Job Search in the Age of AI

Also watch and listen

The signals

• Christine: The resume stopped being a signal. A good resume used to signal a good candidate, the same way good writing signaled a good writer. Now anyone can upload a job description and generate a polished resume that matches it exactly, and everyone using the same tool on the same posting converges on the same words. The polish is an anesthetic: it looks great, which numbs you to whether the substance is there. What used to be signal is now noise.
• Lee: Are your resume, LinkedIn, and portfolio the same person? Lee ran black-hat thinking across his own three assets and Claude asked, are you sure this is you. They had drifted apart since 2015. Multiple signals that do not line up read as noise. Pick one focus and align every surface to it instead of wiggling all of them at once.
• Sam: AI writes you toward the average. AI is strong in the middle of the distribution and weak at the tails; the [Mount Sinai study](https://nature.com/articles/s41591-026-04297-7) found it good on common medical questions and worse than humans at the edges. An AI-drafted resume makes you look like the average of every resume out there, which is perfect if you want the middle of the pile and fatal if you want the top five percent. The memorable candidates are corner cases: the small-town newspaper editor who could actually write, the cruise-ship costume designer who could improvise a show in thirty minutes.

The subtractions

• Christine: Stop delegating the whole document. Do not push a button, generate a resume, and send it. Chunk the work, keep a master document you control, and transcribe the AI output by hand so your voice survives; her fingers will not let her type something she would not say. Every AI-written bullet is a story you will have to defend in an interview you never rehearsed.
• Lee: Unpublish the portfolio you will not maintain. If you are not going to keep it current, delete it, or rebuild it as one clean, simple, narrative page and cut everything unnecessary. It feels like spring cleaning, and a stale portfolio that contradicts your resume costs you more than no portfolio at all.
• Sam: Do not dump the resume pile into a chatbot. Handing a stack of a thousand resumes to ChatGPT to pick your five is illegal in most places, and it leaks data that applicants entrusted to you. Match the conversation to the channel, secure the traffic in between and not just the endpoint, and remember that local models keep the sovereignty in your hands.

About this episode

This week host Sam Rogers streams from Cancun with cohost Lee Rodrigues and guest Christine Rodrigues, partners in life and in business, to work through what AI did to the job hunt from every side of the table: the seeker, the hiring manager, and the recruiter.

The throughline: AI raised the quality floor, which also raised the noise floor. When everyone can generate a beautiful, perfectly-matched resume, the beautiful resume stops meaning anything, and the human parts of the process become the only real signal left. Christine calls it thought sovereignty, the discipline of keeping the original thought, the voice, the taste, and the judgment even while using the tool. Lee's version is alignment across your surfaces; Sam's is aiming for the tails of the distribution instead of the average.

The current-events beat lands on data hygiene: Lee's example of the man whose AI chat logs ended up in a murder case makes the point that there is no attorney-client privilege with the tool on your phone, which is the same reason you never feed a pile of applicant resumes to a public chatbot. Jobs are human things. The move is not bigger numbers, it is the right numbers: a phone call, a warm relationship, a referral outside the herd.

This week's links:

• The Mount Sinai study on ChatGPT Health (Nature Medicine) — strong on the common questions, worse than humans at the edges
• Former NFL player consulted AI chatbot after murdering his girlfriend — Lee's no-privilege example from the show
• Easy, Awry — Sam's comedic essay on one-click job applications, receipts from nearly a year ago
• System2Focus — Lee and Christine's workflow-based approach to the job search
• R&P Associates — strategic planning and marketing for nonprofits

Sponsored by System2Focus, Lee and Christine's workflow-based approach to the job search. Next week: Sabino Marquez on the CISO perspective in the age of AI. Cohosts JD Dillon and Markus Bernhardt join the rotation next month.

Want to bring your own signal and subtraction? Find yours. Sponsored by System2Focus.

The newsletter

Issue 60 · Monday 20 July 2026 · sent on Substack and LinkedIn.

One signal, one subtraction, one analogy, in five minutes. It draws on this episode but stands on its own. Every issue.