The Second Decision

Now that I have this wealth, what do I want it to do? We call this the second decision. The first decision is often about creating wealth. The second is deciding what that wealth is for.

A New Kind of Planning

Recent reporting on employees of companies such as SpaceX revealed something remarkable. As many employees prepared for life-changing liquidity events, they didn’t simply search for investment advisors. They organized collectively to seek integrated guidance around investment management, tax strategy, estate planning, charitable planning, and family governance.

In other words, they weren’t merely preparing for liquidity.

They were preparing for stewardship.

Perhaps the most revealing question wasn’t: “How should I manage this money?” It was: “How should this wealth shape my life—and the lives of others?”

Managing wealth and stewarding wealth are not the same thing.

Snapshot: A New Reality

More than 1,000 current and former SpaceX employees reportedly joined together to evaluate advisory firms before anticipated liquidity events.

They weren’t looking for a stockbroker.

They were looking for an integrated team capable of addressing investments, taxes, estate planning, family governance, and philanthropy as one connected conversation.

The future of wealth advising may be less about individual transactions—and more about helping people navigate life’s largest transitions.

Beyond the Balance Sheet

A common assumption is that wealth naturally leads to generosity. Experience suggests otherwise.

Many individuals devote years to optimizing investment portfolios before taking time to develop an equally intentional philosophy around generosity, community impact, or legacy.

Money is managed.

Purpose is often deferred.

The opportunity is not simply to build wealth.

It is to steward it with intention.

By the Numbers

·       More than $250 billion is currently held in U.S. donor-advised funds. (National Philanthropic Trust, 2024 Donor-Advised Fund Report.)

·       25.2% was the overall donor-advised fund payout rate in FY2024. (Donor-Advised Fund Research Collaborative, 2024 Annual Report.)

·       88% of affluent clients say it is important to discuss philanthropy with their advisor, and 80% believe advisors have a responsibility to initiate those conversations. (The Philanthropic Initiative, co-sponsored by DAFgiving360™ and Foundation Source, 2025.)

These numbers point to an important shift.

Increasingly, people aren’t looking solely for investment expertise. They are looking for trusted partners who can help them navigate the larger questions that accompany significant wealth.

Lessons from Community Foundations

Community foundations across the country are facing a fascinating challenge.

The question is no longer simply how to attract charitable assets. It is how to help donors put those assets to work in thoughtful and meaningful ways.

Many are responding by creating giving circles, donor learning communities, curated opportunities, and issue-focused philanthropy that encourages action rather than accumulation.

The lesson extends well beyond donor-advised funds.

Whether the assets reside in a charitable fund or arrive through a liquidity event, the opportunity is the same: helping people move from holding resources to activating them.

This evolving work within community philanthropy deserves a deeper conversation (look for more about this from us in the near future).

The Second Conversation

Traditional wealth planning begins with important questions.

How should these assets be invested?

How can taxes be minimized?

How should the estate plan be structured?

Those questions deserve careful attention.

But another conversation deserves equal attention.

What is enough?

What values do I hope this wealth expresses?

What opportunities do I now have that I didn’t have before?

How do I hope my family experiences generosity?

What problems do I feel uniquely called to help solve?

These questions cannot be delegated. Only answered.

One Size Fits One

Every family arrives here differently.

One entrepreneur dreams of transforming educational opportunity.

Another is motivated by a parent’s experience with illness.

Another wants nothing more complicated than raising generous children.

Each story is unique. So is every answer. At H&H, we begin with people - not philanthropic vehicles.

Donor-advised funds.

Private foundations.

Charitable trusts.

Direct giving.

These are powerful tools. But tools are not purpose. Purpose comes first. That’s why our philosophy is simple.

One Size Fits One.

Questions Worth Sitting With

Before deciding where your wealth should go, consider where you hope it will lead.

·       What do I want this wealth to make possible that wasn’t possible before?

·       If someone described my generosity twenty-five years from now, what would I hope they would say?

·       Who should be part of these conversations today—not simply after decisions have been made?

·       Where can my resources create change that feels deeply personal?

·       What is my second decision?

The Conversation

Just as individuals experiencing significant wealth often seek seasoned investment advisors, tax professionals, and estate planning attorneys, many also recognize the value of experienced guidance as they begin to define the purpose behind that wealth.

At H&H, that conversation has been at the heart of our work for decades.

We work alongside individuals, families, foundations, and their professional advisors to help transform financial success into thoughtful, lasting impact—not by prescribing a single model of generosity, but by helping each client discover the approach that reflects their own values, aspirations, relationships, and story.

Because meaningful philanthropy is never one-size-fits-all. It is, and always has been, one size fits one.

Selected Sources

· Donor-Advised Fund Research Collaborative. 2024 Annual Report.
· National Philanthropic Trust. 2024 Donor-Advised Fund Report.
· The Philanthropic Initiative, DAFgiving360™, Foundation Source, with support from The Boston Foundation. The Advisor’s Role in Philanthropy (2025).
· Council on Foundations. CF Insights (2024).
· Reporting on coordinated wealth planning among SpaceX employees by Bloomberg, WealthManagement.com, AdvisorHub, and Barron’s (2025–2026).