There’s a saying attributed to Norman Vincent Peale, “Shoot for the moon. Even if you miss, you’ll land among the stars.” The idea is, by aiming high, even if you fall short of your expectations, you will land further than if you’d had no expectations at all.
While this could make for a good goal setting exercise—and that’s still up for debate—it’s completely counter to Charlie Munger’s advice, “The first rule of a happy life is low expectations. If you have unrealistic expectations you’re going to be miserable your whole life.”
The takeaway isn’t to choose between accomplished misery or mediocre happiness. As human beings, we’re not consistent like that anyway. It’s to understand the driving forces of both trains of thought, to be willing to be flexible, and to take a balance, measured, approach to engaging either stance.
There is a time for either way of thinking.
See also latitudes of acceptance, and intuitive fences.