Matthew, you have written upon a lot of issues here that would beckon scores of threads consisting of several pages each.
I see there are basically three chief issues that you have touched upon and which are interconnected, but are really distinct.
Why are there almost no businessmen/professionals among traditional Catholics?
I have been wondering about this too. I think it varies from Chapel to Chapel, and from State to State, aside from the obvious variation inherent in the difference between individuals and the environments wherein they were reared.
Maybe a sad, misguided attempt to be masculine in a world that has destroyed true masculinity? Masculinity is hard to find these days, as in, there are few true male role models for young men to look up to? So they end up finding crude ideas about what it means to be a man (hunting and fishing).
This is a very good topic to discuss, because it concerns not just the subject of employment but also the formation of Catholic boys and their growth to manhood in its essential aspects (spiritual, cultural, psychological, &c.) whilst they are compassed round about by an aberrant, gynocentric world that lulls women with lies about enfranchisement whilst debasing them to entities that deny their natures (the feminist who uses birth control or aborts because it's "her" body, and thus shall never become the mother she was meant to be) or to the objects of the vilest and most disordered passions of the very "phallocentric oppression" they pretend to oppose (such as women who get involved in the pornography industry). This entails the systematic implementation of a cultural notion of "masculinity" that is unnatural, false, and leads to many abuses. Above all, it robs boys of the ideals to which they ought to properly aspire.
This is a subject which cannot be exhausted in this reply [as it involves very profound cultural, sociological, psychological and, above all, spiritual issues], but it should be the concern of every father and every man who aspires to become a father in the future.
I suppose it's good to have down-to-earth skills, but it seems like traditional Catholics are more melancholic in temperament and/or easily discouraged by the countless obstacles involved in starting a business, or becoming a highly paid professional.
One of the obstacles might be going out into the Big Bad World which many trads tend to isolate themselves from. Also, why go through all the trouble to become a Lawyer when the world is going to end soon, or the Three Days of Darkness are just around the corner?
This is an issue which deals more with the trend many have perceived in traditional Catholics regarding their proclivities in general, and it has to be contextualized by present day factors in order to be correctly gauged.
Telesphorus discussed in his reply the socio-economic contingencies that explain why some men have difficulties in attaining to financial stability, as well as the systematic attempt of alienating Catholics from every aspect of modern life (as it has been corrupted thoroughly in its culture, art, philosophy, &c.). I agree with what he says regarding this (and he has discussed this issue many times before), because I myself am experiencing this too.
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These three topics cement in my mind even more the moral indispensability and absolute duty for traditional Catholic who is called to the married state of establishing and maintaining a household based upon the profession and practice of the Catholic faith, especially the Family Rosary.
It will be parents who thus raise their children who will ultimately save Western civilization. They may have to make many sacrifices and see their "double income, no kids" neighbors enjoying "the greener side," but the latter are doomed to be unwitting victims of the anti-Christian machine that has given them their tangible "success," while the latter shall see the fruits of their labors in this life and in the next if they persevere.