Year-end holidays bring together the people who matter most: parents, adult children, siblings, grandchildren, and future heirs. The house is full, the pace slows down, and for once, everyone is in the same room.
And yet, most families never take advantage of it.
Holiday gatherings are the best moment all year to talk about family money, legacy, health, and future plans.
These conversations aren't heavy. They aren't awkward. They aren't about judgment. They're about clarity, protection, and connection.
Here are the 10 conversations every family should have before the year ends — but almost nobody does.
Wills, trusts, powers of attorney, healthcare directives, insurance policies, property deeds, passwords, and digital instructions only help if people know where to find them.
You don't need numbers. You simply need to know how to access critical instructions during an emergency.
Clear direction prevents confusion and conflict at the worst possible moment.
Parents often assume their children "know what to do." Most don't.
Outdated beneficiaries are one of the most common estate mistakes — and beneficiary designations override wills.
Ask everyone at the table: "Has your beneficiary information been updated in the last 12 months?"
This isn't about spreadsheets — it's about beliefs.
The OBBBA made many major TCJA provisions permanent — preventing the 2026 tax hike many expected. But it also introduced new rules around deductions, credits, bonus depreciation, and SALT that impact 2025–2026 planning.
Most parents want a smooth transition. Aligning intentions early supports a strong estate planning strategy.
Most children want to honor their wishes. The missing piece is alignment.
Especially helpful for younger adults:
Risk management rarely gets discussed — but it should.
Ask aging parents whether long-term care preferences or coverage have changed in the last 24 months.
Move the family from uncertainty to forward momentum.
Maybe the most important conversation of the entire holiday season.
For additional non-commercial guidance on navigating financial decisions as parents age, the CFPB offers helpful tools for financial security as you age.
You can keep things light and still be productive.
Try one of these openers:
Yes. The OBBBA prevents the major TCJA sunset, keeps current brackets intact, maintains a higher standard deduction, and preserves several business and pass-through rules. Families should plan using today's rules, not outdated assumptions.
Absolutely. Even without a sunset, estate planning remains essential — especially for wealthy families, blended families, and those with real estate or equity comp. And remember: Congress can always change the law.
Roth conversions, AMT projections for ISO exercises, capital gains/loss harvesting, maximizing pre-tax contributions, reviewing RSU withholding, and planning charitable gifts using appreciated stock or donor-advised funds.
Use the moment: "Since we're all here, can we take 10 minutes to align on a few things?" Keep the conversation high-level and focused on logistics, not numbers.
Yes — and it's usually overdue. Discuss preferences, coverage, expected caregiving roles, and who will help manage medical and financial decisions.
Review remaining Section 179/bonus depreciation opportunities, profit distributions, cash balance plan funding, payroll adjustments, S corp compensation reviews, and informal succession planning.
The end of the year moves fast — and the right decisions before December 31 can save taxes, reduce stress, and protect your family for decades.
If you want an expert to guide you or your family through these decisions, we're here to help.