Moshe Rabeinu begs of HaKadosh Baruch Hu to enter Eretz Yisrael. Hashem replies, "Dont speak to Me anymore on this subject. The Midrash (Yalkut Shimoni, 819) explains that Hashem was saying, "Don't worry you have a tremendous amount of reward waiting for you."
Why tell Moshe about this now? If his big portion in the world to come is supposed to serve as a source of comfort then he should know about it when the decree not to enter the land was first issued. Why wait until now?
Based on the words of the Shir Ma'on of Erloi Hy"d we can explain this interaction.
We know that the Gemara opines that one who is commanded to do a Mitzvah and does it is greater than one who is not obligated yet volunteers. גדול המצווה ועושה יותר ממי שאינו מצווה ועושה The Mefarshim explain that this is because one who is directed to do has his natural human rebelliousness incited within him and therefore the fight with the Yetzer HaRa to do the Mitzvah is greater.
Even though this is true, there is a plus side to not being commanded. He who is אינו מצווה ועושה can be more sure that the Mitzvah is not being done out of habit. He is doing the Mitzvah strictly out of a desire to make Hashem proud.
Once Hashem decreed that Moshe would not enter Eretz Yisrael, Moshe automatically became an אינו מצווה in regards to the Mitzvos that are connected to the land. The Gemara explains that Moshe wanted to enter the land not because he wanted to soak in the scenery and eat from its decadent fruits - rather he wanted to fulfill the מצוות התלויות בארץ - the Mitzvos that can only be fulfilled in Eretz Yisrael.
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By showing Hashem that we wanted to go into Eretz Yisrael as an אינו מצווה ועושה he retroactively displayed that all of his Mitzvos throughout his life were all with pure love even though there was a commandment compelling him to do so. Only now that he Davened to be allowed to do Mitzvos that he was not obligated in was he a מצווה ועושה who attained the love of an אינו מצווה ועושה.
That is why this is the moment that Hashem told Moshe that there is much reward waiting for him, because this moment amplified the reward of all of his previous Mitzvos.
Taking on a Chumrah is a sensitive subject. But when done in a healthy way and with guidance it shows that we are not doing this (what ever the "this" may be) just because we have to. By taking on something a little extra, by stretching our comfort zone a bit it shows the world - and more importantly ourselves - that Mitzvos are important to us. It adds an element of אינו מצווה ועושה into the Mitzvos in which we are מצווה ועושה.
(We will not address now why the Tefilah didn't work and if this answer comforted Moshe. That is hopefully for a later article.)
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