Are We Using AI Backwards? An Improv Coach Says We’re Doing It Wrong. (Substack preview)

Are We Using AI Backwards? An Improv Coach Says We’re Doing It Wrong. (Substack preview)

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 without a single technical note, just told her to sing like Beyoncé. The persona did more work than any correction could, and it's the same principle Josh thinks we're missing with AI. Josh breaks down three improv games Aidan uses with clients, and turns each into a way of prompting AI that pushes past the obvious answer. The real question was never how to get AI to finish your thought. It's how to get it to argue with you instead. Follow The Job Sh*t Show investigation at https://joshlevine.substack.com [https://joshlevine.substack.com/] About The Job Sh*t Show The Job Sh*t Show [https://joshlevine.substack.com/] is an investigation into how finding, keeping, and doing work is changing faster than anyone is admitting — and what that actually looks like for real people on the ground. The Sh*t List is a paid Substack for leaders who want to stay ahead of what AI is doing to the workplace — and actually do something about it. Every other week, subscribers get a new AI Manager Skill: one practical, field-tested move for leading your team better in an AI world.

Will We Ever Stop Work-Maxxing? The False Promise of Infinite Productivity

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 time or energy for the work already on their plate. One fractional executive on a call put it plainest. "I'm 53 and I am tired." Josh's grandfather used to joke that owning a business meant working any 24 hours you wanted. Josh built a bot this year to book his own podcast guests. It's faster. He's not any less tired. The question was never how to work faster. It's what happens when a species that needs sleep gets asked to keep pace with something that doesn't. Josh shares where he's drawing his own line between speed and rest. Follow The Job Sh*t Show investigation at https://joshlevine.substack.com [https://joshlevine.substack.com/] About The Job Sh*t Show The Job Sh*t Show [https://joshlevine.substack.com/] is an investigation into how finding, keeping, and doing work is changing faster than anyone is admitting — and what that actually looks like for real people on the ground. The Sh*t List is a paid Substack for leaders who want to stay ahead of what AI is doing to the workplace — and actually do something about it. Every other week, subscribers get a new AI Manager Skill: one practical, field-tested move for leading your team better in an AI world.

Should AI Be Allowed In School? We’re asking the wrong question. (Substack preview)

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 publishers who pulled Mia Ballard's horror novel Shy Girl over AI accusations her author denied — aren't protecting learning. They're avoiding the harder conversation about where the guardrails actually belong. Anne figured out her own. Research, yes. Writing, no. Checking a paper for errors, yes. She named her AI Otis. And by semester two, she'd built a working relationship with it that her distributed, at-times-lackluster teachers couldn't come close to matching. The question was never should AI be allowed. It's where do we install the guardrails — and who gets to decide. Josh shares a framework for developing your own boundaries around AI use, for yourself and your team. The full essay and the framework are on The Sh*t List at https://joshlevine.substack.com [https://joshlevine.substack.com/] About The Job Sh*t Show The Job Sh*t Show [https://joshlevine.substack.com/] is an investigation into how finding, keeping, and doing work is changing faster than anyone is admitting — and what that actually looks like for real people on the ground. The Sh*t List is a paid Substack for leaders who want to stay ahead of what AI is doing to the workplace — and actually do something about it. Every other week, subscribers get a new AI Manager Skill: one practical, field-tested move for leading your team better in an AI world.

Is AI changing hiring for better or worse? Yes.

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 the same questions. No primacy bias, no 4pm fatigue, no inconsistency. Done well, it might actually be fairer than what we have now. The second is a Stanford study on algorithmic bias that found 26% of Black applicants and 15% of Asian applicants applied to positions where AI discriminated against their racial group. Over 60% of Fortune 100 companies use the same third-party hiring algorithm. When one vendor mediates hiring at that scale, bias doesn't just exist — it compounds. Quietly. Invisibly. Across every company using the same tool. The third is what happens when candidates stop trusting the process. They go around it. Build something. Show up with proof of work instead of a resume. It's smart. And it's also a signal. Because if it's a process people don't trust, it will become a process people game. And a process people game stops working for everyone. The question in the future isn't whether AI should be involved in hiring. It's what kind of AI, built by whom, and accountable to who. Nobody's answered that yet. But at least now we're asking. About The Job Sh*t Show The Job Sh*t Show [https://joshlevine.substack.com/] is an investigation into how finding, keeping, and doing work is changing faster than anyone is admitting — and what that actually looks like for real people on the ground. The Sh*t List is a paid Substack for leaders who want to stay ahead of what AI is doing to the workplace — and actually do something about it. Every other week, subscribers get a new AI Manager Skill: one practical, field-tested move for leading your team better in an AI world.

Has Scarcity Mindset Already Won?

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 Block's workforce and then told the world most companies would follow within a year. That's not a prediction — it's a frame that spreads. The story of not enough jobs, not enough capital, not enough time is landing in boardrooms and news feeds and heads at 11pm. And if you're a leader absorbing it, it is reaching your team whether you mean it to or not. But at a roller derby match in Portland, Josh met a software engineer from Stripe. Same industry. Same moment. Completely different tone. Cautious. Deliberate. Not panicking. And $2.2 billion in free cash flow. The difference isn't resources. It's the mindset behind the decisions. Josh introduces a new framework — the panic trap — a two-by-two that helps leaders identify what kind of decision they're actually making before they make moves that can't be undone. Because some decisions you can walk back. And some you can't. About The Job Market Sh*t Show The Job Market Sh*t Show: How AI Broke Hiring and What Might Be Next [https://joshlevine.substack.com/] is an investigation into how hiring actually works now, how AI and automation have upended the process, and why the old rules no longer apply. It blends reporting, analysis, and firsthand stories from inside a labor market that’s increasingly algorithmic, opaque, and indifferent to the people moving through it—while asking what, if anything, might replace a system that no longer seems to work for humans on either side of the process.