Much has been written about the “Great Wealth Transfer,” the unprecedented shift of wealth from Baby Boomers to younger generations. With an estimated $84 trillion set to transfer to heirs by 2045, this movement represents the largest wealth transfer in history.

But what has been far less explored is how the wealth management industry has missed the mark in preparing for – and responding to – this seismic transition.

Family Wealth Report: We’ve all seen the projections about the great wealth transfer, but from your perspective, what exactly has the industry gotten wrong about it?
Olson: Almost everything. Modern families don’t always follow the traditional blueprint that older estate plans assumed: married parents, biological children, generational continuity. Now, there are more single individuals, couples who choose not to have children, blended families, adopted children – and people who define “family” more by love and responsibility than by lineage.

We also see a shift in priorities. Younger generations often ask: How is this wealth creating impact? What is it doing for the world, not just for me?

Many want to invest in sustainable companies, give to causes they care about, and steward money in ways that reflect their values. ESG strategies, gender-lens investing, community impact – these aren’t just trends; they’re shaping how wealth is managed and what legacy means.

FWR: That evolution in mindset is profound. But many families still have estate plans drafted decades ago. How does that mismatch create challenges?
Olson: Many families created their estate plans years – or even decades – ago. They did it thoughtfully, with care, and with the best information available at the time. But times change. And families do too.

We’re seeing more cases where the structure of a trust is solid, but the assumptions underlying it no longer reflect the real world. The values that guided earlier generations – around family, wealth, responsibility, and legacy – were shaped in a different cultural moment. Today’s rising generation often holds a different view of what wealth is for. This isn’t a judgment. It’s an observation. And it matters.

FWR: Can you share some of the real-world consequences that can result when a plan doesn’t evolve with the family?
Olson: A trust may limit beneficiaries to “lineal descendants,” but the next generation includes adopted children who are legally and emotionally part of the family – yet not qualified under the trust’s terms.

A generation-skipping trust might have been designed for grandchildren, but the middle generation never had children. The assets now sit idle or get redirected in a way that no longer serves the family’s goals. Or perhaps a patriarch’s investment strategy is hard coded into a trust, with no room for modern ESG principles or more inclusive decision-making.

These aren’t abstract concerns. They’re real. And they often lead to conflict, legal challenges, or just a quiet sense that the plan doesn’t match the family anymore.

FWR: So, when families find themselves in this situation – where the plan no longer reflects who they are – what’s the best course forward?
Olson: It starts with this: planning can’t be one-and-done. Families need space for reflection – not just on assets and taxes, but on purpose. Here’s what we’re encouraging:

Review trust language with an eye toward inclusion and flexibility. Revisit family mission statements with the next generation at the table. Build in mechanisms for adapting investments, beneficiaries, or purposes over time.

Acknowledge that values evolve – and that legacy can too.

Most importantly, recognize that what worked before might not work now. That doesn’t mean the old plan was wrong. It means that the world has changed, and it’s time for the planning to catch up.

FWR: That’s a compelling call to action. As this transfer accelerates, what should families and advisors keep top of mind?
Olson: The largest wealth transfer in history is underway. That’s not just a financial moment – it’s a human one. The plans we put in place now will shape how the next generation leads, gives, invests, and relates to one another.

The goal isn’t just to pass on wealth. It’s to pass on wisdom – and the flexibility to make it meaningful in a changing world.