"Meaning" and "winning" are two different things. Even presupposing that the world is meaningless, some states may be preferable to the individual actors inside of it.

Those actors might take steps to maximize those states, and their success or failure in the short term (ie. the duration of their own life) can easily be considered "winning".

That's one way to look at it, sure, my problem with the term "winning" is that it implies an inflexible, omni-important, and universal metric. We're all clear who "won" a given event or game, but that's not how life works, and if you try to gamify life you're prone to justifying just about anything in the name of "winning" by whatever metric you choose. And if you make the world a worse place because of it? Well, what were you supposed to do, lose?

In the context of life, it is ok to lose. It is ok to not be the best, to not ever find your niche, to never really feel like you've succeeded, be lazy, or make mistakes. It's even ok not to give it your all. You don't have to be the winner, it's ok just to be.