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ESPP Tax Consequences

Employee Stock Purchase Plans (ESPP) are one of many stock incentive programs employers use to compensate employees. They typically give the employee a discount when purchasing the company's stock but often vary as to the details such as amount of the discount, the market price used to calculate the discount and subsequent purchase price, and purchase dates. Frequently payment is withheld from the employee's paycheck over a period such as six months, and shares are purchased at a discount at the end of the six-month period. If the employee sells the purchased shares immediately, the gain is the amount of the discount offered at purchase. For example, if a 15% discount off of the market price at the time of purchase is used, the employee receives a 15% return (less taxes) on their investment if the shares are immediately sold. This 15% gain is called the bargain element.The amount of tax depends on the length of time the stock is held as well as whether the shares are sold as a qualifying disposition. To be a qualifying disposition, the shares must be both of the following criteria:

• Shares sold more than one year after the purchase of the shares.
• Shares sold more than two years after the offering date.

This results in four primary tax consequences:

1. Shares sold less than one year after the purchase date (Short-term Disqualifying Disposition): The bargain element, or discount received, is taxed as ordinary income (i.e. your normal tax bracket). Any gain above the bargain element resulting from an increase in the stock price is taxed as a short-term capital gain at the same tax rate as ordinary income.
2. Shares sold more than one year after the purchase date but less than two years from the offering date (Long-term Disqualifying Disposition): The bargain element is taxed as ordinary income and any gain from the increase in stock price is taxed as long-term capital gain, which is typically a lower rate, currently at 5% or 15% depending on your tax bracket.
3. Shares sold more than 1 year from the purchase date and after two years from the offering date, and the stock price decreased from the offering date to the purchase date (Long-term Qualifying Disposition): The portion of the gain taxed as ordinary income is the lesser of a) the discount multiplied by the market price at the offering date or b) the difference between the selling market price and the discounted purchase price. The remaining gain is taxed as a long-term capital gain. This allows a portion of the bargain element to be taxed as long-term capital gain.
4. Same as (3) above but the stock price increases from the offering date to the purchase date: The portion of the gain taxed as ordinary income is the market price at the offering date multiplied by the discount. The remaining is taxed as long-term capital gain. This also results in a portion of the bargain element to be taxed as long-term capital gain.

For some examples of the above situations, refer to this TurboTax article.

As with any stock purchase, the risk lies in not knowing whether the price will increase or decrease over the period you intend to hold it. Many are of the opinion that a quick sale after the ESPP shares are purchased will at least guarantee a return in the amount of the discount (e.g. 15%) less your applicable ordinary income tax bracket rate. If you are in the 25% tax bracket, this is a return of 11.25% (15% x (1 - 25%)). Not a bad return.

Healthcare Reform Impacts Your FSA

There were plenty of changes included in the healthcare reform act signed earlier this year. One that will start impacting everyone beginning January 1, 2011, is the change to items eligible for payment with flexible spending account dollars. The primary change is that FSA amounts cannot be used to purchase over-the-counter drugs.

Many employees across the country will have open enrollment for their benefit plans over the next couple of months. Keep this in mind when you are estimating your out-of-pocket expenses to determine how many pre-tax dollars to set aside for your FSA. You will still be able to use your FSA for co-payments, deductibles, prescription drugs, but for OTC drugs you will need a note from your doctor (essentially a prescription) in order to use your FSA account for it. If you have money left in your current FSA account for 2010, you may want to use it up by stocking up on all the OTC drugs you typically keep at your home. Take the tax discount on your drugs now since you won't be able to beginning next year.

In the future, limits on the maximum amount that can be contributed to an FSA account will also be imposed. In 2013, that limit will start at $2,500 per individual. That should get you thinking about whether you have any substantial healthcare needs and whether they should be addressed before 2013 when larger amounts can be contributed to an FSA account.

List of current FSA eligible expenses.

A Little Savings, Consistently, Can Go a Long Ways

If you have difficulty setting aside money each month, whether it is for an emergency fund, education, or retirement, the important thing is to remember that time is on your side. This is more evident when looking at real numbers and using your own actual examples. The Financial Literacy and Education Commission has a useful website with several tools at MyMoney.gov. The Savings Tool allows you to see how much you will have in the future if you can just scrape together even $100 per month. Play around with it and use a realistic rate for what you currently receive for your investments. You might be surprised how quickly it can grow with a consistent contribution. It could be just the motivation you need to increase your savings each month.

Personal Balance Sheet

This is a great starting point for understanding and being in control of your personal finances. Summarize what you own and owe to see your net worth. The USAA Educational Foundation has a simple form to fill out to get you started.

What is Dollar Cost Averaging?

When it comes to investing, dollar cost averaging refers to investing an amount of money in a stock or mutual fund at regular time intervals. The idea behind this investment strategy is that you are getting a lower price when the market is down even though you are paying a higher price when the market is up and, overall, the average price you pay is lower than what get from investing a lump sum. At first, this may not look consistent with my previous post on The Golden Rule... of Investing: Buy Low, Sell High, but let's take a look at an example to see how you can benefit from this strategy.

Assume you invest $100 every month for five months into a given stock. The stock price at each of these purchase dates is as follows (with the number of shares purchased):

Jan.: $20 (5 shares purchased)
Feb.: $14 (7.1 shares)
Mar.: $13 (7.7 shares)
Apr.: $15 (6.7 shares)
May: $23 (4.3 shares)
Total: $85 (30.8 shares)

The $500 invested purchased 30.8 shares, resulting in a cost per share of about $16.23. This means that when the stock price is above $16.23, there is a gain on the investments.

