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I agree in the sense that small problems which have technical solutions should be pointed out and overcome. However, in later-stage startups and in larger companies, trying to change the direction might not be the wise thing to do. This highly depends on your position, but as an individual contributor and even as someone in the lower management lane (manager, director), your job most of the time is implementing the CEO's vision, whatever that is. If you find yourself disagreeing with that vision, it might be best to change jobs.[1]

In smaller startups, where you might be able to steer more aggressively, you should still ask yourself whether the company is clearly in the wrong direction only from your perspective or if there are factors which you don't have any insight into (no matter how close you are to founder(s)) which would re-contextualize the issue.

Not disagreeing, but these are some caveats which I found useful to keep in mind.

[1] - There was a story about someone from Apple(?) here a while ago who was let go after a lunch with <someone important> where he expressed his dissatisfaction with the company's direction. He then took up japanese caligraphy. Maybe someone remembers and can link it here.



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