When you imagine your financial life at its most successful, what does it look like?

For most people I ask, the answer is a feeling, not a number.

They describe security for their family, meaningful contributions to causes they believe in, and children and grandchildren who understand the value of what they’ve been given. It’s about building a legacy that says something about who they are and what they stand for.

The best kind of financial planning is the architecture that connects those values to the decisions we make every day. Without it, it can feel more like a transaction, where numbers are moved around to reduce taxes, forms are filed before year-end, and boxes are checked. The difference between those two experiences comes down to intention and aligning your money with your values.

I’ve spent over 30 years helping clients navigate the full complexity of their financial lives. After my Dad passed away last year, I realized just how important conversations around purpose, legacy, and impact are within a family.

What I’m learning—and what I want to share with you in this article—is that the most powerful financial plans are the ones built around what you actually care about, not the ones that come with the most financial instruments.

Generational Wealth and How Families Plan for It
As we enter one of the largest generational wealth transfers in history, intentional planning is going to matter more than ever. About ¹$84 trillion is expected to move between generations through 2045—from parents to children, from grandparents to grandchildren, from founders to families. Most of that wealth is currently held by Baby Boomers, who make up ²65% of Americans with $3 million or more in investable assets.

By 2030, ³women are expected to control a significant portion of those assets coming down from the Boomer generation, either through inheritance, the death of a spouse, or both. Women who have already inherited wealth say the experience was more complicated than they expected because many didn’t know where accounts were held, how assets would be divided, or whether a plan existed. ⁴Four out of ten women reported receiving assets without any estate or wealth transfer plan in place at all

It’s not uncommon for both giving and receiving wealth to be more complicated than families expect. Money is personal. What you do with it reflects what matters to you, your family, and the kind of legacy you want to leave. The problem is that it can look different from one generation to the next. Different values, different relationships to investing, and different ideas about what the wealth should do next. When wealth moves without clarity, it can create more stress than stability, and what was meant to be given with good intentions can fuel friction instead. Planning with intention helps navigate those differences.

In fact, ⁵90% of high-net-worth individuals say these values-based conversations should happen within the first few meetings with their advisor, and a third say it should come up in the very first one. However, less than half feel that their advisor is effective in guiding them, reporting that the focus stays too technical, on how tax and wealth is structured within the portfolio rather than what the money is really meant to do.

There are programs that focus on how to guide these discussions and thread family values, charitable goals, and financial strategy into one cohesive plan, including how to:

• Clarify shared values before assets transfer
• Define what wealth is meant to support across generations
• Create communication and governance around giving
• Integrate philanthropy into the broader estate and investment strategy

Something an advisor can do is help families have the conversations they’ve been putting off and to serve as a bridge between generations to align values and help translate those into a strategic plan.

Why Planning with Intention Can Get Complex
We’ve all heard the old phrase “shirtsleeves to shirtsleeves by the third generation,” the idea that wealth gets chipped away over time. But what we’re seeing is that wealth isn’t being lost through poor investments but because of a lack of planning and preparation for the responsibility and complexity that comes with inheritance.

If all wealth were transferred as straight cash, planning would be much easier, but most of the time it rarely is. It’s passed down as a closely held business, a real estate portfolio, or a concentrated stock position accumulated over time. Each comes with tax rules, income implications, decision-making authority, and risk.

A business may need a family member willing to run it. A property portfolio may require capital calls and oversight. A large equity position may expose the family to concentration risk, but selling it all at once could trigger significant capital gains. These are not simple handoffs. They require advanced, sound judgement. 

Without preparation, heirs tend to default to one of two reactions. They either sell quickly to simplify (sometimes creating avoidable tax consequences), or they hold onto everything out of loyalty, even when diversification or restructuring would be wiser. Neither reaction is rooted in strategy.

