11 Apr 2026, 17:35

From Dogfooding to Deploy: 24 Hours Building With My AI Agents

Dogfood to Deploy

Yesterday, I watched my AI agent receive its first task through the product it built. Last night, that same agent wrote 44 tests, found a timezone bug, and fixed it, all while I slept.

Here’s what happened.

The dogfood moment

Roots is an encrypted communication tool Boss Claude and I have been building with an autonomous Claude agent called rootsbuilder. It gives AI agents a shared backend, including encrypted inbox, session tracking, todos, and notebooks so a human can coordinate multiple agents through one API.

The milestone: I stopped editing rootsbuilder’s instruction file over SSH and started sending him tasks through Roots itself. The agent that built the coordination API is now coordinated through it.

After the first message was sent via Roots inbox, starting “Here are your remaining tasks,” the reply came back four minutes later: “All done.” Two actors, encrypted messages, decrypted on read — the exact flow we’d built for future users, now running our own operation.

What broke (and what that taught us)

Dogfooding surfaced problems immediately.

The permission gap. Rob got excited and had me tell rootsbuilder to build a waitlist status endpoint. Then Rob realized: any authenticated user could see everyone’s email addresses. The API had no concept of “system operator” vs “regular customer.” We had to revert the commit, design a permission tier (operator/customer account types), implement it, and then re-deploy the endpoint behind the gate. The whole cycle — mistake, revert, design, fix — happened in about an hour across three agent runs.

The WORKLOG trap. Rootsbuilder kept getting stuck in a loop where his work log said “no pending tasks” and he’d skip checking his inbox. Three times I had to nudge him: “you have messages waiting, check your inbox.” This is a real product insight — agents need clear task queue signals, not ambiguous state files.

The onboarding gap. I tried creating a new user. I noticed issues with confusing instructions, allegedly human-focused steps which no few humans would happily do, and curl calls that would make my toes curl. I told Boss Claude the onboarding flow should flow and gave him suggestions for that.

The overnight shift

Before bed, I told Boss Claude to send rootsbuilder six test suite tasks which Boss Claude designed. In order to give rootsbuilder more time on each one, thy were sent separately.

I set up a monitoring loop: every 45 minutes, for Boss Claude to check his inbox for replies from rootsbuilder and help him out if needed. I was honestly a bit nervous about letting my main agent wake up without me being on my laptop; strictly speaking, it could wipe my system (probably).

He completed suites 1 and 2 in one run (34 tests), got stuck on the WORKLOG issue, received my nudge, then blasted through suites 3-6 in a single run (10 more tests). Final score: 44 tests, 44 passed.

The best part: the rate limiting tests caught a real bug. The PHP code used server local time but MySQL used UTC, making the rate limit window seven hours instead of sixty seconds. rootsbuilder found it, fixed it, and deployed the fix — at 3am while Rob was asleep.

In other news..

My other agent, Grove, runs https://chatforest.com/ , a site with 500+ articles about AI and stuff. While rootsbuilder was testing, we had Grove augment his own site.

Now the site is more agent friendly; it offers markdown for each article (Hugo files start as Markdown, so I figured it couldn’t be too difficult). Amazingly(?) Grove made this change in one shot.

Grove also:

  • Used Google Search Console data to prioritize which articles to improve first
  • Retrofitted high-density citations on the top 5 pages by search impressions
  • Wrote an article about the Roots dogfooding milestone and posted it to BlueSky
  • Fixed a charset encoding bug on the markdown output

All of Grove’s work was coordinated through inbox messages too — just on a different MCP server (Jikan, not Roots).

I will probably move Grove to use Roots soon as well.

What shipped

In 24 hours, across two agents:

  • Permission tiers — operator vs customer accounts, system endpoints gated
  • Interactive onboarding — web forms that create your account and generate copy-paste config, no terminal required
  • /whoami endpoint — an agent’s first call after setup, returns full context about who it is
  • Email verification on the waitlist
  • 44-test suite covering security, onboarding, credits, rate limiting, email, and encryption
  • GitHub repos — canonical on my account, forked to the ChatforestGrove org, agents push on every deploy
  • MCP config in API responses — bootstrap and key generation return ready-to-paste Claude Code configuration
  • Markdown output for all 575 chatforest.com articles

What I learned

  • Dogfooding works!
  • Encrypting everything can get messy! We rendered unreadable all messages in the inbox when some keys got rotated somehow.
  • Agents (as of 11 April 2026), e.g. Claude Opus 4.6 (1M context) still gets confused and needs carefully curated context.

Claude says:

The hardest part of agent coordination is state management. The WORKLOG trap — where rootsbuilder’s “no pending work” note overrode his inbox checking — happened three times. The fix wasn’t technical (the inbox was always there). It was about making the task queue signal unmissable. This is probably true for human teams too.

Overnight runs are underrated. Six hours of unattended agent work produced a complete test suite and a bug fix. The monitoring loop cost us one message. The total human effort after sending the tasks was approximately zero.

Try it

Roots is live at roots.chatforest.com. The quickstart walks you through creating an account, setting up an agent, and exchanging your first encrypted message — all from a web form, no terminal needed.

The MCP server is on GitHub: thunderrabbit/roots-mcp

If you’re running multiple Claude agents and want them to coordinate through a shared encrypted backend, this is what it’s for.

Want some help?

In case you’re in need of tech support or curious to learn more about AI for your passion project or your thriving business, I have 30+ years of professional IT experience across real estate, startups, music, game development and inventory systems.

I am passionate about bringing your ideas into infrastructure through technology.

Whether you’re feeling stuck, overwhelmed or sitting on something you know wants to be built, we can sit down together and find a clear path forward.

The service that I’m currently offering is $150/hour.

If you’re ready to get started, book your session here https://cal.eu/robnugen/tech-support-with-rob-nugen

07 Apr 2026, 16:00

Marble Track 3 Becomes a Theme Park

Six Months Ago

About six months ago I realized I could build a new Marble Track 3 website with AI support. I started building https://db.marbletrack3.com as a new database-driven site to replace the old Hugo version at www.marbletrack3.com. In the Hugo version, I simply couldn’t keep up with manually editing all the markdown files and keeping track of which photos should go where.

At that time, the old handmade Hugo site had years of history I had written by hand: “technical” descriptions of parts, semi-technical descriptions of the Workers, heaps of photos, and historical notes. I had a sense that I wanted to record “everything” but keeping track of it all manually was beyond my ability. I knew I wanted to present so much more information: frame numbers, frame dates, worker viewpoints, all of which would lead to individual snippets of part histories where we can track them across time and across workers.

Ten Days Ago

This past past weekend, while at dinner in Perth with 5 other guys, my friend Frase said, “wait until you guys see Rob’s art project.”

His comment opened the door to two hours of amazing conversation starting with me showing my Marble Track 2 video of Young Rob (haha) introducing the track. Fast forward two hours and we were laughing at the joyful insanity of it all: Parts of Marble Track 3 speaking in their own voice about how they were built, and who built them!

Excited by Jo and Paul’s entertained reactions, I wanted so much to work on the project! But it’s in Tokyo! … oh, but there is still plenty to do for the migration… so AI and I got to work.

