# 10 Job-Search Rules That Just Broke

Page: https://stenobird.com/podcast/the-skip-podcast-5971055/10-job-search-rules-that-just-broke
Text version: https://stenobird.com/podcast/the-skip-podcast-5971055/10-job-search-rules-that-just-broke.md
Podcast: [The Skip Podcast](https://stenobird.com/podcast/the-skip-podcast-5971055)
Published: 2026-05-20T14:00:00+00:00
Episode link: https://theskip.substack.com/p/10-job-search-rules-that-just-broke
Audio file: https://api.substack.com/feed/podcast/196624701/2723af2ab667dd9dc6d37b8d41d7ba32.mp3
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JSON: https://stenobird.com/v1/public/podcasts/the-skip-podcast-5971055/episodes/10-job-search-rules-that-just-broke
Duration seconds: 3561

## Resource

In this episode, I sit down with three senior product leaders who just came through the senior job search in this market: Dana Ingraham from Harvey, Briana Ings from Atlassian, and Pei-Chin Wang, who’s founding her own company. While the search itself continues to be exhausting, I was surprised to learn that everything else has changed: the playbook is completely out of date, in at least ten different ways. All three reported feeling something I’ve started calling smiling exhaustion: working hard, going long, and surprised by how good it feels. If you're a senior leader, sitting in a stable role debating a move, weighing how you can ride the AI shift, or quietly wondering if founding finally belongs on your career path, this conversation is for you. Key topics: • How AI agents have flipped the first year at a new role from headwind to tailwind, and are even bringing joy to the first year of a new role • The new founding math: fast, fun, and skill-additive, with a much lower downside than it used to be • How to navigate the job search when you don’t live in San Francisco—and remote jobs are dwindling • Why structured AI learning is the wrong move, and what to build instead, so your fluency is hard to fake • How to signal hard boundaries to a new boss, and differentiate between real respect and performative virtue-signalling • Why holding your professional identity loosely matters when the role of senior leader is getting reformatted in real time Referenced: • Airbnb: https://www.airbnb.com/ • Atlassian: https://www.atlassian.com • Claude Code: https://claude.com/product/claude-code • Harvey: https://www.harvey.ai • Loom: https://www.loom.com • Modern Animal: https://themodernanimal.com Brought to you by: • Guru—Trusted knowledge for every AI tool and team: https://www.g…

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## Transcript

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