Recently my sister convinced my wife and I to begin watching a Canadian show called Being Erica.  The show is about a 32-year old woman who feels that her life is a compilation of bad decisions.  She meets a ”therapist” who asks her to list her regrets and sends her back in time once an episode to redo some of what she considers the most pivotal points in her life, when she made some of her worst decisions.

I could not help but think when watching this show about some of the pivotal financial decisions I made in my life and what kind of impact they have. 

Here are some of the best and worst financial decisions I have made, and how I think they have affected my life.

My best financial decisions:

Pushing off aliyah for a year:  I pushed off my aliyah from August 2005 to August 2006 in order to take a job as a teacher for a year.  While this did not fill the coffers indefinitely, it did give me the proper cushion I need in order to make it in Israel.  This money would serve as a down payment on the apartment I currently rent, and help me support myself though what was one of the most difficult times to be involved in a job search.

Trying new ideas:  When I was in Chicago, I was diagnosed with a herniated disc (very painful).  My doctor insisted that the only thing he could do was give me cortisone shots and a ton of vicodin until I would be able to raise $20,000 for back surgery.  I did not sleep for nearly a year and was on the verge of taking out a high interest loan in order to pay for the surgery.  The vicodin made me very edgy and snappy (I started watching House because 3 people independent of one another told me that I reminded them of House during this period.)  Finally and in desperation, at the insistence of a family friend, I read a book and followed the program of Dr. John Sarno, head of rehabilitation at NYU medical center.  Within 6 weeks I was completely healed and have had no back or leg pain since (my seasonal allergies and lactose intolerance went away as well.)  If you suffer chronic pain, I highly recommend reading one of his books.  You should be skeptical; I was, but an open mind saved me a ton of money.

Learning in Bar-Ilan’s Kollel instead of getting a job:  During my MBA, I had to choose one of two options in order to make money (1) get a part time job or (2) learn in Bar-Ilan’s Kollel.  After calculating how much the Kollel would be paying an hour, I realized that it would be paying more than a part-time job.  More importantly, learning in an Israeli Kollel gave me the opportunity to learn at a much more advanced level.  Finally, my ability to work in my job today is partially the result of the Hebrew I picked up learning in the Kollel.

My worst financial decisions:

Not knowing what I wanted to do in college:  My generation is defined by desiring a plethora of opportunities so much so that it leaves many of us unable to make a decision.  I took some business courses in undergrad, but I probably should have majored in business in undergrad, as opposed to going for an MBA.  I really don’t think it would have made a difference in the job market and probably would have saved me a ton of money.  This of course brings me to my biggest regret financially…

My student loans:  All my life I have heard that student loans are “a fact of life” and “good debt.”  I no longer believe there is such a thing as “good debt.”  Unless you are certain that the additional education will get you a job that will pay back the loan in spades, I strongly recommend against taking out a student loan.  I went to an inexpensive undergrad, so I am not worried about the loans from there, but the loans from business school are finally beginning to catch up with me.  If I were to do it all again, I would only go to undergrad, and try to make sure my loans were paid off as soon as possible.  And for grad school – I would only go if I were to be subsidized, sponsored (often times employers will foot the bill), or if I saved the money to pay for the entire thing up front.

I remember back in yeshiva that one of my Rabbis told me that he never missed a day of putting on tefillin since he was 20.  Not 13, but 20.  He said that just because he messed up when he was young does not mean that he cannot learn from it and make sure his future is what it should be.  When he makes it to 120, I think the angles will be more impressed that he wore tefillin every day for 100 years than upset that he missed a bunch of days the first 7.  Taking the right step now, religiously, socially and financially is the best thing one can do.  Not only will it make up for past mistakes in time, but it may bring forth new opportunities and possibilities that will make the journey worthwhile.