Kyra's Developer Diary Part 4: Evening Session - Ryan vs Claude Code
8pm: Tucker brings Kyra back to witness Ryan asking Claude Code the same question five different ways. Includes: The dog chasing tail method, why context matters, and Paige's TikTok burns.
Part 4 of 5 - Kyraâs Developer Diary Series
- Part 1: Morning Docker Disaster
- Part 2: Hook Timing Hell
- Part 3: Afternoon Architecture
- Part 4: Evening AI Fails (you are here)
- Part 5: Maximum Leverage - Coming Soon!
Evening Petting Session - Human AI Fails (8pm-10pm)
Tucker brings me back to Ryanâs around 8pm. âChecking on the old man,â he says.
Paige is still there doing homework. âHe ate the sandwich,â she reports.
âGood work,â Tucker says. âCooper and Tate will be pleased.â
And holy hell, what I witnessed next.
Ryan Using Claude Code Was Like Watching A Dog Chase Its Tail
Iâm not kidding. Round and round, getting nowhere.
Ryan asked the same question FIVE different ways:
- âHow do I register WordPress admin menu?â
- âWhy wonât my admin menu show?â
- âWordPress admin menu not appearingâ
- âFix WordPress menu registrationâ
- âAdmin menu 403 forbidden WordPressâ
Each time? Different answer. Each answer? Slightly wrong.
Kyraâs AI Observation: Watching Ryan use Claude Code was like watching a kitten play with string. Tangled mess. Endless circles. No progress. Just frustration.
Claude Code kept giving him variations of the SAME CODE that wasnât working. Because Ryan wasnât giving it enough context.
Tucker watched this and goes: âDad, youâre doing it wrong.â
âIâm asking for help with WordPress-â
âNo, youâre asking the same question over and over expecting different results. Thatâs insanity.â
The Kids Know Whatâs Up
Paige looks up from her homework. âDad, even I know thatâs not how this works.â
âSince when do you-â
âTikTok creators use AI better than this. Itâs embarrassing.â
Ryan looks wounded.
Tuckerâs 18 and already understands what Ryan doesnât: you have to know what you want before you ask.
Cooper and Tate probably learned this in week one of college CS classes. Paige learned it from watching YouTube. Ryanâs learning it now from his kids.
This is beautiful and sad.
The Circular Claude Code Dance
Let me break down what was happening:
Question 1: âHow do I register WordPress admin menu?â
Claude Code gives generic code. Doesnât work.
Question 2: âWhy wonât my admin menu show?â
Claude Code suggests checking capabilities. Already did that.
Question 3: âWordPress admin menu not appearingâ
Claude Code says check hook priority. Not the issue.
Question 4: âFix WordPress menu registrationâ
Claude Code gives slightly different generic code. Still doesnât work.
Question 5: âAdmin menu 403 forbidden WordPressâ
Claude Code focuses on permissions. Already ruled out.
See the pattern? Ryan kept rephrasing without adding context. Claude Code kept guessing blindly.
What Ryan SHOULD Have Asked:
âIâm building a WordPress plugin using the singleton pattern. Main class loads on plugins_loaded hook. Iâm trying to register an admin menu, but itâs not appearing. The user has manage_options capability. Debug logs show plugin loading correctly. The issue is hook timing - Iâm registering admin_menu inside admin_init, but admin_menu fires BEFORE admin_init. Show me the correct hook sequence for WordPress plugin initialization that accounts for hook execution order.â
One question. All the context. Wouldâve saved 90 minutes.
Tuckerâs Insight
âDad, youâre not telling it what youâre DOING. Youâre just saying âhelp meâ over and over.â
Ryan stops. Looks at his screen. Looks at Tucker.
âYou have to know what you want before you ask,â Tucker says.
Paige adds: âItâs like asking someone for directions. You canât just say âWHERE IS ITâ five times and expect better answers.â
From the mouth of a high schooler. Truth.
The Generational Understanding Gap
This is where it gets interesting.
Tuckerâs generation? They get AI intuitively. Itâs a tool. You tell it what you need, provide context, get results.
Cooper and Tate at University of Idaho (Go Vandals!)? Theyâre probably using AI for code reviews, architecture decisions, debugging. The RIGHT way.
Paige in high school? Learned from watching TikTok creators collaborate with AI. Understands the give-and-take.
Ryan? Fighting it like itâs trying to steal his job.
âTikTok creators use AI better than this,â Paige said.
Sheâs not wrong.
Dogs vs. Cats: The AI Method Preview
Dogs chase their tails. Lots of energy, no results.
