After months of demanding work and endless context-switching recently, it got me thinking: out of the 1001 personal learning topics, build ideas, and reading lists I’ve been wanting to tackle over the past 7-8 months - what have I actually achieved? How am I progressing? Have I drifted? Are those still the priorities I remember? What even are they anymore?
I realized I’d lost track. And time keeps slipping by.
So I wondered: for someone who’s not the most organized person - someone who tends to be random and follows what they want to do impromptu - how can I have a better, systematic way to handle and track all this? Something that gives me insights when I need them, lets me reflect on where I’m heading, and tells me if I’m still on track. But most importantly, keeps the flexibility a…
After months of demanding work and endless context-switching recently, it got me thinking: out of the 1001 personal learning topics, build ideas, and reading lists I’ve been wanting to tackle over the past 7-8 months - what have I actually achieved? How am I progressing? Have I drifted? Are those still the priorities I remember? What even are they anymore?
I realized I’d lost track. And time keeps slipping by.
So I wondered: for someone who’s not the most organized person - someone who tends to be random and follows what they want to do impromptu - how can I have a better, systematic way to handle and track all this? Something that gives me insights when I need them, lets me reflect on where I’m heading, and tells me if I’m still on track. But most importantly, keeps the flexibility and openness I need to explore new things as they come.
My first thought: not another task tracker. Not the 999th document or note tool or app that I’ve tried and given up on (or forgotten about) within a week. How can I make this more fun? Something that suits my way of thinking - how I actually feel motivated? Challenge. That was my first thought. But how do I build it? I need help. Since I’m a big fan of Claude Code day-to-day, is there something I can do with it differently?
So I decided to give it a try. I had no idea what would work - only time would tell. If this system makes me remember it and stick with it for more than a week, it works. I started brainstorming and designing with Claude. One thing on my long list was exploring how Claude Code skills could be used in different scenarios. No apps. No tools. Just a Claude Code skill - simple enough that I can "inject" it into my beloved Claude Code to help me with this.
After letting the brainstorming juice flow, I ended up with this skill: GitHub
What it does: every day I check in, log progress, track ideas, and try to maintain momentum. But my original workflow was locked into a specific folder structure and only worked for "building" type challenges.
What if someone wanted to track a fitness challenge? A reading goal? A meditation habit?
I decided to build a Claude Code skill that could track any type of challenge. After discussing with friends, there seems to be a working pattern that’s open, flexible, and adaptable enough regardless of challenge type - fitness, learning, habits. We all have some aspect of our life we hope to improve. It seems to fit just right with what Claude Code skills can do.
How It Ended Up
My previous /daily-checkin workflow worked great for my 30-day AI/ML challenge. It had:
challenge-log.mdfor tracking progressdaily-context.mdfor setting up each sessionideas-backlog.mdfor things to try - whenever my random brain pops up with an idea, I just throw it in the backlog. Or if I’m lazy, I tell Claude in scattered-brain chatting style and it logs it in a structured way for me.preferences.mdfor my stack and tools
But it was hardcoded for tech challenges. Questions like "what did you ship?" and "tech stack used?" are useless if you’re tracking a workout routine or trying to read 12 books this year.
I wanted something that:
- Works for any challenge type (learning, building, fitness, creative, habits)
- Asks the right questions based on what you’re tracking
- Keeps the same useful file structure but adapts the content
- Detects connections across different challenges (compound learning)
The Approach
Instead of building separate trackers for each domain, I realized the file structure could stay universal - only the content needs to adapt.
Think of it like this: A preferences file is useful whether you’re tracking code or workouts. For code, it stores your stack and tools. For fitness, it stores your equipment and workout types. For food, maybe cuisine and diet type. Same purpose, different content.
This led to the "type-adaptive" design:
- Same files for everyone (
preferences.md,backlog.md,today.md, etc.) - Different sections filled in based on challenge type
- Guided creation flow that asks type-specific questions
How It Works
Challenge Types
The skill supports 6 types:
| Type | Best For | Check-in Questions |
|---|---|---|
| Learning | Courses, books, skills | "Any aha moments?", "Progress on milestones?" |
| Building | Projects, shipping | "What did you ship?", "Any blockers?" |
| Fitness | Workouts, health | "What exercises?", "How did your body feel?" |
| Creative | Art, writing, music | "What did you create?", "Any inspiration?" |
| Habit | Routines, consistency | "Did you complete it?", "How did it feel?" |
| Custom | Anything else | You define the questions |
Type-Adaptive Preferences
When you run /streak new, it asks type-specific questions and pre-fills your preferences.md. For example:
For a Learning challenge:
## Topics & Resources
- **Learning:** Rust programming
- **Resources:** Rustlings, The Rust Book
- **Tools:** VS Code, cargo
## Learning Style
- **Approach:** hands-on with reading
- **Practice:** exercises after each chapter
For a Fitness challenge:
## Workout Style & Equipment
- **Focus:** strength training
- **Equipment:** home gym - dumbbells, pull-up bar
- **Workout types:** push/pull/legs split
## Location & Schedule
- **Where:** home gym
- **Best days:** weekdays morning
- **Rest days:** Wednesday, Sunday
Same file structure. Different content. Works for any domain.
