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A question that arises here is, which one of the two praised types of hope is greater in reward?  
The scholars differed which of the two is greater and more rewarding: is it the one of the person who performs good deeds and hopes to be rewarded, or the one of the person who sins but then repents and hopes to be forgiven?

A group of the scholars ruled the first type to be better, because the reasons for the person being hopeful are strong as he performs righteous deeds and his hope is realistic. On the other hand, another group of scholars ruled the second type to be better, because such a person feels a great need for Allaah The Almighty and experiences shame and mortification whenever he remembers his sins; this type of hope has no room for arrogance or (self) deception, because such a person did not yet perform good deeds by which he could be deceived.  
Both opinions may be true, but a Muslim should maintain a balance and combine between the two types of hope. Whenever Allaah The Almighty blesses him and enables him to perform good deeds, then he can hope for the reward of these deeds and he can hope to be admitted into Paradise. However, if he slips and commits a sin, then he should repent and have hope that Allaah The Almighty will forgive his sins.

The different levels of hope
Hope has three different levels and they differ in the outcome:  
First: The hope of a person who exerts hard efforts in worship:  This generates certain sweetness to the worship despite the difficulty and hardship accompanying the deed. He who knows the reward and outcome of the effort he is exerting will exert even more. The one who hopes to attain high profits as a result of a trip, will endure the hardships he faces during his journey. This is just like a businessman who travels, stays up at night and puts up with many difficulties because of the profit he is expecting as a result of the journey.

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Sheikh Muhammed Salih Al-Munajjid

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