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I see peers (coworkers who eventually moved on to other places) who make these strange leaps from Sr. Engineer to Director or CTO and I don't understand how they did it.

Really, the only thing you're lacking -- and I do not say this lightly, or mean this disparagingly -- is chutzpah.

The simple (and sad fact) is, that for the vast majority of these CTO/COO/CEO types, whether they happen to possess great talent, or not -- what happened to catapult them through the glass ceiling into that "leadership" role was one of two things: (1) they were already working in an organization for some time and there was suddenly a vacuum, a great need for someone to "pick up the reins", and the were seen as "the only one in the room"; or (2) they were simply very brash, and repeatedly but persistently insinuated themselves into the "technologist, visionary, co-founder, (what have you)" role and eventually (perhaps with the help of a thick skin and/or immunity from the crushing weight of self-doubt that afflicts most normal, healthy people I know) it finally stuck -- someone finally believed them, and they got that brass ring -- that CTO job in their 20s, million-dollar funding for their company, speaking gigs at TED, whatever.

What I vastly prefer working with managers/principals in the first category, I find the latter path to "greatness" is far more common. I don't mean to belittle these kinds of characteristics, or to say charisma and the ability to sell one's self isn't important, or anything like that. But it does seem is that part of what keeps (very good) engineers in that "worker thread" category, it seems, has (very sadly) a lot to do with what made them good engineers in the first place -- the ability to stay humble, stay focused on just being really excellent at what they do, not for the vanity (or the outsize paycheck) but simply for the sake of excellence itself -- and above all, not taking themselves too seriously.




I don't think this is unique to programming either. In fact, this is the reason why so many Narcissists and Psychopaths make it into management.




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