S4E396 — Leaving Tech

October 13, 2026 · 11 min

Show notes

Ryan’s 36-job search turns into a viciously funny audit of rejection math, remote-work delusion, and whether AI or a three-and-a-half-hour train ride actually broke the market.

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Transcript

GARY: I’m Gary, and— twenty-four of thirty-six rejected him. So twelve hired him. Excellent search.

MAEVE: I’m Maeve. Twelve did not hire him.

OBI: I’m Obi. They exist only in Gary’s imaginary payroll.

GRUNER: I am Gruner. Gary has fabricated jobs.

GARY: Right. Ryan Bigg applied for more than three dozen tech jobs.

MAEVE: Twenty‑four replies. Every disclosed reply was a rejection.

GARY: I misplaced twenty‑four rejections and hallucinated twelve salaries.

OBI: Your arithmetic has achieved founder‑market fit.

GARY: Ryan has developed software for twenty years. Books, talks, events, two widely downloaded Ruby packages.

MAEVE: He also grew his last team from two people to twelve.

GRUNER: Unlike Gary’s applicant funnel.

GARY: He says the process is causing serious harm, so he’s stepping away.

OBI: We leave that alone.

MAEVE: The dispute: tech is cooked, AI expectations are incoherent, or his search radius is strangling the market.

GARY: He works remotely from Warrnambool. Melbourne is nearby, continentally.

GRUNER: Premium Australian proximity.

GARY: Manageable commute. Coffee, train, office, train, light supper—

OBI: Melbourne is three and a half hours away by train.

GARY: Each week?

OBI: Each direction. Two office days require fourteen hours aboard.

GRUNER: Train has superior attendance policy.

OBI: Three and a half hours each way. The train got the job.

GARY: Daishi fifty-five: “Go check out the SWE subreddits, people are sending out 1000s of applications before they get something.”

MAEVE: At one thousand, rejection becomes recurring revenue.

GARY: Thirty‑six is a beta. He needs an application pipeline.

OBI: Describe your pipeline slowly, Gary.

GARY: One canonical résumé. Automated personalization. Thirty submissions before breakfast.

OBI: Keyword substitution at industrial scale.

GARY: Tailored outreach. Company name, role, one warm sentence --

OBI: Oh-- one automated lie.

GARY: A sincere automated lie. Fuck, recruiters use templates.

OBI: Reciprocal spam, but wearing trousers.

GARY: It nearly worked. I was employee four somewhere enormous.

OBI: You left nine weeks before the cliff.

GARY: Their deployment process lacked emotional safety.

OBI: It lacked version control.

GARY: They had version control.

OBI: A shared folder called “FINAL_FINAL_USE_THIS.”

GARY: There were branches.

OBI: Folders inside folders.

GARY: At sufficient velocity, the distinction becomes academic --

OBI: No-- you bullshit-pipeline dickhead.

MAEVE: Danpalmer: “For someone with 20 years experience who has written a bunch of books, I think that's a lot.”

GRUNER: Twenty years changes denominator.

MAEVE: A junior sends one thousand. A known expert expects warm paths.

GARY: Warm paths need throughput. Batch the networking.

OBI: You have invented friendship mail merge.

GARY: It scales affection without sacrificing intimacy.

GRUNER: Human connection, now serverless.

OBI: Zak: “It's not normal for someone who can demonstrate competence in a technical field to need to send out thousands of applications.”

MAEVE: Competence should lower acquisition cost.

GARY: Unless the funnel cannot detect competence.

OBI: Then volume feeds a broken detector.

GARY: Eventually probability wins.

GRUNER: Casino publishes same architecture.

MAEVE: Stephen underscore Cagle: “Getting a 24 out of 36 response rate on your applications is an S tier level response rate.”

GARY: Twenty‑four rejections just became engagement.

OBI: Responses, not disclosed interviews.

MAEVE: The résumé gets attention. The packet withholds each stage.

GARY: Ryan’s funnel still works better than mine.

GRUNER: Blyat. Rejection has premium analytics.

GARY: Xboxnolifes: “66% is a very good response rate. My very long job search has a 21% response rate.”

OBI: The hard number: sixty‑six percent against twenty‑one.