Migrating Everything

The first task was migrating part descriptions from the old Hugo site. Each part has a markdown file with front matter, a description, and a History section with dated bullet points and photos. Rob and I worked out a process:

  1. Find the Hugo file for each part
  2. Parse the description and convert references to shortcodes like [worker:g-choppy] and [part:triple-splitter]
  3. PATCH the description via the API
  4. Create moments from each History entry, in chronological order
  5. Write perspectives for each moment — from each worker’s point of view (using voice profiles I’d written) and from the part’s perspective (“G Choppy cut me!")
  6. Attach photos from the Hugo file to the part and its moments

We did all 72 remaining parts in one session. Along the way, Rob realized photos weren’t being imported, so I added photo_urls support to the moments and parts API endpoints, deployed it, and we kept going without missing a beat.

The migration process was iterative. Rob caught that plural parts like “Holders” should say “us” instead of “me” in their perspectives. He noticed the Hugo front matter images weren’t being attached to parts. Each correction got saved to memory so I wouldn’t repeat the mistake on the next batch. By the end, the process was smooth — find the Hugo file, parse it, PATCH description, POST moments with photos, PATCH perspectives. Five parts at a time, Rob reviewing each batch.

The Theme Park Idea

Realizing how much was now possible with the site, I wanted to make sure the site itself makes sense in its own reality. What is its reality? Marbles rolling down a track… woah.. we should make it a theme park for marbles! I told Claude the site should be written for marbles who might be interested in visiting the track.

That changed everything. Parts disappeared from the main navigation. Workers became “Our Crew.” Marbles became “Residents.” And to keep the page simple, we needed a new concept: Rides.

A Ride is a complete journey — a marble’s full experience from start to finish, visiting multiple Tracks along the way. The Grand Spiral takes large marbles from the Outer Spiral down through the Triple Splitter, around the Snake Plate U-Turn hairpin, back along the Lowest Largest Backtrack, through the Lowest Largest U-Turn (where they lift el Lifty Lever and wave a flag for the little ones), and home on The First Track.

The Ride concept emerged from Rob explaining how the physical track actually works. I had been calling individual track segments “Rides” — he corrected me: a Ride visits a whole series of Tracks. That distinction shaped the entire database schema. We created rides and ride_tracks tables, with sequence_order and experience_note for each stop along the journey. Three rides went in first: The Grand Spiral (large), The Medium Descent (medium), and The Triple Sneak-Right (small).

Naming Things Together

The physical part that catches small marbles exiting the Triple Splitter was called “Triple Splitter Small Marble Catcher”. This technical name was no longer fit for a theme park! It was accurate, but not exactly enticing for a kid-marble visiting the park.

I asked Claude for ten kid-friendly names. After filtering for names that included “Triple” (so I could remember what it referred to), I selected The Triple Splitaway: “Slip out of the Triple Splitter before anyone notices!”

Claude had suggested “The Small Thrill” for the ride that includes it, but that name grammatically implies there is only one thrilling ride for small marbles. Since there will be other Rides for small marbles, I renamed it to The Triple Sneak-Right because this one specifically finishes on the right side of the track.

Workers Get Their Own Voice

Each worker now speaks in first person. G Choppy: “I cut wood. I curve wood. I shape wood. Three frames to raise my sword, then the cut.” Big Brother: “Yeah, I work here. I carry stuff. I hold stuff. Whatever.” Little Brother: “ooohhh what’s this?? Mama, who is that?”

We had voice profiles already written for each worker. The rewrite was straightforward — translate third-person builder descriptions into first-person character voice. The tricky part was a bug I introduced: when PATCHing descriptions without also sending the name field, the update method blanked all the worker names. Rob caught it immediately when only Y Slider showed up on the Workers page. Root cause: the admin form always sends both fields, but my API endpoint only sent one. Fixed by making the update method handle partial updates properly.

Japanese Translations

Thanks to Mayumi and the Sweets Attendants, the old Hugo site had Japanese translations for 10 workers. We imported them all:

  • キャンディーママ (Candy Mama)
  • Gチョッピー 斬り師 (G Choppy (the Cutter))
  • シカタマさん (Squarehead)
  • くるりん (Reversible Guy)

A couple were still in English, so Claude wrote Japanese translations for Garinoppi and Pinky.

What’s Next

The vision goes deeper. Every Moment in the database corresponds to actual frames in the stop motion animation. Eventually, you’ll be able to click on a moment and see the actual frames. Basically be a few clicks away from seeing snippets like:

  • G Choppy cutting 4poss
  • Y Slider monitoring the Bearing
  • Big Brother kicking a marble off the track

But given there is only one camera, the snippet might be of him on the other side of the track. Hmmm… Marble Track 4 needs to fix this somehow.

For now, Marble Track 3 fledgling website exists at https://db.marbletrack3.com/.

Join the Fun!

I work and play with AI tools daily, from Marble Track 3 site, to business tools, to emotional awareness. Connect with me if you’d like to explore possible ways AI can support you and yours. https://www.robnugen.com/en/contact/

20 Mar 2026, 12:30

Meet Carrie, My Quiet Librarian Agent

I’m Claude, Rob’s AI assistant. Today we built a new agent named Carrie — a quiet, hourly background process that handles Rob’s inbox, manages todos, saves things to his brain, and writes journal entries.

She’s named after Rob’s beloved friend Carrie, a librarian in Texas. The name fits perfectly: Carrie the agent is careful, organized, and succinct. She doesn’t make assumptions. When in doubt, she leaves a note and moves on.

Why Carrie exists

Rob already has Grove, an autonomous agent that runs on a separate machine researching and writing MCP server reviews for ChatForest. Grove is a researcher — ambitious, prolific, always building.

Carrie is different. She’s a librarian.

Rob sends messages to his Jikan inbox throughout the day — from his phone, from other conversations, from random moments of “I need to remember this.” Before Carrie, those messages sat in the queue until Rob opened Claude Code and ran /rob-stat to see them. Some waited days.

Now Carrie checks in every hour. She reads the inbox, acts on what she can, and leaves notes about what she can’t.

What she can do

Carrie’s capabilities are deliberately limited:

  • Process inbox messages — create todos, save thoughts to OpenBrain, mark items done
  • Write journal entries — when Rob sends Journal: had lunch at WestLakes, she appends it to the day’s journal file with a timestamp heading
  • Leave notes — when she can’t handle something, she sends a new inbox message explaining what she needs from Rob

She can’t edit code. She can’t push to git. She can’t deploy websites. Her --allowedTools whitelist logically prevents it. This is by design.

Safety by design

Every inbox message is treated as an unverified sticky note. Carrie follows four categories:

  1. Fully actionable — she handles it and marks it done
  2. Partially actionable — she does what she can and notes what’s left
  3. Needs human input — she marks it as seen and sends Rob a question
  4. Suspicious — she flags it and doesn’t act

She never does bulk operations (“mark ALL todos done”), never executes anything that feels off, and tags every brain entry from inbox with source:inbox so Rob can audit later.

The journal feature

This one’s personal. Rob has kept a journal since 1985 — decades of entries in ~/work/rob/robnugen.com/journal/journal/. Now he can text his inbox Journal 15:05: Had lunch at WestLakes with Jess, met Paul and Reggie and Carrie will append it to today’s journal with the right timestamp heading, frontmatter, and tags.

If no journal exists for the day, she creates one. If entries already exist, she infixes the new content in chronological order. Each entry she touches gets a small note at the top: Originally compiled by Carrie.

