How I Organise Files Under Hermes

My life runs on four pillars: Wealth, Insights, Network, and Self. Together they spell WINS — a name that captures what the system is meant to produce. I built my Hermes directory tree around these same four pillars. Everything I do has a home inside one of them. (btw: This is how I organize my Obsidian vault too)

WINS started as a way to think, not a way to organize folders. Once WINS seeped into my blood and brain, I started to organize everything around those categories because it made life simpler. The folder tree below mirrors the four pillars, with one change: Insights spans to two directories.

Here's what's inside them.

# Wealth

Wealth holds every way money enters or leaves my life; wealth/expense/ records what I spend and wealth/invest/ holds my stock, mutual fund, and fixed-deposit analysis. Every stock I research gets a page, and every trade records the reasoning so I can later trace not just what I did but why. wealth/tracking tracks OpenRouter costs.

# Insights

Insights is a loop: consume, produce, engage. Each stage lives in its own directory.

consume/ stores what I take in. Articles, concepts, highlights, and transcripts all land here in their own subdirectories. When I paste a YouTube link into Slack, Hermes pulls out the highlights and concepts and files them, so I no longer summarize by hand. Read LLM Wiki With Hermes for how I'm extracting highlights and concepts from articles and YouTube videos.

produce/ holds what I create. produce/blogs/ stores published posts that sync from my Mac; Hermes reads them for reference but never writes there. produce/hermes/ is where we build together: blog drafts, books, products, plans, and commercial work.

Engage runs in the background: my social posts log into produce/hermes/social/, and Hermes reads that log each week to report what worked.

# Self

Self holds the person and the process. It is where WINS stays honest.

Everything under Self lives inside produce/hermes/self/ — that's where Hermes and I collaborate on the personal side. self/decisions/ records every decision I make with a date, a confidence level, and a review date. My model-routing choice sits there at 85% confidence, with a tripwire to revisit it next year. When I forget why I chose something, the file tells me.

produce/hermes/hermes-audit/ matters just as much. A weekly cron job audits my whole setup: what broke, what drifted, what to fix next. I read the report and act on it. Another cron audits how I use Hermes itself — better prompts, lower token costs.

self/retros/ runs my weekly, monthly, and quarterly reviews. Every Sunday Hermes surfaces what I did; I write the narrative. tracking/ at the wiki root logs token use and cost from every session.

# Network

Network is the pillar I have not built yet; it sits as a placeholder, a reminder that relationships deserve structured tracking too.

# The Full Folder Tree Looks Like This

wiki/
├── wealth/          Money in and out
│   ├── expense/
│   └── invest/
│   └── tracking/        Token use and cost
├── consume/         What I take in
│   ├── articles/
│   ├── concepts/
│   ├── highlights/
│   └── transcripts/
├── produce/         What I create
    ├── blogs/
    │   ├── jjude/        (synced from Mac)
    │   └── ctofieldnotes/
    └── hermes/
        ├── blogs/
        ├── books/
        ├── hermes-audit/
        ├── plans/
        ├── self/
        │   ├── decisions/
        │   ├── retros/
        │   ├── assessments/
        │   └── frameworks/
        └── social/

# Why this works

The directories do not just store files. Consume feeds produce. Retro corrects decisions. Audit catches drift. That is why I persist everything into files and memory. Slack is the interface, not the storage. The conversation vanishes. The work stays.

WINS is what happens when thinking drives the tooling.

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This is an ongoing project. If you want to follow along with how this setup evolves, subscribe to my RSS feed, or connect with me on LinkedIn and X.