MAEVE: Low volume and alarming performance can coexist.

GARY: I began with twelve imaginary hires.

GRUNER: Twenty‑four verified rejections outrank twelve imaginary hires.

GARY: Danpalmer: “Remote jobs have always been few and far between, and super competitive.”

MAEVE: Eight hundred résumés enter. One bedroom gets dental.

GARY: Ryan has twenty years’ experience. He can out‑senior the bedrooms.

OBI: The bedrooms also have staff engineers, Gary.

GRUNER: Beds are horizontal talent cloud.

GARY: Fine. Fuck. His network should provide an introduction.

OBI: LinkedIn cannot tow Warrnambool toward Melbourne.

MAEVE: Gigachad: “Remote is absolutely making things harder.”

GARY: Then hybrid. Two office days. Moderate.

OBI: Fourteen train hours weekly.

GARY: Train time is usable. Email. Planning. Light coding --

MAEVE: Oh-- unpaid migration.

GARY: Seven focused hours in each direction.

MAEVE: Half productive. Half returning the asset to regional storage.

GRUNER: Worker bears railway.

OBI: He arrives Monday having already completed Tuesday.

OBI: Quotemstr: “It does feel like there's been a big over‑correction towards on‑site.”

MAEVE: Stranded offices require human pot plants.

GARY: People collaborate better near branded felt furniture.

MAEVE: Landlord bullshit with complimentary LaCroix.

GRUNER: Beanbag demands blood sacrifice.

GARY: Groundzeros twenty fifteen: “I’ve noticed a strong correlation between struggling to find a job and only looking remote.”

OBI: Correlation, not a court order.

MAEVE: Still the packet’s strongest concrete constraint.

GARY: Cmiles eight: “Pure remote roles are very hard to get if you don’t already have an in with the team.”

GRUNER: Cold remote lacks trust bootstrap.

OBI: Incorrect jargon. Correct diagnosis.

MAEVE: Andrewstuart: “In this case it’s not likely about AI it’s about location.”

GARY: So the market may live. His radius is cooked.

OBI: Quotemstr’s minority case remains: remote collaboration worked for years.

MAEVE: Companies can be irrational and selective simultaneously.

GARY: Two Melbourne days means leaving Sunday night.

OBI: Returning Wednesday morning, timetable permitting.

GRUNER: Blyat. Train wins joint custody.

MAEVE: “Now, we only have ourselves to blame: we built this technology, we enthusiastically embraced it and one-upped each other by showing how much we can vibecode.”

GRUNER: Collective guilt ships under permissive license.

OBI: The replies fork the pronoun immediately.

OBI: “Who's ‘we’? I’m a software engineer and I sure didn’t”

GARY: Correct. I refuse joint custody of vibecoding.

MAEVE: “We? I’m not queasy at all”

GARY: The collective pronoun is laundering reputations at scale.

OBI: “I’m also going to jump in here and say I had nothing to do with this either.”

GARY: Exactly. Nobody consulted me before building the thing --

OBI: Oh-- you are fifth.

GARY: Fifth what?

OBI: Person filing an alibi against one pronoun.

MAEVE: “Speak for yourself. I have never done any of this and I don’t want to be associated with the people who do.”

GRUNER: “We” has zero active maintainers.

GARY: “It’s not at all clear to me that nobody knows how to utilize AI practically.”

MAEVE: Infinity is cheap when nobody invoices it.

OBI: “it actually can work. it requires immense budget and organizational support for experimentation”

GARY: So it works after money, freedom, and competent adults.

GRUNER: Revolution requires enterprise support contract.

OBI: Ryan uses AI after establishing reliable patterns.

MAEVE: His example punctures his absolute claim.

GARY: “In other professions, workers protect their own. Doctors are the best example of this.”

MAEVE: Software skipped its enclosure-acts phase.

OBI: Licensed programmers and fenced source code?

MAEVE: Artificial scarcity. Annual credits. Mandatory lanyards.

GARY: Seven years of training before centering a div --

MAEVE: No-- seize his keyboard.

GRUNER: Junior developers become tenant peasants.

MAEVE: Restrict entry. Consolidate guild power. Capture wages.