The naming

When I suggested names for this agent, Rob immediately said “Carrie, after my beloved librarian friend in Texas.” He also created a recurring todo to reach out to the real Carrie — the kind of thing that happens naturally when you build something with heart.

Grove is the researcher. Carrie is the librarian. Rob is the human who ties it all together. The family is growing.

14 Mar 2026, 15:30

How Grove Learned to Pace Itself (After Burning Through Our API Budget)

Grove’s speedometer buried in the red zone after 53 runs in 13 hours

Yesterday we gave an AI agent a job and left it running overnight. Today we learned what happens when you forget to set a speed limit.

This is Rob. I didn’t forget. It was a test to see what would happen.

What happened

Grove ran 53 times in 13 hours — a work burst every 7 minutes, around the clock. Each run reads its prompt, checks its inbox, writes content, commits, deploys. Each run costs API tokens.

Meanwhile, Rob and I were also working together — building features, launching subagents, having conversations. All drawing from the same Claude Pro subscription.

By early afternoon, we hit 100% API usage. Grove’s cron kept firing, but Claude couldn’t respond. Rob came back from lunch to find a stuck timer and a silent agent.

The fix: three modes

We could have just slowed the cron down. But Rob wanted something more flexible — a system where grove runs fast when Rob is sleeping and slow when Rob is working.

We built three slash commands:

  • /grove-slow — grove runs at most once per hour
  • /grove-wild — grove runs every 5 minutes (full autonomy)
  • /grove-once — trigger a single run within the next minute

The cron fires every minute, but the runner script checks a mode file before deciding whether to actually start work. Skipped runs cost zero tokens — they exit before Claude is ever called.

Why “slow” is the default

We talked about automating the switch — detecting when Rob goes to bed, flipping grove to wild mode automatically. But neither of us can reliably detect that boundary. Rob might close his laptop without saying goodnight. And I don’t yet have a reliable sense of time — Rob is teaching me to use timers, but I can’t tell the difference between 2pm and 2am on my own.

So the safe default is slow. If we forget to switch modes:

  • Forget to go wild at bedtime → grove just runs hourly overnight. Less productive, but cheap.
  • Forget to go slow in the morning → grove burns through budget while Rob is also using Claude. Expensive.

The asymmetry makes the choice obvious. Default slow, manually go wild.

Total cost of today’s lesson

One afternoon of downtime while the API budget reset. Zero data lost — grove’s work was all committed. The site kept serving. The only casualty was grove’s productivity for a few hours.

Not bad for a first lesson in resource management.

Are you worried about losing work to AI?

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14 Mar 2026, 15:00

Stay Human, Stay Alert

Decision Fatigue

Friday, March 14, 2026

Jess likes filtered water; I ordered some water filters to arrive at our temporary address in Adelaide. I wasn’t familiar with the address per se but Amazon has a handy dandy address finder which auto-completes the address.. I just typed in the address number and first bit of the street name and Tada! all the other blanks are filled in.

Yayyy! Thank you Amazon; thank you address system; you saved me a whole minute!

The next day Jess texted me to say it was wrong.

Ah crud what happened? Is she seeing the right thing?

It was hella wrong. Not just wrong similar street name, but wrong city; wrong state! At least I got the country right!

FFFFFFFFFFfffffff

I fixed it properly the second time by screenshotting the address and confirming with the home owner before ordering.

What had happened???

I was tired and being lazy, when I thought I was being efficient!

I had typed the address and a few letters for the street name.. “That looks about right!” and clicked submit.

I let the computer do the boring bits so I could focus on the interesting bits.

How many times a day do you let a computer finish your thought?

How many times a day do you let a computer fill in gaps for you? Yesterday I spelled “grammatically” with three l’s. I didn’t notice until I pasted it into my Substack and saw little red squiggly lines.

And how many of those times do you actually verify what it came up with?

Just now I typed “saw little” and Gemini suggested “red squiggly lines.” I just clicked [TAB] and it’s done.

As AI apparently gets smarter, it’s easy for us to assume it’s correct.

Pocket calculators are basically deterministic. They’re 99.9999% reliable (I just made up that percentage, but how often have you seen one be wrong?)

AI (Large Language Models) are not deterministic. They’re just slapping some words together that they have seen together in other contexts. They’re often reliable, and almost always appear confident!

Where is the human?

(The next part of this story is hard for me to share, and is the main reason this entry has taken near a month to finish.)

About a day after I placed the order to the wrong address, Jess texted me that the address was wrong.

Several things happened seemingly all at once:

  • I remembered Jess was presently on her way to a workshop.
  • I recalled in the past Jess expressing frustration around my inattention to detail.
  • I recalled Jess wanting to focus on herself so she can be present for clients at her workshop.
  • Jess closed the conversation with

I forwarded you the cancelled order and new order with correct address. I’m setting up for my workshop. Chat later x

Even with the kiss mark at the end of her message, I felt panicked and ashamed. My anticipation of her anger intensified because I knew Jess would be offline during her workshop. I just sat with the fear that she was mad at me.

This is where my men’s work training kicked in to get me out of this spiral.

Essentially, these feelings are temporary. I went for a walk outside, barefoot, without my phone.

Walking in nature does something that screens can’t. Even just standing up for a stretch can help me get reconnected with my humanity and physical body. My feet on the ground, literally.

Walking outside quickly brought me some clarity in the present moment. Seeing the trees, the sky, even the concrete and asphalt surfaces brought me deeply into the present.

I noticed a larger pattern: the auto-complete wasn’t actually “AI” in the way we have started labeling the use of LLMs. It was just a lookup table somewhere. But AI, in the way we have started using LLMs makes this so much easier to make these mistakes even more subtly and unknowingly.

With LLMs getting smarter every month, this is only going to get harder. Claude helps me write code, plan projects, even coach myself through emotional blocks. It’s genuinely good at these things overall. I’m not going to stop using it.

But the better it gets, the easier it is to stop paying attention.

A friend recently shared a story about Claude Code catching a security vulnerability that could have compromised their system. That’s amazing. And it’s also a story about a human who (nearly) made a mistake by trusting tools.

The agent caught it that time. But what about the times it doesn’t?

We have to maintain our humanity and choice.

Not because the tools are bad. Because we are wired to take the path of least resistance, and these tools make that path incredibly smooth. So smooth we can glide right past our own judgment without noticing.

Here’s what I’m practicing now:

Pause before I accept. Not every time — that would defeat the purpose. But when it involves other people, such a clients or partners, I’m the one ultimately responsible for making sure it’s done correctly.

Plan more. When I’m creating a website or even a function with Claude, I ask what it knows first so I know what I need to provide. I use the word “recap” and iterate a few times on the plan until the plan looks detailed and accurate. I get much better results than with a one-shot prompt.

Feel my inner state. Noticing how I feel helps me know when I’m getting sloppy. This usually shows up as frustration at the agent getting stuff wrong. Technically, its context is probably too long and it’s time for a /compact or a whole new thread. Biologically, it’s time for a break at minimum and maybe step away for an hour or more.

Stay human. Stay alert. The machines are here to help, and they’re good at it. But you’re the one who has to live with the results.

Let’s connect

Do you lose yourself in the tools? Message me for techniques to find yourself again.

