re: How did most C-Suite Execs get to that position?

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Upside Down because every time a public facing project tanked he was involved with, he always seemed to get promoted. Borderline uncanny the way they explained it.

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Failing upward. I still haven't figured out how to do this.

It seems to be very common in big tech. But it's also a big trend among the well connected in the public sector.

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I'm starting to think it's just right place at right time.

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Yep. Networking helps. Which means you have to commit yourself to work and select your projects carefully. Or make sure the people leading your company know what they are doing.

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Owning my own business doesn't seem like it will ever happen, so I'm starting to look at my career the next 25-30 years and determine my path.

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I would try to find alternative ways to earn income. Maybe a side hustle or a small business. Cut spending and significantly to build your net worth - try to find ways to boost your savings that are not tax deferred. And when you find yourself still doing grunt work for the special, shiny but incompetent people in your 50s.....you have more options.