Bucketlist
Turning group-chat ideas into plans that actually happen
Friends float plans in group chats constantly — a trip, a concert, a restaurant someone saw on Instagram. Almost none of them happen. We designed an iMessage plug-in that catches those ideas where they’re born, without anyone having to become the planner.
Role
Product Designer
Team
5 Product Designers
Timeline
6 weeks, 2025
Scope
Concept → hi-fi prototype
TL;DR
We interviewed 10 young adults and found out why group-chat plans fall through: ideas get buried, dates stay vague, and one person ends up doing all the planning.
We designed an iMessage plug-in that catches plans as they come up, finds when everyone’s free, and uses a planning bot to split roles across the group.
Early usability testing with 9 users led us to make the entry point obvious and interface elements easier to recognize.
↑ 58%*
Navigation success
↑ 44%*
Progress clarity
7 / 9 users
Found this helpful
* Final design compared with the mid-fi prototype in usability testing.
Research
10
Interviews
Ages 22–28 · 3 with ADHD
06
Competitive analysis
Across 8 key features
02
Personas
Planner vs. Follower
Research Artifacts
Affinity map · Empathy map · User journey map
“
Figuring out availability is a nightmare.
I’m okay with planning, but if no one responds it makes me really stressed out.
— busy grad student, 24
“
If I didn’t initiate, things wouldn’t happen.
— overworking Software engineer, 26
Why plans so often fall through
01
Plans disappear when they lose visibility
Without a place to hold ideas, reminders, and updates, plans get buried in the conversation.
02
Friends talk about “sometime,” not exact dates
Demanding exact dates kills the spontaneity in the group chat that made the idea appealing.
03
No one wants to be the planner every time
When one person has to coordinate everything, planning quickly starts to feel like work.
The design question
How might we turn group-chat ideas into plans without relying on one person to coordinate?
DESIGN APPROACH
Each research insight led to a clear design direction
What we learned
What we decided
01
Plans disappear when they lose visibility
→
Capture ideas before they disappear
Make it easy to save spontaneous plans without interrupting the conversation.
02
Friends talk about “sometime,” not exact dates
→
Reduce coordination effort
Minimize the work needed to find a time, organize details, and keep everyone updated.
03
No one wants to be the planner every time
→
Share planning responsibility
Distribute tasks across the group so planning doesn’t fall on one person.
mid-fi prototype + usability testing
We tested the concept before going high-fidelity
We built a mid-fidelity paper prototype and ran live, moderated sessions with 9 participants.
We tested the core planning journey: Capture an idea → Turn it into a plan → Stay on top of it
What we learned
Users liked planning directly in iMessage, seeing shared availability, and having reminders and responsibilities built in.
Users weren’t always sure where Bucketlist lived or how to enter the planning experience.
Users had trouble understanding the banner’s purpose and recognizing the poll interface.
Testing helped us identify areas for improvement and refine the final experience
01
Make the next step obvious
We surfaced suggested actions above the keyboard, giving users a clearer way into the flow.
mid-fi prototype
→
final design
02
Make the experience feel native to iOS
Instead of a new polling interface, we used familiar iOS patterns, so users understood the interaction without learning anything new.
mid-fi prototype
→
final design
Final design
event creation feature
Turning ideas into a plan
Smart Plan Detection
Bucketlist detects planning messages in your group chat and prompts you to create a plan or save the idea for later.
Availability Finder
Bucketlist syncs calendars to show who is free on which days.
Guided Plan Creation
Bucketlist walks you through adding the location, dates, and an AI-generated to-do list.
home page feature
Your beachside homebase
Bucketlist / Plan Cards Tabs
Browse your bucketlist, or switch to plan cards to track upcoming plans and to-dos.
The “Bucket”
Quick access to all saved bucketlist items and an easy starting point for creating new plans.
The “Starfish”
Discover bucketlist items you share with friends and get inspired to create new plans together.
The “Sand Dollars”
Earn rewards for completing tasks and use them to unlock fun avatar customizations.
planning assistant feature
Bucketlist chatbot
Availability Polls
For voting on dates and sharing availability.
Event Reminders
For nudges about upcoming deadlines, actions, chosen dates, or trip milestones.
Event Card Previews
Every event notification comes with a preview card, so users never have to dig through the plug-in to stay updated.
role selection feature
Choose your role
The bot guides the group to pick AI-generated roles, with each person taking charge of one area of the trip and earning sand dollars as they complete their tasks.
event completion feature
Share to complete
After the trip, the bot nudges everyone to add photos to the shared album to complete it and earn sand dollars.
Key Decisions
iMessage over a standalone app
Plans already begin in iMessage. Moving people into a separate app would only add friction to an already fragile process.
- Keeps planning where conversations already happen
- Reduces switching and lowers the barrier for the whole group to participate
- Limited to iOS users
- More flexibility and advanced features
- Adds app-switching, sign-up, and group adoption friction
A dedicated bot over in-chat features
Reminders and tasks needed a home that wouldn’t interrupt everyday conversation.
- Keeps plans, reminders, and tasks organized
- Keeps coordination more private
- Adds another space to check
- Keeps planning and conversation in one place
- Can interrupt the flow and clutter the group chat
Shared roles and rewards over a single planner
We didn’t want to be just another when2meet — we wanted to help people reach their goals.
Roles spread the planning workload across the group, while rewards (and a little peer pressure!) encouraged everyone to follow through.
What I learned
Early testing saves significant effort later
Even with a rough prototype, lightweight testing uncovered fundamental issues before they became costly to fix, a small investment that saved design and engineering effort later.
A native experience is about fitting into the ecosystem, not just matching the UI
Building on familiar iOS patterns lowered the learning curve and made us more thoughtful about when and where planning should appear in a conversation.
UMI CHEN
Product Designer
© 2026 UMI CHEN