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The problem is with this system he only worked with unlucky people.
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I thought this was only an old urban legend; some people actually use this technique? Especially in a trade supposed to be led by people trained in sciences?
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Given how often it's been mentioned here, it's likely that this is an urban legend that people are pretending to have first-hand knowledge of for karma. In a trade that's supposed to be led by people trained in sciences, no less!

(A more charitable interpretation would be that aforementioned CTO was making a joke that didn't land.)

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or its so old, people would make the joke and interns would repeat it unwittingly. no one has to consciously be lying for this type of meme to continue spreading.
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That'd be pretty gross for a CTO if it were real.
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It's OK! We can disguise it as the Secretary Problem and it'll be fine, we could even write a post on the company blog about it. /s

https://en.wikipedia.org/wiki/Secretary_problem

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