"Facing Current Challenges" by R’Yehuda Levi is an absolutely fantastic sefer which I recommend that everyone buy and read. His breadth and depth of knowledge in all aspects of Torah is simply phenomenal. The topics covered range from Jewish Nationalism to Ecology to Chinuch. One can read a book review by R’YGB here.
There is a whole series of essays on the topic of working for a living. Below are some extracts that I think highlight some pertinent themes and ideas that require thought and analysis:
Essay 29: Torah and Livelihood (pg 205)
Two hundred years ago the author of Sefer Heberith [1] expressed himself in the strongest terms concerning the common misinterpretation of R.Nehorai statement:
In the same chapter of Sefer Heberith the author exaplins that “the cornerstone and foundation” of Divine service is “to have a craft by which to earn a living through ones own efforts, and not to need the support of other people”. He goes on to say:
The author of Sedey Chemed thought so highly of these remarks that he copied the entire chapter into his book [4]
[1] Update: Sefer HaBrit – Rabbi Pinchas Eliyahu of Vilna: First printed in 1797. A compendium of the scientific knowledge of the time (astronomy, geography, physics, chemistry, biology, etc.) together with a presentation of the kabbalistic worldview {Thanks to Shy Guy for that information}
[3] Maharsha on Kiddushin 82A: “R.Nehorai.. certainly does not dissent, for everyone must learn a trade; rather, his words may be interpreted thus: “I put aside teaching a trade as a fixed occupation, and I teach Torah by a fixed schedule and a trade when I find the time”
[4] Sedey Chemed, Kelalim, Alef #230, Peiath Sadeh, ibid. #160