Chazal (Brachos 32b) tell us that four things require chizuk (encouragement): Torah, good deeds, prayer, and your livelihood (see Rashi on the gemara). Sefer Musar N'vi'im explains this to mean that even though one does not see bracha from his efforts, don't give up. Rather, one must double and redouble one's efforts in these areas; in the end he will see bracha from his efforts. The gemara brings p'sukim as proof to each of these four areas of endeavor. It seems to me that the first three are self explanatory. Those are area where one often does not see bracha and so the Torah comes to tell us that they require special encouragement. At first glance, though, I am not sure why my livelihood needs a pasuk to encourage me. If anything, my livelihood is the last thing that HaShem needs to tell me to work at; I am plenty encouraged myself, thank you.
Ok, I thought about it; after I learned (Torah), davened mincha (T'fillah), and cleaned up the kitchen (G'milus Chasadim). Then I went back to the gemara and Rashi. Whenever someone tells you, "Rashi is basically saying such and such", don't believe him; especially if it is yourself telling you that. Rashi doesn't "basically" say anything. Each word of Rashi is there because it needs to be there to express the thought/explanation that Rashi wants to convey. If it could have been said in different or fewer words, it would have been. Rashi says that "chizuk" means that a person must strengthen himself in this area constantly with all his power (tamid b'chol kocho). Rashi only comments on one of these four specifically: derech eretz; on which Rashi says, "if he is a crafstman he must work on his craftsmanship, if a merchant he must work on his merchandise, if a warrior he must work on his battle skills". That's a lot words. I looked around and didn't see anyone explaining this Rashi, so I am going to take a stab at it. Your mileage may vary.
When it comes to a livelihood, there are two traps into which one can fall: "kochi v'otzem yadi" or "no matter what I do, HaShem will provide, so I'll just go through the motions". On the "kochi v'otzem yadi", Rashi is explaining Chazal to be saying that you don't need to keep trying different occupations, whatever you are doing is fine. No matter what the occupation, some are rich and some are poor. The occupation is only a vehicle for HaShem to deliver your parnassa (Kiddushin 82a). On the other hand, hishtadlus (effort) is a real obligation. You are not free to simply go through the motions; you actually have to try with all your effort and ability. All the while knowing that your efforts are not actually producing the results.
The world stands on three things: Torah, Avodah, and G'milus Chasadim; and those require constant renewal of effort. It seems that besides that, HaShem expects us to also try with all our might to make it look natural.
Ok, I thought about it; after I learned (Torah), davened mincha (T'fillah), and cleaned up the kitchen (G'milus Chasadim). Then I went back to the gemara and Rashi. Whenever someone tells you, "Rashi is basically saying such and such", don't believe him; especially if it is yourself telling you that. Rashi doesn't "basically" say anything. Each word of Rashi is there because it needs to be there to express the thought/explanation that Rashi wants to convey. If it could have been said in different or fewer words, it would have been. Rashi says that "chizuk" means that a person must strengthen himself in this area constantly with all his power (tamid b'chol kocho). Rashi only comments on one of these four specifically: derech eretz; on which Rashi says, "if he is a crafstman he must work on his craftsmanship, if a merchant he must work on his merchandise, if a warrior he must work on his battle skills". That's a lot words. I looked around and didn't see anyone explaining this Rashi, so I am going to take a stab at it. Your mileage may vary.
When it comes to a livelihood, there are two traps into which one can fall: "kochi v'otzem yadi" or "no matter what I do, HaShem will provide, so I'll just go through the motions". On the "kochi v'otzem yadi", Rashi is explaining Chazal to be saying that you don't need to keep trying different occupations, whatever you are doing is fine. No matter what the occupation, some are rich and some are poor. The occupation is only a vehicle for HaShem to deliver your parnassa (Kiddushin 82a). On the other hand, hishtadlus (effort) is a real obligation. You are not free to simply go through the motions; you actually have to try with all your effort and ability. All the while knowing that your efforts are not actually producing the results.
The world stands on three things: Torah, Avodah, and G'milus Chasadim; and those require constant renewal of effort. It seems that besides that, HaShem expects us to also try with all our might to make it look natural.
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