Someone left a comment (thank you!) suggesting that these two views may be at the crux of the machlokes between R’ Shimon bar Yochai and R’ Yishmael (Brachos35) as to whether one should immerse oneself in learning full time and rely on Hashem to take care of one’s needs or whether one must allow time for work as well. I assume the idea here is that if bitachon means you can trust that everything will work out well, then if you are a big enough ba’al bitachon, you can quit your job and rest assured that G-d will help pay your mortgage, tuition, and food bill. But if bitachon only guarantees that G-d is in control, then there is nothing to say that if you quit your job you won’t starve, so better to keep working if you want to eat.
I was taken by the idea, but don't think it works and wanted to explain why. The machlokes RSb”Y and R”Y is not about bitachon – it’s about hishtadlus. Bitachon and hishtadlus are *not* two sides of the same coin. Whether you hold you have to put in a significant degree of hishtadlus (like R”Y) or can get away with no hishtadlus (RSb”Y), in either case the requirement for complete bitachon and trust that G-d alone will determine the outcome remains the same.
Chazal tell us that Yosef was a great ba’al bitachon, but at the same time (in the same Midrash!) they criticize his request of the Sar haMashkim to remember him. Yosef erred in making that type of hishtadlus, but there is no doubt that he had full faith and trust in G-d no matter what the outcome.
Who has the greater bitachon challenge – the person who goes to work to earn a living, or the person who is torasam u’mnasam? It’s the person who goes to work. The person who has no other means of support is forced to rely on G-d, and hence comes to bitachon easily. “There are no atheists in a foxhole” means that when you have nothing else to rely on, you naturally turn to G-d. The person who goes to work however can fall prey to the illusion that the effort he/she puts in to their job is what brings them the rewards of money, a nice house, nice clothes, etc. In truth, they are just as completely dependent on G-d as the person with no job. The difference is just in the degree of hishtadlus being made, not in the degree of bitachon required.