Why do you consider it your endgame? Top salary? Interesting problems? Making a difference?
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.
I guess you just find the level you want to coast at. I haven’t won the start up lottery either. But I have been able to be fully employed as a contractor with a very good hourly rate for quite a long time. Which probably means I’m coasting right now. But I still manage to bump my rates up every so often, so maybe not.
Sometimes that means coasting and spending more time on your hobbies or with your family. Can’t see anything wrong with that.