Three Months With Claude Code: What 35 Jobs and 26 Killed Ones Taught Me

Bottom line up front. AI support cut 90% of my writing time. Three months in, I built 35 automation jobs and killed 26. Volume alone doesn't make money — that part I confirmed the hard way.

• 3 months in
• 35 jobs active
• 26 killed
• 90% writing time saved

01 · What I have to show for 3 months, in numbers

Start with the tangible stuff. This is the automation surface I've built up over three months. Every morning, launchd runs the lot without me touching anything.

• 35 LaunchAgent jobs (26 killed)
• 12 project folders (5 blogs + α)
• 3 custom skills (only SKILL.md loads)
• 19 slash commands (/run-daily & co.)

On top of that: 13 CLAUDE.md files (1 main + 12 per-project) and 3 hook scripts. Every job ships with a wrapper, plist, and log file — so the actual file count is well past 100.

02 · Five things that actually save tokens

In Claude Code, context tokens are the bill. After three months, these are the five habits that stuck.

1. /compact — the moment the context warning fires. When the alert pops, hit it immediately. Keeps the gist, drops the rest.
2. Split out agents — separate roles for detail and deep work. Main session is the coordinator; details go to a sub-agent. Keeps the context from getting polluted.
3. /clear — every time the task switches. Going from blog work to infra debugging? Clear, no exceptions.
4. Keep CLAUDE.md slim — only the must-reads. It auto-loads every session. Push the rest into separate files and reference them only when the task calls for it.
5. Skill split — load only SKILL.md. My three custom skills sit in their own files. The full text stays out of context until needed.

03 · The three I actually use every day

Out of 19 commands, 3 skills, and a pile of plugins, these are the three I genuinely reach for daily.

The frontend-design plugin in particular changed what I can ship. Before it, I was hand-rolling CSS and the readability suffered. Now Hero, VS, and impact blocks come out clean in one pass. Eleven days in, the lift in visual quality is immediate.

04 · Automation ≠ revenue — the hardest lesson

"I assumed automated posts would mean automated income. Three months later, it's the opposite."

Root cause: automation cuts repetition cost. Revenue is built on trust. You can ship 5 posts a day, but if every one reads like a textbook, readers click and bounce.

Look at the asset count again. 35 active + 26 killed. Those 26 are the ones I built on the assumption that volume alone would pay off.

Early assumption (26 killed jobs):

• "Auto-publish daily"
• Generic / textbook tone
• Conversion flatlined

After the pivot (35 active jobs):

• Experiment logs + lived experience
• Drafts → my own review
• Reads trending up

Automation cuts repetition cost. Revenue compounds from trust. Two completely different mechanisms — I had to kill 26 jobs to internalize that. Volume without trust is worse than zero posts.

05 · CLAUDE.md ≠ memory — keep them separate

Two different contexts auto-load every session. Mix them up and things break.

The split rule is simple. "This needs to work in the next session" goes in CLAUDE.md. "Who the user is, where they work" goes in memory. Don't trust memory for operating rules — always pin them in CLAUDE.md. I caused several incidents over three months by getting this wrong.

One more thing: don't put it in either place. Concrete values (cash balances, prices) or transient state. They go stale fast — push them to a file or a database instead.

06 · Pull quote

"You still need a human's lived experience. Trust beats volume. But AI support did cut 90% of my writing time."

— Eddie, 3 months with Claude Code

07 · Six follow-ups I'll go deeper on

This post is the index. Each topic gets its own case-study post next.

1. Token saving deep dive — each of the 5 habits, in practice
2. Slash commands deep dive — how /run-daily differs across 5 blogs
3. 3 custom skills deep dive — why I built them, how they're shaped
4. Running CLAUDE.md — how I let incident logs accumulate
5. frontend-design plugin — the 30-day review
6. Hooks, memory, agents — the rest of the stack

Productivity and trust aren't substitutes. AI buys back the time. The human fills in the trust.

Disclaimer: personal 3-month retrospective. No ads, no affiliates.

Originally published at jessinvestment.com.