Hacker News Books

If you liked When Breath Becomes Air I'd also recommend Do No Harm by Henry Marsh - it's similar in style (maybe like the book Kalanithi would have written at the end of his career). It still touches a lot on mortality. Here's a great chapter from it: http://lithub.com/aneurysm/

I'd also add Hitchens book "Mortality" as a suggestion too.

Do No Harm by Henry Marsh is a great book that gives some perspective on what it’s like to have to make these decisions. In both their success and failure.

Here’s an excerpted chapter: http://lithub.com/aneurysm/

I'm in the middle of The Road To Character, and it's a bit too much "people used to be better" for me so far - but still it has some good points here and there.
Wodehouse (also listed in the OP) makes me happy to read, they're hilarious and glowingly warm books.

Here are some recommendations from me in a similar vein, (non-fiction) books that positively influenced my outlook:

- Lamott's Bird by Bird, it's reflections on how to be a writer, but the advice works on "living" and "working" in general

- Werner Herzog - A Guide for the Perplexed: an updated long interview with Herzog on his life and his craft, extremely passionate. There are so many minor stories and bits of wisdom that positively influenced my outlook on humanity and the work I do.

- Bakewell's How To Live: If you don't have time or leisure to read Montaigne's Essais (I'm still not finished with those), Bakewell's book is a bit of a primer/summary of Montaigne's lessons interwoven with Montaigne's life.

- Marsh's Do No Harm: it's the autobiography of a "famous" neuro-surgeon at the end of his career. If I'm 50% as honest and humble about the mistakes I've made at the end of my life (mistakes in his operations turned several patients into people who need constant care for the rest of their lives) then I can die contempt.