A few days ago I was having drinks with a new friend who was on a quest to find her own way off the beaten path. I told her that where I’ve ended up today in many ways is the byproduct of a series of really bad decisions.  In some ways my resume appears a bit more like a criminal rap sheet than a resume. I’ve mentioned before that there are 8 failures that have led me to where I’m at today.  In addition to those failures, I made some bad decisions, but I made a point to learn from each one of those decisions.

  • Choosing my major in college: When I got to college, I was determined to get into the business school. I thought I wanted to be a business major. Truth be told, I find most aspects of business other than entrepreneurship fairly boring. But, “getting into the business” school was one of the most prestigious things I could have happen at Berkeley. It wasn’t long before I had less than average grades and my dreams of attending the Haas School of Business became an afterthought. The ego driven pursuit of a life that looks good on paper started long before I ever entered the working world. The idea that you should follow your passion sounds like cliched advice. But I think far too many people neglect that advice and do something “practical.”  Considering that I don’t feel like I use my degrees at all in my job, I realize that I should have studied something that I was actually interested in.
  • Choosing the wrong job for 5k More: I’ve said before that being a paycheck player can be really detrimental to your success. I chose my first job out of college, even though deep down I knew there was something off about the situation because it offered me an additional $5,000.00. The cost of that decision was IBS, ADHD, and uphill career battles which lasted close to 8 years. Don’t assume that a little bit more money is always a good thing. The ultimate irony of this is I probably would have made tons more money if I had opted for a little less in the beginning. As I said when I wrote about finding a company that lets you be you, don’t chose based on money.
  • Staying in a relationship too long: With both girlfriends I’ve had, I stayed in each relationship far too long. I let it to get the point where it was more painful to stay in the relationship than to end it. One of those relationship ended up costing me a fortune and I spent money I didn’t have because the girl I was dating wanted to enjoy things I couldn’t afford. Out of fear of being alone, I didn’t make smart decisions financially. If anything I’ve learned decisions in your relationships made based on fear will ultimately cause the relationship to end. The minute you start making any decisions based on fear, it’s a slippery slope.
  • Spending like I was an NBA basketball player: Losing all my money (literally) and having to move back to my parents house at the age of 31 was the best personal finance lesson of my life. While I didn’t quite spend like an NBA basketball player, I did live well beyond my means. When I had a summer internship that included corporate housing, instead of saving money I would have spent on rent, I assumed I had  $1000 more to spend on entertainment. But times have changed. Fortunately, I’ve learned that you can have almost everything you want if you just save a bit every single day for the things you want. ING direct has really taught me how to save for every single thing I want to buy.

Often, our worst decisions can be some of our greatest teachers. Have you made any bad decisions that ended up being great life lessons?

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