As I was re-reading the “How it Started” section, as well as writing the “Getting your Spouse on Board” post, I realized that one of the fundamental issues facing how I deal with money comes down to fear.  I am not sure how many other people have this issue, or if anyone has done any studies on it, but I know for sure that I would be in a much better place if I was not so afraid of failure.

The whole reason following the set path out of high school (college, then grad school) was fear of not being able to get the job that I really wanted.  Once in college, I was afraid of dropping out, or delaying a year to get more funding, because if I did I would have “failed.”  I was afraid of quitting my job because I was not sure how I would afford more schooling if I didn’t keep working.

Once out of college, I was afraid I had ruined my future, so I ran away to a foreign country to figure out what I was going to do next.  It turns out that was great for me, and I decided I would just have to try harder, and study hard for the LSAT.

By the time I enrolled in law school however, the fear came right back.  If I didn’t follow the path everyone else was following (moot court/journal, unpaid internships, all the networking events possible, working under a professor, and then summer intern at a large law firm) I would be un-hireable and therefore, a failure.  I thought, in order to succeed, I had to take the loans to live on so that I could concentrate on studying, and get through everything in three years.

Of course, I can’t at this point go back and do it over.  I do think, however, that if I had been more honest with myself earlier on, I wouldn’t have taken on so much debt.  I could have worked and gone to school part-time, which would have defrayed some of the costs.  I could have understood that if I didn’t want to work at a large firm, I didn’t have to be chasing the same rings as everyone else, which would have freed up my time to study the topics I found more interesting (hi tax and securities!  I still don’t know you as well as I would like!).

The basic lesson for me would be to stop being so fearful of failure.  I’m not sure how to implement it yet, but you can be sure it’s something I will be working on.