Devil’s Advocate Column

If you read enough personal finance news articles or watch enough television, you’ll notice the pundits telling you the same exact principles. Buy for the long term, invest in index funds, don’t try to time the market, your home is the best investment you can make, etc. In this column, we argue the other side of conventional personal finance wisdom to shed light on whether these beliefs are justified or merely the echoes of nicely dressed parrots. Sometimes these articles are paired with an Angel’s Advocate post.


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 Devil's Advocate 
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You Don’t Have To Be The Best

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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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 Devil's Advocate 
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Don’t Save Your Money

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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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 Devil's Advocate 
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Don’t Donate Money To Charity

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This is a Devil's Advocate post.

Donation BoxThis 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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 Devil's Advocate 
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Timeshares Are Good Investments

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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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 Devil's Advocate 
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401(k)’s and IRA’s Are For Suckers

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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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 Devil's Advocate 
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Failure Is Good

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This is a Devil's Advocate post.

Cant Fail CafeThis 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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 Devil's Advocate 
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Don’t Bring In Your Lunch

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This is a Devil's Advocate post.

Brown Bag Lunch BoxThis Devil’s Advocate post attacks one of the of the hallmark money saving ideas for the working professional: bring in your own lunch. The money you save by not buying a $5 – $10 lunch every day amounts to over a thousand dollars a year in savings ($5 x 48 weeks x 5 days = $1200). It’s hardly bad advice and practically unassailable from a financial standpoint, but there are many reasons why you shouldn’t bring in your lunch every day and eat it at your desk.

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 Devil's Advocate 
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Time The Stock Market!

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This is a Devil's Advocate post.

Screw the experts, screw the planners, screw all those smart people who told you that you shouldn’t the time the market. Timing the market is the name of the game! Why wouldn’t you use all of the available information to your advantage? Why buy shares each and every month if the sky is falling? While I respect the thinking that the averages work out over the long run, reality is that no one lives in the long run and you can’t keep throwing good money after bad. If something is a bad investment, the experts say forget the sunk cost and cut loose. So if the stock market is a bad investment, why do they argue that you should keep investing when the smart money says you should take a break?

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