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I'm new in this industry, but based on my life, the experience of some close friends, and anecdotes like this, my impression is that you need enough career security and cash savings that you can just ignore stupid requests from your boss and not care about the fallout. Of course that is probably unsustainable outside of entry level jobs, so I am sort of convinced that I should have a 6-10 year plan to exit it

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That's an interesting way of thinking about it. I'm not very assertive, so perhaps If I stood up to management a bit more everyone would be better for it anyway. Although it's easier to stand up to your boss when it falls under your domain (technology), but when it's their domain (managing people) it's harder to be assertive.

Also what happens when it just becomes a self fulfilling prophecy? Regardless, if you experience terrible management you should probably be finding another job anyway.

You're absolutely right. But sometimes it's just the confidence and competence. If you're actually good at your job and you know that, you can push back on insanity and not panic if you come up craps.

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