Cross-Challenge Insights
This is where it gets interesting. If you’re running multiple challenges, the skill detects connections - Claude handles the semantic relationship:
Compound Learning Detected
Your "Learn Rust" challenge (Session 12) where you learned async/await
directly enabled your "Build CLI Tools" challenge (Session 3) where
you built a concurrent file processor.
Or even cross-domain (this is experimental - don’t take my word for it happening 100% as expected):
Your morning workout (Fitness) correlates with higher productivity
in your coding sessions (Building). Sessions after workouts show
30% more completed items.
I don’t know if this insight detection will be accurate enough in practice, but the structure is there to try it. This skill itself is meant for experiment and learning for all of us, right? :D
Installation (2 Easy Steps)
Prerequisite: Claude Code installed.
Get from: GitHub
# Add the marketplace
/plugin marketplace add ooiyeefei/ccc
# Install the skills collection
/plugin install ccc-skills@ccc
How to Use
Create Your First Challenge
/streak new
The skill walks you through:
- Pick a type (Learning, Building, Fitness, Creative, Habit, Custom)
- Set your goal and cadence (daily, every 2 days, weekly)
- Answer type-specific questions
- Files are auto-generated with your answers pre-filled
Daily Check-in
/streak
You get:
- Status (on track, due, overdue)
- Type-specific questions
- Auto-logged to your progress file
- Insights generated after each check-in
Other Commands
/streak list # See all challenges
/streak switch [name] # Switch active challenge
/streak stats # Progress and achievements
/streak insights # Cross-challenge analysis
/streak export-calendar # .ics file for reminders
Example 1: Learning Challenge - "Read 12 Books This Year"
Goal: Finish one book per month, track key takeaways.
Setup:
/streak new
→ Type: Learning
→ Name: read-12-books
→ Goal: Finish 12 books this year
→ Cadence: Weekly
→ Resources: Kindle, local library
→ Milestones: 3 books, 6 books, 9 books, 12 books
Weekly check-in asks:
- What did you read this week?
- Any aha moments or key learnings?
- Progress on milestones?
Your preferences.md includes:
- Reading preferences (physical vs kindle vs audiobook)
- Typical reading time
- Genres you’re focusing on
Example 2: Fitness Challenge - "Morning Workout Habit"
Goal: Build consistent strength training habit, 5 days a week.
Setup:
/streak new
→ Type: Fitness
→ Name: morning-workout
→ Goal: Build consistent strength training habit
→ Cadence: Daily (rest days built into routine)
→ Equipment: Home gym - dumbbells, pull-up bar, resistance bands
→ Workout types: Push/pull/legs split
→ Constraints: Recovering from knee injury - avoid heavy squats
Daily check-in asks:
- What workout/exercises did you do?
- How did your body feel?
- Any PRs or progress?
Your preferences.md includes:
- Equipment available
- Workout split
- Rest days
- Constraints/injuries to track
What I Learned After Using It for 2 Weeks
Follow your mood sometimes. Yes, we all want control, focus, and "productivity" as much as possible. But sometimes, listening to your body and subconscious mind helps. If I don’t feel like doing the top priority that day, I just explore whatever else I’m in the mood for. The effectiveness and experience are so much better when you’re in the mood and get into "flow."
It doesn’t have to be perfect all the time. The idea is bite-sized. Even a small baby step helps - we can always continue from there. Logging helps because it brings back context and recaps what’s been done previously, very quickly. Claude even surprises me with suggestions sometimes. It detects progress on certain topics and suggests next steps I’d logged before, after asking how much time I have that day.
Type-specific questions matter. Asking "what did you ship?" to someone tracking meditation is useless. Asking "how did it feel?" makes sense. The guided creation flow captures domain context upfront.
The results so far? Two weeks in: 10+ micro-apps and builds shipped, 5+ new technical concepts outside my comfort zone. Topics that had been sitting on my "someday" list for months. Bite-sized daily progress adds up fast.
Try It Out
Got something you’ve been meaning to improve on and track? Give it a shot:
/plugin marketplace add ooiyeefei/ccc
/plugin install ccc-skills@ccc
/streak new
Let me know what works and what breaks. I’m particularly curious if the type-adaptive preferences make sense for domains I haven’t tested (fitness, creative, habit).
Links: