The holiday season often inspires reflection. As families gather, conversations naturally turn to traditions, values, and the future. For Joe Dowling of Dowling Financial Services and Wealth Management, it’s also the perfect moment to begin another kind of conversation, one that extends well beyond holiday dinners or gift exchanges. It’s the conversation about legacy.
“Legacy planning is the process of organizing how your assets, values, and wishes will be passed on after your death—ideally as easily as possible and with the least amount of taxes. It includes estate planning, wealth transfer, charitable giving, and preserving personal values or business interests to ensure your legacy reflects your goals while reducing burdens on your loved ones,” Joe explains.
For Joe, the idea of a legacy isn’t reserved for the wealthy or those with sprawling estates. It’s something everyone can, and should, consider.
When asked why he believes a financial legacy is one of the most meaningful gifts someone can give, Joe doesn’t hesitate. “A financial legacy is a great gift because it provides lasting support, security, and opportunities for your loved ones or causes you care about. It helps ease financial burdens, allows future generations to build on your success, and can empower them to pursue education, start businesses, or contribute to their communities.”
While holiday gifts may be unwrapped and forgotten, thoughtful planning can support children, grandchildren, and charitable organizations for decades. For families new to legacy planning, Joe emphasizes beginning with clarity. “The first step is for families to come together and define their goals for the next generation,” he explains. These discussions might include what assets will be passed on, which charitable organizations are important to the family, or what personal values or traditions they hope to preserve.
Once goals are identified, assembling the right team is essential. “It is important to work with a professional who specializes in legacy planning, not just investment management,” Joe says. “Often, the best approach is collaborative, involving a financial advisor, CPA, and estate attorney working together on a comprehensive and tax-efficient plan.”
Tools such as trusts, insurance, and investments each play strategic roles. Trusts can help avoid probate and may protect assets from long-term care costs. Life insurance can provide tax-free benefits to heirs and help cover estate taxes. This is particularly relevant in Illinois, where the state estate tax threshold is $4 million, compared to the current federal exemption of $13.99 million per person.
On the investment side, Joe often highlights Roth IRAs as powerful vehicles for multi-generational planning. “When structured properly, they offer tax-free growth and, under current law, can continue growing tax-exempt for up to 10 years after inheritance,” he notes.
Yet, even with excellent tools available, the biggest obstacle Joe sees is silence. “One of the most common mistakes is families not talking openly about money,” he says. “Without communication, children may be unprepared to manage what they inherit, or may not understand the intentions behind certain decisions.”
He encourages families to approach these conversations gently and with reassurance. The holiday season creates a natural opportunity. “This time of year brings families together in a relaxed environment. People are more present and open to meaningful conversations. It does not have to be a formal meeting, just a thoughtful discussion about the future.”
Joe often advises clients to let their family know that their plans are in place and who to contact if needed. Over time, these conversations can help generations work together. “Many clients’ children end up working with us as well, after seeing how we supported their parents,” he says.
Ultimately, Joe reminds families that legacy planning is not only about finances. “At its core, it is about peace of mind,” he says. “It is ensuring your loved ones are cared for and your values are carried forward.”
In a season focused on giving, Joe suggests that the most lasting gift may be the conversations shared around the table, the kind that ensures love and security continue for generations.