But what if the May stock price was still down around $15 as it was in April; what are the results then?

Total: $77 (33.2 shares purchased)
The $500 invested purchased 33.2 shares, resulting in a cost per share of about $15.06. A gain would exist when the stock price is above $15.06. The May price is not above that price so there is no gain until the stock increases.

So what do we learn from these examples? That Dollar Cost Averaging is not necessarily going to give you better returns; it completely depends on the stock performance over the given period. So does that mean I should just invest the $500 all at once? Well, if you did that in Jan. in the example, you would be even worse off since your cost per share would be $20 instead of $16.23 or $15.06. If you invested the $500 in Feb. you would be better off with only a $14 cost per share. Since we don't know how a stock or mutual fund will perform, investing continuously over a period diversifies away much of the market risk (the risk of market fluctuations). Also, most individuals do not have enough money to make a single investment now to carry them through to retirement, but rather have smaller amounts set aside each month as income is received. Another way to take advantage of continuous investing is by reinvesting dividends rather than having them paid out. This can be done automatically by your financial institution or brokerage.

Converting a Traditional IRA to a Roth IRA: Why Now?

Beginning in 2010, the IRS is allowing everyone to convert a traditional IRA to a Roth IRA. (Refer to previous post to learn more about the IRA Basics.) Prior to 2010, only taxpayers with a modified adjusted gross income (MAGI) that was not more than $100K could make the conversion. The main reason to make the conversion is to gain the tax advantages of a Roth IRA, which is tax-free growth and tax-free distributions. The catch to making the conversion is that the IRS requires you to pay tax on the amount you pull out of the traditional IRA that would have been taxed had it been taken out as a normal distribution from the IRA account. That means that the growth or earnings in your traditional IRA account is included in gross income for the year in which you convert it to a Roth IRA. For 2010 only, the IRS is allowing that amount to be split evenly and included in your 2011and 2012 gross income. The benefit here is that you can spread out the taxes you have to pay for the conversion over 2 years rather than only in the year of the conversion. Even with the IRS allowing you to soften the tax blow when converting to a Roth IRA this year, make sure that you have the money to be able to pay these taxes before deciding to make the conversion. The bottom line is that you pay the taxes now rather than later.

There are also estate tax impacts to converting a traditional IRA to a Roth IRA. If your estate is large enough to incur estate taxes, both traditional IRA and Roth IRA assets will be taxed at the estate tax rate. Once the beneficiary has received the assets, distributions from IRA accounts are still taxed according to their taxable nature. In other words, distributions from a traditional IRA are taxed and distributions from a Roth IRA are tax-free. This results in double-taxation of the traditional IRA. Yet another benefit to a Roth IRA. If you have the cash to pay the tax on the IRA conversion, your beneficiaries may thank you for making that conversion. The bottom line here is that you pay the taxes now rather than your beneficiaries paying the tax later.

The Golden Rule... of Investing: Buy Low, Sell High

It sounds intuitive if you want to make money in the stock market, or anywhere else for that matter: buy low and sell high. The difference is your gain (or loss) on that investment. Even though it sounds intuitive, people often do not take advantage of the opportunity. The typical reaction to a slower economy is to sell stocks before the losses get any worse. This may be a good rule of thumb to avoid further losses if you are nearing retirement or are depending on that money in the near future, but what about long-term investors? This presents a great buying opportunity. The recent recession is obvious when looking at the Dow Jones Industrial Average over the past five years. Investing at the market low in March of 2009, would have resulted in some pretty hefty gains as of today. People often choose to stay away from riskier stock investments during a slow economy due to their volatility, but for the long-term investor, that can be the opportune moment to invest.

Quick Tip: Take Advantage of a 401(k) Match

Most employers offer a matching contribution to a 401(k) account up to a certain percentage of your gross salary. Whether it is a dollar for dollar match or a 50% match (i.e. $0.50 contributed for each $1.00 you contribute), that is money ready to be handed out to you simply for setting aside money for retirement. And that is something that you should be doing anyway. Bloomberg reports that 91% of 401(k) participants belong to a plan that offers a match. Make sure you are enrolled in your employer's 401(k) matching program and increase your contribution percentage to the maximum matched by your employer. The earlier you start saving, the more you will have for retirement.

How To Improve Your Credit Score

A few tips to keep in mind if you're trying to improve your credit score.

• Only apply for new credit when absolutely necessary. Too many new applications for credit can hurt your credit score.
• Close any unused credit cards but only if they were recently opened. This goes along with the previous tip to help you ensure you do not have too much recent credit open.
• Keep any old credit cards open even if they are unused. Not only is too much recent credit bad for your score, but having a longer history of credit is beneficial for your score.
• Avoid transferring debts to other accounts. This, too, creates more recent credit accounts rather than keeping older accounts. Paying off debts while under the original account is better than transferring it and then paying it off. There may be a trade-off with this since you may be able to lower your interest rate by transferring the balance and, thus, making it easier to pay off more quickly.
• Pay all bills and debt payments on time.
• Check your credit report at least annually to ensure there are no mistakes. Correct any mistakes you may find with the credit reporting agencies.