Obsidian Ai Tutorial

Become a master at creating documentation with Obsidian and AI. This guide shows you how to plan your work, refine it with chat AI, and then use CLI tools to turn your ideas into clean, organized Markdown you can actually publish.

Version 1.0.0Updated 12/29/2025, 07:00 PM EST

Stop Prompting. Start Building.

Most people use AI like a vending machine.

You type something in.
Something comes out.
You stare at it and think, “That’s… not quite what I meant.”

That’s not because you’re bad at prompting. It’s because AI is not a designer. It’s an executor.

So the real workflow is not “open AI and ask for stuff.”
The real workflow is:

Design first. Delegate second.

This guide shows you how to do that, end-to-end, from “idea in your head” to “files created in your Obsidian folder by a CLI agent.”

The Big Idea

AI is extremely good at following instructions and extremely bad at guessing what you want.

If you skip planning, the AI will still produce something. It just might be the wrong “something,” confidently, at high speed.

So your job is to turn fuzzy ideas into clear instructions.

You do that in stages:

  1. You design the work (without AI).
  2. You use a chat AI to tighten the plan and generate a clean prompt.
  3. You use a CLI agent to execute that prompt inside your project folder.
  4. You review and iterate.

Step 1: Think Before You Touch AI

Before you open any AI tool, pause.

On paper, in Notes, or in your head, answer these four questions:

  • What are you building?
  • Who is it for?
  • What is in scope?
  • What is out of scope?

This is your blueprint.

If you skip this, you will spend your time arguing with AI instead of building with it.

Step 2: Use Chat AI as a Design Partner

Now you open a chat-based AI, like:

  • ChatGPT (web or app)
  • Claude (web or app)
  • Gemini (web or app)

Important: you are not using chat AI to “do the whole project” yet.

You are using chat AI to:

  • clarify your idea
  • expose missing details
  • tighten scope
  • produce a high-quality system prompt you can hand to a CLI agent

This is where you talk to the AI.

Step 2.1: Describe the Idea

Tell the chat AI what you want to build and why. Keep it simple.

Do

I want to create a beginner-friendly how-to guide that teaches people how to plan with a chat AI first, then run a CLI agent that writes Markdown files into an Obsidian folder.
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Do Not

Make me something cool about AI.
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Why: the “Do” version gives the AI a clear deliverable. The “Do Not” version forces it to guess what “cool” means.

Step 2.2: Define Scope and Boundaries

This is where you prevent chaos.

Do

This is for complete beginners. Keep it step-by-step.
Only cover the workflow: planning, chat AI, Obsidian setup, terminal navigation, CLI execution, review loop.
Do not go deep into machine learning theory.
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Do Not

Cover everything about AI and all tools and all platforms.
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Why: “everything” is how you get a 5,000-word tangent you never wanted.

Step 2.3: Ask It to Challenge You

You want the AI to act like a reviewer, not a hype person.

Do

Ask me clarifying questions.
Challenge assumptions.
Point out missing steps a beginner would get stuck on.
Do not just agree with me.
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Do Not

Sounds good, just write it.
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Why: beginners do not know what they don’t know. This step forces those gaps to surface.

Step 2.4: Iterate Until Clear

You go back and forth until it feels obvious.

A good rule: if you can’t explain it in two sentences, it’s still fuzzy.

Do

Keep asking questions until the plan is specific enough that a beginner could follow it without guessing.
If something is unclear, stop and ask before proceeding.
Click to copy

Do Not

This is probably fine. Just ship it.
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Why: “probably fine” is how you end up debugging your own instructions later.

Step 2.5: Ask for the Final Prompt

Now you turn the plan into a reusable instruction set.

This is the handoff point from “chat” to “CLI.”

Do

Turn everything we agreed on into a single system prompt for an AI agent.
Include: scope, tone, file structure, and output rules.
Output it in Markdown so I can save it as system.md.
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Do Not

Start writing the project files now in the chat.
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Why: the chat is for planning and prompt generation. The CLI is for execution in your folder.

Step 3: Install Obsidian and Create Your Project Folder

You want a place where files can be created and reviewed easily. Obsidian is great because it is basically a clean UI on top of normal Markdown files.

Install Obsidian

  1. Go to: https://obsidian.md
  2. Download Obsidian for your operating system.
  3. Install it like any normal app.
  4. Open Obsidian.

Create a Vault

When Obsidian opens:

  1. Click Create new vault.
  2. Name it something like AI-ProjectsClick to copy
  3. Choose where to store it (Documents is fine). Remember this location, you will need it in an upcoming step.

A vault is just a folder on your computer. Obsidian watches it for Markdown files.

Create a Project Folder Inside the Vault

Inside Obsidian:

  1. Look at the left sidebar (the File Explorer).
  2. Right-click your vault name.
  3. Click New folder.
  4. Name it based on the topic you are generating.

