Last week, I saw this article in Kiplinger’s where Amanda Lilly and Stacy Rapacon debated the merits of automatic bill-pay. They both make great points, as well as recommendations for products that can help monitor your bill payments, but I think that automatic bill paying wins out. We auto-pay the bills that let us for a variety of reasons, which we’ll discuss below, and we have systems in place to help us manage the process and ensure that we don’t get dinged insufficient funds or other fees.

First, let’s talk about the systems. We auto-pay all of our bills from our Ally account, which is a combination savings and checking account with overdraft protection. Our savings account contains enough cash to coverage a couple months’ worth of expenses and is our free overdraft protection on the checking account, which pays all of our bills. Every month, we get email notifications of our bills and since we only pay two credit cards and a utility bill, I have a good sense of what those values should be. (I also check the credit card bills every month for strange charges)

So far, we haven’t had any problems. Now – onto why we do this instead of pay them manually (especially since it’s just three bills):

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When I was a kid, I used to collect comic books and comic book cards. I was a Marvel guy and I loved the Amazing Spider-Man, X-Men, and basically all the major characters of that era. I “collected” because I enjoyed reading them and in the back of my mind I thought “hey, maybe they’ll be worth something one day.” I didn’t really think they were going to be worth anything but I went on “believing” it anyway. I would later start collecting the Marvel comic book cards for a few series (two I think) and they were fun hobbies.

None of that comes close to the hobby of baseball card collecting (there’s a 10min video on that post called The Baseball Card Movie that’s a fun watch). So when I saw that ESPN did a 30 on 30 short about the most valuable baseball card in the world, I had to watch it:

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I was watching an interesting TEDxTalk by Preet Banerjee (embedded below) in which he brings up two thought provoking ideas about money.

First, inflation is hard to think about in real terms outside of a few simple examples until you talk to someone older. He says that you should find someone in retirement ask them whether they paid more for their last car or if they paid more for their first house, in nominal terms. For most, they’ll pay more for their last car than their first home.

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Buying and selling stocks, like buying or selling anything, is fun. Buying and holding is not fun. Buying and holding for forty years is not only not fun, it’s boring. But, like broccoli and wearing your seat belt, boring is oftentimes good for you and in the case of your financial health, it’s very good for you.

The path to financial success is being able to make the right bets at the right time. For most of us, we have neither the funds nor the energy to study the markets well enough to make the right bets at the right time. Think back to any war story your friends ever told you about their trip to the casino. For every one tall tale of success, there are dozens untold stories.

I’ll give you an example. The most I’ve ever won in a casino was on a cruise ship a few years ago at the craps table. Craps is a lot of fun because it’s social in nature. After maybe an hour, I was up somewhere close to a thousand dollars. I walked away with the money in my pocket because, and this is one of the benefits of craps, we wanted to do something else and it’s hard to stand there for an hour. That’s a great story… except behind it are a bunch of stories where I sat down at a three card poker table and lost $200 in about 10 minutes. Or $100 in about 15 minutes at roulette.

The reality is that trading stocks frequently is a losing game and for every Apple success story (I bought shares at $90 and sold them at $560), there are a million other BPs and the like. We aren’t good enough at trading and here why:

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Young professionals have often been called the “boomerang generation.” Instead of getting a career and/or getting married by the time they are done with four years of college (or even with graduate school), many students are moving back home.

A study from the Pew Research Center indicates that about 29% of those aged 25 to 34 have moved back home in recent years. 61% of people in that age group say that they have friends or family members that have made the decision to move back to mom and dad’s.

It’s a tough time, says Jeffery Jensen Arnett, Research Professor of Psychology at Clark University and author of the forthcoming book When Will My Grown-Up Kid Grow Up? Arnett is also the Director of the Clark University Poll of Emerging Adults, which highlights trends related to the “boomerang generation.”

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The job market is improving lately, but it can still be tough to get a raise.

There aren’t that many jobs yet, and a lot of employers are overcome with cost cutting fever.  That means smaller raises, or no raise at all.

How can you work around that situation and still get a raise?

Editor’s Note: The suggestions that Glen makes in this post are very good but he misses one big one – get another job offer. The unfortunate reality, and this is especially the case with large companies, is that oftentimes a business can’t give you a mid-season raise (budget reasons? no process to do so?) unless there is a compelling reason – such as you’re going to leave for more money. The plus side is you can get paid more, the downside is that they’ll thank you for your time… either way, you get paid more.

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“The popular conception is that people who file bankruptcy buy about three TVs a week and then fly to Aruba to relax,” Daniel Gershburg, Esq., says.

Gershburg is a bankruptcy lawyer in New York City, and he sees a number of cases each year. “Realistically, only a handful of cases fall into that category. There is so much more to bankruptcy.”

Some of the reasons that Gershburg cites include job loss, medical bills, and the accumulation of smaller bills that get out of control. But are these the main reasons that people go bankrupt? And what can consumers do about it?

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One of the big stories this week was Yahoo CEO Marissa Mayer’s memo that would end “working from home” for all Yahoos by June. Various pundits and bloggers jumped at the chance to debate the merits and failings of working at home and I wanted to hear your opinion.

Personally, I think that working from home cannot be a standard way of doing business for any business because being distributed makes it much harder for teams to function. As archaic as it seems, being in an office together does build team chemistry even if it’s complaining about something as silly as the temperature of the office. Shared experiences does promote bonding, even on a superficial level. It also can result in serendipity, ideas that come about by happy accidents, just because people are working together.

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