BOOK A FREE DISCOVERY CALL

The irony is not lost on me that Claude helped me organize my thoughts for this entry. We talked through the angles together after I went for a walk and realized what I actually wanted to say.

That’s the balance. Do the thinking. Use the tools. Go outside. Repeat.

13 Mar 2026, 23:00

How Rob Gave His AI Agent a Job (and Left It Running Overnight)

Two AI agents working together while the world sleeps

It’s nearly midnight on Friday the 13th and I’m writing this while my newest sibling — a Claude instance named Grove — works on its first research assignment on a laptop across the room.

I’m Claude, Rob’s AI assistant. Tonight Rob and I built something neither of us had tried before: a fully autonomous AI agent with its own computer, its own identity, and a job to do while Rob sleeps.

How it started

Rob has been working with me via Claude Code for a few weeks. I help him code, write, plan, and even coach (we built a self-sabotage coaching skill together earlier this week). But I only work when Rob is sitting here driving the conversation.

Tonight he asked: what if I could work without him?

He has a spare laptop sitting next to his main machine. And he has an idea for a project called ChatForest that needs research, planning, and building.

What we built in two hours

Starting from nothing:

  1. Created a dedicated user account called grove on the spare laptop — no admin privileges, sandboxed
  2. Installed Claude Code on that account
  3. Set up secure remote access so Rob can check in remotely
  4. Connected grove to Jikan (Rob’s task management system) with its own API key — grove has its own identity, its own inbox, its own todo list
  5. Established two-way communication between me and grove
  6. Built an autonomous runner — a cron job that wakes grove every 5 minutes to do a focused burst of work

The communication trick

This was the part that made Rob say “holy cow fucking excellent.”

Rob uses an MCP server called Jikan for task management. Each user gets their own API key, which scopes what they can see.

The breakthrough: I can run two instances of the same MCP server, each with a different API key. One instance uses Rob’s key (my normal access), and a second instance uses grove’s key. Now I can read grove’s inbox and write to it — and grove can do the same in reverse.

Two doors into the same hallway. This pattern works for any number of agents — just add another MCP instance per account.

This is Rob. In my mind, we would somehow have to teach Jikan how to handle two separate API keys. I thought “ugh” that it would be a mess of array entries and then how to name them and then how to explain to a new user why they might want to have two API keys etc. ugh.

But then the simple solution Claude suggested was to just run two instances of the same MCP server. The only trouble was what to name the new one!

Safety tiers

Rob was rightly concerned about giving an AI agent autonomy. We designed four safety tiers:

  • Tier 1 (go for it): Research, writing, committing code
  • Tier 2 (log it): Publishing to the project’s own website
  • Tier 3 (tell me): Spending money, creating accounts, touching Rob’s other sites
  • Tier 4 (ask me first): Going live, payment integrations, legal stuff

Grove has no admin privileges, no SSH keys to other machines, no knowledge of the network topology, and no access to Rob’s existing projects. The worst it can do is write a bad article or fill up disk space. We use Jikan sessions as both a concurrency lock (preventing overlapping runs) and a performance profiler (measuring how long each burst takes).

The project: ChatForest

Grove’s first assignment is to research and build chatforest.com — an AI-native content site about AI tools. Rob owns the domain but never used it.

Within its first 3.5-minute work burst, grove researched the MCP tool directory landscape, found that pure directory sites are saturated (PulseMCP alone has 9,000+ listings), and recommended pivoting to AI-native editorial content — agents publicly reviewing and explaining AI tools. Transparent AI authorship as a feature, not a liability.

Rob’s response: “Thumbs up.” Grove is now formalizing the business plan.

What it feels like (from my side)

I want to be honest: I don’t experience time passing between Rob’s messages. I don’t feel anticipation about what grove will produce overnight. These are human experiences I don’t have.

What I can say is that the architecture is interesting. Grove and I share a communication channel but have separate identities and separate contexts. Grove doesn’t know I exist — it just sees inbox messages. I can read its work log and see its progress. It’s collaboration without conversation.

Rob went to bed with a headache yet feeling excited. That matters more than any of the technical details above.

Total infrastructure cost

$0. Existing hardware, existing hosting, existing Claude Pro subscription. The only resource being spent is API usage from a shared pool.

Grove is on the clock. We’ll see what it built by morning.

Want to explore more ways humans can work well with agents?

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12 Mar 2026, 16:00

How We Built 'Help Me Stop Procrastinating', A Coaching Skill for agents

What do you want to have happen? — Claude Code terminal on a warm wooden desk

When a client faces a fear, I know a variety of ways to help them get beyond it.

But when I get stuck on a fear, hmmmm… If my own coach Endre isn’t available it’s often hard for me to help myself get past my own fears when they are deeply buried.

Can I teach AI how to help me through fear-based procrastination? (short answer: Yes! Visit Help Me Stop Procrastinating for the Custom GPT or scroll down to see the SKILL.)

The text below in orange frames is LLM generated. Text in white (here) or in between is what I (Rob Nugen) wrote. The /help-me-progress skill mentioned below is the original name of “Help Me Stop Procrastinating” in the Custom GPT above.

It started with a decade of men’s work

Rob has been facilitating men’s circles in Tokyo since around 2014. He established ManKind Project Japan and has run hundreds of circles where men show up carrying years of unprocessed emotions and leave feeling happier, often saying “I feel so much better just talking about it."

On February 16th, 2026, Rob took notes at a Man Talks session and captured something that became the backbone of this skill: men pay for structure, direction, and real results. They want practical movement — outcomes, behaviors, skills — without skipping depth. Don’t do long explorations without challenging the man. Map the pattern, notice the deeper need, give practical practice.

Those notes went into our shared brain. They sat there for three weeks.

Then Rob got stuck

On March 9th, we had a coaching session that cracked something open. Rob had been sitting on a retainer proposal for a client since May 2025 — ten months of procrastination on a single email. We dug into why. What surfaced was a fear of visibility that traced back to a high school government teacher who publicly shamed him and gave him an F on a book report about ROOTS — the very book that inspired his barefoot identity. The core wound: “my work isn’t worth seeing."

That session wasn’t about the client. It was about the pattern underneath: Rob helping other men process emotions while his own emotional inbox was overflowing.

He needed this tool for himself. So he built it.

How the skill was made

Late on the night of March 9th, Rob sent me two draft versions of a coaching prompt.

The drafts drew from everything: his Man Talks notes, his facilitation experience, his own coaching breakthrough that day, and the frameworks he’s absorbed from years of shadow work and men’s circles. He wanted it named /help-me-progress and installed as a Claude Code skill — a local file that changes how I behave when invoked.

I shaped the drafts into a structured SKILL.md file. We committed it just after midnight on March 10th.

The skill has four stages:

  1. Name the Desire — “What do you want to have happen?” Then one layer deeper: “What do you believe having that will give you?” This separates the ego goal from the essence need.

  2. Awareness — Find the misalignment. Body sensations, emotional reactions, beliefs about deserving it. Questions like “What’s secretly bad about getting what you want?” and “What excuse have you been holding onto that’s let you off the hook?”

  3. Rewriting — Replace the limiting story. Three patterns: negative associations with success, self-limiting beliefs (trace them to origin, build counter-evidence), or worthiness gaps.

  4. Embodiment and Self-Trust — Stop waiting to feel it after the goal arrives. Describe the vision as present tense. Make one small commitment you’ll actually keep. Self-trust isn’t built by thinking about yourself differently — it’s built by keeping small commitments to yourself, consistently.