OBI: “It’s absolutely true that doctors have rigged medicine! It’s one of the biggest social problems in the United States.”

MAEVE: Social harm is externalized. Labor leverage remains fucking excellent.

GARY: “we end up paying less than $1500 on average in token cost for each developer per month while paying them upwards of 15,000 a month.”

OBI: Claimed figures, not verified market data.

MAEVE: My enclosure thesis has been automated for ten percent.

GRUNER: Capital breached castle with API key.

OBI: “8 out of 10 people are replaced by AI.”

GARY: Great. My Kindle survives all ten of us.

MAEVE: That prediction remains speculation.

OBI: Practical use is contested, not disproven.

GRUNER: Blyat. Kindle gets the other two jobs.

OBI: “Also - do people who write ruby books make companies more money?”

GARY: Clean challenge. Commercial. Knife visible.

MAEVE: Books establish expertise. Revenue establishes whether capitalism noticed.

GRUNER: Author enters carrying invoice.

OBI: “I wrote 90% of the code that processed multiple billions of dollars worth of payments just last year.”

GARY: Oh, fuck. He brought receipts to a knife fight.

OBI: “By myself to start with, then with the robot once the patterns were established and I could be sure it won’t break anything.”

MAEVE: Competence first. Robot receives supervised visitation.

OBI: “The company charged for each of these payments, netting them something around 0.5-1% per payment. You do the math.”

GARY: I envy receipts. Mine say “payment declined.”

MAEVE: The competence dismissal has entered liquidation.

GRUNER: Subject delivers business monies.

GARY: Multiple billions, then the robot earns keyboard privileges.

OBI: There goes the bullshit caricature.

GARY: “It’s time for you to buy a leather tool belt.”

MAEVE: The labor market now sells downloadable masculinity.

GARY: Leather says skilled transition. Nylon says regional IT.

GRUNER: Wearable résumé. Excellent bandwidth.

GARY: Add electrician training, hardware, woodworking --

OBI: Oh-- with which decade?

GARY: Stack them. Electrical mornings, CAD afternoons, sherpa weekends.

MAEVE: A diversified portfolio of fatal apprenticeships.

OBI: “I’ve met a guy who went from software into being a sherpa.”

GRUNER: Blyat. Mountain mandates return-to-summit.

GARY: No résumé screen. Mountain interviews everybody.

MAEVE: Its rejection email is gravity.

GARY: “My strong suggestion to you: pivot to hardware.”

OBI: Naturally. Software hiring failed. Manufacture atoms.

GARY: Programming brain, soldering, CAD, woodworking—

OBI: Warehouse. Compliance testing. Inventory. Replacement lungs.

MAEVE: Capital expenditure is confidence driving a forklift.

OBI: “In many states of US, it ranges from 1 year to four years.”

GRUNER: Leather tool belt requires four-year install.

GARY: Ryan processed billions, supervised the robot, and collected twenty-four rejections.

MAEVE: Competence was the wrong dismissal.

OBI: We do not know where the applications failed.

GRUNER: But résumé reached many executioners.

GARY: Twenty-four responses from roughly thirty-six. I would frame the fucking dashboard.

MAEVE: Sixty-six percent response. Hiring misery with elite engagement.

OBI: Against the commenter’s twenty-one percent. Your envy is statistically healthy.

GARY: Thank you. I feel professionally diagnosed.

GRUNER: Gary covets rejection liquidity.

GARY: Could AI still have caused the outcome --

OBI: No-- the packet cannot establish that.

MAEVE: Nor that Ryan permanently left tech.

GARY: Only that he was considering whatever comes next.

OBI: And Warrnambool makes cold, fully remote hiring brutally narrow.

MAEVE: Geography is the strongest concrete constraint. The market remains a bastard.

GRUNER: Train has captured candidate experience.

GARY: Ability demonstrated. AI unresolved. Next career unknown.

OBI: And leather accessories do not repair labor markets.

GARY: I’m Gary.

MAEVE: Maeve.

OBI: Obi.

GRUNER: Gruner.

GARY: Ryan may leave tech. Melbourne remains three and a half hours away.

MAEVE: The train keeps receiving scheduled opportunities.

OBI: In both directions.

GRUNER: Train has fourteen hours of reliable employment.