This is a Devil's Advocate post.

We are led to believe that the best place to invest our money is in the stock market. Low barriers to entry, low barriers to exist, plenty of information, high probability of success in the long run and a lot of success stories. We also hear some of the horror stories of people who day traded tech stocks in the early 2000s, gamblers who lost it all on penny stocks, and all the chop shop, pump and dumpers like in the movie Boiler Room. However, through it all, we’ve been taught, over and over again, that if you buy for the long term, you will always win.

For today’s Devil’s Advocate post, we’re going to break down the stock market and show why we really are just little guppies hoping not to get eaten by the sharks.

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This is a Devil's Advocate post.

The allure of automation is obvious. Look at the famous Ronco Rotisserie catchphrase – “Set it and forget it!” Automation is appealing because it lets computers do the work and lets you do something else more interesting. Set your 401(k) contribution each month, set the allocation, and then go spend time with your family. Set credit cards on auto-pay, go all electronic for the statement credit and for the environment, and spend more time playing video games and watching television.

I get it and I love automation too, but there’s something you should know… automating your finances can lead to bad habits, bad habits can lead to tragic losses and big mistakes. In this Devil’s Advocate post, I explain why automating all of your finances can be an expensive mistake.

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This is a Devil's Advocate post.

A few years ago, when the housing market was sizzling hot, everyone and their mother talked about how their home was a fantastic investment. They talked about how a home that sold ten years ago had quadrupled in value over the last five and cursed themselves for not buying more. I knew someone who owned four rental properties, all bought on ARMs, and was making a “killing” on the rents and appreciation. I knew someone else who was looking at his paper riches and marveling at how wonderful homeownership was.

Then the housing market stalled. ARMs reset. People were in rough shape. Those who overextended learned something the prudent have always understood, as much as your home is a great place, it’s not an investment.

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This is a Devil's Advocate post.

The conventional wisdom is that you should check your credit reports at least once a year and your score only when you need it. However, with services like MyFICO and Credit Karma, checking your credit score “all the time” has become just as cheap as checking it infrequently once a year.

Credit Karma is 100% free and they give you a TransUnion credit score using TransUnion data. It’s not technically a FICO score but it’s free and good enough for the reasons I give for monitoring your score all the time. You will have to provide sensitive personal information, since they will be accessing your actual TransUnion credit report, but you’ll never need to pull out your credit card.

MyFICO is run by Fair Isaac Corporation, the creator of the FICO score, and it costs money, about $9 a month. You get an Equifax FICO score every week, among other services. I don’t think it’s important to get an official FICO score all the time if you can get a credit score from one of the three credit bureaus (Experian, Equifax, TransUnion).

This is part one of a two part Devil’s Advocate, Angel’s Advocate article in which I argue both sides of an issue. This is the Devil’s Advocate post, here is the Angel’s Advocate post arguing why monitoring your credit score all the time is a bad idea.

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This is a Devil's Advocate post.

Do you play a sport? My favorite sport to play is basketball. There’s something about hearing the ball swish through the net that brings a smile to my face. There’s something about threading that perfect pass that makes me just a little bit giddy. Oh and setting a good solid pick to get my guy free? Love that too. While I love all the other aspects of the game, I love winning the game above all else. I don’t care how many points I score or how many assists I get, the point of the game is to win and if you don’t win, none of that other stuff matters.

It’s not like that in life. In life, you don’t always have to be the best. In this Devil’s Advocate post, I talk about how in personal finance, you don’t have to always get the best offer, sometimes good enough is good enough.

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This is a Devil's Advocate post.

If you read the news, you’d think that our economy was in shambles, that our financial world was ending, and that we should be buying toothpaste and toilet paper, preparing for the Thunderdome. As Devil’s Advocate in this post, I think that saving all of your money is a mistake. I believe our situation seems dire and that an emergency fund is, as always, a requirement for any sound financial plan, but saving every last penny is the last thing you should be doing. Now is the time to buy the things that you’ve been putting off because every signal is telling you to save.

The laws of supply and demand are in your favor because no one else is buying, which means the people who are will be getting incredible deals if they are willing to negotiate and put in the time. No one is spending their money, they’re saving… which means banks won’t be giving you great interest rates because they don’t have to, they have too much money! That’s only the beginning…

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This is a Devil's Advocate post.

This Devil’s Advocate post will cover something that’s bound to elicit a lot of discussion – here are four reasons why you shouldn’t donate money to charity. That’s right, you read that correctly, I have four reasons why donating your hard earned money to a charity is a bad idea and chances are there is at least one reason here that you didn’t even consider. If there was ever a Devil’s Advocate post to end all Devil’s Advocate posts (don’t worry, it’s not the last one), this would probably be one of them!

Americans are one of the most charitable groups in the world, having donating $306 billion in 2007 according to the Philanthropy Journal, an increase of 3.9% over the year before. While the donation amounts in 2008, a period of economic uncertainty, are not yet known, chances are Americans will still be sending hundreds of billions to philanthropic organizations… so in the face of that, I present to you four reasons why you shouldn’t donate money to charity.

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This is a Devil's Advocate post.

This Devil’s Advocate post comes from my friend Lazy Man of Lazy Man and Money, owner of a timeshare in Aruba.

Almost every personal finance guru will tell you that it rarely makes sense to buy a timeshare. They often cite scary fine print, travel inflexibility, and difficulty in selling the timeshare. These are legitimate concerns for some timeshare owners, but not all. Back before I was heavily into personal finance, I considered a timeshare. And my girlfriend (now my wife) on a trip to Aruba actually bought one. Was it a bad decision? I don’t think so. Why? Well here are a few details that make our purchase seem “worth it.”

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This is a Devil's Advocate post.

This Devil’s Advocate comes straight at you and assails the one last bastion of hope for a prosperous retirement – 401(k)s and IRAs. While it probably doesn’t feel that way with the volatility in the market, conventional wisdom says that the best way to save for retirement is tax-advantaged accounts like 401(k)’s and IRAs. The power of having that money grow tax free trumps all other options.

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This is a Devil's Advocate post.

This Devil’s Advocate post is really borderline Devil’s Advocate because it’s not entirely in the spirit of taking a position against something that’s considered prevailing wisdom. You could say that the prevailing wisdom is that failure is bad, success is good; but as the advocate I’m not advocating that you should try to fail. I’m merely saying that failure itself is not a bad thing, much like success itself is not always a good thing; it’s all in context.

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