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Man’s Search for Meaning by Viktor Frankl is a quick book that goes into how we internalize meaning that drives happiness from purpose that helped me figure out this out better than many other “journey > destination” books.

Bed of Procrustus by Nassim Nicholas Taleb is a bunch of quick aphorisms that takes less than an hour to read and gives good insight into Taleb’s form of critical thinking.

Between the Devil and the Dragon by Eric Hoffer has essays from a self-educated, laborer philosopher and has helped me to understand much about how I think through things and why.

[Balgair]

Aside: The True Believer is well worth the read. Though I may have some issues with Hoffer's conclusions in his work, I've never regretted the time spent reading him.

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True Believer is included in Between Devil and Dragon.

I like how you stated “I’ve never regretted the time spent reading him” as I don’t agree with many of his statements and sometimes his writings seem a bit self-involved or exegesis in need of a peer review, but I’ve found it valuable to read through and think the power of some of the ideas I keep, or just strongly disagree, are worth all the material I discard.