Answered by Shaykh Faraz Rabbani
Something is bothering me concerning a very important decision I need to make. Can I perform the Prayer of Seeking Guidance more than once?
Answer: Walaikum assalam,
I pray this finds you in the best of health and spirits.
It is permitted to repeat the Prayer of Seeking Guidance (Salat al-Istikhara)—as it is a prayer (dua) of turning to Allah, and it is encouraged to turn repeatedly to Allah for one’s needs.
However, this is balanced with the sunna of being decisive—and leaving indecisiveness, doubts, hesitations—and trusting in Allah.
Thus, the early Muslims would recommend not repeating the Salat al-Istikhara more than seven times, as a general guideline. [Ibn Abidin, Radd al-Muhtar, others]