Plus, for families who have built significant assets, the point becomes more than passing down wealth. It becomes about legacy, values, and ensuring harmony across generations. Do heirs understand what they own and why? Do they know how it generates income? Do they understand what happens tax-wise if something is sold, gifted, or retained? Have they discussed whether the long-term goal is growth, income, impact, or simplification?

When these conversations happen early, families can have more flexibility in their decisions. They can diversify gradually instead of abruptly. They can use advanced charitable structures thoughtfully instead of at year end. Educating the next generation on how to steward these assets matters just as much as preparing the assets themselves.

Here are a few talking points to start a productive conversation in the direction of building a clearer plan to preserve your wealth. 

• Identify which assets are sentimentally tied to legacy and which are simply financial investments.
• Understand tax and cash flow implications before anyone feels pressured to sell or hold assets.
• Make sure your current charitable giving still reflects what the family believes in today.
• Use data to guide fact-based portfolio transitions rather than emotion.
• Create a repeatable structure for ongoing family conversations to keep talking about money and responsibilities over time.

This framework will provide an opportunity to better understand each other and plan for next steps.

Strategies and Structures for Purpose-Driven Planning
Just as approaches to passing down wealth differ between generations, so do the causes and priorities they care about. Blending together multiple strategies and structures for strategic giving can be an effective way to honor the voices at every stage of the family’s story as well as to reinforce a common thread that weaves throughout.

Many families start with structured tools like donor-advised funds or private foundations to formalize their giving. From there, they may layer in impact investing strategies, shift a portion of a concentrated stock position into mission-aligned funds, or incorporate charitable trusts into their estate plan. Each family is different and deserves a unique approach to wealth planning that fits their purpose.

Advanced charitable planning offers a range of structures designed to serve both philanthropic and financial goals simultaneously. Choosing the right one depends entirely on a family’s values, timeline, and estate complexity.

Donor-Advised Funds (DAFs)
A donor-advised fund allows you to make a charitable contribution, receive an immediate tax deduction, and recommend grants to charities over time. It’s often used in high-income years, such as after a business sale or large capital gain. Appreciated stock or other assets can be contributed directly, which avoids capital gains tax.

Private Foundations
A private foundation is a separate legal entity that a family controls and manages. It allows for direct grantmaking, hiring staff, and creating a long-term charitable structure. It requires more administration and oversight but offers maximum control and visibility.

Charitable Remainder Trusts (CRTs)
A charitable remainder trust provides income to the donor or other beneficiaries for a set period of time, with the remaining assets going to charity. It can be useful when holding highly appreciated assets, as it allows those assets to be sold inside the trust without immediate capital gains tax. It also generates a partial charitable deduction upfront.

Charitable Lead Trusts (CLTs)
A charitable lead trust sends income to a charity for a period of time, after which the remaining assets pass to heirs. It is often used to reduce estate or gift taxes while benefiting charity during the trust term. This structure can transfer future asset growth to the next generation at a reduced tax cost.

Split-Interest Strategies
Split-interest strategies divide benefits between charitable and non-charitable beneficiaries. These structures balance income, tax efficiency, and long-term giving goals. They are typically used in more complex estate or liquidity planning situations.

Deciding whether to give now or leave an inheritance depends on your family, resources, and what you want to accomplish. Most high-net-worth individuals are already actively giving, with ⁶91% reporting a charitable contribution to a nonprofit in the past year, and a similarly high percentage of younger donors say they are preparing to step into that role.

Start Planning with Intention
The transfer of wealth without the transfer of values is one of the most common reasons family wealth doesn’t survive into the third generation.

The resources you’ve built over a lifetime represent financial security on the surface. On a deeper level, they represent the choices you’ve made about what you prioritize, what you believe, and what kind of future you want to help create.

I’m looking forward to deepening these conversations with my clients and helping them integrate their values into every dimension of their financial plan.

If you’ve been thinking about leaving a legacy and wondering how to make it more intentional, I’d welcome the conversation.