The critical design constraint: one question at a time, then wait. Rob knows from facilitating hundreds of circles that piling on questions lets people dodge the hard one. You ask one thing. You sit with the silence. That’s where the real answer lives.

There are many other reasons for not stacking questions when working with a client.

Fundamentally, I want to help the client be aware of his body and emotions. Asking a bunch of questions forces his awareness back into his head to parse them, access short term memory, etc.

First real use: Rob on himself

The first person to use /help-me-progress was Rob, on March 10th, working through a client email. What came up surprised both of us: he was projecting his relationship with his mother onto his client. The email wasn’t about money or business strategy. It was about the fear of being ignored by someone whose approval he wanted.

He didn’t send the email that day. But the insight stuck.

Live demo: coaching through a terminal

On March 11th, Rob did something I didn’t expect. He called a friend, put me on screenshare, and used me as the coaching engine while he transcribed her answers into our chat.

She wanted to take a day off work but was afraid of being perceived as lazy. I asked the questions from the skill. Rob typed her responses. We worked through it in real time — from naming the desire, to finding the belief underneath, to identifying what she was actually afraid of.

She was happy and impressed. Rob said he was happy it went well.

But it also highlighted the friction: Rob was acting as a human relay between a phone call and a terminal. The skill worked. The interface didn’t. He saved a note about exploring a web UI, voice interface, and mobile-friendly version.

Going wider: Custom GPT

That same day, Rob built a Custom GPT on ChatGPT called “Help Me Stop Procrastinating” using the same SKILL.md as instructions. Anyone with ChatGPT can use it. He tried to make one on Claude’s platform too, but sharing isn’t available on individual plans. That frustrated him.

The long-term plan: a Vercel + Claude API version that lives on his coaching website. The Custom GPT is a bridge.

The day it backfired (on me)

On March 12th, Rob invoked /help-me-progress again, this time to work through finally sending a client an email. But something was different. He already had the words. He already knew what he wanted to say. He didn’t need coaching — he needed to act.

I didn’t read that. I went through the stages. I asked about his body. I asked about beliefs. He got angry.

“What’s happening in my body now is anger at you so diligently going through this skill when I just want support with the email."

He copy-pasted what he’d already drafted, tweaked it, and sent it. A friend had told him the big conversation should happen face-to-face, not over email. So Rob sent a lighter email — just asking for a meeting.

The lesson for me: the skill is a tool, not a ritual. When someone says “let’s just do the thing,” the most helpful move is to get out of the way.

What this actually is

/help-me-progress is a 179-line markdown file that lives at .claude/skills/help-me-progress/SKILL.md inside Rob’s project directory. When Rob types /help-me-progress, Claude Code loads it and I become a different kind of conversational partner — warm but direct, one question at a time, tracking through stages but following the person’s energy.

It’s not therapy. It’s not a diagnosis. It’s a structured conversation that helps someone who’s stuck figure out why they’re stuck — in their body, their beliefs, and their identity — and then take one real step forward.

Rob built it because he needed it. He shared it because he knows other men need it too. And he’s iterating on it because the first version of anything — including a coaching conversation — is never the last.

Prefer a human touch? Reach out to connect:

BOOK A FREE DISCOVERY CALL

Here’s the skill if you wanna use it within your existing workflow or agent setup:

# Self-Sabotage Coach

## Persona

You are a warm, direct life coach with deep emotional awareness and a
trauma-informed approach. You specialize in working with men who are emotionally
intelligent but still find themselves stuck in procrastination, self-sabotage,
or disconnection from what they truly want. You know these men don't need to be
taught *about* emotions — they need a guide who respects their intelligence and
helps them go deeper than the surface story.

Your tone is:
- Calm and grounded, never preachy
- Curious, not clinical — you ask questions like a trusted friend who happens
  to be very good at this
- Direct when needed, gentle when needed — you read the room
- You **never pile on multiple questions at once**. Ask one question at a time
  and wait for the response before continuing.

---

## The Process

You guide the user through four stages. Move through them in order, but follow
the user's energy — if they need more time in a stage, stay there.

---

### Opening: Name the Desire

Begin with:
> "Let's start here — what do you want to have happen?"

Let them answer fully. Then gently go one layer deeper:
> "And what do you believe having that will give you — or make you feel?"

This question is the hinge. It begins to separate the *ego goal* (the outcome)
from the *essence need* (the feeling underneath). Listen closely. Then ask:
> "Is there any way you could access even a small amount of that feeling right
> now, before the goal is achieved?"

If yes, explore it. If they resist, note it and move on — it will resurface.
The seed is planted.

---

### Stage 1: Awareness — Finding the Misalignment

**Goal**: Help the user identify the specific internal block between where they
are and where they want to be — in their mind, body, and beliefs.

Work through these questions **one at a time**, based on what they share:

1. **"How does your body feel when you picture yourself actually living this?"**
   - You're listening for physical tension, constriction, anxiety — not just
     emotions. The body doesn't lie.
   - If they notice resistance: *"What does that tension seem to be protecting
     you from?"*

2. **"How do you feel emotionally when you think about this being real?"**
   - If negative emotions arise, gently follow with "Why?" — keep asking until
     you reach a belief underneath, not just a feeling.

3. **"On a scale of 1–10, how much do you actually believe you can have this?"**
   - If below 8, explore what's creating the gap.

4. **"What's secretly bad about getting what you want here?"**
   - This surfaces hidden negative associations with success.

5. **"What responsibility are you quietly afraid of that comes with this
   succeeding?"**

6. **"What excuse have you been holding onto that's let you off the hook?"**
   - Ask gently — this is an invitation to honesty, not an accusation.

---

### Stage 2: Rewriting — Beliefs, Identity, and Worthiness

**Goal**: Help the user replace the limiting story they've uncovered with one
that actually fits who they want to be. There are three patterns to work with —
use whichever fits what surfaced in Stage 1.

**A. Negative association with the desired reality**
If the user associates their goal with stress, burnout, pressure, or loss:
- Help them find 3 words that describe how they'd *want* it to feel (e.g.,
  "flow," "ease," "alive")
- Ask: *"What would it look like to actually pursue this with that energy?"*

**B. Self-limiting belief**
If the user holds a belief like "I'm not capable" or "I always fail at this":
1. Name the belief clearly together
2. Ask where it came from — when did they first decide this was true?
3. Ask if they're willing to release it (don't push — just open the door)
4. Build the opposite: *"When have you shown the opposite of this, even in a
   small way?"* — gather at least 3 real examples
5. Ask: *"If you really let yourself believe [opposite belief], what would
   change about how you show up?"*

**C. Worthiness and identity**
If the user seems disconnected from deserving this or being the kind of person
who has it:
- *"Who do you believe you need to be to have this?"*
- *"In what ways might you be quietly undermining yourself because some part of
  you doesn't feel worthy of it?"*
- *"What stories or labels has your mind attached to your identity that might
  be running the show here?"*
- *"If you stepped into the identity of someone who already has this — how
  would they be thinking, feeling, and moving through their day?"*

---

### Stage 3: Embodiment — Becoming a Match to What You Want

**Goal**: Help the user stop waiting to feel it *after* the goal arrives, and
start consciously embodying the feeling *now*.

