Long-Term Capital Gains: Is It Worth It to Wait?

Source: Phillip Ingham via Flickr

Investing for the long term has many benefits. By identifying the stocks that will have bright prospects for years and even decades, you can maximize your chances of earnings explosive gains for your investment portfolio. Another big benefit of holding on to your stocks longer is that the IRS rewards long-term investors with reduced capital-gains taxes for investments held longer than a year.

Despite your best intentions, though, you'll sometimes find yourself wanting to sell a stock before you get past that one-year mark. If you already have paper profits on that stock, you'll face a tough decision: Should you sell now and pay higher taxes, or hold out for the lower long-term capital gains rate and hope the stock doesn't drop in the interim? Let's take a closer look at how you should think about that critical decision and the risks and rewards it entails.

Why long-term capital gains are such a big deal
Ordinarily, most investors prefer not to focus on tax considerations in making their investments. When you invest in an IRA or other tax-deferred account, you don't have to think about taxes, and that frees you to make buy and sell decisions irrespective of how long you've owned a stock.

But for taxable accounts, the difference in taxation of capital gains is truly huge. For taxpayers in the highest income brackets, each $100 of capital gains can cost you $39.60 in regular income taxes plus another $3.80 from investment-income surtaxes, adding up to a 43.4% rate on short-term gains. By contrast, the top tax rate on long-term capital gains is 20%, and although the 3.8% surtax on investment income still applies, a little patience can cut your tax bill almost in half.

Source: John Morgan via Flickr.

Moreover, you shouldn't conclude that only wealthy taxpayers benefit from long-term capital-gains rates. Those who are in the 10% or 15% tax brackets generally pay their regular rate on short-term gains, but they don't have to pay any taxes at all on long-term capital gains so long as they remain in those tax brackets. Above that level, the 15% maximum rate on long-term gains for all but top-bracket taxpayers compares favorably with the 25% to 35% rates that apply to regular income and short-term gains.

Finally, some states have their own beneficial rates for long-term capital gains. In Massachusetts, for instance, long-term gains get taxed at the ordinary 5.2% rate, but short-term gains pay a higher 12% tax.

Finding the right balance between risk and reward
Ordinarily, these huge potential tax savings make holding a stock for the long run a smart move. But occasionally, you'll quickly earn a big paper profit on a stock just months after you buy it, and the resulting high valuation might make you nervous about hanging on to it long enough to pay lower long-term capital-gains taxes when you sell.

Source: Wikimedia Commons

Resolving that dilemma doesn't have to be complicated, though. In general, if the reason you bought the stock hasn't changed, then even sizable short-term gains are usually just the tip of the iceberg compared to the long-term returns you're hoping to achieve. Selling early might make you feel good to lock in a quick gain, but it doesn't just boost your immediate tax bill; it can also lead you to miss out on a much larger long-term rise in the share price in the years to come.

On the other hand, if the fundamentals of a stock or other investment have changed, then selling early can mean the difference between earning any profit on your stock and suffering a loss. During the tech bust of the early 2000s, for instance, many investors were reluctant to sell highflying Internet and technology stocks because of the admittedly large tax bills they would have incurred by selling. In the process, though, many waited too long and ended up losing all of their gains and then some. It's always better to earn income that will be taxed than it is to give up that income entirely.

Overall, the incentive to hold on to investments long enough to benefit from lower capital-gains taxes on long-term holdings makes it worth thinking twice before selling quickly, as it really is usually worth it to wait. But if a truly game-changing situation comes up, don't hesitate to pull the trigger on a sale -- it can save you from even more costly losses.

Take advantage of this little-known tax "loophole"
Recent tax increases have affected nearly every American taxpayer. But with the right planning, you can take steps to take control of your taxes and potentially even lower your tax bill. In our brand-new special report "The IRS Is Daring You to Make This Investment Now!," you'll learn about the simple strategy to take advantage of a little-known IRS rule. Don't miss out on advice that could help you cut taxes for decades to come. Click here to learn more.

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Comments from our Foolish Readers

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  • Report this Comment On September 03, 2014, at 8:48 AM, dmkap wrote:


    Is there a reason you didn't offer the following solution?

    You made 3 main points:

    1) If you sell early, you may miss a lot more upside?

    2) On the other hand, if you don't sell, you may lose everything you gained, and more, while waiting for the year to end.

    3) The tax disadvantage of selling during the year.

    Couldn't all these problems be dealt with in the following way:

    Let's say I bought 100 shares of TSLA at 200 and now they're at 280 and I'd like to sell but I still have another 5 months left till the year is up.

    I would consider buying 1 PUT, for let's say, January 270. (Like insurance)

    This solves all 3 problems.

    1) If the stock continues going up, I enjoy the gains.

    2) If it goes down to what I bought it, I protect most of my money.

    3) I don't have to sell it during this year.

    The only downside is the price of the PUT, but no one said insurance is free. I think this is as close as you can get to solving your issue mentioned above.



  • Report this Comment On September 03, 2014, at 9:32 AM, RodgerKing wrote:

    Why sell in the first place. You pay zero taxes up until the time you sell a stock. Why pay 43.4% or 23.8% if you don't have to. No one can time the stock market so hold on to your stock until you die - than the capital gains tax goes away. If you need some income, simply sell enough to meet your needs. This is why Warren Buffet is in such a low tax bracket, his paper gains are never taxed.

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Dan Caplinger

Dan Caplinger has been a contract writer for the Motley Fool since 2006. As the Fool's Director of Investment Planning, Dan oversees much of the personal-finance and investment-planning content published daily on With a background as an estate-planning attorney and independent financial consultant, Dan's articles are based on more than 20 years of experience from all angles of the financial world.

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