I've always felt that this philosophy, and others like it, ultimately boil down to "you're going to lose no matter what, so try not to care about the game."
That's really not it at all. Have you heard the story "who knows what's good or bad"?
Something happens, and we judge it good and feel good about it. Then something else happens, and we judge it bad and feel bad about it. And so on. Our feelings are put on a roller coaster according to our judgements. But we don't have enough information to judge anything good or bad. It always remains to be seen. Deeply internalizing this results in equanimity.
There are plenty of things that are pretty unequivocally good or bad. When we anticipate one of these things happening, our emotions change accordingly and this helps to guide our actions in avoiding or encouraging the thing in question. That's what emotions are for. If you have any control over the course of events that affect you, you should experience an emotional response. Anything else just seems like learned helplessness.
> There are plenty of things that are pretty unequivocally good or bad.
Could you name one? For maximum utility in this conversation, can you pick something likely to happen more than once in an ordinary life, some common case?
I am not the GP but I will give it a try. Unequivocally bad:
Death of a loved one.
Unequivocally good:
Birth of a child.
Most people tend to experience these things more than once in a normal life. They represent a reality more real and more final than even psychedelics could manage: life and death. Impermanence.
Imagine how it would be if we didn't die. So is death good or bad?
I have a family friend whose first wife died of cancer. After mourning for years, he found another woman and married her. Unlike his first wife, she was insistent on having a baby. When their baby was born, he told us that, having held his child in his arms, he understood now that it would have been a huge mistake not to have had a child as he originally planned with his first wife. So was the death of his loved one good or bad?
> Unequivocally good: Birth of a child.
My sister was born and it must have been a very happy event. When she died it was very hard for my parents. Was her birth good or bad?
This is what the story is getting at. It doesn't make sense to assign good or bad to things. We don't have enough information yet. And we never do. It perpetually remains to be seen.
It's not apathy or learned powerlessness to accept the fact of reality that you just don't know enough to say whether something is good or bad. It's wisdom.
You're being obtuse. If losing a loved one before their time isn't "bad" then your definition of the word "bad" is useless, or at least irrelevant to our current discussion.
It's closer to 'try not to be attached to specific outcomes'. It's fine to play the game, as long as you don't get so hung up on trying to 'win' that you can't enjoy your life along the way. It's highly unlikely that you'll get to a point where you think that now you've won and can just enjoy, so focusing too much on the game means you will eventually lose - you're not going to live forever. The 'wins' are happening along the way, and if you look, you'll find many of them at times when you're 'losing'.
Something happens, and we judge it good and feel good about it. Then something else happens, and we judge it bad and feel bad about it. And so on. Our feelings are put on a roller coaster according to our judgements. But we don't have enough information to judge anything good or bad. It always remains to be seen. Deeply internalizing this results in equanimity.