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Protecting Your Private Files

For somebody who makes a living online, I’m decidedly low-tech. I just got a scanner for the first time a couple weeks ago, and I’ve been scanning and shredding all my paper documents like tax returns, health insurance statements, and so on.

The downside of scanning such private documents and storing them on your hard drive is that they’re not safe. If your computer dies unexpectedly–or, worse, if somebody steals it–you’ve got a problem.

Fortunately, there’s an easy (and free) solution. (Hat tips go to personal finance blogger Nickel and the members of the Bogleheads forum for their help.)

Dropbox

Dropbox is a free service that allows you to store files online. I’ve been using it for quite a while now, and I’m very happy with it.

When you install Dropbox, it creates a folder on your computer that looks and works just like any other. That folder, however, is linked to your Dropbox account. When you save something in that folder, it automatically saves it online as well. And if you’ve linked other computers to your Dropbox account, it automatically updates the version of that file that’s saved on those other computers.

The problem with using Dropbox to store files with sensitive information is that there’s no option to password-protect the Dropbox folder on your computer. If somebody stole your computer, anything in that folder would be immediately accessible to the thief.

Enter Truecrypt

Truecrypt is a free encryption program. It allows you to create a “volume,” which is essentially an encrypted (password-protected) folder for storing files you’d rather keep private.

To the naked eye, your Truecrypt volume doesn’t even look like a folder. It just looks like a file with no file type (which you’ve ideally named something very unimportant-sounding) that gives a rather unhelpful error message when somebody tries to open it.

But when opened via Truecrypt (and using the appropriate password), the volume opens and works just like any other folder on your computer.

Truecrypt + Dropbox = Happy Storing

So, by creating a Truecrypt volume that holds all your sensitive files, then saving that volume in your Dropbox folder, you’ve backed up your important files online while at the same time keeping them safe from malicious users.

A few final notes:

  • Dropbox’s normally lightning-fast upload speed slows to a crawl on large transfers, so be prepared to wait patiently if your Truecrypt volume is a big one.
  • Dropbox isn’t necessarily the only solution. I’m sure there are other online storage services that would work equally well–perhaps even better.
  • Nor is Truecrypt the only solution. There are several high quality free encryption programs.
  • Truecrypt isn’t exactly intuitive to use. Fortunately, the online user manual has a super step-by-step walk through.
  • Be sure not to lose your Dropbox password or the password to your Truecrypt volume.

Investing Blog Roundup: Saving Too Much for Retirement?

Happy Friday, everyone. :)

Another week, another collection of my favorite personal finance articles from around the web. Please feel free to share your own favorites in the comments section below!

Investing and Retirement-Planning Articles

Tax-Planning Articles

Other Money-Related Articles

Blog Carnivals

Thanks for reading!

Your Personal Rate of Inflation

The Consumer Price Index (specifically, the Consumer Price Index for All Urban Consumers) is the most common measure for inflation. But when attempting to predict how your own spending will change throughout the course of retirement, there are two reasons that historical CPI figures might not be a perfect predictor:

  1. Future changes in CPI may not be similar to past changes in CPI, and
  2. Your rate of spending change doesn’t necessarily match that tracked by the CPI.

What Does the CPI Track?

The CPI measures a specific bundle of goods, as determined by a survey of several-thousand families regarding their spending habits. Per the Bureau of Labor Statistics’ website, the following categories are included in the calculation. (Note: The items provided in each group are just examples. They’re not the only goods measured in that group. For the full list, see page 11 of this pdf.)

  • Food and Beverages (breakfast cereal, milk, coffee, chicken, wine, full service meals, snacks)
  • Housing (rent of primary residence, owners’ equivalent rent, fuel oil, bedroom furniture)
  • Apparel (men’s shirts and sweaters, women’s dresses, jewelry)
  • Transportation (new vehicles, airline fares, gasoline, motor vehicle insurance)
  • Medical Care (prescription drugs and medical supplies, physicians’ services, eyeglasses and eye care, hospital services)
  • Recreation (televisions, toys, pets and pet products, sports equipment, admissions)
  • Education and Communication (college tuition, postage, telephone services, computer software and accessories)
  • Other Goods and Services (tobacco and smoking products, haircuts and other personal services, funeral expenses).

Those may not be the goods that you spend money on. For example, as somebody who doesn’t own a car, doesn’t use prescription drugs, doesn’t smoke, cuts his own hair, and has a rather unusual diet (vegetarian, gluten-free), the CPI isn’t exactly a perfect fit for my own spending habits.

