Overview

Stay Reflective is a reflection and journaling app for iOS, Mac, and the web. You start with a guided reflection or a blank page, and the app asks thoughtful follow-up questions based on what you wrote. It’s built to help you think, not to hand you answers.

The Problem

When tools like ChatGPT arrived, I was excited by what they could do for reflection and disappointed by their habit of jumping straight to advice. I wanted an AI journaling tool that would meet people where they were and help them explore and reframe their own thoughts.

What Happened

• First pilot in January 2024 with Foothill College’s Music Technology program.
• 3,000-4,000 people have taken a reflection on it since.
• The key finding: facilitated reflection works. On their own, few people built a daily habit. But when a coach, teacher, or workshop leader invited their group into a short multi-question reflection, first-time users regularly spent 20-40 minutes and wrote 300-1,000 words in their first session.

The value showed up inside a relationship, not alone. That lesson has shaped how I think about health and behavior change products since.

My Role

I designed and built it end to end (Flutter, Firebase, LLM integration), wrote the reflection journeys, and ran the pilots with partners.

Status

Live and maintained, with a few dozen people reflecting each month. Stay Reflective Company is also the home for my other products, including Playback Pilot and Yesteryard.