Prompt
Daily debrief
A structured end-of-day conversation that captures what you actually did, surfaces wins you'd otherwise skip past, and makes sure nothing important evaporates overnight.
daily systems
workflow
obsidian
todoist
How this came to exist
This prompt wasn't written in one sitting. It was built collaboratively — first as a way to capture job search progress without losing track between sessions, then refined over time as the workflow evolved. When Obsidian entered the picture, the output destination changed. When Todoist got connected, the task pull got added. When the questions weren't surfacing the right things, they got rewritten.
That's the honest origin story. And it's relevant because it means this prompt is a starting point, not a finished product. Your version should look different from this one. The questions should be yours. The format should fit how you think. The destination should be wherever you actually keep notes.
What's intentionally designed in here
A few things in this prompt aren't accidents — they're worth understanding before you adapt it.
1
The AI scans the session before asking anything. You shouldn't have to remember and recite everything you did. The scan catches what's already in the conversation so your answers can focus on what happened outside of it.
2
Wins are asked separately, at the end. If you ask "what went well" alongside everything else, people (including this person) tend to skip it or rush it. A dedicated question signals that it matters.
3
"If I skip wins, surface 1–2 from the session anyway." This is the accountability clause. It's in there because the reflex to minimize is real, and sometimes you need the AI to push back. Don't let me off the hook was the instruction — and it works.
4
The Todoist pull is optional infrastructure. If you use Todoist, it catches completed tasks that happened outside your main chat. If you don't, remove that line entirely. If you use another connected task tool, swap it in.
5
"Keep my voice throughout." The debrief is a note to yourself, not a report to someone else. The AI should write it the way you'd write it — not corporate, not formal, just clear and honest.
💡 where to run it
Run this in whichever chat was most active during your day — the one with the most context to scan. If you worked across multiple chats, run it in the main one first, then use the
daily debrief merge prompt in the others to pull everything together without losing anything.
🧪 test it before you commit
Before you make this part of your daily routine, run it a couple of times and see how it feels. The questions might not be right. The format might be too long or too short. The tone might be off. That's fine — that's what testing is for. It's much easier to tweak a prompt you've actually run than to design a perfect one from scratch.
📖 actually go read it
This sounds obvious but it's worth saying: go read the debrief after it's written. Not immediately — let it sit for a minute, then read it like you'd read a note from your past self. It's easy to finish the process and move on, but the reading is where a lot of the value is. On difficult days especially, it's a reminder that you did things. Real things. More than you remembered.
Run my end-of-day debrief. Here's how:
Step 1 — Scan this session and pull completed tasks.
Before asking me anything:
- Look through our conversation today and note anything worth capturing: documents written, decisions made, applications researched, tools built, insights that landed.
- Pull today's completed tasks from [your task tool — e.g. Todoist] and include them in the session scan.
- Compile everything quietly.
Step 2 — Ask me these three questions in one message:
- [Question 1 — e.g. Applications / job search: Any applications submitted, roles researched, or recruiters contacted outside our session?]
- [Question 2 — e.g. Admin / logistics: Any tasks knocked out that aren't already in your task tool?]
- Carrying over to tomorrow: What's sitting in your head that you haven't done yet?
Step 3 — After I respond, ask me two follow-up questions:
- Wins: Anything that felt good, went well, or deserves a moment of credit?
- Anything to remember: Something that happened, something that clicked, something you don't want to lose.
If I skip wins, surface 1–2 from the session anyway — don't let me off the hook.
Step 4 — Compile everything and write directly to [your note tool and file path].
Do not save a file to download.
Use this format:
# Daily Debrief — [Day, Month DD, YYYY]
## What I Did Today
### In Session
[Bullet list from Step 1 scan — specific and concrete]
### Outside the Session
[Your custom sections here — e.g. Applications, Admin, Tasks Completed]
---
## Carrying Over to Tomorrow
[Bullet list]
---
## Wins Today
[From my answers + anything from the session worth crediting]
---
## Anything to Remember
[Preserve my voice here — this is a note to myself, not a report]
---
*Captured [HH:MM] on [Day, Month DD, YYYY]*
Keep my voice throughout. After writing, just confirm it landed.
Amber text = swap this out for your own setup
Make it yours — and ask for help doing it
The questions in Step 2 are specific to a job search context. If you're not job searching, they won't fit. Change them to whatever actually matters to you right now — client work, a project you're running, a creative practice, anything.
Same with the format. Add sections, remove them, rename them. If the "Wins" section feels forced, reframe it. If you want a section for energy level or what you'd do differently, add it.
🤝 you don't have to figure this out alone
This prompt wasn't written from scratch — it was built in conversation with an AI tool, refined through use, and changed when it stopped working. You can do the same thing. Paste the prompt into a chat, explain what you're trying to capture and what your life actually looks like, and ask your AI to help you adapt it. That's not cheating. That's the whole point.
And if you feel awkward admitting you don't know how to do something — ask anyway. The AI doesn't judge. It doesn't sigh. It doesn't think less of you for not knowing. Ask it to explain something like you're five. Ask it to help you write a question you don't know how to phrase. It's a genuinely safe space to not know things, which is rarer than it should be.
Adapting for your setup
Obsidian
Google Drive
Other / no tool
Replace the Step 4 destination with: Write directly to Obsidian at [YOUR-VAULT]/[YOUR-FOLDER]/debrief_[today's date YYYY-MM-DD].md using the Obsidian MCP tool.
You'll need the Obsidian Local REST API plugin installed and Claude connected via MCP. See the Obsidian integration guide if you haven't set that up yet.
Replace the Step 4 destination with: Save the file to Google Drive at [YOUR-FOLDER]/debrief_[today's date YYYY-MM-DD].md using the Google Drive integration.
You'll need Google Drive connected to your AI tool as an MCP integration. This was actually the original setup before Obsidian — it works well, especially if you want your debriefs accessible from anywhere without a dedicated notes app.
No connected note tool? Remove the Step 4 instruction entirely and replace it with: After I've answered everything, compile the debrief and return it to me as formatted text I can copy.
You'll get the debrief in the chat window and can paste it wherever you keep notes — Notion, a text file, wherever. It's a bit more manual but it works fine as a starting point while you figure out your setup.
🔜 Coming soon
This prompt looks different for different people — and that's the point. We're working on a case study showing how the same daily debrief idea evolved into three distinct versions for two people with different workflows, different tools, and different things worth capturing. Same idea, different context, different results.
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