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Wow!!! Good to hear someone ask the million dollar question!!!
The simple answer is (and you may not like it), the system is the system, doesn’t have to make sense, but those are the facts as they are. I myself, before I got married, ran a successful Amazon business which bh is currently my main parnasah and day job. I learnt a serious 1st and 2nd seder. I worked during lunch, and night times (I didn’t do night seder… My nights were friends weddings/vorts, dates, and work + some social life..) I put serious gedarim in place, my phone remains in my car during seder, and only once a seder during coffee break did I check for anything urgent on my phone.
However, knowing the yeshiva system and how these things work, I was very private about my business, and was very vague to my closest friends. They weren’t stupid, but as long as I didn’t say it straight up, I wouldn’t get that שם, of ‘This bochur does Amazon’. Did it affect me? A little. One girl, when I told her on a 5th date about it, felt uneasy and for other reasons also we stopped dating. My wife however, loved the fact that you can be a serious learner, AND earn a parnasah on the side without compromising on 1st and 2nd seder…
So, sorry for boring you with my personal story, you are 100% right!!! I’ve spoken to many people including Rebbeim, and no one was able to say anything was wrong. The best answer I heard, was “If it would be totally acceptable to work and learn, bochurim that can shteig, and are just lazy, will all drop out of learning”.
Just to finish off… Just a little proven fact for all uneducated people out there about the yeshiva system. A very big percentage of bochurim out there (and some yungerlite) would learn MORE working on the side and learning a serious seder or two, than those ‘learning a whole day. I’ve seen this by many people I know…
Thanks for bringing up this important and informative topic, Hatzlacha Raba, and may you find the girl that will see your work as a plus, not a minus!!!