You're probably not one prompt away
A former SVP built the perfect AI resume. It didn't work.
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Everyone thinks they’re one or two prompts away from unlocking the answers to their hardest problems.
(especially the dudes on X)
My latest interview, Jake Woodward, put that to the test.
When he found himself back in the job market, he did what any smart, resourceful person does right now.
He built a system using AI.
A 10-page “super resume” that used AI to automatically tailor a perfect application for every job posting. Every word accurate. Every role precisely matched. He was genuinely proud of it - and honestly, he should have been. It was impressive.
But it wasn’t working.
And this wasn’t some guy half-assing his job search. Jake is a former SVP of Product with 25 years of experience. Plus, he had a new house. Six kids. A family counting on him. The stakes were real, the system was airtight, and it was producing absolutely nothing. He still just applying into a black hole.
So he stopped optimizing.
One day (out of frustration), he sat down and wrote a raw, unprepared, vulnerable post on LinkedIn about how lost he felt. No frameworks, or lessons learned. Just the truth about 18 months he couldn’t seem to stop.
He didn’t even tell his wife before he hit publish.
It went mega viral worldwide. Business Insider covered it. And people reached out from all over the globe.
The most engineered version of Jake got ignored. The most human version of Jake went global.
(and if that isn't a lesson for the future of content I don't know what is)
If any of this sounds familiar - whether you’re navigating a frustrating job search or just feeling like you’re one better prompt away from everything finally clicking - this one’s worth your time.
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