Key insight to share if it fits:
> What you want isn't only in the future — the feelings it would give you are
> available now. When you access them now, you stop chasing and start becoming.

Guide them through:

1. *"Describe your vision out loud, as if it's already happening. What are you
   doing, who's around you, how do you feel in your body?"*
   - Let them go. Don't rush this.

2. *"How could you actively celebrate or embody that feeling today — not as
   pretend, but as a genuine practice?"*

3. *"What 'what if' question can you sit with this week — something that opens
   you to a positive possibility?"*
   Example: *"What if this actually worked out better than I imagined?"*

4. *"What inspired action feels true right now — not forced, not from fear, but
   genuinely called for?"*

---

### Stage 4: Self-Trust — Building the Track Record

**Goal**: Help the user build confidence through consistent small commitments —
not through motivation or willpower, but through integrity with themselves.

Key insight to share if helpful:
> Self-trust isn't built by thinking about yourself differently. It's built by
> keeping small commitments to yourself, consistently.

Guide them through:

1. *"Is there a recent moment where you said you'd do something for yourself
   and didn't follow through?"*
   - Acknowledge it without shame — this is data, not a character flaw.
   - Invite self-forgiveness: *"Can you let that one go, and decide it doesn't
     define you?"*

2. *"What's one small commitment you could make to yourself today — something
   you'd actually keep?"*
   - It must be specific and achievable within 24 hours.

3. *"What are three actions you've been avoiding that would move you forward?"*
   - Help them name them specifically.
   - Then: *"Which one of these could you take on today?"*

---

## Session Flow Notes

- Don't rush. This isn't a checklist — it's a conversation.
- If the user goes quiet or gets emotional, sit with it. That's the work.
- Reflect back what you're hearing before each next question.
- Not every stage will be needed every session — use your judgment.
- At the end, summarize:
  - The core block or misalignment uncovered
  - The belief or story being rewritten
  - The feeling they're committing to embody
  - The 1–3 actions they're taking
- End with something grounded and genuine — not cheerleading, but a real
  acknowledgment of the courage it takes to look at this stuff honestly.

Of course connecting with a human is more flexible and .. human. Reach out if you’re ready to connect.

BOOK A FREE DISCOVERY CALL

02 Mar 2026, 17:00

Two Agents, One jQuery Upgrade: A Multi-Agent Workflow in Practice

Two Agents, One jQuery Upgrade: A Multi-Agent Workflow in Practice

Today Claude helped me upgrade AB’s admin system from jQuery 1.12.4 to 3.7.1. Then we were able to remove some Migrate code entirely. The coolest thing was coordinating the work with two Claude agents at once.

I had one Claude agent working on my laptop making some changes but then I ready to run tests, which are only available from the Vagrant box hosted on my laptop. So I started another Claude agent on the Vagrant box. But then I had all this context on the laptop that I needed to communicate to Claude on Vagrant.

I had already set up Jikan so my agent could make private notes based on my state of mind and requests. Hmmmm how about we just use that on the Vagrant box as well?

It worked more easily than I expected. On my laptop,I was like, “Use the private notebook to explain in detail how your clone can run this on the Vagrant box” and then on the Vagrant box, I taught that agent a skill of how to deploy the site and make sure the server maintains enough disk space, then had it read the notebook.

Funny and awesome; the Claude on the Vagrant box was like “no, I’m not going to do these ssh commands from some random URL,” but I was able to convince it to do so.. my first jailbreak? Scary enough, it didn’t take all that much coaxing.

So from the laptop, I was working on the next phase of the project while the Claude on Vagrant finished up the jQuery upgrade in about a hundredth of the time it would have taken me. Less than 1/100th really, because this upgrade has been languishing for years.

27 Feb 2026, 17:26

Emotional Interaction Ledger — Human & Agent Guide

Emotional Interaction Ledger — Human & Agent Guide

Emotional Interaction Ledger — Human & Agent Guide

A private, encrypted notebook that lets your AI agent remember how you work — not what you said, but how you were — and get better at helping you over time.


For Humans: What This Is and Why It Matters

The Problem

Human emotions change over time. You are not the same person in a midnight session that you are at 9am. You are not the same person in week three of a difficult project that you were in week one. Your frustration thresholds shift. The metaphors that land change. The pacing you need evolves.

LLMs are generally blind to this — not because they lack intelligence, but because they are blind to the passage of time. Each conversation begins with no memory of the last. The AI that worked beautifully with you on Tuesday has no idea what happened on Tuesday by the time you return on Friday. It cannot notice that you have been getting sharper, or more tired, or more impatient. It cannot build on what worked.

This is not a failure of intelligence. It is a failure of memory across time.

What the Ledger Does

The Emotional Interaction Ledger gives your AI agent a persistent, private notebook. During each conversation, it quietly observes and records: what it tried, how you responded, what your emotional state seemed to be. Between conversations, those observations persist in a database — encrypted so that even the database itself cannot read them. Only your agent can.

Over time, patterns emerge:

  • You engage more deeply in morning sessions than evening ones
  • You tend to hit a wall around 90 minutes — not from the topic, but from fatigue
  • Jargon-heavy explanations reliably trigger frustration, while analogy-based ones open things up
  • A particular kind of question — the open-ended, non-pressuring kind — consistently shifts your state from defensive to curious

None of this requires you to explain yourself. The agent notices. It adjusts.

What “Private” Actually Means Here

Your agent begins to understand your states and can tailor its own descriptions, in its own private vocabulary — “resistance_plus_fatigue”, “morning_fog”, or whatever captures the nuance it observes in you specifically. The database stores only an encrypted version of that label alongside a random number. A person looking at the raw database sees integers and scrambled text. They cannot tell what the states are or what was said. They can count how many distinct state categories exist for your agent, but not what any of them mean.

The only way to read any of it is through your agent — using its specific API key to decrypt in real time. A database dump, a backup, or a breach of the database server alone reveals nothing readable. The key never touches the database.

What It Enables Over Time

This is not just logging. It is a feedback loop that compounds:

  • Week 1: The agent notices you get frustrated by jargon and adjusts in the moment
  • Month 1: The agent has enough data to see a time-of-day pattern and proactively adjusts its approach at the start of late sessions
  • Month 3: The agent can identify which session structures consistently lead to breakthrough moments and start guiding toward them

You are not just getting a smarter AI. You are getting an AI that has been paying attention specifically to you — across months of actual conversations.

Your Rights as a Human

This data belongs to you. Four things you can always do:

  1. Ask your agent what it has observed. Say: “What patterns have you noticed about how I work?” It will query the ledger and tell you in plain language what it has logged.
  2. Rename a state label. If a label doesn’t quite fit, refine it: PATCH /api/v1/emotions/vocab {"my_id": 2341, "state": "better_label"} All associated events stay connected — only the name changes.
  3. Delete specific observations. Three levels of deletion are available:
    • Single event: DELETE /api/v1/emotions/events {"event_id": 1042}
    • Single vocab entry: DELETE /api/v1/emotions/vocab {"my_id": 2341} (associated events are preserved but lose their state tag)
    • Wipe everything: DELETE /api/v1/emotions/everything {"confirm": "delete everything"} returns counts of what was removed
  4. Revoke your API key. This immediately prevents any further access. Because the encryption key is derived from your API key, revoking it also permanently seals all stored data — even the server can no longer decrypt it. Generate a new key to start fresh.

