Contextual Journaling
Bridging reflection and conversation through AI-driven insights.
2024 | Kin Ai
Time frame: 1 month
My roles: UX, and UI designer
Contextualizing
Kin already offered a conversational experience where users could talk about their day, challenges, and emotions. Over time, users started expressing the need for a dedicated space to journal. A place to write or speak more freely, without the back-and-forth nature of a chat.
While the chat worked well for conversation, it wasn’t ideal for longer reflections or structured journaling moments. This feedback revealed an opportunity to extend the product beyond conversation, without breaking the continuity that users already valued.
Opportunity
Users wanted to journal, but the existing chat experience wasn’t designed for focused reflection. Long entries could feel fragmented, hard to revisit, or lost within the conversation history.
The opportunity was to create a dedicated journaling space that still felt deeply connected to Kin’s conversational experience, allowing users to reflect privately, while keeping the option to continue the conversation afterward.
Design Goal
Design a journaling experience that:
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Feels like a natural extension of the chat, not a separate product
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Supports both written and voice-based reflection
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Uses AI to add structure and meaning without taking control away from the user
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Enables a smooth transition between journaling and conversation
Solution Overview
A new journaling experience was introduced and made accessible directly from Kin’s home, which is centered around the chat.
Within the journaling area, users can:
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View past journal entries
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Start a new entry using text or voice
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Receive contextual prompts based on previous conversations
After completing an entry, AI helps organize the content by generating a title, highlighting related entities, surfacing key points, and preserving the full entry. From there, users can either return to their journal or continue the conversation with Kin, receiving feedback based on what was shared.
Role of AI
AI plays a supporting role throughout the experience:
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Suggesting relevant prompts based on conversational context
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Structuring journal entries through titles, tags, and key points
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Bridging journaling and conversation by enabling meaningful follow-up discussions
The focus was on using AI to enhance clarity and continuity, while preserving user ownership over their thoughts and reflections.
Impact & Metrics
The percentage of users engaging in journaling grew from 6% to 15%, with noticeably higher retention and stickiness among journaling users. This increase in engagement positively impacted overall product health, contributing to improved D1 and D7 retention rates across all users, not just those actively journaling.
Key Considerations
Balancing proactivity and intrusiveness was essential, particularly around timing, frequency, and tone of prompts and AI-generated feedback. Accessibility also played an important role, requiring clear hierarchy and readable components within the journaling and chat experiences.
Clear differentiation between journaling, prompts, and conversational feedback was necessary to avoid confusion. Scalability was another key factor, ensuring the experience could support different journaling formats and future expansion without increasing cognitive load. Finally, alignment with Kin’s Design System and long-term product strategy was critical to ensure consistency and sustainability.
Learnings
Designing contextual journaling highlighted how reflection and conversation serve different user needs, even when closely connected. This project deepened my understanding of how AI can support self-reflection by organizing and contextualizing thoughts, rather than interpreting or judging them.
It also reinforced the importance of restraint when designing AI-powered experiences. The most valuable moments came from subtle support, helping users reflect more clearly while always keeping them in control.