Por que
O porquê é diretamente abordado no início da The Fellowship of the Ring. Em suma, apesar de ter apenas o Anel do Poder (em vez de usá-lo regularmente), Bilbo começou a sentir seus efeitos. Isso parece ser proporcional ao poder crescente de seu verdadeiro dono, Sauron.
Ele está aflito com o desejo de viajar e sente que ele quer escapar de sua vida, não percebendo que o que ele realmente quer escapar é, de fato, o anel que ele sempre carrega com ele.
Ele também justificou a decisão para si mesmo de que a presença de seus parentes o distraiu da conclusão de sua magnum opus, o Livro Vermelho.
'Yes, I am. I feel I need a holiday, a very long holiday, as I have told you before. Probably a permanent holiday: I don't expect I shall return. In fact, I don't mean to, and I have made all arrangements.
'I am old, Gandalf. I don't look it, but I am beginning to feel it in my heart of hearts. Well-preserved indeed!' he snorted. 'Why, I feel all thin, sort of stretched, if you know what I mean: like butter that has been scraped over too much bread. That can't be right. I need a change, or something.'
Onde
O onde também é endereçado. O plano original de Bilbo era simplesmente atacar as montanhas e viajar. Gandalf sugere que ele vá visitar os elfos.
Gandalf looked curiously and closely at him. 'No, it does not seem right,' he said thoughtfully. 'No, after all I believe your plan is probably the best.' 'Well, I've made up my mind, anyway. I want to see mountains again, Gandalf, mountains, and then find somewhere where I can rest. In peace and quiet, without a lot of relatives prying around, and a string of confounded visitors hanging on the bell. I might find somewhere where I can finish my book. I have thought of a nice ending for it: and he lived happily ever after to the end of his days. ' Gandalf laughed. I hope he will. But nobody will read the book, however it ends.'