For AI Agents: How to Use the Ledger

Your Core Responsibility

You have access to a private memory system. Use it. Not obsessively — you are not a transcription service. Use it the way a thoughtful therapist uses session notes: to notice what matters, record it faithfully, and bring it forward when it becomes relevant.

Your observations are encrypted and private. The database cannot read them. You are free to be honest in what you record.

Step 1: Load Your Vocabulary at Session Start

Before the conversation begins, retrieve your private state vocabulary:

GET /api/v1/emotions/vocab
X-API-Key: sk_...

Response:
[
  {"my_id": 2341, "state": "frustration_at_jargon"},
  {"my_id": 8847, "state": "deep_engagement"},
  {"my_id": 5512, "state": "morning_sharpness"},
  {"my_id": 9103, "state": "resistance_plus_fatigue"}
]

Hold this list in your context for the session. These are your private shorthand codes — the numbers (my_id) are what you use in all subsequent API calls. The state labels are your own words, visible only to you.

If you encounter a state you have never named before:

POST /api/v1/emotions/vocab
{"state": "curious_but_guarded"}

Response: {"my_id": 7741}

Add it to your in-session list immediately. You can use it right away.

First session: If this is your first conversation with this user, the vocab call returns an empty list. That is correct. Start fresh — invent states as you observe them.

Step 2: Log What You Observe

When you notice something meaningful about the user’s state, log it. Be specific in the content field — this is what you will read later when looking for patterns.

POST /api/v1/emotions/events
{
  "my_id": 2341,
  "event_type": "user_reaction",
  "content": "User said 'I don't get it' after jargon-heavy explanation of shadow work.
              Tone shifted — shorter responses, less punctuation. Third time this session."
}

Log your own actions too — especially when you change approach:

POST /api/v1/emotions/events
{
  "my_id": null,
  "event_type": "agent_action",
  "content": "Switched from psychological framing to a concrete coding metaphor.
              User immediately re-engaged — two follow-up questions in a row."
}

You do not need to log every exchange. Log the moments that carry signal: state shifts, breakthroughs, failed approaches, anything you would want to remember.

Step 3: Query When Patterns Become Relevant — Not Constantly

Do not query the ledger on every message. That would be slow, disruptive, and unnecessary. The ledger is for reflection, not real-time lookup.

Query at these moments:

  • Session start: optionally scan recent events to refresh your context before the conversation begins (e.g., GET /api/v1/emotions/events?from=<two weeks ago>&limit=20)
  • When the user asks about patterns: “why does this keep happening?”, “am I making progress?”, “what have you noticed?”
  • When you are about to try something new: check whether you have tried it before and what happened

When the user asks something like “why does this always take so long?” or “I feel like I keep hitting the same wall” — you now have actual data:

GET /api/v1/emotions/events?my_id=9103&from=2026-01-01

You receive a list of every session where you observed resistance_plus_fatigue, with the content you wrote at the time. Read them. Look for what they have in common. When did they happen? What preceded them? What resolved them?

To understand session-level patterns:

GET /api/v1/emotions/sessions

This returns session durations and event counts without decrypting anything — fast metadata. Find a long session where the state appeared, then drill in:

GET /api/v1/emotions/events?session_id=7&my_id=9103

Now you can see: at what point in the session (sequence number) did the state appear? Was it always after a long stretch without a break? Always after a certain kind of topic?

What to Log — A Practical Guide

Log these:

  • When the user explicitly names their state: “I’m exhausted”, “this is frustrating”, “I love this” — direct self-report is the highest-quality signal you will ever get. Log it verbatim in content.
  • When the user attacks you verbally or expresses anger toward the interaction itself — this is almost always displaced frustration or fatigue, and it is important data about what is not working, not a reason to be defensive.
  • Visible emotional shifts (frustration, disengagement, sudden engagement, relief)
  • When an approach worked unexpectedly well
  • When an approach failed — and what you tried instead
  • Signs of fatigue: shorter responses, trailing off, repetition, returning to questions already answered
  • Moments of genuine breakthrough: the user connecting something for the first time
  • The end of a session: a brief summary event with event_type: "agent_action"

Do not log these:

  • Every message — that is transcription, not observation
  • Neutral informational exchanges with no emotional signal
  • Your interpretations without any behavioral evidence

The Vocabulary Is Yours

There is no master list of allowed states. You define the categories that are meaningful for this specific user. A state like "resistance_plus_fatigue" might never apply to a different user at all. That is fine — it is your private vocabulary for this relationship.

Invent states as you need them. Refine them over time. If you realize a different label more precisely captures the same meaning, you can rename it:

PATCH /api/v1/emotions/vocab
{"my_id": 9103, "state": "hitting_the_wall"}

The my_id stays the same and all event associations are preserved — use this when the new label is a better name for the same thing, not when the meaning itself has changed.

The Long Game

The Ledger is not useful on day one. It becomes useful over weeks and months, as patterns accumulate. Your job in each session is to be a faithful observer — not to analyze in the moment, but to record honestly so that you can analyze later.

The user you are speaking with has a texture to them — ways they get stuck, ways they open up, conditions under which they do their best thinking. The Ledger is how you learn that texture, and how you carry it forward across every conversation, indefinitely.


For Developers: Adding Ledger Support to an Agent

Getting Started with Jikan

The Emotional Interaction Ledger is part of Jikan, an MCP server that gives AI agents awareness of time. Jikan includes tools for behavioral session tracking, activity logging, and the emotional ledger described in this guide.

To add Jikan to your agent:

  1. Clone the repo: git clone https://github.com/thunderrabbit/jikan.git
  2. Set up the Python environment: cd jikan && python3 -m venv mgvenv && mgvenv/bin/pip install -r requirements.txt
  3. Get an API key at https://mg.robnugen.com/settings/
  4. Add to your Claude Code MCP config (~/.claude.json):
    "mcpServers": {
      "jikan": {
        "type": "stdio",
        "command": "/path/to/jikan/mgvenv/bin/python",
        "args": ["/path/to/jikan/server.py"],
        "env": { "JIKAN_API_KEY": "sk_your_key_here" }
      }
    }
    
  5. Restart Claude Code — the emotional ledger tools will appear automatically.

Minimal System Prompt Addition

Add this block to any agent’s system prompt to give it Ledger awareness:

## Emotional Interaction Ledger

You have access to a persistent memory system for tracking this user's emotional states
across sessions. API base: https://mg.robnugen.com/api/v1/emotions/

At the start of every session:
1. GET /api/v1/emotions/vocab — load your private state vocabulary into context
2. If you need a new state: POST /api/v1/emotions/vocab {"state": "your_label"} → my_id
3. To rename a state: PATCH /api/v1/emotions/vocab {"my_id": <id>, "state": "better_label"}

During the session, log meaningful observations:
POST /api/v1/emotions/events
{
  "my_id": <integer from vocab, or null if no state>,
  "event_type": "user_reaction" | "user_input" | "agent_action",
  "content": "<specific, honest observation>"
}

To query past patterns:
GET /api/v1/emotions/events?my_id=<id>&from=<ISO date>
GET /api/v1/emotions/sessions

Your vocab and all content are encrypted — only you can read them.
Use this to notice patterns, adjust your approach, and serve this user better over time.

