The holidays and life’s big milestones have a way of inspiring generosity. A wedding, a new baby, a graduation, a first home — these moments make many people want to help in a meaningful way. Sometimes that help is a check tucked into a card. Other times it’s something much larger: a transfer of stock, a piece of property, help with a down payment, or even a family home passed along early.

Those gifts can be beautiful, life-changing acts. But when the assets are substantial, the outcome isn’t always as simple as “give and forget.” Large gifts can carry tax consequences, legal requirements, and long-term effects for both the giver and the recipient. That doesn’t mean you shouldn’t give. It just means you shouldn’t give without a plan.

Estate planning is often thought of as something you do to prepare for the future. But it’s just as much about making smart decisions while you’re here, especially when you’re thinking about transferring wealth during your lifetime. With the right structure, gifting can support the people you love today and strengthen your overall plan. With the wrong structure, the very same gift can create avoidable burdens, confusion, or even family tension down the road.

One reason gifting needs extra care is that different types of gifts are treated differently. Cash gifts, investment gifts, and property gifts follow different rules, and each can affect taxes in distinct ways. A gift of appreciated assets may lead to different outcomes than a gift of cash. A property transfer can involve valuation, title considerations, or future responsibilities that aren’t obvious at the time of giving. Even gifts made with the best intentions can create surprises later if the tax or legal details aren’t handled properly.

There’s also the big-picture question most people don’t stop to ask: how does this gift fit into your broader estate plan? A generous spur-of-the-moment transfer might feel right in the moment, but it can unintentionally shift the balance of your long-term plan. For example, a gift to one child today could affect what feels “fair” later,  especially if expectations aren’t clearly documented. A well-designed gifting strategy avoids those issues by making sure your generosity works in harmony with your goals.

This is where estate planning and tax guidance become essential. An estate planning attorney can help you explore ways to gift that align with your long-term intentions, protect your assets, and support your family in the way you truly want. In many cases, there are options beyond a simple, outright gift: options that give you more control, protect the recipient, or reduce unnecessary risk. A tax professional can then help you understand the potential tax impact, timing considerations, and reporting requirements tied to your specific situation.

Think of it this way: a major gift is not just a financial transaction. It’s a legal and tax event. And when something is both meaningful and high-impact, it deserves a quick conversation with the right experts before you move forward.

If you’re considering gifting something significant this season, including money, investments, real estate, or another valuable asset, take a moment to pause and plan first. A short consultation now can help you avoid costly surprises, preserve family clarity, and make sure your gift delivers the benefit you intended.

Generosity is a wonderful thing. With thoughtful planning, it can also be one of the smartest parts of your estate plan. If you’re thinking about a substantial gift, we’d be glad to help you explore your options and coordinate with your tax advisor so you can give confidently, wisely, and in a way that protects everyone involved.