4 Estate Planning Lessons Every Family Should Carry Into 2026

As families prepare for a new year, many intend to “finally get their estate plan done.” This past month, I spoke with several advisors from the Trust & Will Contributor Panel to understand the biggest estate planning lessons they’re carrying into 2026. Their collective insights revealed clear patterns in what families misunderstand, what creates confusion, and what ultimately helps them move forward with confidence.

Across conversations, the same themes surfaced:

• Misconceptions about who would become guardian

• Couples assuming courts will “know what they meant”

• Out-of-state guardians chosen without a realistic plan for day one

• Old documents treated as permanent solutions

• Families experiencing firsthand how powerful proper documentation actually is

This year made one thing unmistakably clear: assumptions create chaos; clarity creates calm.

Here are the lessons we’re carrying into 2026.

Lesson 1: Incremental progress beats waiting for the “perfect” plan

Shared by: Al Faber, CFP®, Founder of DIWY Financial Planning,

Estate planning used to feel overwhelming, something families did once every decade or two. But in 2025, Al found that clients make far better decisions when they take an incremental approach instead of waiting for the perfect plan.

Clients respond well when he encourages them to start the process, document initial decisions, and revisit the plan as life evolves. Even working through the first set of questions inside the estate planning (a la Trust & Will) workflow Al has implemented helps families uncover important decisions around guardians, successors, and trustees.

2026 reminder: A first draft is always better than no draft.

Lesson 2: Many families misunderstand guardianship

Shared by: Charles Thomas III, CFP®, Founder of Intrepid Eagle Finance

Charles saw an increase in clients with incorrect assumptions about guardianship, including beliefs that courts would automatically appoint the person they intended, that distance didn’t matter, or that informal wishes carried legal weight.

Families also tend to overlook the immediate logistics. When a guardian lives across the country, few parents consider who would step in during the first 24 hours to care for their children or manage their routines.

2026 reminder: Families benefit from understanding not only the legal process but also the practical realities their decisions create.

Lesson 3: Couples often disagree–and don’t realize it until they talk about it

Shared by: Matthew Ricks, CFP, founder of Haystack Financial Planning

Matthew observed a recurring pattern this year: many couples discover they have different assumptions and expectations about guardianship, backups, and succession roles only after they begin the estate planning process.

Some assume their wishes will naturally be honored, not realizing that proper documentation is what ensures their intentions are followed. Matthew also noticed that families often have more honest, productive discussions during natural gathering times, like the holidays.

2026 reminder: Couples rarely align by accident. Advisors can help guide these essential conversations before documents are finalized.

Lesson 4: The importance of planning becomes clearest when a plan is actually needed

Shared by: Chitra Patel, CFP®, CPWA®, Founder of WealthWorth

Chitra experienced one of the most profound reminders of estate planning’s value when a long-term client passed away in October. Supporting the family through the estate-settlement process made the purpose of this work unmistakable.

Because the documents were properly in place, the family had direction, clarity, and structure at a moment when everything else felt difficult. The plan worked exactly as intended, allowing loved ones to focus on what mattered most.

2026 reminder: Real-life examples reinforce that estate planning isn’t theoretical. Estate planning is deeply meaningful protection for families.

Today’s families are more dispersed, their digital lives more complex, and their caregiving responsibilities more layered than ever. With modern dynamics like out-of-state guardians, blended families, multi-factor authentication, and digital account access, estate planning can no longer be treated as a one-time event.

Instead, think of estate planning as a clarity system, one that benefits from regular review and updates. Tools like Trust & Will help advisors build this system right into their practices.

What Advisors Can Do Right Now

1. Encourage progress over perfection.
Help clients take the first step, knowing the plan will evolve.

2. Explain what happens in the first 24–48 hours.
Realistic context leads to better decision-making.

3. Use natural moments for alignment.
Holidays and year-end reviews create meaningful openings.

4. Help clients choose practical backups.
Alternate guardians and successors matter as much as primary choices.

5. Surface unspoken assumptions between spouses.
Alignment rarely happens without intentional conversation.

6. Share real stories (anonymized) to motivate action.
Chitra’s experience is a powerful reminder that planning truly works.

Final Thought: Estate Planning Is Family Care

If 2025 taught us anything, it’s that estate planning is one of the most meaningful acts of protection a family can take. It brings order to uncertainty, reduces conflict, and provides clarity during the hardest moments.

As we move into 2026, the goal isn’t perfection. At Trust & Will, we’re here to help you make your goal a clear, current, and adaptable plan that reflects a family’s values and protects the people they love most.

Interested in partnering with Trust & Will to enhance your own clients’ estate planning needs? Learn more about how you can join over 20,000  financial advisors and firms who are delivering peace of mind to their clients by offering a comprehensive estate planning solution. Schedule a free demo today.

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