This folder is where your CLI agent will write files.

Step 4: Open a Terminal in That Folder

You want to run commands “inside” the folder so the AI outputs files in the right place.

macOS

Open Terminal, then:

cd path/to/your/ObsidianVault/Ollama
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Tip: In Finder, you can right-click a folder and look for something like “New Terminal at Folder” (availability depends on settings and macOS version).

Windows

You have two main options:

Option A: Windows Terminal / PowerShell (native)
Option B: WSL (Linux inside Windows)

If you are a beginner and you plan to do more dev work, WSL is often smoother, but it is still another thing to install. If you want the simplest path, start native.

If you use WSL, your Windows drive is usually mounted like this:

cd /mnt/c/path/to/your/ObsidianVault/Ollama
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Linux

Open Terminal, then:

cd path/to/your/ObsidianVault/Ollama
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Step 5: Install and Use AI CLIs (Codex, Claude, Gemini)

Below are common CLI paths people use. Commands can change over time, so treat these as the “current typical approach,” and verify with each tool’s official documentation.

No matter which CLI you use, the pattern is the same:

  1. Install the CLI
  2. Verify it runs
  3. Run it inside your project folder
  4. Provide the prompt (often from a file like system.md)

OpenAI Codex CLI

Typical install (Python):

pip install openai-codex
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Sanity check:

codex --help
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Common execution pattern (example):

codex run --system-prompt system.md
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Note: many agent-style CLIs ask for confirmation before writing files or executing actions. If Codex prompts you to approve steps, that is normal.

If you want “less interactive” behavior, check the CLI help for flags related to approval (search for words like approveClick to copy, yesClick to copy, autoClick to copy, or non-interactiveClick to copy):

codex --help
codex run --help
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Anthropic (Claude) CLI or SDK-driven CLI

Anthropic commonly provides SDKs, and many people use CLI wrappers or build simple scripts around the SDK.

Typical install:

pip install anthropic
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Sanity check:

python -c "import anthropic; print('anthropic installed')"
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If you are using a Claude CLI wrapper (some tools name the command claudeClick to copy), always check:

claude --help
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Some CLIs have an “allow” or “dangerous” style flag to let the agent execute without constant confirmation. These flags vary by tool and are easy to misuse, so treat them carefully:

  • Only use them in a safe folder
  • Only when you understand what it will write or run
  • Prefer interactive mode when you are new

Google Gemini (Python SDK)

Gemini is commonly used via SDKs, and you may run it through scripts or agent tools that integrate it.

Typical install:

pip install google-generativeai
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Sanity check:

python -c "import google.generativeai as genai; print('gemini sdk installed')"
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If you are using a Gemini-specific CLI or agent wrapper, use:

<your_command> --help
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Because the naming and interface depends on the wrapper, not just the SDK.

What About Grok and Meta

As of today, the common situation is:

  • Grok: often accessed via web app or API, not a mainstream official “agent CLI” people run locally in a folder.
  • Meta: commonly provides model weights (like Llama) and tooling around running models, but not a single universal “chat CLI” for this workflow.

In other words: you can still use them, but it is usually through APIs, local model runners, or third-party tools, not a simple “official CLI agent” you install and run like Codex.

Step 6: Run Your Agent in the Obsidian Folder

This is the “rocks and rolls” part.

  1. Save the final prompt you generated in chat into a file named:
system.md
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  1. Make sure your terminal is in your project folder:
pwd
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You should see something like:

.../ObsidianVault/Ollama
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  1. Run your CLI agent using the prompt file.

Example with Codex:

codex run --system-prompt system.md
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  1. Watch what it creates.

When it writes .mdClick to copy files into that folder, Obsidian will show them almost instantly.

Step 7: Review, Fix, Repeat

You are not trying to get perfection in one run.

You are trying to get:

  • a solid draft
  • correct structure
  • consistent formatting
  • minimal confusion for beginners

When something looks wrong, you have two choices:

  1. Fix it manually (fast for small edits)
  2. Go back to chat AI and adjust the prompt (better for systemic issues)

A healthy workflow looks like a loop:

  • run agent
  • review output
  • improve prompt
  • run agent again

The Pattern (In Simple English)

Here’s the pattern you are teaching:

  1. You plan the work without AI.
  2. You use chat AI to pressure-test the plan and produce a clean prompt.
  3. You use a CLI agent to execute that prompt inside a real folder.
  4. You review results and iterate.

Why this works:

  • planning reduces ambiguity
  • chat AI is great for thinking and clarity
  • CLI agents are great for structured output and speed
  • review keeps you in control

Final Thought

You are not “prompting.”

You are building a pipeline:

  • Idea → Plan → Prompt → Execution → Files → Review

Once you do that a few times, AI stops feeling random and starts feeling predictable.

And predictable is where the real power is.