3 Strategies for Addressing Appreciated Stock

This blog was originally posted to Pathway by Willow.

While portfolio growth is a good indicator that your investment strategy is working, having highly appreciated stock can put you between a rock and a hard place—either sell and take a big tax hit or hold indefinitely and risk exposing your portfolio to additional volatility.

Fortunately, there are a few strategic ways to manage appreciated stock that don’t involve paying more tax than necessary. Whether your gains come from long-held company shares, a concentrated position, or just successful stock selection, below are some appreciated stock strategies to consider.

The Challenge With Selling Appreciated Stock

When you sell appreciated stock within a taxable account, you likely trigger capital gains tax. This taxes the difference between what you paid for the stock (your basis) and its fair market value (FMV) when you sell. Depending on how long the stock was held before being sold, your capital gains tax could be as high as your ordinary income tax rate. For long-term capital gains (meaning the stock was held for at least a year), the tax rate tends to be lower, usually up to 20%, but as low as 0% depending on your other taxable income.

And for those in higher income brackets or experiencing a liquidity event (such as selling a business or exercising stock options), that tax bill can be even steeper. That’s why it’s important to have a plan in place before you sell.

Strategy #1: Donate to a Donor-Advised Fund (DAF)

As we explored in our previous article, a donor-advised fund (DAF) can be a powerful way to reduce your tax liability (particularly when it comes to appreciated assets) and support causes you care about.

Rather than sell your shares outright, pay capital gains tax, and donate what remains of the proceeds, a DAF enables you to make charitable contributions out of your appreciated stock—without triggering a taxable event. Not only can you potentially receive a charitable deduction for the full FMV of the stock, but you may be able to mitigate some of that capital gains tax liability.

Strategy #2: Gifting to Family

If you have older parents or young adult children, you might consider gifting appreciated stock to those family members in lower tax brackets. This strategy is most effective when your loved ones have a lower taxable income and aren’t subject to the same capital gains tax rate as you are. They will inherit your cost basis, but should they choose to sell the stock right away, their total tax liability should be lower (since they’re subject to less capital gains tax than you).

If you do consider this avenue, just be mindful of annual and lifetime gift tax limits. In 2025, you can give up to $19,000 per person without triggering gift reporting requirements.

Strategy #3: Strategic Selling

If you prefer to sell your shares outright, consider waiting to sell until you’re experiencing a lower-than-usual income year. Or, space the sale of multiple appreciated assets across different tax years. You can also pair it with tax-loss harvesting in other parts of your portfolio to offset gains.

Preserving the Value of Your Appreciated Stocks

To see what works best for your unique situation, explore your options with a financial advisor who can help you evaluate what fits your broader goals. If you’re curious about using appreciated stock to fund a donor-advised fund or want help building a tax-savvy giving strategy, we’re here to help.

Disclaimer: This content is for educational purposes only and should not be considered personalized investment advice. Individual circumstances vary, and executives should consult with qualified financial and tax professionals before making investment decisions.*