The correct view is that after one prays Istikharah and recites the Du`a, a sign that one should go ahead with the matter is when Allah makes things easy. The existence of obstacles and difficulties is an indication that Allah is pushing His slave away from doing it.

There are three reasons why praying Istikharah is important: 1- To show our desperate need of Allah alone, disconnect any hope except in Allah, and put our trust in Him. 2- To make the right choice, be successful in what one is striving to achieve, and to be helped by Allah in one’s efforts. 3- To accept divine decree and be content.