> Cynics feel smart but optimists win.

That's not been my experience. Optimists also tend to assume the best motivations behind the actions of others, and that will nearly always bite you in the ass in any sizeable organization.

I've been the ultra-cynic before, and agree that doesn't work either. People don't like working with you, and don't trust you.

I think we need to be realistic on order to be successful, and neither ultra-cynicism nor optimism fits the bill.

I would suggest that a healthy, reasonable amount of cynicism is a part of being realistic about how the world works.

Blind optimism is silly. But time and again we’ve shown that tit-for-tat is the best strategy in repeated games.

Start optimistic. Stop if it doesn’t work. In the long-term you don’t need to win every iteration, just enough for a positive expected value. And make sure you don’t get wiped out in any single iteration.

The weeks are short but the decades are long and the industry is smaller than you’d think :)

>I've been the ultra-cynic before, and agree that doesn't work either. People don't like working with you, and don't trust you.

Is the issue being that one isn't being cynical enough? If you are very cynical about how things will turn out, and share that with others who don't appreciate it (even if you are right), then you are being optimistic in thinking it will change things. Controlling one's displays to others to appear as whatever gets one their best outcome is being even more cynical, to the point of abandoning any attempts at open honest relationships, but it likely works the best if one can pull it off.

Though that might be a very big if, and getting caught faking this likely is worse. Then again, is forcing oneself to adopt optimism just an attempt to do this indirectly, a sort of 'fool yourself so you can better fool others' approach when more direct manipulation doesn't work, given that drive for the optimism is to get better outcomes?