Over the past two months, we have traveled a remarkable road together. In June, we met the men who put their fortunes on the line for a new nation, Benjamin Franklin, Alexander Hamilton, Robert Morris, and Haym Salomon, and explored the financial philosophy that helped build a country from nothing. In July, we watched that foundation scale into something remarkable: a growing middle class, the birth of retirement, and the power of markets and compound interest working throughout generations. This month, we arrive at the question that sits underneath all of it. What happens to what you built when you are gone? What do you leave behind, and for whom?
This is the Legacy Chapter. And it may be the most important one yet.
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"The Legacy Chapter"
Lessons from the Modern Era and Looking Forward (1980s — Today and Beyond)
Every generation we have explored in this series sacrificed for the next. Franklin wrote for colonists he hoped would one day be free. Morris and Salomon bankrupted themselves for a nation still being imagined. The factory workers of the Industrial Age built wealth they prayed their children would inherit. The veterans who came home after World War II used the GI Bill to buy homes and send children to college, not because it was easy, but because they believed the next generation deserved a better start.
Legacy isn't a financial product. It is a decision. It is the choice to think beyond your own lifetime and to build something that outlasts you. Two hundred and fifty years into this American experiment, that choice is still available to every one of us, at every income level and every stage of life.
Generational Wealth: What It Actually Means
The term "generational wealth" can feel intimidating, as if it belongs only to families with old money, large estates, and teams of attorneys. It does not. Generational wealth is simply leaving the next generation better positioned than you found yourself. You think it starts with a dollar amount, but it's really about your decision to get started.
The GI Bill generation understood this intuitively. They did not think of homeownership and education as luxuries. They understood them as tools, the same tools that would give their children a foundation to build on. In many families, that one generation of access changed their family financial trajectory and legacy for generations to come.
Consider Ida Mae Fuller of Ludlow, Vermont. A legal secretary who had paid into Social Security for just three years, she walked into her local Social Security office in January 1940 and received the very first Social Security retirement check ever issued, for $22.54. She lived to be 100 years old, collected benefits until 1975, and received a total of roughly $22,000 over her lifetime.¹ She did not plan to be a symbol. But her story illustrates something essential about what this generation built: a system designed so that no American would have to face old age alone, and one that every generation since has inherited and relied upon. That is generational wealth in its most democratic form.
But we cannot tell this story honestly without acknowledging its gaps. Families who were systematically shut out of those same tools, through discriminatory lending, segregated schools, and denied benefits, faced a steeper climb with fewer handholds. The wealth gap that exists in America today is the result of policies that excluded entire communities from the wealth-building era we celebrated last month. Reducing that gap begins with access, awareness, and the kind of intentional planning that every family deserves regardless of where they start.
Generational wealth starts with a conversation. It starts with deciding what you want to leave behind, and then building a plan to get there.
Estate Planning, Gifting, and Leaving a Financial Legacy
Here is a sobering fact. Studies consistently show that the majority of Americans do not have a will.² Not because they do not care about what happens to their assets, but because the conversation feels complicated or uncomfortable. The result is that the courts, not the family, often make the most important financial decisions at the most difficult moment.
The modern era has reshaped how Americans plan for the future. The Tax Reform Act of 1986 formalized the IRA and accelerated the rise of the 401(k), completing the shift from employer-managed pensions to individual retirement responsibility that we explored last month.³ For the first time, the tools of retirement and estate planning were within reach for ordinary working Americans, not just the wealthy. In 2019, the SECURE Act updated retirement rules for the first time in decades, expanding access to retirement plans for part-time workers and changing the rules around inherited IRAs.⁴ SECURE 2.0, passed in 2022, went further still, raising the age for required minimum distributions and creating new pathways for younger Americans to save.⁵ The framework keeps evolving because the need keeps growing.
Estate planning isn't just for the wealthy. A will, a trust, beneficiary designations on retirement accounts and life insurance policies, these are the basic architecture of a financial legacy. They are the instructions you leave behind so that what you built goes where you intended.
There is also the matter of living legacy. The annual gift tax exclusion authorizes individuals to give a meaningful amount each year to children, grandchildren, or others without triggering gift taxes. You do not have to wait until death to begin passing wealth forward. Some of the most powerful financial gifts are given while you are still alive to see their impact.
But the most enduring legacy is rarely the asset itself. It is the values and knowledge that accompany it. The parent who teaches a child to save before they spend. The grandparent who explains compound interest over the kitchen table. The family that talks openly about money, debt, and planning from generation to generation. These conversations are more valuable than any inheritance.
Redefining "Enough": What a Rich Life Looks Like at Every Stage
John Bogle, the founder of Vanguard and one of the great democratizers of investing in American history, spent his career helping ordinary Americans build wealth for the long term.⁶ In the 1990s, as the bull market roared and mutual funds became household names, Bogle stood apart. While Wall Street chased fees and short-term gains, he championed strategies built for the patient, long-term investor. He understood that wealth built slowly and deliberately was the only kind that lasted. But he also understood something that balance sheets cannot capture. The point of building wealth is not the building. It is the living.
