The Job Sh*t Show

Uber burned through its entire 2026 AI budget in four months and still can't tie the spend to results. Starbucks pulled its AI inventory agent. Ford hired back 350 engineers to clean up after automated inspection. So what's actually going on? I think most of us are stuck in mode one and mode two thinking — using AI to automate tasks or do things faster ourselves — when the real payoff is in mode t...

My friend Lindsey Caplan buys professional services. She also sells them. Recently she opened a deliverable from someone she's paying real money, and found AI output staring back at her. What she landed on is something I keep coming back to. We've confused what we actually pay professional services people for. It was never really the output, even if it looked that way for years. It's the judgment,...

LinkedIn is noisy, frustrating, and often feels like a job search dead end—so why are we still using it? In this episode, Josh unpacks the tension we all feel about the platform, exploring what still works (profiles, networks, discovery) and what definitely doesn’t (spam, false leads, and the chaos of too much noise). Plus, a glimpse into how job seekers are starting to reclaim control—one Slack o...

Managing an AI agent is like speed running my worst management habits. I get frustrated, I start micromanaging, and I catch myself acting like the boss I used to complain about. Boris Berenberg, founder of Zero AI, told me we're turning everyone into a manager now. There's no such thing as a non managerial role anymore. Jack Dorsey disagrees. He called middle managers "an information routing proto...

Josh's instinct is always to reach for a matching disaster from history. He thinks that's a trap, because by the time you pick the analogy, you've already picked the answer. He found the proof in a New York Times episode his wife sent him. The chief economics correspondent Ben Casselman laid out two futures for AI. One matched the internet, which displaced travel agents slowly enough that most jus...

The instinct is always the same. Ask AI to complete the task, assemble the deck, execute the command. Josh thinks that's backwards, and the bill for that mindset is already coming due. So Josh went looking for a different way to use the tool, one built on opening ideas up instead of closing them down. He found it in leadership coach and improviser Aidan Nepon. She once coached a singing student wi...

In this episode, Josh challenges the question everyone keeps asking about AI and work, and makes the case that it's the wrong one. The framing is always the same. AI helps us do more, or it burns us out. Faster or exhausted. Pick one. But that's a biology problem, not a software problem. Microsoft's 2025 Work Trend Index shows the split. Eighty percent of the workforce says they don't have the tim...

In this episode, Josh challenges the question everyone keeps asking about AI in school — and makes the case that it's exactly the wrong one to be asking. The yes-no binary is a dead end. AI in school: allowed or banned. AI in writing: authentic or cheating. These are crude frames for a genuinely complicated problem. And the institutions drawing the hardest lines — the grad school deans, the publis...

In this episode, Josh weaves together three stories about where AI-driven hiring is actually headed — and why the answer to whether it's making things better or worse is: yes. The first is a conversation with someone building a high-volume AI hiring tool for a major tech company. The premise is simple: skip the resume, go straight to an AI-hosted interview. Everyone gets to speak. Everyone gets th...

Josh hit a Claude Design usage limit this week. Four hours locked out of a presentation he was mid-build on. The feeling that came with it — that he didn't own it, couldn't just keep going — told him something about the moment we're all in. In this episode, Josh argues that scarcity thinking isn't just a feeling. It's becoming a leadership strategy. And it's contagious. Jack Dorsey cut 40% of Bloc...

This week Josh covers why AI is doing something economists didn't see coming — collapsing the coordination costs that made large firms powerful in the first place. It starts with a 1937 paper by economist Ronald Coase called The Nature of the Firm. His argument: companies exist because coordinating through the market is expensive. Search, negotiate, contract, repeat. It's cheaper to just put it al...

If a person produces X and AI produces X faster and cheaper, the math is simple. Replace people with AI. Except the equation isn't true. This week Josh covers AI Leadership Skill #4: Know the Value of Your People — the latest entry in The Sh*t List , the paid Substack companion to The Job Sh*t Show. It starts with a simple question: what does a doorman actually do? Holding the door is the job desc...

