Seven minutes into Saturday’s live, Cory Blumenfeld was describing the system that records every conversation he has, when he stopped mid-sentence. He had forgotten to turn on his own recording. I told him I’d send him the file. Which is about where everyone stands. Three years into AI being used at work, nobody is an expert. The person with 30 years in a field has three with the tools, at most. Cory’s read is that this is the opening, and he had receipts: a friend in Playa del Carmen who went from unemployed to running AI at a company, a CTO who used to be good at searching Stack Overflow and is now just fast, our mutual friend John Brewton who went from looking for his next thing to CEOs lining up by giving his time away, and IKEA, which retrained roughly 8,500 call-center employees after its chatbot took the routine questions, then watched the remote sales business those people moved into grow past a billion euros. My side of it: the fear is real and the diagnosis is wrong. AI eats the task layer. The job still needs a person. The people squeezed hardest are entry-level, and the companies not hiring them are borrowing from the future, which is the argument I had with Neha Kabra in August. The people who benefit most are mid-career, because they know enough to tell the model what an FP&A analyst does. And the thing employers now pay a premium for is the messy cross-functional problem nobody owns. Also: my AI told me I was right so many times that I now ask it to push back, and I still owe New York extra tax because Claude invented an address... You will disagree with at least one of us. Colin did, in the chat, with one word: judgment. Tell me where in the comments. Full conversation above. Timestamps: 00:00 Cold open: Saturday, two founders, button-up shirts 01:19 Is the fear real? Jobs are being repriced, not erased 02:16 Nobody has 20 years of AI experience: the opening for self-learners 04:40 No real experts yet, and the home-vs-work tooling gap (Claude Code at home, Copilot in Word at the office) 07:02 The systems we built: recording every call, requesting our chat archives, Cory’s second brain 10:14 The hiring signal: how do you use AI outside work? 10:33 “AI will never” is a losing recipe, and the “AI wrote this” red flag 12:12 Early vs mid-career: who benefits most 14:36 Colleges cutting tuition in half, self-taught websites, Gary Vee’s cold-call play, and what “clipping” is 18:44 Everything is relationships: how consultants actually get hired 19:31 From struggling to CEOs lining up: content, courses, and giving time away 21:43 The promotability test, and “business is one giant trust fall” 23:34 “I don’t even work here”: directness, and culture fit before skill 25:48 Lonely CEOs, an AI that always says you’re right, and the founder’s rabbit hole 27:44 Chat question: what employers pay for next, the messy problem nobody owns 28:53 Orchestration without authority; paying for outcomes, not hours 31:20 IKEA retrained 8,500 call-center reps and opened a new revenue line 33:48 One move this week: the Rooms Inventory, and using AI in your own life first 36:04 The dark side: a bank balance posted to Slack, a hallucinated tax address, start small 38:16 Wrap Mentioned in this episode * The AI Job Panic Is Missing the Point (the repricing thesis): https://alexrandallkittredge.substack.com/p/the-ai-job-panic-is-missing-the-point * I Asked a McKinsey Partner Which Skills AI Is Repricing. She Named Three. (Neha Kabra on cutting junior hires): https://alexrandallkittredge.substack.com/p/a-mckinsey-partner-told-me-what-ai * How to Build a Career Moat in the Age of AI (the promotability test): https://alexrandallkittredge.substack.com/p/career-moats-in-the-age-of-ai * “I Don’t Even Work Here” Is the Most Powerful Sentence I Say at Work (the Guest Pass): https://alexrandallkittredge.substack.com/p/office-politics-for-consultants * The Rooms Inventory (the worksheet, paid): https://alexrandallkittredge.substack.com/p/the-rooms-inventory-the-worksheet * The Rooms Inventory workbook on Etsy: https://www.etsy.com/shop/ARKStrategy * What I Wish Someone Had Told Me About S-Corps (the hallucinated address): https://alexrandallkittredge.substack.com/p/s-corp-election-fractional-operator-2026 * Our July live, Your Job Already Moved Overseas, They Just Haven’t Told You Yet: https://alexrandallkittredge.substack.com/p/your-job-already-moved-overseas-they * IKEA’s retraining of about 8,500 call-centre employees (Fortune, via People Matters, Aug 2026): https://www.peoplematters.in/news/ai-and-emerging-tech/ikea-uses-ai-to-reskill-8500-employees-instead-of-cutting-jobs-51222 * Cory’s essay Business Is One Giant Trust Fall https://substack.com/@coryblumenfeld/p-214061550 About Cory Cory Blumenfeld is the founder of Blumoso, which matches businesses with virtual talent and manages them. He writes Taking My Time Back on Substack has built two tech companies, and runs the business from Playa del Carmen. He is Canadian, which you will hear every time he says “out.” If you want the worksheet Paid subscribers get the Rooms Inventory, the career worksheet behind most of what I said on Saturday: the rooms you have stood in, what each taught you, and the one capability you would defend if the floor dropped tomorrow. The Founding tier includes two 1:1 sessions a year. Alex Randall Kittredge writes the Substack ARK Strategy and is the founder and Managing Director of APR Strategic Consulting. He has advised 9+ CEOs, integrated workforces, and redesigned organizations across hedge funds, startups, and industrial companies. He is a graduate of Columbia University and the University of Cambridge, and mentors entrepreneurs & startup founders through Oxford Entrepreneurs Network, CamEntrepreneurs, and Plug and Play Tech Center. He is a Director of The Oxbridge Method Ltd, and is the author of the forthcoming book, How Your Side Hustles Will Save You: Creating a Durable Career that Transcends the Corporate Ladder. Compliance Statement: All views and opinions expressed are solely my own and do not reflect those of any current or former employer, client, or organization with which I am or have been affiliated. This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit alexrandallkittredge.substack.com/subscribe
