Recently I've been taking another look at the Book of Privy Counselling, in A.C. Spearing's translation. It's obviously by the same author as The Cloud of Unknowing, and is often bundled with it in editions of The Cloud. Privy Counselling is shorter and more practically direct than The Cloud, and I've enjoyed noticing what I underlined at my last reading, guessing at what must have been on my mind at the time. Sometimes I also think that the close association of The Cloud with Centering Prayer has led us to read it through that lens, sometimes to the detriment of the text.
Some of my favorite parts:
When you come to be by yourself...put aside good thoughts as much as evil ones..and see that nothing remains in your active consciousness but a naked purpose reaching out to God.
And so descend to the lowest level of your understanding (which some, on the basis of actual experience, hold to be the highest)
You are your own cross. This one reminds me of my favorite quote from St. Augustine, Factus eram ipse mihi magna questio, from Confessions 4.4.9, which I like to translate, "I became my own big problem."
The household of the spirit is marvelous, because its Master is not only the doorkeeper himself, he is also the door. He is the doorkeeper through his Godhead, and the door by his Manhood.