the work answer already covered the working side with berachos 35b, many did like rabi yishmael and succeeded. what is not covered is the ordering between work and marriage.

1. the gemara in kiddushin 29b brings a braisa: a man should learn torah first and then marry, and if he cannot manage without a wife he marries first and learns after. then rav yehuda says in the name of shmuel that the halacha is marry first and learn after, and rabi yochanan pushes back, how can a man learn with a millstone around his neck, meaning the pressure of supporting a family. the gemara says there is no argument, one practice was for bavel and one for eretz yisrael. so practically which side is the halacha like, and which one was for which place?

2. the gemara in sotah 44a learns an order straight from the pesukim in devarim 20:5 to 7: a person should build a house, then plant a vineyard, and then marry a woman. and the rambam paskens it openly in hilchos de’os 5:11, the way of sensible people is first to set up a way to make a living, then a place to live, and then marry. does that mean marrying with no parnassah at all is actually against the halacha, or is it an ideal way and not an obligation?

3. and kiddushin 29a puts it on the father to teach his son torah, to marry him off, and to teach him a trade, and says a father who does not teach his son a trade, it is as if he taught him banditry. so inside the halacha itself, which really comes first, the trade or the marriage?

bottom line: if a young man today asks what he should set up first, work or marriage, what does the torah actually answer?