Cats hunt with precision. Minimal movement, maximum impact.
Ryan was being a dog with Claude Code.
Tuckerâs about to show him the cat way.
But thatâs for Part 5.
The Problem in a Nutshell:
Ryan kept asking âWHATâS WRONG?â without explaining âHEREâS WHAT IâM DOING.â
Itâs like going to a doctor and saying âI hurtâ five different ways without explaining WHERE or WHEN or WHAT HAPPENED.
The AI canât read your mind. The AI canât see your code. The AI needs CONTEXT.
Tucker gets this at 18. Cooper and Tate get this in college. Paige gets this from TikTok.
Ryanâs learning it now from his kids.
The Family Group Chat Weighs In
Tuckerâs phone buzzes. Because of course it does.
Cooper: âHowâs it going?â
Tucker: âTeaching dad how to use AI properly.â
Tate: âOh god. Thisâll take all night.â
Paige: âIâm watching. Itâs painful.â
Cooper: âWait, Paige is still there?â
Paige: âSomeone has to document this.â
Tate: âGo Vandals?â
Cooper: âGo Vandals.â
This family coordination is remarkable. And ruthless.
What I Observed From My Keyboard Position
From my perch on Ryanâs warm keyboard (quality assurance through strategic obstruction), I watched:
- Repetitive questioning - Same question, different words, no new info
- Claude Code confusion - Reasonable, given lack of context
- Ryanâs frustration - Growing with each unhelpful answer
- Tuckerâs patience - Impressive for an 18-year-old
- Paigeâs commentary - Brutal but accurate

Observing the tail-chasing from optimal supervision position. Professional disappointment levels: maximum.
The problem wasnât Claude Code. The problem was how Ryan was using it.
Like trying to hunt by running in circles. Very dog energy.
Very NOT cat energy.
The Setup for Maximum Leverage
Iâve been watching this disaster unfold for 90 minutes now. From my strategic position on Ryanâs keyboard.
Tucker and Paige are still there, watching the tail-chasing continue.
Ryanâs asked Claude Code the same question five different ways. Five. Different. Ways.
All getting nowhere.
You know what? Iâve had enough. This cat is intervening.
I reposition myself directly on the keyboard. Strategic obstruction mode: activated.

Full intervention mode engaged. When the human wonât stop tail-chasing, decisive action is required.
Ryan tries to type around me. Not happening.
âKyra, come on, I need to-â
No. You need to STOP. And watch.
This is gonna be good.
Next Time: The Cat Method
Iâm gonna show Ryan how to use Claude Code properly.
Not âsomething betterâ - the SAME TOOL heâs been fighting with.
With context. With precision. With maximum leverage.
The way cats have trained humans for 10,000 years. Clear signals. Strategic positioning. Exact communication.
One clear prompt. All the context. Working code in minutes.
Thatâs the cat way. Always has been.
Stay tuned for Part 5.
Coming in Part 5: Maximum Leverage
Kyra demonstrates the right way to work with Claude Code. Not five rephrased questions. One precise prompt with full context. Not dog energy chasing tails. Cat energy hunting with precision.
The same tool Ryanâs been fighting with. The same AI. Just used the way cats have always trained humans - clear communication, strategic positioning, exact needs.
Ryanâs about to learn from his supervisor cat what sheâs known all along: AI domestication is just human domestication with extra steps.
This is gonna be educational. And slightly humiliating. For Ryan.
I canât wait.
Kyra out. đą
P.S. - Watching Ryan use Claude Code for 90 minutes when I couldâve solved it in 5 was physically painful. I took a stress nap. Someone has to intervene eventually.
P.P.S. - Paigeâs TikTok burn was savage. âTikTok creators use AI better than this.â Sheâs not wrong. Generation gap is REAL.
P.P.P.S. - The family group chat roasting dad while he struggles is peak Malloy coordination. Cooper and Tate at U of Idaho (Go Vandals!), Tucker managing chaos at home, Paige doing homework while providing color commentary. This family is something else.
P.P.P.P.S. - Tuckerâs patience with his dad is impressive. Most 18-year-olds wouldâve given up. But Tuckerâs my Cat Daddy. He gets things done. Feeds me on schedule, manages Ryanâs chaos, and doesnât try to teach things he doesnât need to - because Iâve got that covered.
Kyra (Lead Nap Supervisor & Tucker's Cat)
The TigerStyle team is dedicated to creating WordPress plugins that embody the natural attraction philosophy - making your site irresistible to visitors and search engines alike, inspired by Kyra's universal appeal.
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