John E. Chapman
Chief Executive Officer
Family meetings have a reputation for being something only the wealthiest families, like the Roys in the series Succession, would bother with. In reality, they’re just as useful for families of even modest wealth when done thoughtfully. The holidays are the rare stretch where everyone is home, the pace finally drops, and you have a shot at conversations that matter. Think of it like the quiet moment at the end of Home Alone when the whole family finally gets on the same page.
These ten prompts help open that door. You don’t need a $100M balance sheet to use them. You need the intent to align before the new year begins.
1. Are we still structured the right way for the next decade
Life moves fast. Families change. Goals shift. Taking inventory of how your accounts, titling, trusts, and ownership structures are set up is one of the simplest ways to make sure your plan still matches your life.
2. What is our real cost of lifestyle going into the new year
December naturally puts a spotlight on spending. This is the moment to talk about what your lifestyle actually costs, what feels right, what feels heavy, and what adjustments make sense for 2026. This isn’t necessarily about limiting spending. It may even reveal room to increase lifestyle if circumstances have improved. More communication is better here.
3. What is our shared vision as a family
Wealth transfer is just as much about the transfer of values as it is the transfer of dollars. Values define priorities and shape what you want your family to stand for. Whether you’re building a legacy or just trying to stay organized, a shared vision makes everything easier.
4. Are our kids prepared for what’s coming their way
Financial readiness isn’t about inheritance. It’s about confidence. Do they understand saving, investing, credit, and basic financial choices? For many HNW families, this is a neglected topic. The holidays are a natural time to gauge whether they’re ready for the next stage of life.
5. What do we want our giving to look like in 2026
Charitable giving, supporting relatives, or backing causes you care about. December is the best time to align on what “impact” means to your family and how you want to show up next year.
6. What big decisions are ahead of us next year
Home purchases, college decisions, business structure changes, retirement timing, caring for aging parents. Getting these on the table early can allow for better planning and better support. Many of these decisions also need to be relayed back to your Clearwater Capital team as we build your 2026 plan.
7. How do we want to communicate going forward
Most family conflict comes from silence. Talk about how often you want to check in, who needs to be informed about what, and where key documents should live.
8. Are there risks we’re not thinking about
This is broader than the market: health events, job changes, insurance gaps, cyber risks, and elder care. One honest conversation now can remove years of uncertainty later.
9. Are our legal and financial basics in place
Beneficiaries, wills, powers of attorney, insurance coverage, and digital access. These aren’t glamorous topics, but they’re foundational. We can help review your current documents and identify any gaps.
10. What lessons do we want to pass to the next generation
Stories, mistakes, values, and the principles that shaped you. These matter more than net worth, and they age a lot better than any Christmas sweater.
How Clearwater Can Help
These conversations don’t require extreme wealth. They just require intention and a willingness to start. That’s where Clearwater steps in.
We help families turn ideas into structures. If you want to open custodial investment accounts for kids or grandkids, we can handle the setup and use the process to help teach them the basics of long-term investing. If your family wants a shared approach to philanthropy, we can help design the framework, set up the right giving vehicles, and align it with your values.
Suppose you want to revisit your financial architecture, organize your accounts, update beneficiaries, stress-test your plan, or prepare the next generation for real responsibility. In that case, we can guide you every step of the way.
Nothing here is reserved for the ultra-wealthy. These are practical actions any committed family can take. The holidays are the perfect moment to begin. When you’re ready,
Clearwater can help you turn these conversations into action, without any of the chaos of the McCallister family running through O’Hare.
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