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CommentaryWealth

Navigating the Great Wealth Transfer: building confidence across generations

By
Massy Williams
Massy Williams
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By
Massy Williams
Massy Williams
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November 27, 2025, 9:00 AM ET
Massy Williams
Massy Williams, principal, head of Wealth Management, Vanguard.courtesy of Vanguard
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Over the next 25 years, nearly $124 trillion will change hands, marking the largest wealth transfer in history, according to Cerulli Associates. This transition will happen in stages: first to spouses (predominantly women), then to Gen X, Millennials, and Gen Z.

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Yet with so much information—and so many competing voices—many inheritors won’t know where to begin. Financial jargon, complex strategies, and a lack of trusted relationships often leave individuals feeling overwhelmed. Confidence suffers when expectations aren’t met because every investor engages with wealth differently. That’s why families need tailored tools, conversations, and strategies to feel prepared.

Let’s explore the challenges inheritors may face, and practical actions families can take to navigate this journey with clarity and confidence.

Family Dynamics: Talk about wealth, early!

Families must proactively pursue conversation and connections ahead of the wealth transfer event. While it can be incredibly difficult to think about wealth and death, we’ve seen tremendous success when families discuss the values first (not the dollars), communicate the intentions of their wealth, and bring the inheritors into the dialogue early and often. Better yet, rehearse the transfer. Families that practice the plan by walking heirs through what would happen at incapacity or death reduce chaos and the stress for the people left behind because it’s one less thing they must figure out while grieving. It is with that thought in mind that my husband and I had this emotionally charged conversation not only with our boys, but also with their godparents. These are complex topics, and investors do not have to do it alone. The right wealth manager will guide you through this. 

Women: Leading the wealth transfer

Women are statistically more likely to outlive their husbands, and Cerulli reports that nearly $40 trillion will first be transferred to widowed women. Yet many feel unprepared because they’ve never had to manage the details of family finances. The barrier isn’t just access—it’s confidence. That starts with building financial acumen before stepping into conversations. Here’s how to flip the script:

  1. Build Your Financial Readiness First – Learn the basics of investments, taxes, and estate plans. Even a foundational understanding changes the dynamic from intimidating to empowering. 
  2. Get Involved Early – Once you have the knowledge, join discussions with your wealth advisor and ask questions. Engagement becomes easier when you feel informed.
  3. Turn On Your Superpower – Bring your perspective—clarity, transparency, and emotional intelligence—to make wealth conversations collaborative and values-driven.

Here, too, a good wealth manager will enable these discussions. For example, at Vanguard, our Women and Financial Empowerment program provides education and resources so women can gain the confidence and skills to lead their financial future—not just inherit it.

Next-gen HNWIs: Evolving expectations 

Over the next several years, wealth inheritance among next-gen, high-net-worth individuals (HNWI) will accelerate, bringing with it complex decisions around taxes, estate planning, succession planning and preserving wealth. To successfully navigate those wealth transfer events, next-gen will expect an evolved service and engagement model.  

My two sons, both Gen Z, remind me daily that methods of communication are changing. They digest information in short, frequent volumes, often via social media. And they’re not alone. If you’re a Gen X or Millennial, you are likely to value some version of the same, expecting seamless, tech-driven experiences with transparency and speed.

Beyond the medium of communication, next-gen HNWIs also expect customized products and services from wealth managers such as alternative investments or tailored value-added solutions and personalized guidance on things like private equity, margin strategies, and advanced tax and estate planning. The right strategies can help minimize tax burdens, prevent family disputes, and protect assets from legal or financial risks. It is important to work with a trusted advisor to create a holistic plan, encourage open family discussion, and build financial literacy to help preserve family assets.

A blueprint for all

Inheriting wealth is inherently personal, emotional, and complex. Choose a trusted advisor who prioritizes your long-term goals over short-term gains and provides more than investment guidance. A partner who understands your values and stands by you to navigate complex financial questions is essential.

Discuss inheritance early and often. Don’t assume others know what matters to you. While these conversations can often be uncomfortable, honest conversations with family prevent misunderstandings and ensure your wealth strategy reflects the priorities and values of all. 

Your family’s wealth is a tool to help you live your values and create your legacy. A clear plan aligns your financial strategy with what matters most, whether that’s security, philanthropy, or growth.

Financial advice isn’t just about numbers. It’s about confidence, clarity, and time saved. Our research shows that working with an advisor can help investors stay disciplined, avoid costly mistakes, save time, and feel more secure about their future.

The opinions expressed in Fortune.com commentary pieces are solely the views of their authors and do not necessarily reflect the opinions and beliefs of Fortune.

About the Author
By Massy Williams
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Massy Williams, CFA is a Principal and Head of Vanguard’s Wealth Management business. Prior to this role, Ms. Williams has held various leadership roles within Vanguard, including Head of Retail Relationship Management and Sales, Head of Financial Advisors Services Strategic Operations, Key Accounts Bank Sales Manager, Manager of the Fixed Income and Equity Security Valuation teams, Department Head of the Central Investment-Only RM team in the Institutional Investor Group and Head of Vanguard Global Securities Lending program, where she had oversight for trading, operations, systems, risk management, and client support. 

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