Although people say "money doesn't matter," sometimes it leads us to the most stressful and frustrating situations a person can deal with. What mistakes have you made that have cost you or your family a ton of money? Crashing a car? Losing a ton of money? Spill your financial insecurities here.
Even though this isn't necessarily a mistake per say, a recent medical issue of mine will probably cost my family thousands of dollars even though it was a small thing in retrospect. I can't help but feel guilty in situations like this one. Also, I lost a retainer during a church trip that cost me $200 to replace. By the time I got back, my teeth were crooked enough for me to be unhappy with how they are.