The 2008 financial crisis tested that philosophy in the most brutal way possible. Retirement accounts lost trillions in value almost overnight.⁷ Families who had invested decades building toward a secure future watched those plans collapse in months. It was, for many Americans, their 1929 moment. And like 1929, it carried a lesson. The Americans who panicked and sold locked in their losses. The Americans who held their diversified plans and stayed the course recovered and, in most cases, went on to see their portfolios reach new highs within a few years. Discipline, during the darkest moments, is the most valuable financial asset you own.
At 30, enough might mean an emergency fund, a growing retirement account, and the freedom to take a career risk. At 55, enough might mean knowing your children's education is covered, and your retirement is on track. At 75, enough might mean the peace of knowing your affairs are in order and the people you love are provided for.
The danger of never defining enough is real. There are investors who spend decades optimizing, targeting a future that never quite arrives, always one more milestone away from feeling secure. There are retirees who worked and saved with discipline and then found themselves unable to spend, so conditioned by a lifetime of frugality that enjoyment felt as though a threat. A good financial plan does not just grow your wealth. It gives you permission to live wholly while you have the chance.
This is exactly the conversation a financial planner is built for. Not just in building a portfolio, but in helping you define what enough looks like for your life specifically and then building a strategy around that definition. The best financial relationships are not transactional. They are ongoing conversations about what matters most and how to protect it.
Franklin knew this. He did not write "wish not so much to live long as to live well" as a financial maxim. He wrote it as guidance that the point of a well-ordered life is not the order. It is the life.
A Lesson in History: Build, Grow, Leave a Legacy
Two hundred and fifty years ago, a group of men with very little security and very much at stake decided to build something that would survive them. They argued over foundations, fought over systems, and in some cases gave everything they had for a country they believed in. They did not know if it would work. They built it anyway.
The Industrial Age expanded what was possible. The middle class emerged. Retirement became a concept, then a plan, then a right worth fighting for. Markets opened, crashed, recovered, and proved over time that patience and discipline were the most powerful financial tools available to ordinary people.
The modern era brought new tools and new responsibilities. The 401(k) replaced the pension. And through it all, from the crash of 1929 to the crisis of 2008, the Americans who came out the other side were the ones who planned, stayed the course, and thought not only about themselves but about those who would come after them.
And now it is your turn. The legacy you leave does not have to be grand. It has to be intentional. A will that reflects your wishes. A beneficiary designation that is up to date. A conversation with your children about money that breaks a cycle or starts a new one. An investment strategy built not just for your retirement but for the generation that follows.
Franklin built a philosophy. Hamilton, Morris, and Salomon put their fortunes on the line. Carnegie's era built the middle class. The GI Bill generation built homes and sent children to college. Ida Mae Fuller cashed the first Social Security check and became the face of a promise one generation made to the next. Every generation in this story added something to what came before and left something for what came next.
What will your chapter say?
If this series has stirred some questions about your own legacy plan, your estate, or simply whether your plan is where it needs to be, your advisor is ready to help you write it.
This concludes our three-part Happy 250th America series. We hope the journey through our financial history has been as meaningful for you as it has been for us to share. Here at EBW, we believe that understanding where we came from is one of the most powerful tools for planning where we are going.
If you live in Fairfax County, learn more about 250th events by visiting America's 250th. If you live in Loudoun County, visit Loudoun Virginia 250. In Virginia, visit America Made in Virginia. In DC, visit dc250.us. To find more information on 250th activities in your community, visit the America 250 State and Territory Commissions website.
Footnotes
¹Social Security Administration, "Ida May Fuller, First Beneficiary" — ssa.gov/history/idamay.html
² Caring.com, "Wills and Estate Planning Study" — caring.com. Note: Caring.com publishes this survey annually; verify against the most current year before publication.
³ IRS, "401(k) Plans" — irs.gov; Congressional Research Service, "The Tax Reform Act of 1986" — crsreports.congress.gov
⁴ IRS, "Setting Every Community Up for Retirement Enhancement (SECURE) Act" — irs.gov; U.S. Congress, "H.R.1994, SECURE Act of 2019" — congress.gov
⁵ IRS, "SECURE 2.0 Act of 2022" — irs.gov; U.S. Congress, "H.R.2954, Securing a Strong Retirement Act" — congress.gov
⁶ Vanguard, "Our History" — vanguard.com; CFA Institute, "John C. Bogle Biography" — cfainstitute.org
⁷ Federal Reserve, "Changes in U.S. Family Finances from 2007 to 2009" — federalreserve.gov; PBS Frontline, "Money, Power and Wall Street" — pbs.org