By skyforbes I’ve been trying to build a system where I do:
- A 3–5 minute daily review
- A 30–60 minute weekly review
- And quarterly goals that tie everything together
Each quarterly goal breaks down into smaller weekly or daily tasks. Some goals are projects (like building an app), and others are more habit-based (eating healthier, losing weight, improving my morning routine, etc.).
What I’ve been trying to do is integrate this whole process with ChatGPT in a way that gives me more insight and continuity. Ideally, I want to:
- Look back at a quarterly goal and get a short summary of how it went
- Get weekly tips or reflections based on what worked or didn’t before
- Have a sort of “habit note” that tracks progress, struggles, and wins
- See a bigger picture of ups and downs across projects and habits
Basically, I want my daily reviews to roll up cleanly into weekly summaries, and my weekly ones to consolidate into quarterly reflections. Over time, I’d love for ChatGPT to point out patterns, what helped, what derailed me, and maybe even suggest new strategies to try.
The problem is… I can’t get it to work well.
I’ve tried having ChatGPT summarize my notes, keep rolling context, or maintain a habit tracker note that updates each week. But the summaries always miss key insights, and the “context memory” never really sticks in a useful way.
Has anyone managed to make something like this work?
What’s your process like, and what’s actually helped you get good summaries or insights from ChatGPT over time?
Here are some of the prompts I’ve tried before:
ChatGPT daily to weekly prompt:
Here are my daily reviews for this week, plus the Rolling Context Summary at the bottom. Please summarize:
General tone of the week
Progress or struggles for each goal
Notable thoughts or journaling insights (relationships, emotions, health, learning, etc.)
2–3 moments, quotes, or reflections worth remembering
Update the Rolling Context Summary with 2–3 concise bullets reflecting this week’s themes
[PASTE DAILY NOTES + ROLLING CONTEXT SUMMARY]
Quarterly summary prompt:
Here are my 13 weekly reviews, including the Rolling Context Summary and my Habit History Context notes.
Please:
Summarize progress on each goal
Highlight major struggles and breakthroughs
Extract notable personal thoughts or themes (relationships, learning, pain, health, etc.)
Update my Habit History Context:
Modify or refine the “What Works” and “What Doesn’t” sections based on my history and this quarter’s notes
Add to or refine the “Future Experiments” section with specific and testable ideas, building on past attempts
[PASTE WEEKLY REVIEWS + ROLLING CONTEXT SUMMARY + HABIT HISTORY CONTEXT]