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.
If your work makes you an important person in the company, you have a strong basis for negotiation. Most people just don't use it...
often times companies will opt to pay more as a stop-gap until they find a cheaper replacement
They know the game, no employee ever is going to stay if they're being paid half their market value. "Commitment" my ass lol. But more to the point in order to replace you they have to pay market value for your job. They can only find someone cheaper if your job is beneath you.
Parlaying offers is fine as long as the work they need doing is worth that money. Who are they going to replace you with? Hiring is expensive even if they find a sucker. The only risk is if your market value is higher than they need to pay to get your job done.
Fundamentally the operative variable is: "can they get your job done for less than you're demanding." That's what matters, more than the impression of commitment.
Trying to get a promotion is deciding to compete for one position in one company with essentially every qualified candidate in the world. It’s easy to see how looking for a better job every so often has better odds for success.