I wonder how a successful pessimist would be like. Would he be gloating his failure to foresee his success? Or to delight in the fact success has its serious pitfalls which needs to be managed delicately. What exactly would be a pessimistic response to success? It could be just denial, or the recognition that successes doesn’t teach us anything that helps us improve while actually failure does (though an optimist is more likely to see that).
There’s so much contradiction within being a pessimist when it comes to living life. Do you celebrate the downside of things you have foreseen and prepared for? Or do you celebrate the bullets you dodged? Or success? And what is it about success you celebrate? The transient nature of it? What drives him/her? What does he/she really want out of life?
He (or she) probably doesn’t exist. So choosing to be skeptical about things and paying careful attention, doing due diligence and all is important. But to consistently play the pessimist is simply not the pathway towards attaining success.