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The risk you run here is internally over-emphasizing events that happened more recently as more important. That could make them more relevant to your recent experience but not necessarily something of more value than the problems you were solving earlier in your career.

I have also found increased risk of bikeshedding. The higher you go, the more likely you're working cross-disciplinary with ego-intellects. That also leads to suppressing dissent (hierarchy relationships more than experience-based), leading to worse decisions.

Please don't listen to the HBR articles, they're generally very terrible and often can be summed up by survivorship bias.

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