What you're saying resonates completely, it's the quotes like the one from Steve Jobs above that get me.

If today were the last day of my life, would I want to do what I'm about to do today.

For me, the answer most days is no. Which the quote would then imply that I'm settling and not living the life I should be. To which I can say, no Steve you don't understand, I'm sacrificing so that I can get to a life where that's possible. Then I'm back to the cycle I mentioned above where settling seems to occur because of the need to balance living in the present and trying to create a life that you can enjoy in the future.

But I'm still having to give up living today in a way that I truly want to. Which then begs the question, can life be lived everyday without settling while still accounting for the fact that we have to take care of our future selves?

It's definitely a great topic that's easy to go back and forth on.