent Thinking

Dumped every related idea onto sticky notes — guilt around rest, shame spirals, "catch up days" becoming impossible, energy tags for tasks, leeway accessories, automatic chore completors, the "if plan slips whole day is ruined" mentality, and more. No filtering, just generation.

Stage 2

Convergent Thinking

Clustered all ideas into six groups: Executive Function & Planning, Energy/Attention, Emotions & Self Talk, Environment, Ideas/Tools/Opportunities, and Miscellaneous Reaches. Patterns emerged around shame, recovery, and the gap between intention and execution.

Stage 3

Next Steps

The clusters pointed to a single reframed question — and a solution that gave the whole project its name.

How Might We

"How might we design planning tools that adapt flexibly for students who miss tasks, instead of punishing them?"

The name "Lee-Way" is intentional: it's a double meaning — my last name (Lee) combined with the idea of giving users leeway. Not a blank canvas, but a planner and scheduling assistant that expects you to mess up and need help. Part goal tracker, part health helper.

The Solution

Four features that give you leeway, not guilt.

Lee-Way isn't just a smarter calendar — it's a system designed around human imperfection. The core features replace punishment mechanics with permission, recovery, and adaptability.

AI-Powered Day Planning

Automatically allocate time for tasks based on your energy levels, priorities, and history. When life happens, the schedule adjusts — no guilt, no overdue pile.

Voice Input

Add tasks, goals, or feelings by simply talking. Be as specific or vague as you want — the app figures out the rest. Low activation energy is a feature, not a bug.

Buffer Tokens

5 leeway buffers per week — use one when you need to shift a task without guilt. Token Test results showed perceived shame decreased and recovery rates increased with this mechanic.

Nudge Windows & Reset SMS

Tasks show time ranges instead of exact times — stress ratings dropped in testing. Texting "stuck" to the app triggers a 2-minute reset ritual, increasing task restart rates.

Reflection

What this project changed about how I design.

I learned to see the invisible — the frictions, defaults, and assumptions baked into everyday tools and spaces that users have accepted as normal but shouldn't have to.

Design nudges behavior — streaks, red badges, layouts, and wording all change what people do. Recognizing that made me much more intentional about what signals a product sends.

Power lives in design — who gets centered, who has to adapt, and how rules quietly discipline users. Good HCD means designing for dignity as much as efficiency.

Going forward: involve users early, run scrappy pilots, replace punishment cues with permission, and make rest and recovery count as much as productivity.