Introduction

Like a rich diamond deposit lying undiscovered beneath the ground. Scattered throughout the Talmud and its commentators, there exists a complete, consistent and practical system through which a Torah person can properly understand his relationship to work (melacha).
Like prospectors searching for half-mile-deep treasures using only shovels. For all kinds of reasons, many thousands of fine bnei Torah approach their employment without a sense of direction and without the incalculable benefit of the Torah's eternal guidance.
Let's try to connect this treasure with those searchers.
First, however, there are questions. Are we perceptive and honest enough to understand this system; to draw together all the threads woven throughout the wider Torah tapestry? Are we qualified to intelligently and respectfully apply these timeless teachings to the specific needs of our exceptional age? We can certainly try.
Are there risks associated with earning a living? Of course there are. Is every method of training appropriate for every Jew? Certainly not. Does the Torah prescribe only one path through life upon which everyone must tread using identical steps? Most unlikely. Rather, someone who, after careful consideration and extensive discussions with a talmid chochom, discovers that his circumstances lead him to seek parnassa outside the world of the yeshiva will, hopefully, find in these pages access to some of our holy Torah's guidance.
One important note. Most of the gemara sources I'll explore fall into the category of homiletics (aggada) and not halacha. Please don't think that by choosing a particular interpretation of a particular passage of gemara, I'm claiming that this is the required Torah practice.
And in any case, one can't say that interpretation "x" is the definitive interpretation of gemara "y". Here's an example of what I mean (in general, it should be noted, I will adopt a somewhat loose style in translating Hebrew passages to make them more readable. As a rule, you'll gain from looking them up yourself):
The mishna (Kiddushin 82a) famously records: "Rabbi Nehoray said, 'I would leave all the trades in the world and I would only teach my son Torah...'" The Maharsha ("l'olum...") writes "and Rabbi Nehoray who says later 'I would leave all the trades...' certainly doesn't argue (with the general requirement that a man have a trade) and (in fact) every man must learn a trade. However, here's what he meant: 'I would leave the (attitude of the) centrality (kevi'us) of any trade and I would teach my son Torah with kevi'us and a trade on the side (b'aray).'"
The Iyun Yakov, on the other hand, explains that Rabbi Nehoray really wouldn't have taught his son any trade at all, but only if his son was one of those people capable of teaching Torah and who, by making use of one of the many permitted methods of accepting payment for his teaching services, may still avoid the general need to have a trade. Such a person will never be tempted by crime (as in Kiddushin 30b) but, in fact, he'll be joining his Torah to a melacha (as in Avos 1; 10).
In a third approach, the Ben Yehoyada understands that Rabbi Nehoray advises a father to avoid teaching more than one trade ("I would leave all the trades"), but one single trade, of course, he would teach his son. Alternatively, Rabbi Nehoray would decline to personally teach his son a trade, but would instead hire a tutor, freeing himself, as a father, to concentrate on the teaching of Torah.
Can you say that the Maharsha (allowing for his pre-eminent status) is more "correct" than the Ben Yehoyada or the Iyun Yakov? Rather, each is offering precious Torah advice. We'd be fools to ignore any of it.

Thinking About Work

What does a working ben Torah (by which I mean someone for whom Torah values and study are of prime importance) think about his parnassa?
Even if he must, reluctantly, leave the bais hamedrash for some time each day, Torah, of course, is his main focus. Its words occupy his free time and hang sweetly in the background even while he's involved in other things. "They are our lives and the length of our days." He has specific and ambitious learning goals to maintain interest and commitment.
Our ben Torah surely remembers R' Shimon bar Yochai (Brachos 35b) who insisted that meaningful Torah can only be achieved through total, uninterrupted dedication. But he also remembers R' Yishmoel who understood "you will gather your grain..." (Devarim 11; 14) literally: that Torah must be accompanied by melacha. "Many acted like R' Yishmoel and were successful." Successful, obviously, not only at their melacha, but in their learning as well.
Again: we're not taking sides between Rashbi and R' Yishmoel (or between any two other chochmai Yisroel). We're only trying to understand how, once we're in it, we're to look at melacha.
This is a ben Torah:

• He knows that any trade - no matter what the conventional wisdom might say about its prospects - can generate prosperity (mishna, Kiddushin 82a). His melacha might be his duty, but it's not the actual source of his success, as, in general terms, economic status is decided before birth (Niddah 16b) and the specific details for this year were set last Rosh Hashana (Beitza 16a - Shabbos, yom tov and chinuch expenses being deductible).
• Through self-analysis, he tries to understand how much effort (hishtadlus) is appropriate for his unique situation. He realizes that overly intensive involvement in this-worldly pursuits can badly distract him from his Torah life (and cloud his sense of dependence on G-d). On the other hand, he also knows that if he minimizes his effort, relying wholeheartedly on G-d to meet his needs, he might not yet be spiritually ready to face the disappointment of unmet expectations (even if he's intellectually aware that whatever he's been given is no less than G-d intended for him). The trick is finding the proper balance (see R' Dessler, Michtav M'Eliyahu volume 1, page 189).
• He enjoys his work and takes pride and satisfaction when he does well. "G-d instills in each man's heart a fondness for his parnassa...hence the popular expression: lower a tasty vegetable to a pig and he'll do what he always does (i.e., roll it in the mud as he does with his regular, coarse food - Rashi)" (Brachos 43b). In other words, even a dirty, degrading job can (and should) appear majestic in the eyes of the one doing it (as, according to Rashi "Yafe lo", G-d doesn't want any trade to die out). All the more so a job that provides some useful, constructive service to ease the lives of one's fellow human beings.
• He looks to his work to provide opportunities for Torah growth: "the majority of camel drivers (who regularly face the dangers of the desert and will thereby turn to G-d as their only hope) are kosher, most sailors (who face yet greater dangers at sea) are chassidim" (Kiddushin 82a, see Rashi). In fact, the Chovos Halevavos suggests that one of the reasons G-d Himself created His world with the need for people to work (who said it had to be that way?) was to provide precious opportunities for spiritual challenges and elevation.
• He's confident that his self-reliance and hard work are safeguarding his spiritual accomplishments. "Greater than one who fears heaven is one who benefits from his hard work" (Brachos 8a). Maharsha explains that by earning his own way during his lifetime, a man can ensure that his reward in the next world won't have been prematurely spent miraculously supporting him here.

We should note the approach of the Mesilas Yesharim (in Chapter 21) who writes how, since what's coming to us has already been decreed from Above, we can, when it comes to our material success, simply rely on Him. Why waste any time at all trying to speed things up: our efforts won't help anyway. In fact,

"a person would be able to sit and make no effort whatsoever if it weren't for the fact that it was decreed upon mankind 'to eat by the sweat of your brow,' obliging us to make at least some effort in the acquisition of a livelihood, because thus has the Heavenly King declared. And this is like a tax which every human being must pay and from which there is no escape.... However, the effort is not what helps, but is only an abstract necessity (independent of the Providence that brings us sustenance).

A ben Torah will welcome the enjoyment and sense of fulfillment he finds in his work, but he must never forget that the time spent earning a living - though necessary - is time that can be a distraction from the pursuit of his true purpose in creation.

What to Choose

Chazal list a handful of trades that one should avoid. Curiously, Benedictine monk doesn't seem to be among them. Does that make it a reasonable career option (after all, Shabbos shouldn't be a problem as you're largely free to set your own hours)? Unlikely. Rather, using their familiar brevity and precision, Chazal presented various examples as prototypical models from which each generation is expected to learn. So let's take a look at these models and try to apply the guidelines they provide.


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