It begs an important and interesting question.
Can anyone, ever, really wake another person up?
I think that's probably a misunderstanding of the effect we have in other people's lives, at best we act as catalysts in each other's journey.
A persons waking is entirely of their own timing and is idiosyncratic in nature, the means could be anything, a crisis, a series of synchronicities, a dream, a conversation, a book, a moment of high strangeness etc. We can inspire or point to where someone might find the resources or answers they're looking for but if we press to hard in that direction we are against the current of their own understanding and fighting against the stream, hindering rather than assisting.
A fine tuned sensitivity to another's needs is what's required not what we think waking up is all about and there is a subtle balance to be struck. Eagerness here is likely to be both over emphatic and counterproductive.
I don't think the idea here is not to pass that book at an opportune moment or assist in some other manner but rather to realise that where no such opportunity exists and the doors being closed, not to dissipate energy and move on.
Someone may even profusely feel indebted to you for, as they see it waking them up and that's fine and we can be accepting of that but I would assume in some way they would have had to be ready for that moment and acquiescent of it.
If you can remember a time when you acted as a catalyst in someone's awakening then it might be apropos to realise that the moment was of their choosing and that it really was a great service you participated in.
Let's be grateful for all those who were instrumental in our own awakening.
It might be of interest to hear of any stories where the above was a factor in the lives of anyone and the awakening of another or another as a catalyst in your own awakening.