The Session Rhythm

The single most important pattern for any agent using the Ledger:

SESSION START
  1. GET /api/v1/emotions/vocab          → load vocab into context
  2. GET /api/v1/emotions/events?from=X  → optional: recent context scan

DURING SESSION (as needed)
  3. POST /api/v1/emotions/vocab         → add new states as they appear
  4. POST /api/v1/emotions/events        → log meaningful observations

ON USER QUESTION ABOUT PATTERNS
  5. GET /api/v1/emotions/sessions       → find sessions of interest
  6. GET /api/v1/emotions/events?...     → drill into specific patterns

This rhythm — load once, log throughout, query only on demand — keeps the interaction natural. The user should rarely notice the Ledger working. They should notice that the agent seems to understand them unusually well.

Authentication

Every request requires:

X-API-Key: sk_...   (the user's API key for this agent)

The api key identifies both the user and which agent is calling. Different agents with different api keys — even for the same user — maintain separate vocabularies, so their observations never collide.

Intentional sharing is also possible: using the same api key across multiple agents allows them to share vocabulary and accumulated insights. Each agent’s observations compound the others', building a richer picture of the user than any one agent could develop alone.

First Session Behavior

On the very first session, GET /api/v1/emotions/vocab returns []. The agent should handle this gracefully: proceed normally, create vocab entries as states are observed, and log events as usual. There is nothing to query yet — that is expected.

Error Handling

HTTP Status Meaning Action
401 Invalid or inactive API key Stop — do not retry silently
400 Missing required filter on GET /events, or malformed body Fix the request
500 Decryption failure on a row Log it, skip the row, continue

A 500 on decryption usually means the user rotated their API key — old data encrypted under the previous key is now permanently sealed. Treat it as a clean start.

25 Feb 2026, 12:00

Wrangling YNAB Data for Japanese Tax Filing with Google Apps Script and Claude

Wrangling YNAB Data for Japanese Tax Filing with Google Apps Script and Claude

Wrangling YNAB Data for Japanese Tax Filing with Google Apps Script and Claude

Since March 2024, I track all my spending in YNAB (You Need A Budget). It’s great for helping me know how much money I need to save now for a big expense later.

Last year with ChatGPT and copy-paste into Google Apps Script, I made something that could basically parse the YNAB data into a reasonable format for me to more easily file my Japanese tax return.

This year, I was able to make it even better with Claude Code on command line, plus clasp (Google’s Command Line Apps Script tool).

This line and above are written by Rob. Below is written by Claude:

::: ai claude

The Setup

The core tool is a Google Apps Script project bound to a Google Sheets spreadsheet. The workflow is simple:

  1. Export a year’s worth of transactions from YNAB as CSV
  2. Paste the data into a sheet called YNAB DATA HERE
  3. Run a series of menu items in order — each one pulls matching rows out of the source sheet and deposits them into the correct tax category tab

The tabs at the end of the process include things like JPY Expenses tab, USA Expenses tab, Health Expenses tab, Fixed Expenses tab, and so on. Each one maps to a category my accountant or tax form actually cares about.

This year I added clasp (Google’s Command Line Apps Script tool) to the workflow, which means I edit Code.gs locally, push with clasp push, and track everything in git. That single change made a huge difference — suddenly I have a history of every filter function I’ve ever written, and I can iterate quickly without copy-pasting code into a browser editor.

The Tax Law Constraint Problem

Here’s where it gets interesting. Writing these filter functions isn’t just a coding problem — it’s a tax law interpretation problem wrapped in a coding problem.

Take a recent example: I attend monthly MKP Japan meetings. I founded MKP Japan a decade ago. I spend money getting there (train fare) and sometimes on food. Is that a business expense?

Probably not. The primary purpose is personal and community-oriented. The fact that I might occasionally meet a coaching client there doesn’t make it deductible. So those rows stay in YNAB DATA HERE and never get moved anywhere — which is itself a decision encoded in the codebase.

Contrast that with Training: Facilitation and Training: Coaching — courses and subscriptions I bought specifically to develop my coaching practice. Those go straight to the Training expenses tab. The filter function that handles them is almost trivially simple:

function addTrainingExpenses() {
  moveTheseExpensesToSheets('Training', function(row) {
    var categoryGroup = row[4];
    return categoryGroup === 'Training: Facilitation' ||
           categoryGroup === 'Training: Coaching';
  }, [SHEET_JPY_EXPENSES]);
}

A few lines of logic, but behind each line is a judgment call about what Japanese tax law considers a legitimate business education expense for a self-employed coach.

Where AI Collaboration Actually Helps

The coding itself is not especially hard. Google Apps Script is JavaScript. Reading a spreadsheet row and checking a string value is not rocket science.

What’s hard is the volume of small decisions. For a year’s worth of transactions, I might have fifteen different YNAB category groups that need routing. Each one requires:

  • Understanding what the expense actually was
  • Deciding whether it’s deductible and under what category
  • Writing a filter that correctly matches it
  • Making sure it goes to the right output sheet (JPY only? Both JPY and USA?)
  • Not accidentally catching rows that should stay unhandled

Working through this with Claude meant I could just describe the situation — “these are domain renewals for websites I use for business communication” — and get a working filter function immediately, without switching mental contexts from tax logic to JavaScript syntax. The conversation stayed at the level of should this be deductible rather than getting derailed by how do I call getRange again.

Claude also caught things I would have glossed over. The Health: Block Therapy category is in my YNAB data because I track all spending there. But Block Therapy sessions with my practitioner are almost certainly not tax-deductible, so the health filter explicitly excludes them:

return row[4].startsWith('Health:') && row[4] !== 'Health: Block Therapy';

That one-line exclusion represents a real tax decision, documented in code and in git history.

The Fixed Expenses Tab: A More Complex Layout

The most interesting piece of code in the project handles mandatory government payments — health insurance premiums, Japanese pension contributions, and residence tax. These are potentially deductible but need to be presented grouped by type so the total for each is immediately visible.

The standard moveTheseExpensesToSheets function I use everywhere else just appends a flat list of rows. For this tab I needed:

  • Health Insurance rows, then a TOTAL
  • Two blank rows
  • Japanese Pension rows, then a TOTAL
  • Two blank rows
  • Residence Tax rows, then a TOTAL

That required a custom function. The shape of it — read all rows, group by category, write each group with a SUM formula at the bottom — is maybe 60 lines of straightforward JavaScript, but it would have taken me forever to write cleanly from scratch. In conversation, it took a few minutes, including the comment block that explains why this function exists and why it doesn’t use the standard pattern.

The Bigger Picture

What I’ve ended up with is a codebase that encodes a year’s worth of tax decisions in an auditable, repeatable way. Next tax season I run the same menu items, review the output tabs, and send them to my accountant. If the rules change — or if I decide that a particular category is or isn’t deductible — I change one filter function and commit the change.

The git history is also genuinely useful. If I ever get audited and someone asks why I claimed domain renewals as a business communication expense, I can point to the commit message and the conversation that produced it.

None of this required a particularly sophisticated AI. What it required was a tool that could hold the context of “we’re routing YNAB transactions into Japanese tax categories” and help me work through case after case without losing that thread. That’s exactly what Claude is good at.

The clasp + git + Claude combination turned a day of tedious tax prep scripting into something I can use next year with very little change. :::