I feel stoicism works reasonably well when your life goes generally well. If your life is going very badly, I think it ends up like a lot of positive thinking where you have to live in an almost delusional world where you pretend things are good while they really aren't
My experience is the opposite. Stoicism (and those they influenced like Plutarch, Emerson, Thoreau) helped me in hard times.
It's divine getting to a point where you can at once care deeply about something and yet realize it's fate is out of your control---and so not break when that thing dies. Even approaching that state by degrees is worthwhile, and I found stoic thinking to help with it.
It's not able pretending things are good when they aren't. It's about exercising your will against your mind and controlling your thoughts and behaviors even when you cannot control your external environment. Rich or poor - stoicism is about self mastery.
If I lost everything and was in some terrible situation, I'd rather be a stoic.
