Building a Daily Reflection System That Actually Works
Six questions I answer every day to capture learning moments and friction points before they're forgotten
It’s the end of the first week of January. Some of us are settling back from travels, others are finding rhythm after the holiday lull. Depending on how you respond to the Fresh Start effect, you’re either energized and ready to tackle goals or slowly easing back into routines.
When days blur with back-to-back meetings and constant inputs, insights slip away before you can capture them. Without written data, there are no patterns to identify.
Why Reflection Matters
Daily reflection isn’t just about capturing thoughts. It’s about creating a feedback loop for your own growth. When you consistently document what you’re learning, struggling with, and noticing, you create a dataset about yourself. That dataset can reveal patterns: recurring friction points that need addressing, emerging interests worth pursuing, gaps between what you think matters and what actually moves you forward. Without this practice, you’re operating on gut feel and selective memory. With it, you have evidence to inform how you spend your time and energy.
Five days ago, I felt scattered. Still jetlagged, I felt ideas slipping away. Insights forgotten by the end of the day. So I created a system: six simple questions I’d answer at the end of each day, designed to capture both the learning moments and the friction points before they disappeared.
The six questions are:
What did I learn today? (personal growth)
What surprised me?
What’s one thing I am struggling with?
What are the insights from my work? (professional reflection)
What’s one question I am wrestling with?
What’s one insight from the books I am currently reading?
At first, I started to document my response to these questions at the end of each day in a Google Doc. Then I built a Reflection system in Claude code that integrates with Obsidian to capture my daily reflections. The creation of the system, integration with Obsidian, and the setup process were surprisingly easy and was up and running within 30 minutes.
For example, yesterday’s “What surprised me?” was realizing how much my perceived friction with Obsidian was mental rather than technical. That one observation led directly to taking action rather than continuing to avoid the tool.
After just five days of daily reflection, three patterns emerged:
My productivity depends on clarity. I’m consistently more productive on days when I’ve documented clear learning goals and targets.
Perceived friction is mostly mental. My hesitation to integrate Obsidian and Claude Code wasn’t technical—once I started, it took 30 minutes, and Claude Code basically did most of the heavy lifting.
You can’t find patterns in what you don’t capture. The act of documenting improves both retention and recall, creating a foundation for identifying where I’m actually heading.
Automation takes the heavy lifting out of the system. The Claude Code integration handles file creation and formatting, so I can focus on the thinking itself.
I built this in early January, riding the fresh start effect. But the system works because it’s simple enough to maintain beyond the initial motivation spike.
What system do you use to capture your thinking? Or are insights slipping away before you can act on them?
If you need a system, try mine. The six questions are a starting point. Alter them to fit what you’re actually trying to learn about yourself and your work.