The Most Valuable Inheritance: Teaching Generosity as the Foundation of Legacy
As an advisor, I often talk about balance sheets, trusts, and portfolios. But if you asked me what I believe is the most valuable inheritance I could pass to my children, it would be the values that guide them.
This principle recently came to life in my family. My daughter and her friends came up with an idea for a nonprofit as they discussed how many homecoming dresses, nice garments, and dance outfits they had that were barely worn before they were retired. They decided to find a way to recycle and reuse garments by giving them to those in need.
The girls formed Dress it Up, a student-led 501(c)3 Sustainability Project that facilitates the exchange of garments between organizations. Three years later, their nonprofit is still going strong, serving the Tampa community and recently even making the news alongside United States of America’s Mrs. 2025, Diana Meyer.
The Moment I Saw the True Meaning of Legacy
Another instance crystallized for me what true legacy is all about. Our family went to a local church that donates clothing to children in foster homes. The volunteers there were used to getting a few bags of donations. We, however, dropped off somewhere between 30-40 large boxes of clothing.
As we unloaded vehicle after vehicle, the volunteers were overwhelmed—not with stress, but with joy. They saw not just clothing, but dignity and help for the children they served.
Watching the impact our family’s commitment to service was making, I realized that true legacy isn’t about leaving assets to your children; it’s about leaving values with them.
Generosity as a Cornerstone of Multi-Generational Success
My personal experience only deepened a professional conviction I’ve long held: that teaching the value of generosity is one of the most vital components of multi-generational success.
Growing up, volunteering and community service were always a part of our family values. This focus on helping others only increased when I attended a Jesuit high school where community service was part of the curriculum. In my professional life, being involved with several family foundations and serving as a board member for one has shown me the incredible, systemic impact strategic giving can have.
Tools to Incorporate Generosity
If charitable giving is important to you, consider these practical tools:
Donor-Advised Funds (DAFs): These are perhaps the easiest and most flexible way to get started. You receive an immediate tax deduction when you contribute, and the money grows tax-free. You and your family can then decide when and which charities to support over time. This is a perfect way to involve children and grandchildren in the decision-making process.
Gifting of Appreciated Stock: This is one of the most tax-efficient ways to give. If you own stock that has appreciated in value, gifting it directly to a charity (or DAF) means you avoid paying capital gains tax on the appreciation, and the charity receives the full value.
Charitable Remainder Trusts (CRTs): For those with larger, more complex estates, a CRT can be a powerful tool. It allows you to contribute assets to a trust, receive an income stream for a specific period, and then donate the remainder to charity.
Whether through simple volunteering, setting up a DAF, or establishing a family foundation, the objective is to create a structure for purpose that extends beyond your lifetime.
Generosity is a value that pays dividends that money can’t buy. If you’re currently vetting advisors or wondering how to align your wealth with your family’s values, let’s discuss how purposeful giving can be integrated into your financial plan and your multi-generational legacy.
This material is distributed for informational purposes only. Investment Advisory services offered through Journey Strategic Wealth, a registered investment adviser registered with the U.S. Securities and Exchange Commission (“SEC”). The views expressed are for informational purposes only and do not take into account any individual’s personal, financial, or tax considerations. Opinions expressed are subject to change without notice and are not intended as investment advice. Past performance is no guarantee of future results. Please see Journey Strategic Wealth’s Form ADV Part 2A and Form CRS for additional information.