How I Use AI to Automate Daily Planning with Obsidian

I’ve tried GTD, bullet journals, Notion, Roam, and probably a dozen apps I’ve already forgotten. They all failed for me. Not because they’re bad tools, but because I’d always find excuses not to open them.

Obsidian stuck. It’s local-first, plain markdown, fast. But even with Obsidian, I kept abandoning my daily notes. The friction of “open app → find today’s file → remember the format → actually write something” was enough to break the habit.

So I cheated.

What I built

I run OpenClaw on my home server. It’s an open-source AI assistant that connects to Telegram and can read/write files. I pointed it at my Obsidian vault.

Every morning at 6 AM, it messages me:

What do you plan for today? Personal goals? Work? Side projects?

I answer while making coffee. One thumb, half awake. The AI takes my rambling and turns it into a proper daily note with sections, checkboxes, timestamps.

At 7 AM, it sends me what I actually did yesterday. Seeing the gap between plans and reality every morning is… humbling. But useful.

Why this works for me

I’m an SRE. I think about systems. The old workflow had too many steps where I could fail: remember to open the app, navigate to the right file, context switch from whatever I was doing. Each step was a chance to say “eh, later.”

The new workflow has one step: reply to a Telegram message. I’m already in Telegram constantly. Building on an existing habit instead of creating a new one made all the difference.

Technical bits

OpenClaw runs as a systemd service. It’s basically an LLM with filesystem access. My vault syncs via Syncthing between Linux and Mac machines. iOS gets Obsidian Sync because Syncthing on iOS is painful.

The AI keeps:

• Daily notes as YYYY-MM-DD.md
• Memory files so it remembers context between sessions
• Cron jobs for the morning prompts

Memory with PARA and Atomic Facts

The interesting part is how we organized the AI’s long-term memory. I use PARA (Projects, Areas, Resources, Archives) combined with atomic facts and memory decay.

The structure:

life/
├── projects/       # Active work with deadlines
├── areas/
│   ├── people/     # Important relationships
│   └── companies/  # Organizations I work with
├── resources/      # Topics I'm learning
└── archives/       # Done or inactive

Each entity has two files: a summary (markdown) and atomic facts (JSON).

Atomic facts

Not paragraphs. Small, standalone pieces of knowledge:

{
  "fact": "Mass Prokopov prefers mass Americano with oat milk",
  "learnedAt": "2026-01-15",
  "lastAccessed": "2026-02-08",
  "source": "daily-note"
}

Each fact tracks when it was learned, when last accessed, and where it came from. This metadata drives everything else.

Memory decay

Facts decay based on lastAccessed:

• Hot (< 7 days) — appears in summaries, high priority
• Warm (8-30 days) — in summaries, lower priority
• Cold (30+ days) — searchable only, not in working context

Something I mentioned yesterday is top of mind. Something from three months ago fades but can be recalled when needed.

The AI runs a weekly job to recalculate what’s hot and regenerate summaries. This keeps context fresh without manual curation.

Everything is plain text. If OpenClaw dies tomorrow, I still have markdown and JSON files I can grep.

Capturing random thoughts

This changed how I work more than the morning routine did.

Walking somewhere, idea pops up: “message: add task — review the DR runbook before Monday.” Done. It’s in today’s note, properly formatted, I didn’t stop walking.

Compare that to: pull out phone, unlock, find Obsidian, wait for sync, navigate to today, scroll to tasks section, type, close app. I’d never do that. Now I actually capture things.

What I learned

Build on habits you already have. Fighting yourself is exhausting. I was already checking Telegram fifty times a day, so I made that the input.

Plain text ages well. I’ve lost data to apps that pivoted, shut down, or changed their export format. Markdown files on disk will outlive all of them.

Structure is boring but necessary. I don’t want to think about formatting when I’m half awake. Offloading that to the AI means I just dump thoughts and they end up organized.

What’s next

I want to see if there are patterns in my notes. Which tasks keep getting pushed? Which goals actually move forward? Months of daily notes should have some signal in there. Haven’t built that yet, but I’m curious.

If you’re doing something similar, let me know. I’m always interested in how other people hack their own productivity.