Jabir bin Abdullaah –RadhiAllaahu anhu- said the Messenger of Allaah -sallAllaahu alayhi wa sallam- used to teach us al-Istikharah (a prayer said for seeking blessings in carrying out a decision) for all matters, just like he used to teach us a chapter from the Qur’aan, he would say: If any of you intends to undertake a matter then he should pray two Rakah other than an obligatory prayer then he should say the Du’aa of Istikhaarah.

Learn the Dua of Istikhaara – [Listen] Hisn Al Muslim Min Athkar Al Kitaab Was Sunnah – by Sa’eed Al Qahtani

Ibn al-Qayyim -Rahimullaah- said:
‘So the purpose of al-Istikharah is to rely upon Allaah and entrustment to Him and the capability to fulfill the action with Allaah’s Capability, His knowledge. And that Allaah chooses good for His slave, and this is from those things which necessitate being pleased with Allaah as the Lord. As a person will not taste the flavour of Eemaan if he does not have these things (reliance, entrustment etc), and if he is pleased with destiny after al-Istikharah then that is a sign of happiness.’
[Taken from ‘Za’ad al-Ma’aad’ by Ibn al-Qayyim 2/443-445]

Shaykh Muhammad bin Umar Bazmool said:
‘That al-Istikharah is not done when a person is uncertain about the matter at hand; because the Prophet -sallAllaahu alayhi wa sallam- said: ‘If any of you intends to undertake a matter’ and that the whole of the Dua’ indicates to this point.
So if a Muslim is uncertain about a matter, and he intends to pray al-Istikharah , then he should make a choice between the two matters and then pray al-Istikharah , and then after al-Istikharah he executes that matter, and if it was good then Allaah will make it easy for him and bless him in that, and if it was not good for him, then Allaah turns it away from him and makes easy for him that in which there is good by the permission of Allaah -Subhanahu wa Ta’ala.
[Taken from: ‘Buggeeyat al-Mutattawa’ fee salat at-tattawa’ p.105]

Related Links:

  • Benefits From al-Istikharah Prayer – Compiled & Translated by Abbas Abu Yahya [PDF]
  • Istikharah – Prayer For Seeking Guidance
    A prayer in which a servant if concerned with an affair or is faced with a worldly problem or intends to do something recommended or obligatory in which he has a choice, or when two recommended or obligatory actions conflict each other — which one should he do