1. The more you learn about why your mistakes are really wrong, and the damage they do, the more you'll feel true regret. This is why learning Torah is so critical, and specifically learning everything to do with whatever you are focusing on currently. For instance, someone working on anger, would read the section on anger in The Garden of Emuna, and in other books like The Aleph Bet Book, Aleph Bet of Life (Hebrew), etc. As you come to grips with the damage done by not being perfect in this trait, you'll naturally feel more regret when you still come up short.
2. Excellent! You cannot say you won't do it again – you can only say that you'll continue to pray about it every day, that Hashem should help you not do it again. And yes, you do pray on it daily – that's part of the 30 min of spiritual accounting.
Really, the 30 min of spiritual accounting and the 30 min on one subject, are dealt with the same way – praying for help for the future, increasing the desire to change and apologizing for the past. The only difference is the SUBJECT – spiritual accounting is on yesterday's accounting until today (putting out the burning fires, if you would) and the 30 min is always on one specific thing, until you perfect it and choose something else (dealing with the elephant in the room).
3. Gray areas mean that you have not clarified the truth totally, and you need to keep learning until there are no more grey areas. This is our life's work of course, but understand that as long as there is gray space, you're opening the door to the Evil Inclination. He specifically exploits the gray space, because that's where you are weak – you don't yet have daat and you don't for sure know the truth, so it's easy to trip you up.
2. Anonymous
11/13/2020
3. A lot of things are grey areas and I don't even know if they are right or wrong.
3. Anonymous
11/13/2020
1. I am a bit of a black and white person. When I review my day I see my actions as very factual. I don't feel the regret. I know I did something wrong so I want to ask Hashem to come closer to Him and that I should not do it again. But I don't necessarily feel the feeling of regret.
2. How can I say that I will not do it again if I am using my personal prayer to work on one specific deed and am not ready to work on everything else at once.
11/17/2020
11/13/2020
3. A lot of things are grey areas and I don't even know if they are right or wrong.
11/13/2020
1. I am a bit of a black and white person. When I review my day I see my actions as very factual. I don't feel the regret. I know I did something wrong so I want to ask Hashem to come closer to Him and that I should not do it again. But I don't necessarily feel the feeling of regret.
2. How can I say that I will not do it again if I am using my personal prayer to work on one specific deed and am not ready to work on everything else at once.