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When Paying Taxes Isn’t a Bad Thing

Apr 18, 2022

Why You Shouldn’t Get Too Attached to Appreciated Assets

The goal of any investor should be to buy assets that appreciate in value over time. Thus, the old investing adage: Buy low, sell high. 


Sometimes, however, investors get attached to appreciated assets and don’t want to sell them. This is usually because they don’t want to pay taxes on the increase in the asset’s value. If the asset has been held for at least one year, the appreciation is subject to capital gains tax that’s currently as high as 20%. 


But if the asset is never sold, the gain will never be realized — it will always be a “paper gain.” So it’s important to know when is the right time to sell appreciated assets, realize the gains and pay Uncle Sam what you owe. 


Other Reasons for Hesitation 

There are reasons other than taxes for hesitating to sell appreciated assets. For example, sometimes investors can get emotionally attached to securities. This is especially true if it’s the stock of a company you work for (or used to work for) or if the stock was gifted to you by a loved one. 


Another reason for not selling appreciated assets is simple inertia. It’s often easier to just leave things as they are, especially if they’re working out well. In other words, “if it ain’t broke, don’t fix it.” Yet another reason for not selling is the belief that an asset will appreciate even more in the future. This is sometimes referred to as FOMO — or Fear of Missing Out on even more gains. 


There are dangers to holding onto appreciated assets too long that go beyond never realizing your gains. For example, over time an appreciated stock can end up becoming a concentrated position, knocking a portfolio’s asset allocation out of whack. 


When this happens, it may be time to sell the stock and use the proceeds to buy other assets, perhaps in another asset class (e.g., fixed income or cash) in order to diversify the portfolio and bring things back into the proper balance. This is referred to as portfolio rebalancing.


Be Strategic

Here are a few strategies to consider if you own highly appreciated assets:


Spread out your capital gains and taxes. Eventually you will have to sell assets and realize the gains, unless you die while holding them and they become part of your estate. Given this, you could create a capital gains budget that lets you realize gains gradually over a period of time.


For example, suppose you bought a stock position 10 years ago for $50,000 and it’s now worth $100,000. The taxable capital gain would $50,000, resulting in a tax bill of $10,000 at the 20% capital gains tax rate. You could sell off the position over four years and spread out the $2,500 in capital gains tax over this time.


Donate the assets to charity. Not only will this save capital gains taxes, but you may also receive a tax deduction if you make the donation to a qualified Section 501(c)(3) organization. The charity will receive the full current value of the asset and you’ll be able to donate (and deduct) more than your cost basis (or what you originally paid) for the asset.


One strategy is to donate appreciated assets using a donor advised fund (DAF). This is a pool of money managed by a charitable organization on behalf of multiple contributors. With a DAF, you can make charitable donations now and decide later which charities will receive money from your portion of the fund.


Give the assets to family members. You can give up to $15,000 a year to as many individuals as you want tax-free. Using our example above, you and your spouse could each give $15,000 worth of an appreciated security to a family member each year for three years and then the remaining $10,000 during the fourth year.


Keep in mind the potential tax implications of this strategy on the recipient. For example, the gifts could push the recipient into a higher tax bracket.


Complex Details Require Expert Assistance

The details and logistics of selling and donating appreciated assets can get complicated. Give us a call at (803) 791-1111 or send us an email if you have questions about your specific situation.



Information is provided by William Amick & Blake Amick and written by Don Sadler, a non-affiliate of Cetera Advisor Networks LLC.


This post is designed to provide accurate and authoritative information on the subjects covered. It is not, however, intended to provide specific legal, tax, or other professional advice. For specific professional assistance, the services of an appropriate professional should be sought.


A diversified portfolio does not assure a profit or protect against loss in a declining market.


Re-balancing may be a taxable event. Before you take any specific action be sure to consult with your tax professional.


The hypothetical investment results are for illustrative purposes only and should not be deemed a representation of past or future results. Actual investment results may be more or less than those shown. This does not represent any specific product and/or service.



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