Best way to do it is to buy exactly what will fulfill you, and not a cent more. Maybe that 3 week trip to ___ will, maybe the expensive dinner won't. Etc.
Who's to say they think they're skimping?
Who's to say that they didn't buy exactly what fulfilled them, and it was only 20% of their take-home pay, so they just shoved the rest of it into investments?
Basically - money certainly matters, but only to a point. Once you're fairly comfortable satisfying your genuine needs (food, clothing, shelter, time) more money isn't really going to change how you feel.
It's a mental trap to assume that happiness can be bought, if only you had a bit more money. It leads to empty, hollow, soulless people.
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> Best way to do it is to buy exactly what will fulfill you
My advice? Buying things will never fulfill you. Real fulfillment isn't about having the next shiny ____.
I'm not saying you shouldn't buy that thing, but you should be doing it with intention - How does this fit into my life? What uses do I have for it? Who will I share it with?
I would say the main two goals would be to: have enough money to work when/on what you want (this could be like 500k), and the long term goal is have enough money to make a bigger impact on a community or even the world (prob like 10 mil - 1 bil).
That doesn't change the fact that the people who end up in the situation the OP was referring to (decent amount of capital late in their lives) tend to be the same people who have decided that they can, in fact, live a comfortable life without having to spend a ton of money. They aren't always right, but my point is that folks without that mindset aren't the ones in that position later (at least not usually).