> Fair to say unlucky people are skeptical/pessimistic/realistic and lucky people are naive/optimistic?

Optimism vs pessimism is basically only a valid framing in very neutral times. If things really are significantly tilted towards up or down, then you either notice that or you don't, and only framing that makes sense is realism vs confusion/delusion

People in my life routinely talk about how lucky I am. Its a big enough thing that it's kind of a meme. I think a big part of it is strategic disassociation. You can't do it with every decision in your life but if you pick and choose some focal points where you just pick the choice with the unknown but possibly positive outcome, commit to it fully, and internalize the value of the joy of discovery without worrying about it too hard you often come out ahead.

I'm pretty sure the luck came first because optimism/pessimism is a learned trait.

I say this as someone who considers themselves "Optimistic by nature, pessimistic by experience."

I was born in lucky circumstances but that luck turned in my teens due to factors outside of my control. I have seen firsthand how it works.

Even now, I constantly have to catch myself and force myself to think pessimistically... And my pessimistic projections are usually right or sometimes not pessimistic enough.

But I know I'm a natural optimist by the fact that I don't give up. I've built so much software and startups over the years; most of them I'm still running on the side and keeping up to date even though I know consciously that there is zero chance they will succeed. Deep down I have a deep optimism that something will change and all the opportunities will come at once. Consciously, I know it is delusional but I'm fundamentally motivated by emotions, not thoughts.

It's a weird feeling having built products that work very similarly to (or better than) other products which rake in millions of dollars but not being able to find a single customer due to all sorts of weird contrived socio-political reasons.