We almost didn’t write this column.
Not because there isn’t anything to say, but because we kept asking ourselves how to make a conversation about taxes and charitable giving feel even remotely interesting.
But then we thought about the people we’ve been working with this week, and it’s really not just about taxes.
Now that we’re past the April filing deadline, many are coming up for air after gathering documents and crunching numbers. Maybe you’re even feeling that familiar “tax hangover.” And around now, the questions start. What could I do differently next year? Is there a smarter way to plan ahead?
One donor had been holding stock for years. It had done well, but had grown into a larger position than they wanted to keep. They were thinking about selling, but didn’t love the idea of a large tax bill. At the same time, they cared deeply about supporting youth enrichment through arts, culture and athletics.
Instead of selling, they donated a portion of that stock to establish a donor-advised fund through the Community Foundation of the Florida Keys. Recently, they recommended a grant to a local youth sports organization, helping ensure more kids can participate without financial barriers. They’re having an effect, and doing it in a tax-efficient way.
Another conversation we often have is with retirees adjusting to required minimum distributions from a retirement account. They may not need all of the income and are concerned about moving into a higher tax bracket. Through qualified charitable distributions, they can direct those funds to organizations they care about while potentially reducing their taxable income.
We’re also hearing more from business owners who are preparing for a transition, whether that’s selling a business or stepping into a new chapter. Charitable planning can play a meaningful role here, too. In some cases, donating a portion of business interests or sale proceeds can help offset taxes while also reinvesting in the community. These are more complex strategies, but they can be incredibly effective with the right planning.
Even if none of these scenarios feels familiar, there are plenty of simple ways to give back.
It could be a one-time gift. It could be the establishment of a scholarship to help a local student years from now. It could simply be taking advantage of the new above-the-line charitable deduction — up to $1,000 for individuals or $2,000 for couples — and making a commitment to give in whatever way you can.
In a place like the Keys, those gifts matter. They stay here. They ripple outward through more than 200 nonprofits working every day to care for our neighbors, protect our environment and strengthen our community.
If you already know the causes you care about, this is a good moment to think about how to support them in a way that fits your life.
And if you’re not sure where to begin, that’s part of why the Community Foundation of the Florida Keys is here. We spend our days connecting people to work being done throughout the Keys to make our community a better place to live now and in the future.
We also hope you’ll join us as we celebrate our 30th anniversary at our meeting on May 6 at 6:30 p.m. at the Tennessee Williams Theatre in Key West. It’s an opportunity to hear more stories like these and see local philanthropy in action.This column may have started as a conversation about taxes, but it’s really an invitation – to plan a little earlier, to give a little more intentionally and to see yourself in the stories that shape this community. To learn more, reach out to us at cffk@cffk.org.
