Claude Code as Life Coach: How I Use AI + Obsidian for Personal Growth

Ron Forbes / December 28 2025

Yesterday I had a profound coaching conversation with an AI that synthesized years of my scattered thoughts and helped me realize I'd been holding onto a childhood dream that may have run its course. Here's what happened.

TL;DR: I pointed Claude Code at my Obsidian vault of years of personal notes, and it became an AI life coach—synthesizing patterns I'd missed and helping me realize a childhood dream had run its course. Here's my setup and what I learned, not as an expert, but as someone figuring it out in real-time and applying it to my personal life.

Who Is This For?

Honestly? I'm still figuring that out as I explore. Social media's been buzzing about how Claude Code is accelerating not just software development, but lots of other forms of business. I read a post today about someone using it to plan dates with their significant other. I'm not sure how true the results are, but the buzz is hard to ignore. And maybe that's the real take here: a lot of people are playing productivity theatre with AI agents, but the actual use cases are still emerging.

What I do know: this is not just for software engineers. Despite the name "Claude Code," the capabilities extend far beyond coding. I think 2025 will be remembered as the year Claude Code became a general-purpose agent for getting things done, both in business and in personal life.

How I Got Here

I started using Claude Code for what it's named for: coding. I'd been prototyping websites, apps, and game ideas, bouncing between ChatGPT Codex, Gemini, and other tools. Eventually I landed on Claude Code because, frankly, that's what everyone seemed to be using.

Around the same time, two things happened. Claude added memory (the feature that had been holding me back from making it my default LLM), and my job started allowing Claude Code for work. It became my default for everything.

Then I started seeing tweets and videos about people using Claude Code for non-coding tasks. Which makes logical sense when you think about it: the command-line interface gives it a technical appeal, but underneath it's just a chatbot with access to a file system. There's no reason those files need to be code.

The Obsidian Connection

Something you may not know about me is that I'm a bit of a notetaking nerd. I've been a heavy Notion user since it launched. I love its block-based editor, its databases, how easy it was to publish my notes to the web (in fact, ronforbes.com is built on Notion + Super.so).

Meanwhile, I'd always heard about Obsidian as this more hardcore, anti-establishment notetaking ecosystem that prioritizes privacy and local ownership, and honestly, I've resisted it for years. Its sparse (but highly customizable) UI always scared me back to Notion.

But before long, as I kept building this mega-Notion workspace, I gradually fell into the trap a lot of its users encounter where they spend more time building the productivity system than actually using it. So I eventually migrated to Apple Notes for its simplicity and frictionless integration with the Apple ecosystem.

But Obsidian has one thing going for it in the age of AI agents: local markdown files. Claude Code operates on local files. Obsidian operates on local markdown files. LLMs work really well with markdown. The synergy is obvious once you see it.

What I'm Actually Doing

Here's my current setup:

1. Started an Obsidian vault on my local machine. Need to set it up? Just go to obsidian.md to install it and create a new vault (I called mine RonOS).
2. Pointed Claude Code at that directory so it has full read/write access. Don't have it yet? Get started here. On MacOS, launch Terminal, and type:

cd ~/Documents/RonOS claude

1. Imported years of notes from Apple Notes and Notion using Obsidian's Importer plugin.
2. Started talking to Claude and instructing it to capture its thinking in markdown.

I initially asked Claude to analyze and organize thousands of imported notes. It got stuck—too much to process. But then I asked it to distill key insights from what it had learned, and something interesting happened: it synthesized patterns across different areas of my life that I hadn't connected myself.

Here's the prompt in case you're wondering:

You're a personal knowledge management expert. You're looking at an Obsidian vault of my notes, including imported notes from Apple Notes and Notion. Start building bidirectional links between my notes based on related concepts and keywords. Don't try to do them all at once. Rather, make a plan, and spin up subagents to work in parallel.

