This is an interesting question. I moved into to IT/Security from another sector, and I'm trying to figure out my endgame. At least at my company, there aren't any jobs I covet. Most of the higher ups don't impress me, and they don't seem to know what's going on in their company very well. It seems like if I moved into leadership, I'd have to spend a lot of time lying-via-powerpoint. (that is, taking a complex problem, and both simplifying and misrepresenting in a powerpoint which shows "progress" happening.)

I wasn't a loser in my old career, and I don't want to be a loser in tech. But, it seems like everyone is a loser here. IT/Security is seen as a well-paid janitor; someone you need, but not someone you really care to learn about. Worse, becoming "important" in a company seems to be useful only in so far as you have sway at that particular company. ie, it's a lot of work for some very local, and very useless prestige. And worse, there's no external meaning other than your own status. Why do I care if I have a little fiefdom within company walls? Nothing worthwhile is being accomplished, it's just more sales.