Of course, you may look at my spending choices and think, “Wow, what a weirdo!” But that’s the point. We all spend money on different things.

Even if you do buy most of the goods/services tracked by the CPI, it’s entirely possible that your allocation between those goods/services is significantly different from the allocation used to calculate the index.

Consumption Changes vs. Price Changes

When attempting to determine how much income you need in retirement, it’s also important to remember that your consumption might change, not just the prices of the things you buy.

For example, the price of prescription drugs might increase by 5% per year, but if the rate at which you’re taking them is doubling every five years, then your own prescription drug spending will be growing faster than the rate of change that’s reported by the CPI.

Predicting Your Personal Rate of Inflation

My point here is not that the CPI is useless or that it’s way off base for everybody. Neither of those statements is true. But there is a chance that it won’t align very well with your own rate of spending change.

If you want the most precise answer possible as to how your spending will change over time, my suggestion would be to:

  1. Track your current spending (broken down by category),
  2. Do your best to estimate how your rate of consumption will change for each category, then
  3. Try to estimate how the prices for each category will change.

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Can I Retire Cover

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Roth Conversion Math

When deciding whether or not to convert a traditional IRA to a Roth IRA, many investors overlook the fact that the goal is not to minimize the amount of tax dollars paid. Rather, the goal is to maximize the ending value of the portfolio.

What Am I Talking About?

Let’s consider a simplified example. Imagine that an investor has a choice between paying a 25% tax on her portfolio right now or in three years. And let’s say that her portfolio earns the following annual returns over those three years: +8%, +17%, +20%.

  1. If she pays the tax right now, the math will look like this: Ending value = beginning value x 0.75 x 1.08 x 1.17 x 1.2.
  2. If she pays the tax at the end, the math will look like this: Ending value = beginning value x 1.08 x 1.17 x 1.2 x 0.75.

Note that, due to the commutative property of multiplication, the ending portfolio value is the same in either case–even though the investor will pay more tax if she selects option #2 (because her portfolio value will be higher at the time she pays the 25% tax).

The same analysis applies for Roth conversions: The amount of tax paid doesn’t matter. What we care about is the ending portfolio value.

Roth Conversion Scenarios

Admittedly, this is something of an oversimplification, but Roth conversions can be roughly broken down into three scenarios:

  1. You plan to pay the tax on the conversion out of the IRA (rather than with money from a taxable account), and you’re over age 59.5
  2. You plan to pay the tax on the conversion out of the IRA, and you’re under age 59.5, or
  3. You have enough money in taxable accounts to pay the tax without having to use money from the IRA.

Paying the Tax from the IRA

In the simplest scenario–the one in which you’re paying the tax on the conversion out of the IRA and in which you’re over age 59.5 (such that there’s no penalty for doing so)–things work out like this:

  • It’s a wash if you expect your tax bracket to stay the same. The commutative property of multiplication tells us that multiplying by, say, 0.75 now as opposed to multiplying by 0.75 later makes no difference.
  • It’s a good idea if you expect to be in a higher tax bracket later.
  • It’s a bad idea if you expect to be in a lower tax bracket later.

In the second scenario–in which you’re under age 59.5 and paying the tax out of the IRA–things become slightly more complicated. We have to account for the 10% early withdrawal penalty. For example, if you’re in the 25% tax bracket and you convert a $40,000 IRA and withdraw $10,000 to pay the tax, the 10% penalty will be charged on that $10,000.

End result: You need to expect a higher tax bracket in retirement in order for it just to be a break-even decision. (Specifically, your retirement tax bracket must be at least 1.1-times your current tax bracket for it to make sense.)

Paying the Tax from a Taxable Account

In the third scenario–in which you’re paying the tax out of taxable funds rather than out of the IRA–things get trickier. We have to make assumptions about the after-tax rate of return that will be earned (if you choose not to convert) on the money that would otherwise have been used to pay the tax.

That said, in this last scenario, things usually (though not always) work out like this:

  • If you expect your tax bracket to remain the same, there’s a benefit to converting. It’s essentially a way to use non-tax-advantaged money to increase the size of your tax-advantaged accounts.
  • If you expect your tax rate to increase, converting is a good idea.
  • If you expect your tax rate to decrease, converting is likely (though not necessarily) a bad idea.

