SHAFAQNA – The Grand Ayatollah Sistani answered questions about performing Istikharah.
Question: Is performing Istikharah as is customary among us nowadays, religiously approved and appropriate? And is there any harm in repeating it if it is accompanied with paying Sadaqah (offerings in the way of charity) equal to the number of times the person requests Istikharah?
The Grand Ayatollah Sistani: Istikharah is performed after thinking and consultation, at the time of confusion, and equality in probabilities, and when one probability is not preferred to the other. But repeating it due to confusion is not right unless the situation changes, and Sadaqah is paid accordingly from wealth.
Source: PERSIAN SHAFAQNA