Fear of failure after failure after...

A bad mood suddenly came over me to the point that I had to write it down or just let it pass. It is 10pm, and I am starting to get tired, but what I wanted to communicate is the feeling that sometimes as a person nears the later years of his or her twenties, one looks back and sighs from the important accomplishments one has achieved in the last ten years. My story is not that supreme.

I feel that most of my life, I have been recovering from one shipwreck or another, whereas I would take on a task, work hard at it, and then through external factors, the task would fall apart and I would be left with a disaster on my hands.

In college, I spend four years working hard to get admitted to medical school to become a doctor. One day after years of effort, upon sending out my resume to all of the medical schools I applied to, I noticed that the school sent my transcript out to all the schools with an error so destructive that I had to withdraw all of my applications.

Then I worked a number of home-based businesses and multi-level marketing programs and I lost money on every one, even though I gave each one my best effort. On some, I even was successful in reaching the objectives set out for me by the company, and then the president of the company would run away with all of the money and not pay the commissions due, or he would dissolve the company and everyone involved would lose everything they invested into the business.

Then years later when I went back to school to become a doctor again after working for a few years, my plans were destroyed by external factors because it was at that time that I was beginning to become religious, and I learned that a Cohen (a descendant of the Jewish High Priests, sorry for the crude description) cannot be a doctor. No exceptions. I decided to stay in yeshiva instead and I became religious.

Additionally, there were many other factors in play at the same time, I was dating a girl who was religious, and I had no compunctions to drive over to visit her on Shabbos (Sabbath), because it meant nothing to me at the time because I did not yet know that I was obligated to be religious -- I thought it was just something nice to do and to be. For me, eating kosher was choosing to eat a dairy meal at a non-kosher restaurant. Before I became religious, the girl used to tell me that she couldn't consider a serious relationship with me because I wasn't religious. As I became religious, she broke up with me because according to her I became too religious.

Then I was hired by a mortgage bank who promised a high-five figure salary, but when I did exactly as they instructed and over a period of months I brought in the mortgages and built the mortgage business, the bank (my employer) decided to stop paying the salaries and started having "accounting errors" which deprived people -- myself included -- on their commissions, which amounted to thousands of dollars of salary that I needed to spend almost two years suing to recover only part of it. I continued to work despite the diminished commission status and the disputed amounts owed to me, and then September 11th, 2001 wiped out my business, which ultimately led me to go back to yeshiva for a few good years of my life.

There were many other occurrences, but I suppose the point is that I feel that most of my life has been spent trying to make something of myself, and most of my life has been a whole cholent (slew) of disasters and failures. I have not mentioned most of these stories because I fear that the stories I have already disclosed will certainly tell at least some of the readers from my circles who I am and my true identity, something I wish to keep secret so that I can continue to express myself candidly without fear of hurting people's feelings or needing to conform to someone else's idea of how things should be.

I often wonder if I had known that I would fail in so many areas of my life, would I have worked so hard to invest thousands of dollars in many businesses, would I have given thousands of dollars and thousands of hours of my life to various causes and to various employers, and would I have devoted my life to various ideologies that have failed me over the years?

My whole life has been one big search trying to find Truth, some comfort, and a little bit of peace. This journey has landed me today in my last year of law school, frum, single, and almost into my thirties. I wonder when these failings will stop, and when I will come home to a real life and home that I have built together with someone else, and when I can be able to say good bye to the fragmented painful existence of grinning and bearing one failure after another while I still give my all.

The question is whether I would have done everything I have done had I known that I would have failed over and over again. Then again, at least I can have pride that at least I went for something and I gave it everything I had and even though it failed me, I have the satisfaction that I never failed it, whatever endeavor "it" might have been during my past.

My only fear is that the cycle of failure will not stop and that I will never find a wife and that I will not find a job after law school and I will be a poor, sad, and lonely forty or fifty year old who didn't even live the broken life that his parents lived. At least they lived a family life by the time they were my age, whereas all that I've done is manage one failure after another, and all I do each day is fill it with subjects such as Patent Law, Secured Transactions, Constitutional Law, and bar review.