Thats part of the reason that puddleglum is my favourite character of that book - he never loses faith in Aslan throughout the book when others are unable to. I like what you said about God giving us our faith and hope, as opposed to an attitude because I believe that is totally true! And i reckon puddleglum is a great representation of that

This is so true, thanks for bringing it up - it highlights something I've appreciated about the strong spiritual role models in my life. None of them are what I would call "positive thinkers" - they are all people that are genuinely moved and upset by the world they see. They have a heart for change, and sometimes that heart causes them to suffer. But I feel like they're much closer to God's heart in this way.

Puddleglum is not someone to be emulated with regard to his negative outlook on the weather, your health, your travels or the mundane things. But you are spot on that when it really comes down to it, his outlook on life is defined not by what happens to him but by who Aslan is.

Living life as a complete pessimist is not helpful, but neither is living life with "rose coloured glasses" as they say. Yet theologically, one can be an optimist. Knowing that justice will come and that wrongs will be righted at a future point in history, there is room for an overall optimistic look. But one must understand that the righting of wrongs may not happen in his or her lifetime. We often quote Jeremiah 29:11, but if you read the verses leading up to it, you start to feel like Puddleglum.

It is true that we can have theological justification for an optimistic outlook--we can know that God is actively working all things (the good, the bad and the ugly) for his own glory and for the good of his people.
That said, I'm not opposed to Puddleglum's philosophy of expecting the worst and putting a bold face on it. Pragmatically, it makes a lot of sense...
I've heard it said that the pessimist is always going to be right or pleasantly surprised--that situation seems to be Puddleglum's goal. But underneath it all I think Puddleglum is a distinctly hopeful character--not in the hope of the present life or his immediate circumstances (that much is plain!) but he is hopeful because his hope is built on the faithfulness of Aslan to do and to be all that He has promised.

Puddleglum was actually based on a real person - C.S. Lewis' beloved gardener. While I doubt that Lewis' was making a positive case for consistent negativism, I do think he was allowing himself to find humor and even goodness in folks who are this way. Puddleglum did say after all that he was the most positive Marshwiggle in his community, so he had, in that sense, already broken the mold of who he was trained to be. In his shining moment, we see that Puddleglum may be negative about a lot of things, but Aslan holds the key to his heart - and about that, he is positively convinced!

I love Puddleglum! He reminds me so much of myself. I'm a very pessimistic person, and yes while pessimism, itself, can depress you, maybe harm you, I have to say that positivity is NOT faith. Pessimism and optimism are simply attitudes, neither prove that one has faith.

And sometimes when having faith, you also hurt very badly, sometimes you don't feel positive or happy. That's why I adore Puddleglum.

In his own words,

"I'm on Aslan's side even if there isn't any Aslan to lead it. I'm going to live as like a Narnian as I can, even if there isn't any Narnia."

I've always liked Puddlleglum for that reason. I tend to be rather pessimistic myself. To me, the point is not whether you are optimistic on a day-to-day basis, but whether you have hope about the big things when it counts. That's what I think he is an example of.