Rav Bloch, in his sefer Egeret Al HaBitachon (Page 13) gives a beautiful mashal to understand how bitachon works:
A wealthy man has a very large business, which has certain procedures, and practices. Employees get a certain amount of days off before they deduct from his pay; He has to be in the office at a certain time, and so on.
How much money can you spend on birthday gifts? You don't have to keep asking questions. All these things are worked into the system and you follow the rules. And if someone doesn't follow the rules, he gets fined, or, for something worse, he can get fired. That's the way the business runs, and the system is perfectly made for this business. Everyone under him follows the rules that he made.
Of course, ultimately, he is aware of everything, but he's not necessarily in constant contact with every individual. Then, lo and behold, the owner of the business decides to bring his son in, as is customary for wealthy people. People often bring their children into their businesses, to eventually take over. The son starts out on the bottom of the totem pole. He works in the warehouse packing boxes, so he can learn, from bottom up, how to run the business. But this young man made a very big mistake.
He was negligent and caused a tremendous loss to the company. Based on the systems in place, it was determined that he deserved to lose his job. But of course, there was an appeals system. So he appealed, and the appeal went up the ranks, layer by layer. Even at the highest level, they decided that he should lose his job. Finally, the case gets to the final judge, who happens to be his father.
So the son says, “Dad, besides being the judge, you're also my father, and I'm begging you to have mercy me, like a father has on his son, and tear up this decree. Let me back into the company. You're the one that made the rules and regulations. Everything is done based on you. It's up to you, at any time, to try to change something.”
The nimshal is quite obvious: Even though Hashem made systems for how to run this world, and He's in charge of them and everything goes by the rules, ultimately Hashem has the ability to have mercy on someone. And if someone really relies on Him and turns to Him like a son turns to his father, there’s a different set of rules. That's the Bitachon system. There's a Midrash in Tehilim 118, on the pasuk
Hashem Libo Ezrai- a mashal that two people go to be judged. They were afraid, and someone told one of them, “Don't be afraid. Have courage.״
And this is the example for the Jewish people being judged by Hashem. The angels tell them, “Don't be worried.
He's from your city.” Then they say, “Don't be worried. He's your relative.” Like it says, Bnei Yisrael, Am Kerovo.
Then, Don't be worried. He's your brother. And the final claim is, “Don't be worried. He's your Father.” Like it says, He’s your Father. He's the one that created you. That's why the system is a Bitachon system. It doesn't necessarily work on merits and demerits, like we've said in the past. It says, “There are many pains to the wicked, but the one that relies on God, the kindness of God surrounds him.” That Bote’ach B’Hashem is going back, says the Midrash. This rasha deserves to have many pains, but if he relies on Hashem, he is surrounded by kindness. And this is the understanding that we have to have, on the bitachon track. B’Ezrat Hashem, we will continue with this concept, but it’s an important principle to understand. Because if you don't understand how bitachon works, you really can't rely on Hashem.