As-Salaam ‘Alaikum sister,
Istikhara is a particular form of prayer which is nothing more than a normal du’aa’ in which a person prays to Allah (swt) to guide him/her to reach a right decision. It is not necessarily the case that in response to an Istikhara Allah (swt) will give an answer in the form of a dream, but the answer can also be in the form of a gut feeling or a sense of realization which, when considered on the balance of other research and external factors, may guide you in the right direction.
A dream should not be considered an absolute answer towards a particular direction, but as guidance as within the Shariah a dream is not the binding proof of something. Istikhara enables the relevant person to make a decision which is good for him/her in this world or the hereafter or both. That is why you should make Istikhara yourself and not rely on another person to make it for you even if it is someone as close to you as your own mother because, ultimately, it is your life the decision will affect.
Istikhara does not mean that a person should abandon the consideration of all other matters relevant to the situation. The person should weigh up all the pros and cons to reach a correct decision even after making Istikhara. The actual meaning of Istikhara is “asking what is best and proper from Allah, the Merciful“. Reliance (upon Allah), leaving all of one’s affairs (to Allah) and having a good or favorable opinion of Allah are the requirements before any supplication.
This means that after making Istikhara you must use your own intelligence, and weigh up the situation and think through the possible consequences of any actions you take with the help of research and other people’s advice. It is again going back to the old “have trust in Allah but also tether your camel” philosophy.
I suspect that your depression is a consequence of your consequent difficulties and has immobilized you into feeling helpless and hopeless about your life. This is why you are being caught up in ruminating about what could and should have happened rather than looking at what is and working towards a solution.
My advice would be to stop dwelling on the questions you cannot find answers for and the things you cannot change i.e. why did the Istikhara not work? This is because you will forever be caught up in a spiral of negativity which will have a continuous adverse affect on your mental health and reduce your capacity for coping.
Another way of looking at your current difficulties may be harder, but remember that if you took the decisions that you made on the basis of your Istikhara, then regardless of the difficulties you are experiencing, keep faith in Allah (swt) and submit to your condition as ultimately your submission will yield a greater reward in the hereafter.
If you are still not able to reach satisfaction, then the best thing to do is to once again return to Allah (swt) and ask for “contentment of the heart” and for help to remove all difficulties rather than dwelling endlessly on why the Istikhara has misled you or caused you to make the wrong decisions in life.
Instead seek professional help to overcome your depression and try to search for practical help for the financial difficulties you are currently experiencing as in the end we cannot turn back time or predict the future. But what we can do is live for the present (and the hereafter) which is literally a gift from Allah (swt) – a present which we need to savour and appreciate. I understand that it is easier said than done, but the alternative is that you are going to feel more and more depressed and disillusioned with your life and your resilience will become nonexistent. Remember that things can only get better with the grace of Allah Almighty, so long as you keep your faith and trust as well as be practical about dealing with your problems.
Disclaimer: The conceptualization and recommendations stated in this response are very general and purely based on the limited information that was provided in the question. In no event shall AboutIslam, it’s volunteers, writers, scholars, counselors, or employees be held liable for any direct, indirect, exemplary, punitive, consequential or other damages whatsoever that may arise through your decision or action in the use of the services which our website provides.