By Daniel G. Coman, JD/CPA/MBA | Chief Family Office Strategist, Leelyn Smith
An estimated $124 trillion in wealth is expected to transfer between generations by 2048, according to Cerulli Associates*, with nearly $100 trillion coming from Baby Boomers alone. The scale of this shift is unprecedented, and yet in family after family, the conversations that actually need to happen are not always happening. Not because families do not care, but because the conversations that make the biggest difference are often the ones that are the hardest to start.
Most advisors focus on the technical work: trusts, tax planning, business forecasting and legal documents. But in my experience, these are rarely what keep families up at night; and they are rarely what makes the difference between a plan that works and one that does not. The things that really illustrate why this work matters are often emotional or relational. What do I want my legacy to be? How can I make sure my kids are set up to thrive? How do I live out my values now and into the future?
Why the Technical Foundation Still Matters
Many families, even those with meaningful wealth, have at some point been told they do not need to worry about estate taxes. The federal exemption has grown dramatically over the course of my career, from $600,000 per person in 1987 to $15.0 million per person in 2026, and many families under that threshold have tuned out of estate planning as a result. That exemption, however, has long been a political football, with estimates of the resulting exemption during the last presidential election ranging from $7 million to today’s $15 million depending on the outcome. The current figure was recently made “permanent” with ongoing upward inflationary adjustments, which only means it will hold until a new President and a new Congress decide otherwise. That is precisely the risk. Federal exemptions are set by legislation and subject to change, which is why working with people who monitor these changes closely is essential.
State-level estate taxes can matter even more for many families. The State of Illinois, for example, offers only a fixed $4 million exemption per person for its residents, and because Illinois does not allow unused exemptions to carry over to a surviving spouse, married couples often end up with access to just one exemption rather than two. At a maximum marginal rate of 16 percent, this can create a genuine surprise for families who assume they have no exposure at all. Consider a surviving spouse who passes away in 2026 with $15 million in net assets and no lifetime gifts. Federally, no tax would be owed. As an Illinois resident with all tangible assets located in the state, however, that same family would face approximately $1.6 million in Illinois estate taxes, along with a complicated state filing and meaningful legal, accounting, and appraisal fees.
The legal side is equally easy to let slip. Wills and trusts drafted many years ago may no longer reflect current circumstances, and beneficiary designations set once are often never revisited after a divorce, a death, or the birth of a child or grandchild. For business-owning families, how the business is held has direct implications for how easily it can be transferred and at what tax cost, and a residency change or a second home in another state can quietly trigger the need for a fresh legal review. Decisions that made sense at the time can also age poorly. Naming a parent, aunt, or uncle to oversee assets for the benefit of your children might have made sense when that relative was in their fifties or sixties, and may no longer make sense once they are in their eighties or nineties, facing health issues, or living far away.
Laws change, and families change alongside them, which means the plan that made sense five years ago may not be the right plan today. That is why this work depends on an ongoing relationship rather than a one-time set of documents.
The Fear Underneath the Planning
The most common fear I encounter is not the fear of losing money to taxes. This is especially true among families with newer wealth, built through the sale of a business, RSU or stock option payouts, or a substantial inheritance. The more meaningful fear is what the money might do to their children. For families who built their wealth through discipline and hard work, the idea that a windfall could remove a child’s motivation to build something of their own is persistent and real, alongside the fear of a young person being taken advantage of or losing an inheritance before they ever really had it. Even well-structured trust planning, distributed over time, can still leave room for dependency if it is not paired with mentorship and context.
Conversations about values and expectations, held well in advance while there is still time to mentor the next generation, can make an enormous difference here. The same dynamic often appears when a spouse passes away, particularly if that spouse managed most of the family’s financial life. The loss can bring financial complexity on top of grief, and having a team that has walked with the family for years can steady that transition considerably.
Structures That Carry Your Values
The same tools that seek to protect assets can also carry values, and that reframing changes the entire conversation. A trust, at its most basic, is a structure in which a beneficiary does not directly own the assets held on their behalf. Depending on how it is built, a trust can insulate a descendant or spouse from creditors, litigation, or the fallout of a difficult divorce or a bad business decision. Trusts can also be designed as incentives, tying greater or lesser access to education, charitable involvement, or milestones a family genuinely cares about.
This design work requires flexibility, since none of us can fully know the future. Tying access to a four-year degree may not make sense decades from now if higher education looks entirely different by then, for example. Tying access to continued full-time employment might risk discouraging a granddaughter from staying home with a newborn, even if that was never the intention. These structures should be built to help, not to punish, and getting that balance right is where an experienced team can be so valuable.
Family businesses raise their own set of questions. Is any family member guaranteed a role regardless of performance? Who decides on compensation, or on a future sale? These issues are far easier to resolve when they are discussed well before they become urgent, particularly when children are involved in the business to different degrees. Every family wants its children to grow into people they can be proud of, and a well-built structure can be a genuine expression of what the family stands for.
An Ongoing Conversation
The plan needs regular revisiting, not only because laws change but because families do too. A child marries. A grandchild is born. A parent’s health shifts. A business is sold or a new one acquired. Some families are entrepreneurial and want to keep building; others want the next generation to carve out an independent path before any inheritance arrives; still others believe wealth exists to be enjoyed together now. Every one of these priorities has implications that ripple across an entire financial picture and plan.
Ideally, the next generation is educated gradually, while the senior generation is still present to mentor them on stewardship. Telling children nothing about family wealth rarely works, and telling them everything too soon carries its own risk. What works is a calibrated process that starts with education and builds over time, together. One advantage of a team that has been present across multiple generations is continuity. I have worked with some families for more than thirty years, and when the senior generation passes, I know who they were and what they valued, because we built that understanding through decades of shared conversations with the whole family.
Why the Whole Picture Matters
Beyond identifying a family’s values, I often see families whose advisers are not coordinating with one another through major transitions and decisions. Every layer connects: the trust structure affects income tax, the charitable vehicle affects liquidity, the business entity affects transfer strategy. When these pieces are handled in silos, the burden of coordination falls on the family, and details can often fall through the cracks.
The approach we bring at Leelyn Smith is holistic in the most literal sense: financial, tax, and legal, all grounded in a relationship with the whole family. A plan that optimizes one dimension while ignoring the others is not actually a complete plan.
The families who get this right are rarely the ones with the most sophisticated trust language or the largest tax savings. They are the ones who have done the harder work of naming what actually matters to them, then found a team willing and able to carry that conversation forward through every transition that follows. That is the work we do at Leelyn Smith, turning what you have built into what comes next.
Source: Cerulli Associates, “The Cerulli Report: U.S. High-Net-Worth and Ultra-High-Net-Worth Markets 2024.”
The opinions voiced in this material are for general information only and are not intended to provide specific advice or recommendations for any individual.
This information is not intended to be a substitute for specific individualized tax or legal advice. We suggest that you discuss your specific situation with a qualified tax or legal advisor.