Tax loss harvesting can be a smart tool for investors. But first, you have to learn how it works. Here’s our easy guide to tax loss harvesting.

Even in a period of economic prosperity, not every investment pays off, and there are bound to be losses. Fortunately, as the saying goes, every cloud has a silver lining and so does every investment.

You may be able to turn your investment losses into tax gains, reducing the impact on your financial health. This concept is known as tax loss harvesting.

Tax loss harvesting is one of the few free lunches in the world of investing. With a little planning, you can reduce or even eliminate your capital gains in any given year. In some cases, you may also get a deduction from ordinary income of up to $3,000.

Note from the editor: In this episode of the podcast, Rob tells us about tax loss harvesting, sometimes abbreviated TLH. Learn how it works, its benefits, its limitations, and how you can use it to defer taxes. We’ll also look at the implications for those who use robo advisors that offer TLH services. If you prefer to read rather than listen, we delve into tax loss harvesting below, so read on.

What Is Tax Loss Harvesting?

Briefly, tax loss harvesting is the selling of securities at a loss to counteract a capital gains tax liability.

Capital gains are the additional money an investor receives after the sale of security above its original purchase price. A capital loss is the difference between the selling price and purchase price of a security sold for a loss.

Whenever you make capital gains, the profit is taxable. But if you take a loss on an investment, those losses can be offset against any profit netted from capital gains. The result is you can reduce or eliminate your income tax liability on the capital gains.

A Practical Example

You’re an investor, and after a review of your portfolio, you notice your stocks in the tech industry have risen sharply while your stocks in the energy sector have declined in value.

You realize you want to cash in on the rise of your tech stocks and reduce your exposure in anticipation of a market swing. You sell off some of your tech stocks, and now you have a capital gain and a tax liability due on that gain.

This is where tax loss harvesting comes in handy. If you sell the energy stock in your portfolio that has fallen in value, you can use the loss to reduce the tax you owe on your tech sector gains. This reduces your tax liability.

If the losses you incurred on your energy stocks are greater than the gains you made, the residual amount can offset $3,000 of your taxable income. This is the cap the IRS has set. And if you still have any additional loss left, that amount can be carried forward to offset losses in the subsequent years.

For example, the sale of your tech stocks netted you a gain of $20,000, and you purchased that stock less than a year ago. The time of the purchase is important because short term capital gains (held for less than a year) are taxed at a rate higher than long term capital gains (held for over a year).

The sale of your energy stocks netted a loss of $25,000. Tax loss harvesting would imply that the $25,000 loss would cover the $20,000 gain you made and the remaining amount of $5,000 would offset $3,000 from your ordinary income. The remaining amount of $2,000 is carried forward to subsequent years and can reduce tax liability on capital gains.

How Tax Loss Harvesting Works

Here are a few applications of how tax loss works in your favor.

Strategically Offset Losses Against Gains

In the previous example you sold off two investments, the profitable tech stocks and the loss incurring energy stocks, and paid no taxes. However, there is no rule to sell both investments to utilize the benefit of tax loss harvesting.

The IRS allows individuals to carry forward their losses indefinitely to be utilized at the investor’s discretion. Instead of selling off both positions you could retain your funds and cash them in at a more opportune moment.

How Much Tax Loss Harvesting Can Save You

The money you’re trying to save in taxes through tax loss harvesting mainly depends on two factors; your applicable tax rate and the nature of the revenue stream you’re trying to offset.

The IRS taxes the income realized from capital gains, but the rates vary depending on the period the investment was held by you.

Since short terms gains are taxed higher than long term gains, it makes more sense to offset short term gains against short term losses. It also holds for long term capital gains and using them to offset long term losses.

If, however, you incur a loss in one and a profit in another, tax loss harvesting can still offset the loss. Any remaining amount is carried forward to reduce the taxable income outside the scope of investment revenues.

Taking the first example of tech stocks and energy stocks, let us look through the number you stand to gain from tax loss harvesting.

Let’s assume you fall in the 35% tax bracket. So, $20,000 was your capital gain offset with a further $3,000 deducted from your ordinary income.

($20,000 + $3,000) * 35% = $8,050

You stand to save $8,050 in total savings from utilizing tax loss harvesting.

Things to Keep in Mind With Tax Loss Harvesting

The critical aspect to remember for a successful implementation of tax loss harvesting strategy is to assess what you own and why you own it, identify investments running a loss and then to discard a portion of those investments against capital gains, expected capital gains or even your income.

Keep Reinvesting But be Wary of Wash Sales

After deciding the investments you want to dispose of and offset the loss through tax loss harvesting, you must decide upon reinvestments. But you must be careful of a rule which applies on tax loss harvesting called Wash Sale Rule.

Suppose you invest in the same type of stock you sold to realize a loss. You believe the value will rise or that it matches your desired diversification and risk tolerance. The Wash Sale Rule states that your tax loss harvesting claim will be declared void if you buy back the stock or a contract to buy the stock within 30 days before or after the disposal of the relevant stock.

If you want to keep exposure of the industry in your portfolio, one way to go around the Wash Sale Rule would be to buy stock in a similar company that operates in the same industry and has more or less the same amount of market share. Or you could purchase an exchange-traded fund (ETF) that tracks the relevant sector.

Although some substitutions are allowed and don’t violate the Wash Sale Rule, others can still lead to a void claim. This happens when the IRS deems the substitute as substantially identical to the disposed of investment. Consult a tax advisor if you’re unsure before making a reinvestment.

Wash Sale Rule & IRA Accounts

The Wash Sale Rule applies to purchases inside an IRA. If you sell an investment to create a loss in a taxable account and then buy the same or substantially identical investment in an IRA account within the 30-day window,  the Wash Sale Rule will wipeout the tax loss.

Here’s the deal–

• Section 1091 of the Internal Revenue Code creates the Wash Sale Rule;


• It says NOTHING about IRA or 401k accounts;


• In 2008, the IRS issued Revenue Ruling 2008-5, concluding that the Wash Sale Rule applies if a loss generating investment is replaced in an IRA;


• The ruling says nothing about 401(k) accounts, but the Wash Sale Rule likely applies to purchase in these accounts, too.

You can refer to IRS Pub 550, Investment Income and Expenses (Including Capital Gains and Losses) for more details.

Don’t Sell Off Simply for the Sake of Realizing a Loss

Investors should remember not to let the tax tail wag the investment dog.

If you have stocks or securities in your portfolio performing below par, don’t sell them off immediately to realize a tax loss. Often market swings are fueled by speculation and not economic or financial facts.

That doesn’t mean you keep sitting on a loss-incurring investment hoping for it to increase in value. There’s a thin line between a smart sale and selling due to market pressures to realize a tax loss.

Pros and Cons of Tax Loss Harvesting

Tax loss harvesting is one of the most popular options amongst investors to maximize after-tax returns. But many individuals don’t know this strategy comes with its own risks.

There’s always the lurking risk of selling a stock just about to pick up or is temporarily down due to market speculation. There is also the fact that market analysts believe that the overall effect of selling investments and re-purchasing them again is just a tax deferral and not a gain.

Conventional investors also hold tax loss harvesting in contempt because it goes against the fundamentals of investing which state to buy low and sell high. Selling important stocks pivotal for diversification to save a few dollars on taxes is a hard note for many investment veterans to swallow.

Below, I summarize the pros and cons of tax loss harve