I've always believed in the interconnectedness of the various parts of our lives. When I'm at my healthiest, I can summon the most of my creative / logical / emotional / action-oriented energy into my work, and I show up my best with my friends / family / partner / community, and life just feels the most fun and fulfilling. And the opposite is true as well.

Obsidian + Claude Code starts to bring these connections to life, drawing similarities between my professional life and my personal projects, taking insights from books I'd read long ago and applying them to current-day relationships, drawing from random notes hastily written in the past and turning them into an interconnected narrative of my thinking over the years.

I'm writing this blog post from within that same knowledge base. Meta, I know. And as I write, Claude Code has spun up several subagents that are actively working through all of my imported notes, tagging them based on their topic and creating bidirectional links between related ones based on shared concepts and keywords. It’s kinda cool to watch the graph grow like a knowledge amoeba in real time 🤓

Claude Code as Life Coach

Here's where things get weird. Once Claude Code understood the context of what it was looking at and helped organize the notes with tags and links, I started a new chat and switched gears:

What followed was a very deep, incredibly personal, and profoundly insightful coaching session with an AI living in my computer. Again, I imported thousands of notes from over the years into this knowledge base, so it was able to draw on a lot of my inner thoughts, previous goals, common themes of values, dreams for the future, and guide me toward some deeply insightful takeaways.

Like a lot of kids growing up in the 90s, I grew up loving video games and developing a passion for computers based on dreams of creating my own video games one day. That passion sent me down a path of learning to code from an early age, picking up piano to play the songs from my favorite games, leading project teams in my early career as a stepping stone toward future aspirations as a game producer. And for the most part, that dream's worked out incredibly well!

But a major "aha" moment was seeing years of scattered thinking get synthesized into a clear takeaway: the thing that excites me now is teaching, sharing, seeing my mentees succeed, and inspiring others with what's possible through technology. Having a thought partner to piece together these patterns from across thousands of notes helped make clear that I'd been carrying a goal from my 12-year-old self that no longer fits who I am.

Something we talk a lot about in my work is that writing is thinking. For someone who has years of written notes that I rarely revisit, being able to connect, distill, reflect, and act on them feels like a big unlock, and it feels like I'm only scratching the surface.

Getting Started: Claude Code + Obsidian Tips

Before we go, here are a few tricks in case you're just getting started with Claude Code and Obsidian.

Monitor your context usage. Type /context to see a visual display of how much of the context window you've used. Response quality tends to fall off a cliff as the context window fills up. When you see it getting full, start a new chat to reset.

Organize through linking / tagging over folders. One of Obsidian's most powerful features is its ability to link between notes and visualize those links through its Graph View. Resist the urge to group things into folders, and instead focus on linking notes together. Aside: My mind naturally tends to want to group things into a clean folder structure. Maybe it's growing up on Windows. I hear this may also be a millennial habit, like organizing apps in folders on your phone's home screen, whereas younger people tend to use the search function as a launcher.

Consider voice dictation for even more effortless prompting. I'm actually writing this post on a train, so social acceptability prevents me from using it today, but check out tools like Wispr Flow and Superwhisper which let you talk in conversational language when prompting Claude Code.

What's Next

I'm just getting started with this setup. If you're experimenting with AI agents for personal productivity, I'd love to hear what's working for you.

Follow along: Subscribe to The Degenerate for more experiments at the intersection of AI, productivity, and personal growth.

Find me elsewhere:

• ronforbes.com
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This post was written using the setup I'm describing: Claude Code running inside my Obsidian vault, helping me turn scattered thoughts into something publishable. All text was hand-typed by me, with some light editing by AI.

In this post:

• Claude Code as Life Coach: How I Use AI + Obsidian for Personal Growth
• Who Is This For?
• How I Got Here
• The Obsidian Connection
• What I'm Actually Doing
• Claude Code as Life Coach
• Getting Started: Claude Code + Obsidian Tips
• What's Next

I’m a midlife millennial, storyteller, creator, and product manager working on Meta Quest.

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