Mark Zuckerberg called it a budget trade-off. Jack Dorsey cut 4,000 jobs. Salesforce slashed its support headcount from 9,000 to 5,000. ServiceNow's CEO celebrated agents that don't need lunch or healthcare. The story these CEOs are telling is that AI made the cuts necessary. But the productivity numbers don't show it — and the pattern of how new technology actually gets adopted suggests we've bee...

For 50 years, organizations have chased one thing: efficiency. More output, less friction, faster everything. And it worked — until it didn't. In this episode, Josh sits down with organizational change expert Josh Allen Dykstra at a live conference to trace how we got here: from Milton Friedman's 1970s shareholder mandate to a workplace so optimized for productivity that there's no room left to th...

The résumé was already broken before AI showed up. Now it might actually be on its way out. In this episode, Josh looks at the first viable replacement he's seen — not a shinier LinkedIn profile or a better-optimized PDF, but something closer to a behavioral fingerprint. A system that stays with you across your career, learns how you actually work, and advocates for you to employers using verified...

The last thing your people need is another training. This week Josh previews AI Leadership Skill #2: Let Your Team Lead , the latest entry in The Sh*t List, the paid Substack companion to The Job Sh*t Show. It's built around a conversation with Jeffrey Roach, SVP of Healthcare Solutions at RisePoint, where he helps colleges and universities modernize for the real world. When Jeffrey asks leaders h...

When Anthropic dropped Claude Design and OpenAI released Images 2.0, something shifted. The ability to create professional-grade visuals — the kind that used to require years of training and hard-won expertise — got handed to everyone. In this episode, Josh argues that AI isn't replacing creative experts. It's promoting them. The people with real taste, real vision, and the language to describe wh...

Most leaders are using AI to go faster. This skill is about going deeper. Coach Your People With Better AI is the first entry in The Sh*t List, the paid Substack companion to The Job Market Sh*t Show. It starts with a simple question: what if, before your next difficult one-on-one, you spent 15 minutes with an AI tool working through everything you actually know about that person? This one's built...

Job descriptions are supposed to clarify what a company needs. But what if they’re just educated guesses? In this episode, Josh looks at how AI is quietly breaking one of the most fundamental parts of hiring: defining the role itself. Drawing on stories from job seekers and hiring managers, he explores why candidates are getting rejected for jobs they already had interviews scheduled for, how role...

AI is supposed to help people get jobs. But what if it’s making it harder to tell who’s real? In this episode, Josh looks at how AI is creeping beyond résumés and into interviews—and even the work itself. Drawing on stories of impersonated candidates, AI-assisted cheating in technical interviews, and coordinated efforts to land remote jobs at scale, he explores how trust is breaking down across th...

Job titles used to tell you what a job was. Now they often raise more questions than answers. In this episode, host Josh Levine looks at the rise of strange, sprawling, and sometimes absurd job titles—and what they reveal about how quickly work is changing. Drawing on conversations with job seekers, coaches, and operators inside companies, he explores why organizations often don’t actually know wh...

AI is supposed to reduce work. But what if it just gives us more of it? In this episode, Josh looks at what actually happens when AI hits the org chart—inside real companies, not predictions. Drawing on recent layoffs, historical patterns like ATMs and spreadsheets, and firsthand stories from teams already deep into AI adoption, he explores why automation rarely shrinks work the way we expect. Ins...

AI gets blamed for a lot right now—layoffs, hiring freezes, disappearing entry-level roles. But what if it’s not the whole story? In this episode, Josh looks at the strange “low hire, low fire” job market where companies aren’t hiring much, but they aren’t laying people off en masse either. Drawing on labor data, conversations with business leaders, and a few high-profile layoffs framed as “AI tra...

Is it who you know? How people are and aren't landing interviews. Applying to hundreds of jobs feels like progress—but it might just be noise. In this episode, Josh looks at the two strategies job seekers are using right now: scale and signal. Some people are flooding the system with applications, hoping one slips through. Others are doing the opposite—only applying when they can get a human intro...

AI used to promise better work. Now it’s starting to promise no work at all. In this episode, Josh unpacks a deceptively cheerful Grammarly ad that suggests AI can handle your tasks so you can “get back to what matters.” Cute on the surface. Slightly terrifying underneath. He connects the dots to a viral essay arguing that AI is already replacing large chunks of knowledge work—from coding to law—a...