Tariq Mehanna
Allah said in Surat Al 'Imran, v.135: {"And those who remember Allah and ask for forgiveness for their sins when they commit sins or wrong themselves – and who forgives sins but Allah…?"}
The acts of tawbah & istighfar are traditionally accompanied by emotions of sadness and regret. Indeed, regretting the sin that one is repenting from is a pillar, a key condition of that repentance being accepted by Allah. And reading the books of Ibn al-Jawzi in particular, you come across frequent mention of "the tears of repentance," and "cleansing your sins with the tears of regret." It goes without saying that one should be saddened at the disobedience of Allah, whether on the part of himself or others.
But I would like to point out that once you realize that you've committed a sin, feel regretful over it, and then progress to the point of seeking Allah's forgiveness, the sadness should be replaced by happiness. Yes, a believer should feel sad at the realization that he/she has disobeyed Allah. But committing a sin is like locking yourself in a cage. Repenting from that sin and asking Allah's forgiveness is like the key to unlock that cage and free yourself. Imagine yourself being freed from that cage – the natural emotions you will feel are none other than happiness, joy, optimism. You will not feel sadness while you are being freed. Likewise, repentance should be associated with these positive emotions, rather than the sadness that should accompany the sin itself.
In fact, your repentance is an occasion of joy for none other than Allah, Himself. Anas reported that the Prophet (عليه الصلاة والسلام) said: "Allah is happier when you repent to Him than you would be if you were riding in a desert, your animal escaped from you carrying all of your food & drink, you lost hope in ever finding it, you found a tree and lay in its shade, and suddenly found the animal standing in front of you…" So, if Allah – the One forgiving you – is happy when you repent, it only makes sense that you – the one being forgiven – would feel nothing but joy upon repenting.
So, tawbah & istighfar are occasions to look forward to, and should be performed with a sense of joy.