He has several options in front of him; how should he choose?
Question

I am a Saudi student in Canada, and I want to complete my master’s degree in engineering. But I am confused about which of five master’s specialties to choose. They are: 1- Urban Planning 2- Urban Design 3- Housing 4- Real Estate Development 5- Urban Management. My question is: should I pray istikharah once and mention all of the specialties [in the supplication], or should I pray istikharah five times in a row, once for each specialty?
Praise be to Allah.The meaning of istikharah is that the Muslim asks his Lord to choose for him the one of two things that will be better for him in his both his spiritual and worldly affairs.
Shaykh Ibn ‘Uthaymin (may Allah have mercy on him) said:
What is meant by istikharah is seeking the better of two things."(Sharh Riyadh as-Salihin  p. 792).
He said in Taj al-‘Arus (11/250):
In the hadith of istikharah, it says “Allahumma khir li (O Allah, choose for me), meaning: choose for me the better and most appropriate for me of the two things. End quote.
The basic principle regarding istikharah prayer is that it has to do with one matter, which the person may either do or not do.
Based on that, you have to examine these options, think them over, and consult people of experience, knowledge and reason, until you settle on one thing, then pray istikharah regarding it.
An-Nawawi said: It is recommended, before praying istikharah, to consult someone who is known to be sincere, compassionate and experienced, and who is trustworthy in terms of his religious commitment and knowledge. Allah, may He be exalted, says (interpretation of the meaning): {and consult them in the matter} [Al ‘Imran 3:159]. So after consulting other and deciding to go ahead, then pray istikharah, asking for Allah’s guidance regarding that."(Al-Mawsu‘ah al-Fiqhiyyah  2/243).
Dr. Muhammad ibn ‘Abd al-‘Aziz al-Musnad said:
If the Muslim wants to do something, and he only has one option that he is thinking of doing, then let him pray istikharah and seek Allah’s guidance about doing it, then let him go ahead with it. And if he is thinking of not doing it, then let him pray istikharah and seek Allah’s guidance about not doing it. But if he has a number of options, then first of all – after consulting trustworthy people of knowledge and specialists – he should choose only one of these options, then if he wants to do it, he should pray istikharah before going ahead. End quote.
If you prayed istikharah about one of these options, and Allah did not decree it for you, then move onto the next one and pray istikharah, seeking Allah’s guidance, after examining the matter and consulting others.
If you prayed istikharah once regarding each of these matters, meaning that you repeated istikharah five times, then you decided on one of them, we do not think there is anything wrong with that.
And Allah knows best.
For more information on praying istikharah, please see the answers to questions no. 112151 , 11981 and 2217 .
We ask Allah to help and guide you.