For More Information, See My Related Book:

Book6FrontCoverTiltedBlue

Taxes Made Simple: Income Taxes Explained in 100 Pages or Less

Topics Covered in the Book:
  • The difference between deductions, exemptions, and credits,
  • Itemized deductions vs. the standard deduction,
  • Several money-saving deductions and credits and how to make sure you qualify for them,
  • Click here to see the full list.

A testimonial from a reader on Amazon:

"Very easy to read and is a perfect introduction for learning how to do your own taxes. Mike Piper does an excellent job of demystifying complex tax sections and he presents them in an enjoyable and easy to understand way. Highly recommended!"

Investing Blog Roundup: Debunking Dividend Myths

For one reason or another, there’s been a lot of talk lately in personal finance blogs and other financial media about dividend investing. I, for one, am enjoying this series from Canadian Couch Potato:

If you read any investing or tax-related articles this week that you particularly enjoyed, please share them in the comments below. :)

Investing-Related Articles

Tax-Related Articles

Other Money-Related Articles

Blog Carnivals

Thanks for reading!

Income Tax 101: Tax Brackets and Withholding

To date, there are 573 posts published on this blog on a fairly wide variety of topics. Despite that, approximately half the email questions I receive deal with either tax brackets or withholding. As far as I can tell, these questions stem from the fact that many (most?) taxpayers do not understand:

  1. How tax brackets work, and
  2. How the amount withheld for taxes from one’s paychecks can be different from the amount of tax one actually has to pay.

Let’s take a crack at each of those, shall we?

How Do Tax Brackets Work?

Based on the 2012 tax brackets, we can see that for an unmarried taxpayer, the 10% tax bracket goes from $0-$8,700 of taxable income. For example, if John’s taxable income is $8,700, his income tax will be $870. Nothing tricky there.

But what if John’s taxable income increases by $1 to $8,701 (thereby putting him in the 15% tax bracket)? How much extra income tax will John pay?

Answer: He’ll pay an additional $0.15 of income tax. That is, only his final dollar of income (the dollar that’s in the 15% tax bracket) will be taxed at 15%. His first $8,700 of income will still be taxed at 10%.

Important conclusion #1: Getting a raise at work that puts you into a higher tax bracket will not reduce your after-tax take-home pay. (Possible exception: The raise could make you ineligible for certain deductions or credits, the loss of which could outweigh the increase in income.)

Important conclusion #2: If you’re trying to get an estimate of how much income tax you’ll owe for a given year, do not simply multiply your income by your marginal tax bracket–doing so would overestimate your tax (by a very wide margin in many cases).

How Does Withholding Work?

From every paycheck, your employer withholds some of your salary/wages to go toward taxes. The Federal government requires this because they understand that many people spend every dime that makes it into their bank account (plus some). By making withholding mandatory, Uncle Sam gets his money before taxpayers have a chance to spend it.

It’s important to note that the amount of tax that’s withheld over the course of a year goes to more than just Federal income taxes. It also covers:

  • Social Security tax (6.2% of your earnings, up to $110,100–temporarily reduced to 4.2% for 2012),
  • Medicare tax (1.45% of earnings), and
  • State income tax (if applicable).

In addition, the amount that’s withheld over the course of the year for Federal income tax will not actually equal the amount that you’re responsible for paying that year. This is the result of the fact that your employer doesn’t have all of the information necessary to precisely calculate the tax that you’re responsible for paying. (For example, they don’t know what deductions you’ll claim or how much your spouse earns.)

The fact that the amount that’s withheld does not equal the amount you’re responsible for paying is why tax season is basically a massive “settling up,” during which taxpayers either receive a refund (for the amount by which their withholding exceeded their tax) or write a check to the U.S. Treasury (for the amount by which their tax exceeded their withholding).

For More Information, See My Related Book:

Book6FrontCoverTiltedBlue

Taxes Made Simple: Income Taxes Explained in 100 Pages or Less

Topics Covered in the Book:
  • The difference between deductions, exemptions, and credits,
  • Itemized deductions vs. the standard deduction,
  • Several money-saving deductions and credits and how to make sure you qualify for them,
  • Click here to see the full list.

A testimonial from a reader on Amazon:

"Very easy to read and is a perfect introduction for learning how to do your own taxes. Mike Piper does an excellent job of demystifying complex tax sections and he presents them in an enjoyable and easy to understand way. Highly recommended!"
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