Overview
This article is the result of several years of reading, experimenting, and trying to build a system that helps me stay on track with my goals, habits, and long-term roadmap.
I’ll share my mindset, the tools I use, and how I put everything together into a system that actually works for me.
Before we start, it’s important to say — there’s no one-size-fits-all system. Everyone’s personality, lifestyle, and situation are different. What works for me might not work for you exactly, but maybe it’ll give you a few ideas to use for your own system.
At the end of the day, our life is like a system. If we don’t design it intentionally — for our habits, goals, and progress — things get messy fast. Building a system increases your chances of success in literally anything you aim for.
The Chain of Efforts Rule
For me, one of the biggest keys to success is what I call the Chain of Efforts rule.
It basically means:
Success isn’t one big event — it’s the result of small, boring daily efforts that you keep doing for a long time without breaking the chain.
This idea is talked about beautifully in The Slight Edge book, which I totally recommend.
That’s why I’ve built my personal system around this concept — creating and monitoring a structure that helps me keep my daily chain of efforts strong.
Why Monitoring Matters
Think about it — any system, whether it’s a software, rocket, or business, needs constant monitoring.
A rocket that’s off by just one degree can end up kilometers away from its target.
It’s the same with our goals and habits — even small misalignments can take us in the wrong direction over time.
So if we don’t monitor our roadmap and daily actions, we might be working hard... but toward the wrong target.
How I Build My Roadmap and Habits
Once I choose a specific goal, I break it down into smaller, clearer timeframes:
- 5-year vision
- 3-year milestone
- 1-year goal
- This season
- This month
- This week
At each level, I describe the goal as if it’s already achieved. This helps me visualize success and build the steps backward.
Once the roadmap is clear, I figure out which daily habits will help me move forward toward those goals.
Creating the Right Habits
If you’re new to this, I really recommend starting with Atomic Habits — it’s a classic for a reason.
But the key thing is this:
Your habits should be realistic enough to stick with daily, but meaningful enough to push you toward your next goal.
Don't forget that we need to do our habits for a long run and our brain hates sudden, hard activities, so start small, make it consistent, and let it grow naturally over time to shape the habit.
That’s how I build the “chain of efforts” we talked about earlier.
Monitoring the Roadmap and Goals
After breaking down your goals and setting your habits, it’s time to track your progress.
At every checkpoint (monthly, seasonal, yearly), I review:
- What percentage of goals I’ve achieved
- What worked well
- Where I struggled
- What I can improve next time
This reflection part is critical — it’s where you actually learn and adjust your system. Because we always need to update our system and habits through the time based on our new visions, ideas and philosophy of living.
My Favorite Tool for Goal Monitoring: Obsidian
There are a lot of goal-tracking tools out there, but if you’re a bit techy and like flexibility, Obsidian is amazing.
You can download it here.
At first glance, it’s just a note-taking app for Markdown files.
But what makes it powerful is its plugin ecosystem — you can turn it into almost anything you want.
My Key Plugins
- Dataview – to pull data and stats from notes
- Charts – to visualize progress using the data
- Kanban – to organize tasks visually in boards
My Folder Structure
Here’s how I’ve structured folder and files inside of Obsidian:
.
└── Goals/
├── Week Goals/
│ ├── 2025-06-01 (FIN).md
│ ├── 2025-06-08 (FIN).md
│ └── 2025-06-16.md
├── What to be/
│ ├── 2030-01-01 (5 years).md
│ └── 2035-01-10 (10 years).md
├── 2025-03-31 End of March.md
├── 2025-04-30 End of April.md
├── 2025-05-29 End of Spring.md
├── 2025-08-29 End of Summer.md
├── 2025-11-28 End of Fall.md
└── 2025-02-27 End of Winter.md
Each goal file includes goals for one aspect of my life (career, health, learning, etc.), plus a dynamic progress percentage that updates automatically with Dataview and a small JavaScript snippet.
In my “Statistics” file, I gather the results from all the smaller goals and visualize them using the Charts plugin — it’s super motivating to see progress in one place.
For weekly goals, I use the same structure — and mark completed weeks as (FIN). Those get picked up by the weekly statistics automatically.
You can find my example scripts in this gist link
You can freely use and modify my code to fit your own workflow.
Just copy each code and put in related file like this:
Bonus tip: I also use the Kanban plugin to connect roadmap items with related goals and tasks. It helps me see everything more clearly without extra tools.
Also for syncing obsidian data I use synthing and I'm share the folders between pc and mobile. But you can use many other ways or apps like this to share obsidian and document folder between your pc and other platforms or use other community plugins.
Tracking Habits
You can use Obsidian for habits too, but personally, I prefer a dedicated app for simplicity.
My favorite is Habit Tracker on Android (you can find it here).
It gives you clean weekly and daily statistics — perfect for seeing your “chain of efforts” visually.
And for doing habits or focused work sessions, I use the Pomodoro technique.
My go-to app is Focus To-Do — simple, synced, and effective.
Conclusion
A lot of people focus on making effort, but I’ve learned that the real power comes from building a system that helps you make those efforts wisely and consistently.
Your system doesn’t have to be perfect — it just has to be yours.
I hope sharing mine gives you some new ideas to experiment with and build your own version.
I’d love to hear from you:
👉 What kind of systems do you use to monitor your goals or career progress?
👉 How could I improve mine?
If this article helped you or gave you new ideas, I’d really appreciate your interaction — it helps me share this with more people.
Thanks for reading — and don’t break the chain 💪
Top comments (2)
Hey, thanks for sharing! I think there is a thing or two here I may adopt, especially the Obsidian/Dataview setup.
What I found your system a bit lacks, though, is managing uncertainty and risk. That's where my method shines, so I'll share it for contrast:
My tracking is less about daily habits and more about course tracking and correction. I mentally map out four potential outcomes for my career path: the optimal, the balanced, the sub-optimal, and the catastrophic.
I then track which path I'm moving down in a career journal and plan decisions specifically to push toward the optimal.
I've also found it really helps to pursue goals that you currently think are unreachable within a reasonable time-frame.
It was really insightful, It helped me to get new idea.