The worst financial decision that I made was spending years chasing down a girl that looked like this:
She was beautiful and from a wealthy family (the above photo is not actually her). Her life was like a giant vacation. She spent most of her time taking photos for Instagram. This meant I spent a fortune trying to keep up with her traveling and shopping. I was young and broke at the time, yet I spent thousands trying to keep her attention. The reality is that we didn’t have the same values, other than being attractive, dating her had a lot of drawbacks. It was a constant cycle of spending money so that I could spend more money later on. None of which I could afford.
If I could go back and fix a financial mistake that would be it. It does absolutely no good to put up a facade in order to impress somebody. Find someone that likes you for you and can fit with your lifestyle. You are simply digging a hole in a relationship. When you are stuck in a whole, stop digging. Make changes to your life and find a relationship with someone that you have more in common with. I don’t think there is anything inherently wrong with dating someone with more or less money than you, but it will cause these types of issues an possibly make you incompatible. If you are like me and generally frugal and constantly trying to work to improve your career, it is extremely challenging trying to spend your life with someone who doesn’t have the same values. There is nothing wrong with having a life of leisure if you’ve got the means to support it, but if you don’t, dating someone who does is difficult.
Financial compatibility is very important in a serious relationship. You make financial decisions every single day whether you realize it or not. You choose where you work, where you live, what you buy, and most importantly what you don’t buy. If your partner, especially a spouse, doesn’t value their career or money the same way you do, it will be a constant point of tension.
The best decision was starting a business. I was never going to be happy working for someone else. Even if the job paid well or was enjoyable, I was never going to be happy working for someone else. This proved to be a great financial decision. It allowed me to make more money quickly as well as build up equity that I never would have had otherwise. It was difficult in the beginning, I didn’t really know where I would find clients or if it would work. Ultimately investing in yourself and becoming self employed will dramatically change your life. I also gained a peace of mind knowing that I didn’t ever need to worry about a resume or employer again. I could make it on my own and always find a way to produce money when needed. Knowing this made me worry about money far less. When I had a salaried job, I was constantly living in fear of being fired. One guy who didn’t even know me could make a split second decision and fire me. I was overly paranoid about this happening but it created stress the entire time I worked there. It wasn’t worth it anymore. Today I know that if I follow the system I have in place I will find opportunities and make a good living. Being chained the desk and fed a salary kept me from realizing my potential. Once I cut the cord everything improved dramatically.