Each of these situations is a unique challenge from Hashem. Success can bring a person to hubris and haughtiness and to reject Hashem. And if he isn’t successful, it can make him feel angry at Hashem: “Why do I deserve this?”
These are essentially the challenges of wealth and the challenge of poverty—not only when a person actually has or doesn’t have money. Every person constantly struggles with the essence of these nisyonos. Every time things go exactly the way a person wants them to, he’s experiencing the העושר נסיון, and every time he feels disappointment, he experiences the העוני נסיון not to become angry with Hashem, chas v’shalom.
Remembering That Everything Is a Gift
What is the eitzah for both nisyonos? This very yesod: to remember that he has nothing, and everything is a gift from Hashem.
If we retain this attitude, then even if a person is successful, he feels the בושה of the pauper at the door with his hand outstretched. He thanks the Ribbono shel Olam, and he surely doesn’t reject the pauper. And if he isn’t successful, he doesn’t become upset—because he never thought he deserved anything.
Receiving and Giving Back
This is essentially the yesod of מבורך ה' שם יהי לקח וה' נתן ה', Hashem has given and Hashem takes back, may the Name of Hashem be blessed. The two go together. No one can get up and declare “Hashem took back” if he didn’t believe with all his heart that Hashem gave it to him in the first place.
If a person has never invested in the נתן ה', he won’t be able to properly feel that לקח ה'. He may say it, but his heart doesn’t feel it.
Only if a Yid constantly reiterates and internalizes that Hashem gave him everything—that nothing is his, and everything was given to him by Hashem, and he constantly does actions that remind him of this: he gives tzedakah in order to remember this; he thanks with gratitude constantly for everything that he has; he asks with humility that Hashem should continue to give him—then, if it is ordained that it should be taken away from him, he will be able to declare with all his might, Hashem has given and Hashem takes back, may the Name of Hashem be blessed! He will remain the בחלקו השמח עשירemas as before.
To Recap:
Every person in the world is given reminders from Above whenever he forgets the Ribbono shel Olam. This is part of the design of creation—both for those at the lowest level, those in the middle of the ladder, and those at the very top. Every time a person forgets the Ribbono shel Olam, he will be sent a hint, a reminder to come back to the proper emunah.
The eitzah for this is to awaken in our hearts the feeling of impoverishment. When we feel like a pauper who is dependent on the giver, then we will never forget the Ribbono shel Olam, because the needy person thinks constantly of ways to approach and petition the one who will give him.
If a Yid knows that his עושר is the Ribbono shel Olam, he will feel constantly as though he’s the pauper at the door, and he will constantly remember Hashem. When the Ribbono shel Olam makes a wedding (Kabbalas HaTorah), he will surely remember to attend, and he will feel joy. He participates, and he never forgets the Ribbono shel Olam.
And if he doesn’t forget, he won’t need so many reminders. He will remain the בחלקו השמח עשיר throughout all the situations in his life.