Some financial opportunities are easy to overlook because they sit in different places: charitable giving, estate planning, and employee benefits. But they share a common theme of making more of what you already have.
Give more with your biggest investment winners
Imagine you own ETFs worth $50,000 that originally cost $20,000. Selling them would realize a $30,000 taxable gain.
If you already intend to give to charity, consider donating those shares directly to a donor-advised fund, or DAF. With qualifying investments held longer than one year, you generally avoid realizing the capital gain and may qualify for an itemized deduction based on fair market value, subject to applicable limits. More of your investment can support the causes you care about.
A DAF lets you make an irrevocable charitable contribution now and direct grants to eligible charities. When choosing what to donate, consider the ETF tax lots with the largest embedded gains relative to their value.
One current detail: beginning in 2026, itemizers generally face a charitable deduction floor of 0.5% of adjusted gross income. Coordinating several years of giving may help.
Leave more through a step-up in basis
Those same appreciated ETFs can also play a role in your family’s legacy.
Suppose qualifying ETFs purchased for $20,000 are worth $100,000 when your heirs inherit them. Their tax basis generally resets to the date-of-death value. If they sell immediately for $100,000, there generally is no capital gain on that sale. Meaning, the prior $80,000 of appreciation escapes capital gains tax (applicable only to taxable accounts).
That leaves more for the people you love. Gifting shares during your lifetime generally carries over your basis instead, so timing matters. Estate taxes and ownership arrangements require separate consideration.
Capture more from your ESPP
An employee stock purchase plan offering a 15% discount is a valuable benefit that we should take advantage of if possible.
If shares trade at $100 and you purchase them for $85, selling at $100 produces a 17.6% pretax return on your contribution. A lookback can make it even better: if your quarterly plan applies the discount to the lower of the starting or ending price, a rise from $100 to $120 means buying at $85—a 41.2% pretax gain if sold at $120.
For perspective, repeating a 17.6% quarterly return with full reinvestment mathematically equals approximately 91.6% annually. That is an illustrative annualization.
If cash flow allows, maximizing permitted contributions and selling promptly can capture the benefit while limiting additional employer-stock exposure. Check trading restrictions first. Price changes before execution can affect your proceeds.
Thoughtful planning connects these opportunities to your goals: supporting your community, providing for your family, and making your compensation work harder.