Optimistic-ly Pessimist?

Life is a bundle of roses or a shrub of thorns…(albeit adorned with a couple of flowers atop it ) We come across many such similes and contrived (and at times completely cheesy) metaphors which goads one to look at the ‘positive’ side of things, or life in general.
I cannot be faulted for my naïve ‘optimism’ nor can be labelled as an eternal cynic /pessimist (though most people would find the latter to exemplify my very existence) but I do realise how thin the line can be between pragmatism and pessimism esp. given my natural bais-ness or maybe even desire to be a ‘pragmatist’. The likeness in the terms could be on account of the ‘P’ factor, or maybe it’s how I choose to look at it, but whatever said and done I feel, ‘Optimism’ is a tad bit overrated.
The adage says the optimist wins against all odds so is optimism hope or a very strong hunch? Is it naivety or is it confidence? Does it some in some weird way imply foolhardy-ness…or is it just the pessimist in me talking?
So what is the optimism-pessimism divide really- I often ask myself that when I am faced with some difficult situation (which these days is more often than not) – does my natural inclination to think/prepare for the worst make me less of an optimist- or is it a disguised sense of ‘reverse-optimism’ (driven predominantly by superstition, murphy’s jinx). Would hoping for a miracle when the chips are down and you know ‘you’ve lost this one’ be optimism? Maybe, guess miracle do happen for those who believe in them…I wonder if I really do? Yes, there have been times when I’ve been sure of a break-thorough in the face of the crisis, but somehow I have never felt that is attributed on account of a sense of optimism- always on account of what seems “factual” and “logical” with a strong probability of occurrence (not the mathematical one ). As I write this, I realise I must come across as a self-assured-cocky non-conformist, but I think that is the farthest from reality, on the contrary, I feel it’s my lack of all the adjectives (in most instances) in the previous sentence which tends to make me more of a pragmatist/pessimist whatever way you choose to see- rely on facts/logic when you can’t rely on your hunch/believe. I do not mean to berate my fellow ‘pessimists’ nor cynically uphold the optimist I just want to realise for myself if these are yet again brackets we tend to compartmentalize people in, and at times conveniently so.
The Pessimist, Optimist, or Pragmatist (POP – sic) all reside within us – and it POP-s up depending on how we choose to be in a given circumstance, and I think it’s a selfish need to ‘classify’ people which makes it easier for us tag them or put them in brackets…but is not unfair to them/us???