Eönwë, I misread your sentence and I'm glad I wasn't drinking anything at the moment because I would have spluttered it over the computer screen... even though it even wasn't that funny.
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Originally Posted by Legate
and I don't recall him being an efficient "outdoorsman" or such things
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Well, I don't think it's ever said anywhere, but one could assume him to be rather good in such things since he travelled a lot (and never got lost)...
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Originally Posted by Legate
As it was already mentioned, however, I think he was not that self-assured. Already as Olórin, he was afraid of Sauron.
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Now, that is interesting. Of course he was afraid of Sauron, because he had the wits to be. I don't think he was not self-assured, more likely he was just being realistic. He knew he was less powerful than Sauron (if we think about the word "powerful" narrowly here) and that he had just one way of winning, and there ws only the fool's hope for its success...