The Worst Financial Decisions I Ever Made

It's easy to laud my successes when it comes to money decisions, but not every decision I've made has been beneficial to my financial situation. I've made plenty of mistakes along the way, but I've tried to learn from those mistakes. And, while certain mistakes have been much costlier than others, all have been important in contributing to my financial character and filling my background with valuable learning experiences.

From stocks to real estate, here are what in my opinion, are a few of my worst financial faux pas.

Company Stock Sale

When I started working in the hotel business, the company with whom I was employed offered a stock purchase plan. In short, the stock was offered to employees at a discounted price and was part of the payroll deduction option. I started to put about 10% of my pay into the program for several years until eventually they discontinued it.

Most of the shares I had purchased in the area of $10 to $12 and the stock bounced back and forth between this range for most of the next several years. After a while I got tired of watching the stock do a whole lot of nothing and decided to sell. As I recall I had about four hundred shares or so by this time, and I felt I could do more productive things with my money. So when the stock shot all the way up to $14, I sold.

At the time of the sale I felt reasonably good about the whole thing. I think I had cleared somewhere in the area of $1200, and with my family's poor historical luck with stocks, counted myself lucky to have escaped with any sort of profit. This feeling continued until about four years later when the company was purchased and shares of the stock were bought out somewhere in the $40 to $50 range -- oops!

Home Purchase In 2008

Hindsight being 20/20, it's easy to look back and chastise myself for buying a home at the start of 2008. But at the time it appeared that things had leveled out in the real estate market and that homes in the Chicagoland area weren't going to take as big of a hit as properties in other parts of the country...and in some ways I was right.

It certainly has not been as bad here as in other states -- at least not yet -- but it certainly hasn't been good either. Since my home purchase, property taxes have gone up, our homeowner's property tax exemption has been slashed dramatically (with more to come), and property values have dropped significantly. Pair those issues with the fact that my wife and I don't really care for the location in which we bought (it's kind of boring!), and we now have our home on the market at about 15% less than what we paid for it.

Rolling Over My 401k to an IRA

As I was preparing to leave my career in the hotel business three years ago, I decided I should find out about rolling my 401k over into an IRA. I really didn't know much about doing this, so I called our company's 401k hotline to find out more. The representative transferred me to an adviser with the managing financial institution who began guiding me through the process.

Now I'm not someone to jump the gun on these things and I consider myself reasonably knowledgeable on many areas of investment (although the stock market has never been my strong suit), and I thought I was asking all the right questions -- and maybe I was, but I just wasn't asking them in the right way or getting the right answers. Anyway, long story short, not only did the rollover end up costing me 4% of the entire value of my portfolio to do, but the adviser ended up helping me choose funds that were worse than those in which I was invested in my 401k.

All in all, I should have just left the darn thing alone.

More from this contributor:
Should People Work for Their Unemployment Benefits?
Teaching Your Children About Personal Finance
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Disclaimer: The author is not a licensed financial professional. The information provided in this article is for informational purposes only and does not constitute legal or financial advice. For financial advice, readers should consult a licensed financial advisor. Any action taken by the reader due to the information provided in this article is solely at the reader's discretion.